Why So Many Men Still Dress Like They’re 16

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S1: This ad free podcast is part of your slate plus membership.

S2: I feel like I have a lot of friends who are women and something they do that I’m kind of jealous of that I don’t like. I’m jealous that I don’t have this kind of relationship with my male friends is that they’ll tell me that they’ll like send pictures of themselves in different outfits to their friends and say, hey, how does this look? Do you think I should get this? And I feel like men don’t really do that with each other. 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 like sending a picture of myself to and saying, hey, how does this shirt look on me? Do you think I should get it?


S3: I wish men were more comfortable having those kinds of relationships. Have you ever tried that? No.

S4: Now I feel like you would come across as corny.

S5: So that’s John like me. He grew up skating, collecting banned 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.

S6: 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 our terrified of looking like we’re trying to look good and put together.


S7: And what I’m really wondering is what are we so afraid of?

S8: Hello and welcome to MAN UP. I’m your host. A minute smile. And on this show, we crack questions big and small about manhood. This week, we clean up our closets and whatever is going on in our heads.

S9: So if you had to. How would you describe your look?

S10: My look hasn’t evolved. I’m almost 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 like a T-shirt and jeans.

S3: I was like a skateboarder kid in high school. So I kind of gravitated towards stuff that, you know, looks like that. And since then, most of the shirts I bought as an adult have been. I go to a lot of shows like you see see bands and stuff. And so a lot of the shirts I’ve bought have been at shows either because I like the band or because I just want to support them because, you know, 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 keeping up with dressing my age for lack of a better word.


S11: You know, I can I can so relate almost all of the t shirts that I have pretty much gone for free. They have, like you donated blood logo on them or.

S3: Oh, yeah, I guess of America T-shirts.

S11: I feel like 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 trying to convince you they need to change your look?


S10: I feel like for a long time I felt like I shouldn’t.

S12: It maybe was the cause I grew up with, really influenced by like punk rock music or something.

S10: But I always felt like it would be kind of like arrogant to try to dress nice or or something like that or like I would look like I think I’m trying to be better than other people. And now I’ve kind of shifted my outlook. I don’t really feel that way anymore.


S3: 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 like I want 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, is looking and dressing nicer. And so I guess it’s mostly that. And also part of me just wants to take more risks because I feel like a lot of the reason I don’t really try new things when it comes to close is because I’m afraid I’m not gonna. 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. So does that answer the question?


S11: Yeah. Yeah. What you just said really stood out to me, though, because 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.


S9: Like I look at 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 like 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.

S13: Totally. Yeah. I feel that.

S9: So what else are you looking for in in clothing right now?


S3: I’m trying to. Now that I’m like, you know, an adult with a quote unquote, grown up job, like I I’m trying to also buy clothes that aren’t as disposable.

S4: I feel like this is especially true with shoes because most of my life I’ve always bought like pretty cheap shoes and they usually don’t last long. And so I’m trying. I guess 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 sixty dollars. Even sixty dollars was like a lot. And just recently I bought a pair that was like one hundred dollars, which to some people might not sound like a lot, but 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 it’s you know, I don’t want to just be wearing clothes that are only going to last a couple of months. And I feel like I’m too old for that now.


S11: Dude, I’m starting a sweat, man. I’m thinking like, oh, man, I could relate so hard. I’m wondering if you feel this way, too, because I feel almost nervous for you. Like trying on a whole new look. And public where people will see you and maybe like what you’re really talking about is wanting to change the way people feel about you. Right. Like feel towards you.


S3: So, yeah, well, it’s scary. Yes. But not just the way people feel towards me, but I feel like I’m also trying to change the way I feel about myself. Maybe. So it’s both of those things, I think. Like I say that because even when we were saying just now about wearing trying out new things in public and how scary that can be, that’s 100 percent true.


S12: But I even feel like even just trying things on in my my home or in a dressing room or something is almost scary. Like I’ll look at myself and be like I look like a joke, you know? I feel like there’s something blocking that.

