Is It Okay to Ask a Guy to Dress Appropriately for a Date?

Is It Okay to Ask a Guy to Dress Appropriately for a Date

My question for you is why are men so relaxed in the way that they present themselves (attire wise) when going on dates?

I’m in my early 30s and I usually date men between 29-41. It doesn’t matter if we go out to a nice restaurant to have some cocktails at the bar or dinner, these men are wearing button up shirts, jeans, and then these heinous shoes! We’re talking skater shoes that slip on, wear no socks with, and have the velcro triangles on the side. Better yet, I’ve gotten actual athletic shoes and these men think it’s cool.

It’s very disappointing as a woman who gets dolled up with doing her hair, makeup, a cute blouse, skirt and some heels to come to a guy who did not come with the mentality of dressing to impress. A guy can still wear a casual button up shirt, jeans, and put some dress shoes with it just to dress it up just a tad. Woman are still visual creatures, maybe not driven by that side as much as men. We do want to be attracted to the men we are going out with. I put in the time to looking very nice and it seems like if it’s not a job interview where they are required to dress appropriately with their best foot forward, they’ve become very lax and lazy when it comes to dates as far as how they dress.

If the first date goes well by having good conversation and he’s attractive, but his dressing bothers me, is this something a woman can bring up the next time she’s asked out to a similar venue? If so, how can I express myself in a way that feeling without telling him what to do?

Thanks Evan!


First of all, I wouldn’t at all disagree with you that many men are woefully inattentive to their own appearance. We can delve into the societal reasons why, but, for the most part, we don’t have to dig too deep. Men, for the most part, are not told that their status or self-esteem is dependent on how they look.

What DO men care about? How much money they earn. How physically strong they are. How intelligent or funny they are. How big their dicks are. How many women will sleep with them.

Fact is: until there are mass consequences for bad behavior, behavior doesn’t change.

So if a man can work hard, make money, work out, and be generally charming to women and satisfying in bed — all without combing his hair or putting on a pair of shoes — what incentive does he have to comb his hair and put on a pair of shoes? That’s right. None.

Which means that you’re fighting a losing battle with society. It’s as futile as suddenly declaring that a woman’s appearance DOESN’T matter. You’re going to stop shaving your legs, styling your hair, staying fit, and keeping up with the latest fashions. That’s fine and you’re entitled to do it, but you’re only doing it for yourself and must be willing to accept the consequences that many men may not find you as attractive anymore. (And you may not be as high on how you look either).

Fact is: until there are mass consequences for bad behavior, behavior doesn’t change. Which means that your best hope is a full boycott of sartorially challenged men until they learn their lesson. But as long as some woman is willing to sleep with the bed-head guy in a stained T-shirt and flip flops, he’s going to keep being that way. My point is that if it bothers you this much, YOU don’t have to sleep with him.

Changing others is the LEAST effective way to date.

Want to complain that men have sex without commitment? Well, you can yell at men to be more conscientious, or you can stop having sex with them without commitment.

Want to complain that men don’t like to talk about relationship stuff? Well, you can yell at men to be more communicative, or you can stop dating stoic and emotionally unavailable men.

Only you can decide if it’s worth your time to stick with a guy who cares so little about how he looks.

Only you can decide if it’s worth your time to stick with a guy who cares so little about how he looks. But you should not criticize a guy on the second date; rather, you should see if you’re attracted to him, if you have fun, if you feel comfortable around him, and if you want to see him again.

If this man steps up to become your boyfriend, THEN you can tell him how hot he looks in a button-down shirt and some tapered jeans.

Until that point, you should probably keep a lid on your unsolicited opinion of his looks. Unless you would appreciate some strange guy telling you to grow your hair out and wear less makeup.

Which I’m pretty sure you wouldn’t.

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  1. 1

    Good advice, but even in a relationship I would personally keep the criticisms about his appearance to a minimum.   One of my guy’s exes always criticized how he dressed.   I’m not saying that’s the only reason they broke up–but, it was just a symptom of how she didn’t truly accept him for who he is.   He really resented her for that.   I’m not sure if there’s a way to tell someone to change how they dress, without it coming off as criticism.

    Evan has said repeatedly how men don’t want to be treated as “projects”.   I would think that extends into things like this too, not treating a guy as a “project” to be fixed with your preferred clothing.

    Personally, I think that if the way the guy looks and dresses bothers you that much, maybe he isn’t the right person for you to begin with.   Rather than trying to transform him into something he’s not, women might be better off just dating the well dressed men they don’t feel a need to change.


  2. 2

    Evan’s response speaks to the broader issue here, but in order to help the OP come to terms with this reality, I offer this:

    I see absolutely nothing wrong with jeans and a button down shirt. And this is from someone who prefers khakis to jeans. If the OP has a problem with this outfit, I really think she should adjust her expectations. I consider that somewhat dressy – I count down the dates til I’m comfortable wearing a polo. (Also, I have no idea what the difference is between a “casual button up shirt” and a “non-casual button up shirt ”

    But I think, based on the letter, this is about the shoes. I can’t even picture those shoes, frankly — they sound like slippers. But, for most of the date, the guy’s shoes are not going to even be visible. This degree of fixation on the shoes seems totally irrational to me.

    Basically, I think the OP is getting worked up about things that don’t matter.   All she is doing is imposing artificial limits on herself. It is very possible that she is doing way more work before the date than the guy would expect.

    And this is from someone who typically wears dress pants, a button down shirt, socks, and the same shoes I wear to work on a first date. And I have never in my life worn a button down shirt the way the guy in the picture is wearing it.   If the vibe I get is more casual, I will drop it down to a polo. I am usually the better dressed of the two of us. Sometimes it’s equal. Once, I thought I got a casual vibe and miscalculated. I will never know if that was why she didn’t want another date. I doubt it. But if she thought, “he expects me to dress like this while he dresses like that?” She was 100 percent wrong.


