Why Some Men Still Dress Like They’re 16

It’s not because they’re lazy.

Photo illustration of a man looking at clothing options and scratching his head in confusion.
Photo illustration by Slate. Photos by Getty Images Plus.

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.

Yo, I can so still relate. Almost all of the T-shirts that I have I’ve pretty much gotten for free. They have a “you donated blood” logo on them, or—

Oh, yeah. I’ve got some of those.

Bank of America T-shirts. I also, very similarly, feel a little guilty for that. So I want to know why you feel like that. What part of you is trying to convince you that you need to change your look?

Maybe it was because I grew up really influenced by punk rock music or something, but I always felt like it would be kind of arrogant to try to dress nice, or I would look like I think I’m trying to be better than other people. Now I’ve kind of shifted my outlook, and I don’t really feel that way anymore. I feel like it’s more of an investment in myself and just trying to present my best self to people, and it’s not a matter of wanting to dress nicer because I’m better than anyone else. It’s just I want to present my best self to people, and that involves a lot of things. And part of that is looking and dressing nicer.

Also, part of me just wants to take more risks. I feel like a lot of the reason I don’t really try new things when it comes to clothes is because I’m either afraid I’m not going to look good in it or I just feel like I have no way of knowing if I’m going to look good or not. And so I tend to just stick with what’s inside my comfort zone, which is kind of what I’ve always been wearing.

That hits home for me—not wanting to take too much of a risk because I have no real way of knowing how I look in these clothes. Like I look in the mirror and think to myself, That’s not you, or That doesn’t seem like the look that I was going for exactly. And if I ask anyone that I know, “Hey, what do you think of this?” a part of me will kind of feel corny. Like I’m trying too hard.

Totally. Yeah, I feel that.

So what else are you looking for in clothing right now?

Now that I’m an adult with a “grown-up job,” I’m trying to also buy clothes that aren’t as disposable. I feel like this is especially true with shoes because most of my life I’ve always bought pretty cheap shoes, and they usually don’t last long. And so I’m also shopping for durability now for the first time in my life. Like I never really bought a pair of shoes that was more than $60, and just recently I bought a pair that was like $100, and to me that’s a lot of money to spend on shoes. But I’m hoping that they’ll last longer than other pairs of shoes I’ve bought. So I don’t want to just be wearing clothes that are only going to last a couple months. I feel like I’m too old for that now.

Dude, I’m starting to sweat, man. I can relate so hard. I’m wondering if you feel this way too, because I feel almost nervous for you. Trying on a whole new look in public where people will see you—and maybe wanting to change the way people feel about you—that’s scary.

Yes, but not just the way people feel toward me. I feel like I am also trying to change the way I feel about myself maybe. But I feel like even just trying things on in my home or in a dressing room is almost as scary. I’ll look at myself and be like, “Oh, I look like a joke.” You know? I feel like there’s something blocking that.

What’s really motivating you to want to change up your look?

Not that people don’t, but I want people to view me as an adult and not like someone who’s still wearing the same thing he wore when he was in high school. I think the answer is just confidence. If I feel confident that what I’m wearing looks good, then I think it’ll affect the way I act. If I feel more confident, then I’ll start to be more confident, and then I’ll be more pleasant to be around.

That’s interesting. You want to present your best self. Do you feel like you’re not doing that enough right now?

No. I mean, there’s always room for self-improvement. I’m a goals-oriented person, and I’ve made it one of my goals to dress nicer and to stop not caring. I feel like the way I dress just makes it look like I don’t care. And I don’t want to dress like that anymore. I want to show that I do care.

I just looked up and down at my outfit and I’m like, I really look like I don’t give a shit right now.

Yeah. That’s my outfit most days.

To hear the entire episode—including a style intervention by a vintage boutique owner—subscribe to Man Up on Apple Podcasts, Stitcher, Spotify, or wherever you get your podcasts. Look for the episode “Why So Many Men Still Dress Like They’re 16.”