Auntie SparkNotes: My Boyfriend Dresses Like a Dorky Teen
My problem is not urgent, exciting, or probably anything new, but I decided to write to you because I need your advice! For the past two and a half years, I have been dating the most amazing man. We are both in our early twenties and he is everything I could want in a guy, excepting one fact — he dresses like a 16 year old boy.
When we first started dating in college, I assumed that he just dressed in this fashion because he was a stereotypical broke student, but he’s been working as an engineer for almost a year and a half and nothing has changed. Ill-fitting khakis, light wash jeans, and ratty sneakers are the core of his wardrobe, and when I convinced him to try this super trendy men’s haircut, he still just spiked the front of his hair like Fry from Futurama.
Is there any way I can graciously and kindly let him know how I feel about his clothes and help him become more stylish, or do I learn to accept all his unfashionable quirks? I love him very much but this is something about him that has grated on me for several years now. Poor fashion is not a relationship deal-breaker, but if he could improve his look it would make me so happy!
And I don't blame you, Sparkler. (To be honest, Auntie SparkNotes let out a small shriek of horror when she read the words "light wash jeans," and had to spend a full five minutes looking at gratuitous photos of Henry Cavill in a tailored suit by way of recovery… or maybe it was more like five hours. What day is this? Where am I? IT'S DARK OUTSIDE AND I'M DROOLING.)
And look, before we go any further, let's just get a quick disclaimer out of the way: matters of personal style are often a minefield in relationships, and if your boyfriend actually were a 16 year-old boy, this answer would probably be much heavier on advice to accept his aesthetic for what it is and stop trying to nudge him into a new one. But because we're talking about an adult, employed man in a long-term committed relationship, you certainly have standing to make a loving plea that he please give his wardrobe an overhaul — and there are reasons why it's worth bringing up that go way beyond your personal feelings about it.
Because the truth is, it's not uncommon for guys (and particularly the kind of guys who grow up to be brilliant but badly-dressed STEM superstars) to take a defensive posture as teenagers when it comes to personal style — especially if, as nerdy young men often are, they're insecure about their appearance and uninformed about fashion to begin with. When you feel like you look bad and you have no idea how to look better, it's much easier to cultivate a disdainful attitude toward the entire concept of dressing well (and often, to write off the people who care about it as stupid and shallow) than to admit that you're clueless and intimidated about what to wear, you know? (In extreme cases, which it sounds like yours luckily is not, this cultivated disdain for personal appearance can extend to matters of basic bodily grooming.)
And if nothing ever happens to change that state of affairs, then the end result is that you just keep on wearing the same stuff you've always worn, and replacing your worn-out stuff in the same unflattering style you've always bought, long after you've outgrown all the available young-person's excuses for looking like a slob.
That's not to say that your boyfriend definitely fits that particular psychological pattern (although I suspect he might tick at least a few boxes). But it sounds like his sloppy appearance has similar roots, in that Overgrown Dork isn't his preferred personal aesthetic; he just defaults to it because he lacks the information and incentive to look a different way. And since he's apparently super open to your input on this front — to the point where he was willing to cut his hair per your desires — you should be in pretty good standing to give him a little tough love on the fashion front… with the operative word being "love." These things tend to go over better when you lead with the part where he's super-sexy, and then lead into the part where his wardrobe doesn't do his super-sexiness the appropriate justice. ("You have a great butt, honey — and it deserves better than those khakis. Can we maybe talk about getting you some clothes that fit?") And depending on how that goes over, you can always segue from there into a deeper conversation about why he dresses the way he does, and whether he's really on board with the image his current clothes are projecting, and whether he'd be down with either letting you moonlight as his personal stylist or consulting with a professional one.
Here's the caveat, though: your ultimate goal here isn't to get your boyfriend to dress the way you want him to. It's about helping him to dress more intentionally and develop some style of his own, which is a process that you can kick off but on which he has to ultimately take the reins. (Unless he's utterly and genuinely uninterested, in which case you should go ahead and overhaul his wardrobe yourself, because if he doesn't care what he wears, it's just as easy for him to keep not-caring while wearing something that looks halfway decent.) So when you start this conversation, be prepared to encourage him in whatever direction he chooses to go, be it classic or hipster or vintage or preppy or "the exact outfit the mannequin at the Gap was wearing, down to the pocket square." As long as he's always moving away from the Land of Hideous Pleated Khakis, it'll be a decided improvement.
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