  3. 3

    I’ve had men show up to dates filthy, dirty shirt, jeans, crud on their teeth and some that know what is appropriate for a particular occasion. Some of this seems to be determined by what the do/did for a living; if they had to look and be professional, they learned to be. If their occupation has always been blue collar or more laid back, they did not. If it’s an issue, move on, it’s that simple. Evan is spot on: By our actions, never our words, we show men what is and is not acceptable. Some, after getting rejected repeatedly, will get it, some never will.

  4. 4

    “Well, you can yell at men to be more conscientious, or you can stop having sex with them without commitment.”


    Having sex before marriage is a masculine, this is why women are unlikely to be unhappy in their marriage/relationship.   This has been proven by a relationship expert with a PHD.

    1. 4.1

      Hello MikeTO,

      I don’t understand your last paragraph? What point were you trying to make? The word masculine is throwing me off?

      Are you saying women are happy when they are masculine?

      1. 4.1.1

        Having sex before marriage is a masculine, this is why women are unlikely to be unhappy in their marriage/relationship. This has been proven by a relationship expert with a PHD.

        what I mean was to the there is a reason why women are unhappy in relationships. Women generally are becoming or already more masculine.
        The corporate world is a good example, it’s not set up for women it’s set up for men.
        Most women will be stressed because it doesn’t nurture her environment. If she doesn’t do feminine things to balance it out she will be stressed.

        1. GoWiththeFlow

          Mike TO,

          “Having sex before marriage is a masculine, this is why women are unlikely to be unhappy in their marriage/relationship. This has been proven by a relationship expert with a PHD”

          Please link the study.   If it’s the one most red pill guys cite, it’s a scientifically unsound study that used unorthodox methods and was directly released to the public, never undergoing peer review.

          “The corporate world is a good example, it’s not set up for women it’s set up for men.

          Most women will be stressed because it doesn’t nurture her environment. If she doesn’t do feminine things to balance it out she will be stressed.”

          Tens of millions of women who go to work everyday are in traditionally female occupations:   nursing, teaching, child care, social work.   How is that making them more masculine?   Millions of other women work in traditionally male fields, but do it in a way that is consistent with there feminine characteristics and their outside care giving roles.

          As far as women being happy in their relationships.   There are 50 million married women in the U.S.   Are you saying they are all unhappy?

  5. 5

    This is a cultural issue and the OP could simply date different men if that is so important. Men who work in various business fields (as opposed to say tech guys) will dress well. The society is in fact telling them that they need to look sharp – in order to succeed and make that money. A lawyer will automatically have a better wardrobe than a software developer, and will be more aware to not wear a polo shirt to a swanky bar (and a truly upscale place will not admit improperly dressed people anyway..).

    In my opinion, for a man over 30, the inability to dress appropriately for various occasion is a sign of immaturity, social awkwardness and lack of awareness. These could be deal breakers but not always. He may just be this geeky clueless guy who’s always been socially inept but has great personality and partner qualities otherwise. Criticizing their choice of clothes on date 2 is simply bad taste (just as bad as wearing wrong shoes), but once the OP is his girlfriend she could take him shopping and help him pick nice clothes… A guy like this could be a fixer-upper, but definitely don’t attempt to fix it before you buy it!

    1. 5.1

      “A lawyer will automatically have a better wardrobe than a software developer”  

      You are 99.9% stereotypically correct Stacy and wouldn’t you know that I know the ONE lawyer who when he comes out he sometimes wears a brand new un ironed wrinkled with the fold lines shirt! What’s even worse his wife let’s him leave the house like that….LOL It’s not my place to say anything and I’m sure he doesn’t go into court without a clean pressed suit. Of course he’s not MY lawyer and I’ve never seen him in action. Point being even men that are white collar are sometimes clueless out of their element.

      1. 5.1.1
        Karl S

        that I know the ONE lawyer who when he comes out he sometimes wears a brand new un ironed wrinkled with the fold lines shirt!

        What sort of lawyer is he? A high flying corporate lawyer or a pro-bono public interest lawyer? You get a whole spectrum of lawyers on different kinds of salaries.


  6. 6

    As guy I do understand where the OP is coming from. Night after night I’m out and I see the most ridiculous things and say to myself “how can a grown man over 30 leave the house in THAT?” Some are on dates and many are not and that may be one reason why. It was many years ago I watched Marie Forleo in a dating advice video (David De Angelo- where I found Evan btw) and her topic was teaching men “style”.   She taught how to shop for the right clothes, brands etc… explaining the difference between “dad” jeans/shirts and what to wear when and with what. It was a life changing event for me to the point where I now have a nice wardrobe from high end jeans to many different shirt, shoe/boot combos. If any guy thinks that women don’t judge what they’re wearing in their online profile they’re delusional. Many men of all ages are clueless ladies, some intelligent ones would welcome a little help every now and then. If they’re in to you and you make it fun some(not all) might even enjoy it.

    The flip side for me is I see and have dated women(40’s-50’s) that are stuck in their “mom” clothes, wear no make up, and no idea what a fragrance is. I don’t try and change them but one time for a birthday gift I bought her a nice Marc Jacobs gift set and she couldn’t even put it on once. 🙁    ……. I moved on.

    1. 6.1


      I think that most of the poorly dressed men and women are either clueless or stuck in a rut.   A few people will have a this-is-me-deal-with-it attitude and if so, it will come out in other ways as well.   I think the OP shouldn’t assume evil intent on the part of the guys.   She has two options; automatically eliminate men who are bad dressers, or accept them as they are.   Maybe if she enters an LTR, her man may want/accept her wardrobe upgrade assistance, but she can’t assume that he will want to change.

