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!
Kristin

Kristin,

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.