What Can I Wear To Make My Boyfriend Happy? Ask A Pro

By The Head Pro

Send Head Pro your questions about life, love and sweatpants to [email protected]

Dear Head Pro,

I've been with my boyfriend for almost three years, and every so often he still comments on me dressing differently when I'm with him verses if I'm out with my girl friends. However, when I do dress nice he usually says something like, "wow why do you look so nice?" I get so frustrated because I feel like no matter what I wear, with or without him, it is somehow wrong, (dressing too nice when we stay in, not nice enough if we are going to go out) but I also feel like I'm probably not the only girl who feels this way.

He says he just loves how I look and doesn't want me to feel like I have to wear clothes that cover me up, and that I should show off what I have. I don't want you to get the idea that my boyfriend is making comments on my clothes every time I see him or anything like that or that he is some jerk who makes me change when I'm out. On the contrary, he only makes comments about what I wear very rarely but when he does I feel like he has been wanting to say something for awhile, as if it genuinely upsets him that I dress nicer when I go out to a bar with my girl friends versus watching a movie on the couch with him. So,  I know that all guys are different, but what do guys really want their girlfriends to wear? thoughts on this?

Dear ________________,

Ugh. I don’t think there’s a more annoying topic to cover than girls, their clothes, and how guys feel about them. Like you said, all guys are different - I have no idea what, specifically, your boyfriend wants you to wear. And there’s also the question of why it matters to them in the first place. Assuming your style hasn’t changed drastically since you started dating, he doesn’t really get much of a say in how you dress. Like, do you bitch at him for dressing nicer at work and throwing on pajama pants when he gets home? No, because you’re (I hope) not a crazy person.

I’m going to go out on a limb here and assume that your boyfriend’s random commentary on your clothes has more to do with him than it does you. As in, he may feel that disparities in how you dress are an outward reflection of how much of a priority he is to you, and he’s just not very good at expressing that. He may feel hurt in some way that you get decked out when you go out without him, but on a date with him you opt for jeans, flats and a t-shirt. Because most men are at least aware that clothes matter a lot to girls, in his mind dressing nicer means that going out with your girlfriends is more important than you than spending time with him. I’m not saying that’s right, but that may be how he feels.

This isn’t necessarily a bad thing! It means he thinks you’re hot and wants to show you off. Rather than go insane trying to pinpoint the “perfect” outfits for him, I think you need to help him get a grasp on your relationship with clothes. Explain that going out with a bunch of girls requires putting on that “uniform,” of sorts, and it’s more to fit in than anything else. Explain that part of what you love about being with him is that he doesn’t make you feel like you have to dress up to feel sexy. Explain that looking good as a girl is fucking exhausting, and to please excuse you if you want to throw on some loungewear at the end of the day if you’re not going anywhere.

And hey, if you want to throw him a bone and wear something a little sexier once in a while, that’d be a nice thing to do.

Sartorial Kisses,

Head Pro

Send Head Pro your questions about life, love and sweatpants to [email protected]




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