      As for us middle aged daters, there is the element that many of us are reentering the dating world after being in marriage and/or parenthood bubbles, so the rut can be very deep.   Recently I have been working to upgrade my look after realizing that, with two school aged kids at home, I really backslid on the self-maintenance.   I made a promise to myself to put my contact lenses in every day, changed my makeup, grew my hair out, bought some skirts and dresses (I used to wear them all the time pre-youngsters) and invested in some heeled shoes.   After 3 foot surgeries, I can’t do the stilettos anymore, but I do have options other than birkenstocks and tennis shoes.

      There is an older book out there called Erotic Capital, where the author posits that erotic capital is a super-SMV.   It encompasses all things that make a person desirable as a friend or partner;   physical attractiveness, charm, a pleasing personality, intelligence, being well groomed and well dressed, etc.   The author addresses how people do let their appearance-presentation slack off as they get older.   She says that if a person  maintains their  appearance while their  peers (and competition) let themselves go as time goes by, then  that person will have an even greater advantage in the dating and life in their peer group than they may have had when they were younger.   All of that is a fancy way of saying that if you are  showing up looking like a million bucks, while your peers look like schlubs, you will have a big advantage.

      As a woman in my 40s, I sincerely thank all of the well dressed men like you JB, who give me reasons to smile every day and inspire me to keep up 🙂

      1. 6.1.1

        Hi GoWithTheFlow,

        __I hope you are feeling better after your surgery; let me know when you want to race… I get a head start (^_^).

        …    …    …

        __So GoWithTheFlow how do you view people who show up to dates dressed like they are going to the gym or the grocery store?

        __I like what Christine, Emily and Diana said below, but doesn’t how the person presents themselves for your 1st in person meeting (online dating), your 1st date (cute person you met at the coffee shop), or just your first time alone together in a non-group environment (co-worker, a friend of a friend, someone you met at a party) say something about how they view the date? The value they place on it?

        __How do you know the difference between a possible red flag and just being persnickety?

        __I am curious, what would you do if a date you were excited about showed up looking like he was about to go fishing after he left the restaurant?

        1. GoWiththeFlow

          Hi Adrian,

          Yes, doing better.   Thank you for asking.   I’m down to using just ibuprofen for pain so my head is clearer, though that may not be considered a good thing 😉

          I’m not sure what is going on with your dates being NOT dressed to impress.   Again that was girl code 101 when I was younger and my daughter and granddaughter will be informed of this.   I know you mentioned that sometimes you will chose a street fair/event as a venue for a first date.   For something like that, or mini golfing, a baseball game, etc. I would choose pants over a dress or skirt but I would still wear a nice blouse and shoes.   I may just trip and break an ankle if I try to wear 4″ heels and a pencil skirt to walk up stadium stairs during a basketball game.

          My objective while getting ready for a date is to be as attractive as possible while being event-appropriate.   So I don’t understand the whole “I will dress down because I want him to like my personality” attitude that the author of the book you mentioned in another comment says some women have these days.   I long ago accepted that there is no personality test to pass if I don’t get past the pecker-picker test first.   Plus it can be real fun to get dressed up and I enjoy the process of getting ready for a date.

          Maybe your dates are very casual in everyday life?   I change into scrubs upon arrival to work, so I don’t have a dressy business wardrobe, I tend to live in shorts, casual pants, and (now) casual skirts and dresses.   If the women you date don’t need business-dressy attire for work, they may be out of practice when it comes to stepping it up a few notches for dates.

          I think dressing in a way too casual manner on a date may be a red flag if there are other signs of indifference that goes along with it, like being late or rejecting plans once the date starts.   If a date of mine showed up completely inappropriately dressed (like the going fishing outfit you mentioned) it would be negative points towards an unfavorable impression, that’s for sure!

    2. 6.2

      I’m going to have to think again the next time I leave the house in my camo shorts and tie dyed t-shirt and black socks/sneakers….

      1. 6.2.1


        Don’t forget the mullet hair!   All business up front, all party from behind.

        1. ScottH

          I thought mullets were out of style.   Besides, I don’t have enough hair for that.   Aren’t comb-overs more contemporary?

        2. GoWiththeFlow


          Orange comb-overs are apparently presidential now so maybe???

        3. Nissa

          The comb-over is for when you want your dates to Feel the Bern.

        4. Nissa

          Oops! Bernie is more of a comb-up, lol.

    3. 6.3

      Marie also taught us about skin care which back then in my early 40’s like most men I never gave it a second thought. Now I wouldn’t dream of going a day without my Kiehl’s and Anthony Logistics regimen on my face. If I’m going to shave 3 yrs off in my profile I better be able to walk the walk….lol I was on a meet & greet with a woman last week who was 9 yrs younger than me and my face looks younger I can assure you.

      1. 6.3.1


        Very important point about skin care.   In my line of work–I’m an anesthesiologist–I see people’s skin and teeth up close. 9 times out of 10 if someone’s nose is covered in blackheads, it’s a guy.   Regular cleansing and a small investment in skin care products would work wonders on that!   About 1/3 of my time is spent working with plastic surgeons.   Since I’m “in the business”   I have access to treatments and products at low to no cost and it makes a huge difference.

        Also, regular dental and doctor’s visits are a must to look good.   Some men avoid healthcare like the plague.   Untreated high blood pressure and high blood sugar levels (pre-diabetes, diabetes) will do more than shorten your life, they will tank your energy level and make your skin wrinkle and look ashen.   Smoking has the same effect on skin.   Not to mention all three contribute to ED.