S11: So I don’t know what’s really motivating you to want to change up your look.

S13: Not that people don’t. But like, I kind of want people to.

S3: 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. And I want to, I guess. OK. As I’m talking this out, I’m coming to an answer. I think the answer is just confidence. You know, if I feel confident that what I’m wearing looks good, then I think it will 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. Does that make sense?


S9: That’s interesting. You want to present your best self? Do you feel like you’re not doing that enough right now?

S3: Probably not. No. I mean, there’s always room for self improvement. Yeah, I’m kind of goals oriented person and I’ve made it one of my goals to to dress nicer and not I’m going to wear this really awkwardly to stop not caring.


S2: Does that make sense? Like, I don’t know exactly what you mean by. I feel like the way I dress just makes it look like I don’t care.

S12: And I don’t want to dress like that anymore. I want to show that I do care. So I guess that’s what motivates it.


S14: Damn. You know what I just did? I just had to bend down on my outfit and like, I really looked like I don’t give a shit right now.

S15: That’s my outfit.

S16: Most days after the break, we face our fears and hear from someone who deals with guys like us all the time.

S5: So we need your help with a future episode of Man Up. We’re looking for two or more guys who are our best friends but feel like they’ve been having trouble maintaining that friendship or have drifted apart entirely for any reason.

S17: So if you think that’s you call us at 8 0 5 6 2 6 8 7 0 7. That’s 8 0 5 men up 0 7. Or e-mail us at Man up at slate.com.

S18: Hey, what’s going on, man? How you doing? Good. How are you? I’m good. I’m good. Thank you.

S17: So John and I were just joined by Izzy, who thinks he can help us out is he worked as a professional stylist and now owns and operates his own vintage clothing shop in Jersey City, New Jersey, called Zero Kids. He’s locally famous for hooking up musicians with brand new looks. And he says that he deals with customers like us all the time.

S19: Guys come in and they’re like, I have a date tonight and I have no idea what to wear. Nike to help me make sure let’s you know, let’s get started. Let’s see. Because, you know, you always want to make them feel comfortable as well. But, you know, especially they want to be able to go in to a room with people and just, you know, have a conversation and feel comfortable in what they’re wearing and not have to be in the back of our mind being like, are these people looking at me and what I’m wearing? Are they judging me or are they looking at my t shirt? Are they like, oh, my, are my pants too tight or is someone later? I mean, stuff like that, like. And I think that happens to a lot of people. And that’s I was in the back of their mind. And that causes anxiety, that causes like you kind of don’t want to be there anymore. It makes it hard to be there.


S11: What advice can you give John to start changing up his look?

S20: OK. The best advice I could probably give you is. Start dressing in a way that you feel comfortable in. But start picking out certain pieces to mix in with your wardrobe. For example, try a different color pair of pants. But keep it wearing with your band teacher. That way you’re still comfortable, but you’ve introduced a new item into your wardrobe. Does that make sense?

S10: Yeah, for sure. Can I ask, is there. You mentioned band T-shirts. Shirts are a great place to start. Is there something that like especially with it being fall? Is there something that layers really well?

S20: Absolutely. It’s a denim shirt. Like and that’s where I’m going with switching it out of the. Don’t just wear jeans, wear like pick up some slacks, pick up some, you know, khakis, some cargo pants so you can match with the band shirt and then you can layer that with a flannel, a denim shirt and then a jacket and overcoat, something. But you’re still wearing that band. T-shirt is still at school. Also, accessories. Do you do you have certain certain accessories that you like, just like hats?

S18: OK. Perfect.

S20: I’m in a hat. Most of the year, whether it’s a beanie or five panel or something like that, do you wear what you wear snapback? Do you wear.

S3: Yeah. Like a. Like a flat rim snap back out. I don’t know if pushing 30. I don’t know if I’m too old for those or not at all. But I feel I really like the way they look.

S20: And like I said, paired that nicely. You can definitely wear a band, tee shirt, a blazer and one of those hats and you look great. Cool.


