Why Some Men Still Dress Like They’re 16

Why Some Men Still Dress Like They’re 16

On a recent episode of Man Up, Aymann Ismail and a listener, John, talk taking risks with how they dress—and why so many men are afraid to break out of their teenage comfort zones of jeans and T-shirts. This transcript of their conversation has been condensed and edited for clarity.
Aymann Ismail: Like me, John grew up skating, collecting band T-shirts, and making fun of the way that other guys put actual thought into their outfits. I considered myself someone who focused on real things, like doing good in school or being able to jump high enough to dunk a basketball. Putting that much thought into how I looked? No way, that’s desperate.

But now that both John and I are fully grown adults, we’re starting to feel a little left behind. We both have the exact same problem. We want to look good and put together but are terrified of looking like we’re trying to look good and put together. And what I’m really wondering is: What are we so afraid of?

John: I have a lot of friends who are women, and something they do that I’m kind of jealous of, that I don’t have with my male friends, is they’ll send pictures of themselves in different outfits to their friends and say, “Hey, how does this look? Do you think I should get this?” I feel like men don’t really do that with each other, and I kind of wish we did. I have a lot of male friends, but I don’t have any male friends that I’d be comfortable sending a picture of myself to and saying, “Hey, how does this shirt look on me? Do you think I should get it?” I wish men were more comfortable having those kinds of relationships.


Have you ever tried that?

No. No. I feel like it would come across as corny.

So if you had to, how would you describe your look?

My look hasn’t evolved. I’m kind of embarrassed about this, but it hasn’t evolved much since I was in high school and college. I still wear mostly T-shirts and jeans. I was a skateboarder kid in high school, so I gravitated toward stuff that looks like that. As an adult, I go to a lot of shows to see bands and stuff, so a lot of the shirts that I’ve bought had been at shows either because I liked the band or because I just want to support them because they’re trying to get money to get to the next gig. So, I guess, I feel like I should be doing a better job of dressing my age, for lack of a better word.

from Human Interest - Slate Magazine 
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