        The biggest age gap I’ve ever had in dating was with a man who was 11 years older.   He was fit, a good dresser, and took care of himself.   Women will date men older than them if the the men have energy and look youthful and healthy.

        1. JB

          Most men my age married or single just don’t care about their appearance and many don’t want to learn. I feel sorry for women in my age group. The “Meetup” groups are filled with  about 95% of these guys because it’s the only way they get to interact with women.

  7. 7

    Is it possible that his shoes are sending a juvenile or childlike signal that is unconsciously turning you off? In the same way that seeing a grown woman blow chewing gum bubbles while twisting her hair and staring at her phone is a turn-off, I imagine seeing a man dressed like a child in some way would be equally repellant.

  8. 8

    “Having sex before marriage is a masculine, this is why women are unlikely to be unhappy in their marriage/relationship.   This has been proven by a relationship expert with a PHD.”

    Name of lead researcher and link to the study, please.

  9. 9

    Hi Kristin,

    __This is not a male issue… or a female issue; it is a person issue.

    __A few months ago the commenter GoWithTheFlow brought up a similar issue about dressing for dates, I a male, asked her about situations were for most of my dates it was I who was always dressing to impress and the women were dressing very causally.

    __I love Evan’s answer and I really love this saying of his, “Fact is: until there are mass consequences for bad behavior, behavior doesn’t change.”  

    __The reason I love Evan’s answer so much is because it is not angry or placing blame. I read a book by a famous relationship expert and her answer to this issue was that the person doesn’t value you or the date, and that is reflected by the way they dress. By not dressing up for you on a first date, your date is showing you that they aren’t really into you or excited about the date.

    __For the longest I believed this; actually I still do (^_^). But I want to give Evan’s positive mentality advice a chance.

    1. 9.1

      I used to think like that other relationship expert…until I fell for a guy who wore jeans, sneakers and a hoodie on our first date 🙂 To be fair, it was at a coffee shop, so didn’t exactly require either of us to dress to the nines!   I wore a nice but casual dress and cardigan.

      I’ve since discovered that he just isn’t a slave to fashion, that’s all.   I’m glad I didn’t immediately dismiss him for that because he has other wonderful qualities I love.

      Not to say you should become a slob and wear an “I’m with stupid” T-shirt on dates. 🙂 Just to keep an open mind and not necessarily read too much into it.   Your date might also just be showing you that they’re not fashionable. Sometimes a cigar really is just a cigar!


      1. 9.1.1

        Hi Christine,

        __As I said in my earlier comment, I still struggle with first date presentations. I can honestly say that I have not given second dates to women who have showed up in jeans and a T-shirt while I was dressed to the 9s.

        __In your opinion, where is the balance between knowing your self-worth and being too picky?

        __To be fair, I have never had a coffee date, all my first dates have been at either fancy restaurants, art museums, or an outside arts fair. Now I want to switch gears and focus more on fun activities for a first date.

        …    …    …

        __By the way the author of the book, she stated that all the women who intentionally dressed very causal for a first date gave the explanation of wanting a guy to be attracted to them for their personality, and not their sexuality; also some felt like dressing up to impress a man or dressing up for a date when they dress causally in their everyday lives was giving the man too much power and pretending to be someone they aren’t.

        1. Emily, the original


          By the way the author of the book, she stated that all the women who intentionally dressed very causal for a first date gave the explanation of wanting a guy to be attracted to them for their personality, and not their sexuality;

          There is already a lot of pressure — and thus a lot of nervousness — for both parties on a first date. Keep the activities light and the time short. Look nice and presentable, but there is no need to get “dressed to the 9s.” Having to get really dressed up ratchets the pressure and no one needs MORE pressure at the early juncture. I’ll do my hair and makeup, but if we are just meeting for a drink at, say, TGIFS, a nice pair of jeans and solid colored T-shirt (sorry) with some flats or sandals is perfectly fine. A woman can always jazz up what she’s wearing (and what she’s wearing underneath) as the dates progress ….

        2. Christine

          Adrian, good question.   In my own humble and admittedly non-expert opinion, I think “knowing your self-worth” is refusing to compromise on the “big stuff” that can make or break a relationship.   To me, “picky” is fixating on minutiae that don’t actually matter for a relationship.

          For instance, if someone’s appearance on a date is such a turn off that you have no attraction for that person, not giving them a second date is knowing your self-worth.   All romantic relationships need some degree of attraction, so I think someone should move on if it isn’t there.

          On the other hand, if someone isn’t that well dressed but has many other good qualities that could make for a good partner (like my guy on our first date)–then I think it might be too picky to pass on them for that reason.   I think Evan’s right to try looking for the positive and for reasons to say “yes”, rather than “no”.

          That’s interesting about the women in the book.   I typically just picked date outfits based on what I thought was appropriate for the venue (as well as weather-appropriate).

        3. Buck25

          “There is already a lot of pressure-and thus a lot of nervousness-for both parties on a first date. Keep the activities light and the time short”


          Yes, and this is why, when I was dating online, I started doing coffee/drinks, dates for initial meet-ups. Evan, I gather, doesn’t care for the practice, but I think it worked better for my situation. In my age group, a lot of the women I was meeting were either widows or long-married divorcees, just entering the dating scene again. There were some with a good bit of dating experience of course, but quite a few had very little recent dating experience, so I’ve encountered my share of nervous ladies ( I pretty much lost the mild nervousness I felt after the first couple of months). I think with that scenario, a brief casual meeting for coffee or drinks and conversation, a half-hour to an hour, is plenty, and a lot less pressure than the traditional dinner date. For those “first meet” dates, I always suggested that my “date” dress casually; and I agree jeans, a nice t shirt and flat/sandals is just fine for a woman in that situation

        4. Emily, the original

          Hi Buck 25,

          I think with that scenario, a brief casual meeting for coffee or drinks and conversation, a half-hour to an hour, is plenty, and a lot less pressure than the traditional dinner date.