S21: And you just added one piece of clothing to your arsenal, which is the blazer, which now you can wear with different jeans, different pants and different shirts.

S22: I feel like maybe part of the way I dress, too, is to kind of fly under the radar. Like I don’t almost.

S2: Again, this goes back to the fear thing. Like, maybe there’s a fear of people noticing, like if I wear something awkward or something.

S3: So maybe I try to dress a little bit is in a way that maybe people won’t won’t notice me or want comments on what I’m wearing.

S11: But so when you set that goal for yourself to dress better, does that mean that you’re ready to try and not fly under the radar anymore?

S10: Yeah, which is like a it’s kind of scary to say yes to that question because that’s a step outside my comfort zone.

S3: But the answer is yes. I want to. You know, I kind of want maybe people to say, wow, you look really nice like that. Wouldn’t that wouldn’t be a bad thing.

S11: Yeah. I mean, ads like some really stylish friends like crazy stylish where they were and like the latest supreme or brands I’ve never heard of. Whatever. And they’re always getting compliments from girls and other guys all the time. And a part of me gets a little jealous. Yes, I know that sounds like super corny, Billig. No, no, I feel it. Yeah. I think I bought one Supreme jersey because somebody that I know was complimented on the on their Supreme shirt. And I mean, I bought it, used I got it for like a really good deal, so I was like, oh, I’ll I’ll wear this to the next party I go to. I still haven’t put it on once. Like a part of me is afraid that it’s going to look like I’m triangle of a sudden. And a part of me doesn’t want to look like I’m trying.


S10: Yeah, I saw a bartender a few weeks ago who was wearing he was wearing a short sleeved pink button down shirt with pineapples all over it like little images of pineapples. But like the way he wore it and like kind of the confidence he had, like he made it look good. And I don’t think I would wear like a pink shirt with pineapples on it. But I want to like maybe maybe learn how to figure out like, hey, this is kind of a more. This is something very different from what I normally wear. But but it will look good on me. Like you figure out how do you go to tell us something all good out on me, even if it’s something I don’t normally wear?

S3: Does that make sense?

S20: Yes. Do you think the guy looked good in the in the pink shirt because of the way he was carrying himself?

S3: I certainly think that that’s part of it.

S18: Question What if the shirt was black with pineapples? Would you wear it?

S10: I think I’m more hung up on the pineapples than the color. I don’t think I’d be more likely to wear like a pink shirt that didn’t have pineapples on it than a black shirt with pineapples on it.

S18: So why don’t you start there, start there with a little bit of a color pop. OK.

S19: You know, we’ll take away the pineapples and we’ll go with like a little bit of a color pop. And if you don’t want to go as far as, you know, as extreme as a pink, you know what I mean? You can start with something more like a green or like a lighter blue.


S3: So start like slightly outside my comfort zone instead of just going all out.

S19: Absolutely. Because if you go all out, you’re going to be nervous when you go out like I’m going to where I can already tell you to be the moment you start putting the clothes on, you’re going to be in your own head way too much. Yeah.

S11: Yeah. Fun accessories to be the safest way for me to try and express my personality through my look like I’ll have a fleece that I inherited from my dad and like paints that like pants that paint on it. But they don’t have like a brand new really nice watch.

S20: OK. We like, for example, we just describe what if that fleece was just a crewneck sweater? Mm hmm. With everything you have on still, yeah. You know, you see, it’s like you’ve changed one. Only one article and it’s kind of the same fit you’re wearing.

S11: Do you think that’s a universal advice just to try one thing at a time?

S20: Yeah, absolutely. Like you don’t have to sweat. You got to change your whole self in one shot. Start with a piece.

S19: You know, whether it’s a different kind of pants or where you want to try a slim fit instead of a bootcut. Mm hmm. Try with a slim fit. And then you wear thinner sneakers with that. Or you could tuck that into a work, put in the works work boots, you know? I mean.

