"Cool Story, Bro" is an ongoing series in which Jian DeLeon tries to place men's style in the larger context of an apathetic society.
Word, you’re a dude into clothes that can pretty much put an outfit together without looking like a total dickhead. Even better, you’ve managed to find a stable relationship with someone who does not mind that you nerd out about Urotsukidoji-like Yayoi Kusama window displays or the artfully disheveled forms showcasing the latest in blanket-stripe rustic outerwear at the RRL store on Prince St. And you know what? She digs clothes too. But not in the annoying “OMG I love my Isabel Marant sneakers, PS1 handbag and I just died when I saw this Christopher Kane Frankenstein T-shirt” kind of way. In fact, she’s actually more nonchalant about dressing well than you are.
But look, even if you have a bajillion Tumblr followers and scores of guys look to you for style advice and like your Instagram selfies, there are some ground rules for when you and your girlfriend happen to be stepping into a store together. First and foremost, if there is one, don’t make a beeline for the men’s section unless it’s fine with her. I mean yes, she can dress herself, but you are still her boyfriend, which pretty much means that you are obligated to do regular boyfriend duties, like watching her try things on and giving feedback, no matter how terrible they are.
Which brings us to the next point: you are not a judge on Project Runway. You are also not Kenny Powers. Sure, you might know a little about womenswear and, like, flipped through Lula or the gentlewoman a few times, but that does not a Tim Gunn make. You might think that talking about peplum and A-line dresses in the context of your girl’s body makes you look like you know about fashion, but really, it makes you look an insensitive asshole who's definitely not getting laid anytime soon.
If you find yourself in a shop that only carries women’s clothes, just go with it and accept that you’re probably going to be there for a while. You’re not there for the clothes—you’re there for her. Besides, you’ll probably see something you wish they made for dudes. Keep this to yourself. What, you didn’t think floral shirts and polka dot sweaters were strictly a menswear thing, did you? Just don’t be that guy that says things like, “That shirt looks like the Gitman one I have,” or “I have those exact Bass Weejuns for men.” She doesn’t care. No one cares.
Above all, trust her taste and do not try to dress your girlfriend. This is the girl that is willing to be seen with you in public even though you like to wear a double-breasted sportcoat with dad jeans when she would probably rather you wear a heather gray T-shirt and denim jacket, but hey, at least you aren’t wearing a college hoodie, Vibram FiveFingers and convertible cargo pants.