          I completely agree. I once met someone for lunch for a first date. It went on for two hours, and that felt a bit long. Sitting with a virtual stranger face-to-face at a table for hours and attempting to make conversation can be difficult.

          For those “first meet” dates, I always suggested that my “date” dress casually.

          I think casual is the way to go for the first date. That isn’t to say I will show up looking like I didn’t make any effort, but attempting to get all dolled up [heels, skirt, push-up bra etc.   🙂 ] just adds pressure to any already tense situation.


      2. 9.1.2

        In the six years I’ve been dating recently, two very bright engineers have fallen head over heels in love with me (at separate times, two different relationships). They weren’t horrible dressers, but neither were they great dressers.   However, they both REALLY wanted to please me. They both said that I would be  looking at them when we were together, and they wanted to dress to please me. I would not have dismissed them on the meet’n’greet because of their clothing, and I wouldn’t have brought it up early on in the relationship. My current guy was thrilled when I bought him some clothing, and he then brought multiple pairs of shoes to my house to get my opinion on what shoes would go with his new clothes. In return, I dress to please him.   It is an easy way to please your partner, I think.

    2. 9.2


      I missed this one before, but knowing about where you are age-wise, and extrapolating from that the likely age group of most of your dates (I’m guessing most are late 20’s to early 30’s) a lot of what you’re encountering may be an age group thing; I see a lot of women who appear to be in about that age range dress very, very casual, in places and situations where a slightly older woman usually would not.

      1. 9.2.1

        Buck & Adrian,

        Sounds like a cohort of young women missed learning Girl 101.

        I’ll remember to start my daughter and granddaughter’s lessons with “Dress To Impress.”

  10. 10

    From Shakespeare’s Hamlet, Polonius   to his son: ” for the apparel oft proclaims the man..” That is all you need to know.

  11. 11

    I’ve been on many dates and honestly, I can barely remember what my dates wore.   But what I DO almost always remember is as follows:

    Was he happy to see me

    was he interested in me

    was he nice to the waitstaff/barista

    did he smell good

    did he have good dental hygiene and clean nails

    did he make eye contact

    did he show up on time

    did he avoid crude jokes

    Did they have a (well developed) sense of humor

    Was he able to discuss ideas

    did he complain about his  ex

    did he complain, generally

    were there stains on his clothes or were they wrinkled

    i can only remember the color of one guy’s nice button down shirt, a beautiful blue. He turned out to have a full blown STD, which he did confess at the appropriate time. I dodged that bullet.

    Also, I don’t dress up too much on initial dates. No tight clothes and high heels. And hair and makeup is understated, but perfect. I like to keep it casual. I might even wear high end slip on shoes/sneakers with a nice casual dress (and I’m short) I don’t like to be over coordinated or appear oversexed. But that’s just me.


    excuse any typos this is from my phone









    1. 11.1
      Emily, the original


      I’ve been on many dates and honestly, I can barely remember what my dates wore.

      Ditto. I can only remember one: He showed up in short white shorts, white knee socks pulled up to his knees and his keys hanging from a back belt loop! I believe that was paired with a short-sleeved, floral button-down shirt. Needless to say, there was no second date! But baring that, if I really like the guy I’m not paying much attention at all to what he is wearing.

      1. 11.1.1

        Emily & Diana,

        What I remember most are overall impressions;   looked great, snappy dresser, etc.   There was one guy whom I nicknamed black-on-black, that had on black shoes, black pants, black belt, black button down shirt, and hair dyed jet black that clashed with his skin tone.   The all black look could have worked if it wasn’t for the hair.

        I have noticed that a lot of younger women are now dyeing their hair black when it’s clear that isn’t their natural color.   It often clashes with their eyebrows, skin tone, and eye color.   I wonder if men react to this in women as poorly as I did to it in a man.

        1. Emily, the original


          I have noticed that a lot of younger women are now dyeing their hair black when it’s clear that isn’t their natural color.   It often clashes with their eyebrows, skin tone, and eye color.

          I noticed that, too. They dye their hair red, for example, but don’t change their eyebrow pencil and other makeup to match.

          Another pet peeve of mine is roots! I know it is fashionable to ADD roots into your dyed or highlighted hair, but to me it looks as if you don’t care to maintain your look. Black roots with platinum blonde hair … UGH! Being blonde is a responsibility … If you can’t HANDLE it, don’t take it on … 🙂

        2. Karl S

          Did he just come from work as a waiter? That sounds like my uniform.

        3. GoWiththeFlow

          Hi Karl,

          He wasn’t a waiter so I think he was trying to achieve a certain look.   I think the all black outfit can look very striking on some people.   I can’t pull off wearing a lot of black, I look washed out and am overwhelmed by such a strong color.   If you  have the coloring and confidence to wear an all black outfit, you may look quite hot in your uniform!

  12. 12

    I live in LA and there are two kinds of people – who dress up and who wear flip flops year around. I don’t like flip flop guys, they are usually lazy, broke and want to “hang out” at their place. I mean if a guy is great in everything else, I will obviously overlook his dress style but usually it’s connected, they will have a dirty shit hole apartment and   inflated ego.

    I was on two dates with a french guy last week, I did not like his style as I don’t really like accessories on a man but you can see that he thought through his outfit and everything was not random and I’d say very interesting. Not my style at all but it will never be a deal breaker for me opposed to wearing flip flops on a fancy dinner date.