S11: Yeah, yeah. I guess part of the reason why I haven’t really experimented too much of my clothing is it sometimes feels like a performance to me. Like like if I were to try and put on pull off that like pink shirt with pineapples on it, I’m going to feel like I’m just pretending to be that bartender. John, what do you think about that? Do you relate?


S13: Yeah, like, I don’t know.

S4: I don’t want to be corny or foolish or or whatever, but it is kind of like I see people wearing some of those outlandish type of things. And I’m like, man, the way they the way they wear it and the way they rocket. I’m almost jealous that day that I can’t, you know, like what’s stopping me from getting a pink shirt with pineapples on it and looking as good as that guy does.

S18: What is stop by, though?

S3: I don’t think I look as good as that guy does. For some reason, I don’t know.

S20: That is that I feel like that’s an internal battle.

S18: Yeah. So how do you help someone get over there that that internal struggle?

S20: I think he should honestly wear the shirt, but maybe not in a situation where he knows as many people maybe just wear where he doesn’t know anybody.

S19: It’s just random people there. And you just they don’t know him. Why would they? You know what I mean is more or wear in a smaller setting with comfortable people and just big. What do you think?

S18: That makes sense to you? Yeah. Yeah. One I never said.

S14: So, John, are you going to go shopping this weekend?

S23: I think so. Yeah. And next time I mean, next time I’m out there, I’m going to hit your store.

S18: Yeah. Deathly come through and now. Duffy, give you some pointers and help you out when you do. Can be awesome.

S5: So it’s been a few weeks, but we got to follow up with John, who’s been putting some of his advice into action.


S23: I’ve been shopping a couple times since we last talked and the first time I went to a vintage store. Oh, cool, John. A couple shirts that I like, both very like work shirts and for going out this. They’re kind of nice enough for for both. Which is good. And then as far as like accessories goes, I’ve never really worn scarves before. But we were at this I was at this vintage store with my girlfriend and she point to a scarf and was like, you try that on.

S24: And I was like, I don’t I don’t know. I don’t know. The worst part is I don’t really, really know how I look at them.

S15: I don’t even really know how to put one on. But she showed me how to how to put it on. And I looked in the mirror and was like, whoa, I look like a million bucks. So. So I’ve been wearing that a lot lately, too. So, yeah.

S9: Have you noticed any change in how people act around you or has anyone made any comments about you changing because your style is changing?

S25: I think that changing up my style a bit has improved my confidence and people can sense when you’re a more confident person. And I think that has changed the way people act around me. I feel like people. Treat me more like a dog. Sounds bad to say this because people treat me more like an adult as opposed to just somebody who’s just afraid and insecure all the time. And I think that has to do with the way I carry myself because of dressing nicer.

S9: It’s so cool that because like at the very beginning, you set a goal and you have described yourself as being a goal oriented person. So how do you feel now that you’ve reached that goal?


S26: It feels good. I’m ready to I’m ready to set the next goal. So he is cool. I look forward to going going shopping for clothes now because it feels more like an experience. And I think there’s anyone out there who dreads clothes shopping the way that I did. If you think of it more like an experience than maybe it’ll be something they look forward to.

S1: Mm hmm. Damn. Can you hear me snapping? Yeah. Yeah.

S27: Hello.

S28: Hi. So I was gonna ask you, how would you describe my fashion sense?

S29: I would describe it as low key, muted tone C casual, cool.

S28: Is it a good style?

S30: I like it. So in a sense, I don’t even need to upgrade anything. I’m good. While you’re still kind of figuring out in the end that they have place to grow with you. I thought you said it was a good again, but it’s a good thing. Keeps changing and keeps, you know, you have to keep experimenting.

S28: And yeah, it really feels like ever since we got together, I’ve been a little embarrassed when I look like a scrub and I’m hanging out with such a fly, honey. So I feel like I needed to upgrade so that we can be seen together in public. So if anything, I have all the credit to give to you for giving me that motivation to look fly.

S30: Yeah. Like I mean even before it needs to air like tires on like t shirt type of thing. I don’t know. I’m just glad that was pretty my day. Okay.

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