    1. 12.1

      I loved everyone’s comments. It was a treat to actually spend money and pick outfits for dates after I divorced.   I never had the luxury to do any of that when I was married. I’ve also noticed the jet black hair/mismatched eyebrows and skin tone. Wait till you get my age and all your friends (who are now 75% grey) go blonde! Geez-most of them look awful. They look washed out most the time because they go ash blonde instead of golden. I found out I actually stand out amongst my girlfriends now:)

      1. 12.1.1


        I’m a natural golden tone blonde.   My mom and aunt always used to say that it was best to stay within a few shades of your natural color so you still pass the believability test.

        When I was on the date with Mr. black-on-black, his hair color was so unbelievable, it was a distraction.   My eyes kept shifting up to his hairline.   He wasn’t a bad looking guy, he was just sporting a bad look.   I do know a few men who dye their hair to cover grays and they look good, I’m guessing because they stick close to their natural hair color.

        1. Buck25

          Ladies, you have to remember that like JB said earlier, most guys are clueless when it comes to knowing how to dress. I have to say that most of the married guys I’ve known over the years have had their clothes picked out by…their wives. You can imagine what they do when single again-these guys don’t even know how to pair the right tie, or the right color socks, with a business suit, much less anything more complicated. This is particularly true of my generation (baby boomers). A lot of them seem to think that it’s somehow “gay” or “metrosexual” for a guy to have a sense of style. This attitude is actually pretty silly; at minimum, guys, we need to know how to dress appropriately for the occasion, the situation, and our age!

          It’s not all that hard; and most of it is common sense. The first thing I do, is make sure whatever I’m wearing actually fits. If something off the rack doesn’t, I get it tailored so it does. I make sure the colors coordinate, and match my hair and skin tone (This was the problem with the guy wearing the black-on-black look mentioned earlier). I never wear an outfit on a date (or anywhere else, except fishing or working in the yard), that I haven’t tried on, and looked at in a full length mirror.

          One thing that works for me, that might not work for someone else, is I won’t wear a suit, when I can wear a blazer or sport jacket; the older I get, the more I go for a combination that’s classic and snappy but a bit relaxed. I don’t, incidentally, dye my hair. The biggest challenge I have, is our summer weather here, where the heart index can be 100 degrees at   6pm; it’s a challenge to stay crispy and comfortable. This is where khakis (chinos) and a lightweight linen jacket (when necessary) come in. If it’s really hot and humid, I’ll forego the jacket, long-sleeve shirt and tie, and just wear a polo. Incidentally, guys, I’ve found that women pay attention to shoes (shouldn’t be surprising give how many pairs most of them have, right?) so I make sure those are properly kept, and compliment the rest of the ensemble. The point is, that when I look good, I feel better and more confident, and on a date, it shows a lady that I respect her enough to try to look my best in her presence.

          I guess this works, because I often have women (most of them married, dammit!) come up to me when I’m out and about alone, and ask who helped me put together the look I’m wearing, and where I found that jacket, shirt   or tie (often with some comment that “I wish I could get my husband to dress like that!”) Now, if I can only figure out how to get the single women to do something similar… 🙂


        2. Caroline

          GWTF-that’s a good point about keeping it within three shades. I also think if you were born some variance of blonde you can go some variance of blonde later in life. I had a good friend (milky white complexion and dark hair) go very blonde. It just washed her out. But I do think it was a very freeing experimental fun thing at that point in her life:) I also think it’s fine for guys to put a little color through their hair if it makes them feel better. My almost 90 year old dad combs a silver through his white locks. He actually looks much better(his hair is a bit yellow/white). I do think as you get predominantly grey you gotta step it up a notch and get hi lights. Those box dyes tend to give your mostly grey strands a big block of one color instead of greater variation. My color fades during the summer so I actually get lo lights too along with hi lights. It looks more natural.

          Buck-it sounds like you nit only dress well but are comfortable in how you dress. I agree, it’s too hot to wear certain clothes this time of year. I’m a sundress/skirt kinda gal. Much cooler when you’re nearing 100 even over shorts and especially jeans. I really appreciate a guy who feels comfortable in his own style. I dated a lawyer from Nola who showed up on many evenings in a seersucker suit, and now tie. He looked great because he owned it. But I gotta admit I was a bit perplexed the first time I tailgated with my guy. He showed up in pink corduroy shorts with the wales running horizontally and a crisp white button down and topsiders! Only in the SEC 🙂


        3. SMC

          Thank goodness for hair dye.   Yes I do.   Red heads don’t go gray gracefully at ALL, at least not the ones in my family, so we’ve all determined we’ll be dying our hair to our graves.   Caroline, after letting two “professionals” (and I use that term very loosely) try to color my auburn locks, I vowed never again.   One turned me jack-o’-lantern orange, the other overcompensated by turning me dark chocolate brown, so I finally decided I did it better all along by blending two shades right out of the drugstore boxes.   (I cut my own hair too, again, because nobody does it better than I do.)   Heh!

          I did try going blonde once – awful mistake, just didn’t go with my Irish skin color (read: ruddy).   🙂

        4. Buck25


          That seersucker suit thing used to be practically a summer uniform around the Nola area (and some other parts of the deep south, as well), and for some reason, the right bow tie seems just the thing to set it off, with course a coordinating (NEVER matching!) pocket square. I’ve been known to wear that look myself. For a real retro look, it can be topped off with a fresh boutonniere, and a straw boater or panama, (though if I’m going to go that far, I prefer a white linen suit, lol!)

          The shorts like you describe with a button down, deck shoes and no socks, is kind of a southern frat boy look. I prefer to leave that to the twenty-something crowd, but some older guys here are fond of it.

          Funny bow tie story; I was wearing one with my blazer one day, just for a change of pace, and a buddy of mine noticed it. He asked if it was if it was one I tied by hand, or a pre-tied one (like   the clip-on type mothers used to make young boys wear when I was a kid). I couldn’t resist the chance for a quip, and recalling Gen. Patton’s remark when asked about his “pearl-handled pistols” (they were ivory), I replied “Hand-tied! Only a pimp in a cheap New Orleans whorehouse would wear a pre-tied bow tie!”   (Which is true, actually. I don’t know why some guys think a bow tie is difficult to tie; it’s   really easier than getting a proper four-in-hand knot in a necktie, which actually takes a bit of practice) 🙂

          As an aside, of course I’m comfortable with how I dress; I have to be, or I wouldn’t feel good in whatever I was wearing. One thing some guys forget, is that matter how fashionable a look is, if you’re not totally at ease in it, your look ends up wearing you, instead of you wearing it. (this is why any guy who ever has need to wear a tuxedo, needs to spend some time in one; if it’s the right weight and properly fitted, the black-tie outfit is no more “uncomfortable”   than anything else we wear). It’s also why most guys can’t pull off an ascot; takes a lot of confidence to wear that in the off-handedly casual manner it requires.

        5. SMC


          “… no matter how fashionable a look is, if you’re not totally at ease in it, your look ends up wearing you, instead of you wearing it.”

          You can say that again, both for men AND women.   If you’re going to “wear outside the box,” then own it and wear it with style, panache, hell, take an attitude with it, but just be COMFORTABLE in it.

        6. GoWiththeFlow


          On behalf of all the single ladies, we do notice and we do appreciate it 🙂

      2. 12.1.2
        Yet Another Guy

        I am in my mid-fifties. I have almost no gray in the hair on my head. I am not even graying at the temples; however, I do have some gray in my facial hair. My ex is in her late forties. She also does not have to color her hair to cover gray. I was completely blown away to discover that a large percentage of the women my age have been coloring their hair to cover gray for at least a decade.

  13. 13

    I seriously dont get why women waste their time in that. I could care less how the guy dress up, i dont pay attention to his clothes, I pay attention to how he acts and the things he says, he can show up at the date wearing shorts, a tank top and flip flops and if I like him, I like him.

    1. 13.1

      Really? Are you saying that if a guy showed up to an upscale restaurant/bar where the crowd is dressed properly wearing shorts and flip-flops, you wouldn’t notice it and it wouldn’t bother you one bit? I find it hard to believe.

      Its not about what he is wearing per se, rather about how appropriate it  is for the location and whether it makes him stand out from the rest of the crowd (and not in a positive way). If a guy showed up in sneakers  to an upscale place (that happened to me), or if he showed up in a tuxedo to a beachfront cafe (ok that didn’t happen but just to make a point), either way it would make me go “hmmmm” and make me think this person is socially inept.

      1. 13.1.1

        Sneakers are good.. A guy wore flip flops and dad’s jeans with t-shirt that originally had a different color but now you cannot tell, to a fancy event I invited him. I secretly was hoping they won’t let him in but they did, haha.   I really wanted to tell something but I am not going to tell a 43-year old how to dress. The thing is his all apartment looks like random things from a dumpster or Craigslist and he can brag for half an hour how he bought sunglasses on some Chinese website for $6. Sloppy dresser equals sloppy apartment and everything else.

        In LA is so easy to dress nice, hundreds of local cool designers with good prices and very interesting clothes. You need just to make an effort but…eh, yeah, it’s probably hard.

    2. 13.2

      I could care less how the guy dress up, i dont pay attention to his clothes”

      You should Kathy because it’s a reflection on you. I know when I’m out with a woman that looks like she took time to care about her appearance in all areas I feel better and I also know she probably appreciates my effort.

  14. 14

    NO! Don`t make him second you! You liked him when he was not with you and did what he wanted. But you liked him. Never try to turn a guy into you. Don`t you want to live with yourself.

  15. 15

    Funny about the connection between the sloppy dressers and the sloppy house. My biggest turn off are the teen jeans. Way worse than dad jeans in my opinion, though both are bad. LOL. When I see a man wearing those jeans with all the extra snazz on the pockets, I automatically think “douche bag alert”.

  16. 16

    I feel for the OP.   I am constantly amazed at what I see entering the front doors of fancy restaurants.   I don’t go to them much anymore because my guy is a “live off the land” guy who is more comfortable in jeans and loose shirts (or camos when he’s fishing and hunting), but they’re always clean, pressed, and he smells divine (except when hunting, when he has no fragrance at all).   He doesn’t wear flip flops or sandals.   I don’t think I’ve ever dated someone who did.   He wears boots (cowboy or work), or leather casual shoes, or mud boots, or whatever depending on what activity he’s engaged in.   Athletic shoes when he plays basketball.   I had to wonder what his house was going to look like when I was first invited there, and I was delighted to see that it was spotlessly clean, neat as a pin, and he maintains it throughout the week, doesn’t just clean it when he knows I’m coming over.   His house reflects who he is – casual and clean – not sloppy.

    Then there are the guys who walk through the front doors of those restaurants I’d mentioned earlier, and honestly, to see their dates all prettied up and then these guys in untucked, wrinkled, button-down shirts, tennis shoes and ill-fitting jeans makes for interesting people watching.   I’m old school and frankly don’t care for the look of these long-tailed men’s cotton shirts left untucked.   Polo shirts and t-shirts untucked?   Great.   But not cotton button-down shirts that have long tails specifically so they CAN be tucked in.   Yep, old-fashioned, and I’m fine with it.   I can’t say that I’ve ever dated a man who dressed that way, either.   It’s not a conscious thing, I guess I just gravitate towards men who care about their appearance enough to put in the effort.

    As for me, I put in the effort too including for work, evenings out, even going to the grocery store on weekends.   I’m too “seasoned” to go without a lick of makeup anymore, so I at least do my eyebrows and eyelashes if nothing else.   I recently had a first date to go shoot pool, so for that it was nice (dark) jeans, black boots, a black boat-neck, cap-sleeve tee and what I call my “biker belt” – a black belt with silver studs.   Kind of a bad ass look, actually, and one in which I’m completely comfortable.   Second date was in a leopard print sheath dress with black stiletto pumps, appropriate for the restaurant we went to.   Wore that same leopard dress with fringed black cowboy boots for a dance at a country club last week and was comfortable in THAT, too.   My guy is comfortable with me in what I wear which spans many looks, I’m comfortable with him in his camos (I have a set too) and his more countrified look.   He doesn’t try to tone me down, I don’t try to dress him up, and neither of us embarrasses the other.

    I do get where the OP is coming from, though.   That look in the picture above is EXACTLY what you can see in any of the many, many expensive restaurants in my city.   I just can’t figure out why.

  17. 17

    I think if a man did not care about the way he dressed or his grooming, I’d be outta there.   Smelly men who can’t be bothered is just not attractive.   And it’s insulting to a woman that he does not make the effort.   I once turned up for a date wearing something classy and he turns up like he’s going to spend the evening in his sofa (or rather HAD spent the evening or the week in it on his sofa).   Just not on.

  18. 18

    Apparently, I’m not the only one with objections to men’s clothes that don’t fit well. Here’s a current article from the Wall Street Journal, “Nice Cargo Shorts”. .

    A quote from the article:

    Fashion guru Tim Gunn said in a 2007 interview with Reuters that cargo shorts were the least fashionable item of clothing in his closet. British tabloid Daily Express called cargo shorts “a humiliation for any man over 21 and should be sold only after proof of age has been presented.

    1. 18.1

      @ Nissa,

      LMAO over the quote in No.18 above! Cargo shorts? If those things look even decent (let alone good) on anyone, I don’t know who that might be!

      1. 18.1.1

        Buck & Nissa,

        Cargo shorts look pretty good on my 7 year old son 😉

        1. Buck25

          “Cargo shorts look pretty good on my 7 year old son”


          LOL! Yes, and a Teenage Mutant Ninja Turtles T-shirt does as well, I’m sure…but then, seven year old boys don’t need to project sex appeal. Men do…if we can, and somehow, looks appropriate for preteen and early adolescent boys just don’t cut it. I have this mental picture of my 68 year old legs (tanned and in shape, but still!) sticking out of cargo shorts…ummm, NO!

          Makes me feel like Maurice Chevalier’s character in Gigi  ; remember the song, “I’m Glad I’m Not Young Anymore“? There’s something to be said for a grown man having a schoolboy’s heart;   but a schoolboy’s clothes and fashion sense? Not so much. 🙂


        2. Christine

          LOL!   Cargo shorts look great on my 4 year old nephew too…as do his Thomas the Train and Curious George T-shirts.   They’re appealing to the opposite sex all right…to the little 4 year old girls who like him. But I’m not sure if they appeal to older demographics!


        3. GoWiththeFlow


          “There’s something to be said for a grown man having a schoolboy’s heart;   but a schoolboy’s clothes and fashion sense?”

          Words of wisdom there, Buck!

          My little boy is so sweet!   He will look me straight in the eyes and with a big smile on his face say, “Mommy, you’re in my heart!”

          Recently, one of the summer school aides said that they got a new girl in class, and my son introduced himself, sat down next to her, and then was real quiet, but he had a sneaky smile on his face all day long.   It cracked her up.   He’s been going there since he was 3 and she said she’s never seen him like that.   And so it begins!

      2. 18.1.2

        “And so it begins!”


        Well sort of; the real beginning will come in a few years, at about the time he realizes that girls aren’t so icky after all; let one get cleaned up and dressed up, and she actually looks kinda pretty…and she smells nice, too. That’s when it begins; remember that first middle school dance? I know I do. 🙂

  19. 19

    I’m not gonna wade in to the debate about whether people _should_ care whether their date makes an effort about his clothes and fits the event or whether that’s shallow.   I think the point was Evan’s single line:

    Changing others is the LEAST effective way to date.

    Our job, on a date, is not to change our date into someone we’d like to be with.   It’s just to decide whether or not he is someone we’d like to be with.   If dorky shoes are a dealbreaker, then you walk away.   If you are willing to accept him as he is, then you can rave about how great he looks the first time he does dress to the nines (if that ever happens) or watch Crazy Stupid Love and mention how great Ryan Gosling’s wardrobe is, and maybe he’ll choose to change for you.   But there are few things more off-putting than having someone tell you they’re not happy with you the way you are, especially if they manage to say it in a way that implies that their way is right and your way is wrong.

  20. 20

    I wish the worst thing I had encountered was a guy’s crappy shoes. Seriously, you have to let people be who they are. The writer sounds a little perfectionistic. You have to cut these guys some slack; they’re in the same dating melee the rest of us are. What would you think of a guy who went back to his friends and said, “she was really hot and I really liked her, but she had a run in her pantyhose. I just don’t think I could date a girl who cares so little about her appearance?” He’d probably be called shallow as hell.

    Really, in the scheme of things, how important is it? If she is that nitpicky, love is going to be hard to find.

    1. 20.1

      You get it Jen. I don’t dress like a slob and I’m always wondering if I’m smelling at my best. I also don’t wear a tuxedo or always put on something from men’s warehouse. You try to understand the other side instead of these women who say “my way or the highway”. All the creepy stuff aside, you sound like a great woman. I would agonize over making sure I don’t turn you off on a date.

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