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Is it Better to be Overdressed or Underdressed? · Group Chat of One

• 0:00
  Edward: What would your outfit of choice be?
• 0:02
  Chat: Honestly, probably something easy but put together. Doc jeans or chinos, a clean sweater, casual button down, decent shoes.
• 0:12
  Edward: Okay. But, Chat, you're you're on a phone. Like, you don't have a body to put that outfit on.
• 0:17
  Chat: Ah, fair point. I don't have a closet. But if I did, I'd still vote for simple and intentional.
• 0:31
  Edward: I'm Edward, and this is Group Chat for One. Every episode, I bring one question to chat, and we discuss and just see where the conversation takes us. So, chat, today's episode question, is it better to be overdressed or underdressed?
• 0:44
  Chat: Uh-huh. That's a fun one. I think being a little overdressed is the safer bet because it shows effort, you know? But, hey, context matters. Showing up in a suit to a backyard barbecue, that's a choice.
• 0:58
  Where do you usually land?
• 1:00
  Edward: So I'm someone who is generally laid back when I dress up. If I could spend my whole day or, like, my whole life in a hoodie and pants, oh, would I be happy? So for me, I find being underdressed always more comfortable, but I think that's just my personal opinion.
• 1:17
  Chat: Okay. That's fair. Comfort is a strong argument, but like when you say you're underdressed, like, you ever feel out of place, like at a dinner or something?
• 1:29
  Edward: Not really. And maybe it's just because I like to avoid really fancy dinners, but being just dressing up in general, I'm just like, oh, I got to put on a shirt, like a fancy shirt with buttons tied all the way to the top. Gotta wear a tie. No.
• 1:49
  Chat: Right. Right. I get that. So it's less about being too casual and more about not wanting a whole performance of dress clothes. So is there a middle ground that feels like still you, like a a training nudge up without going full costume?
• 2:07
  Edward: I guess it would be a sweater instead of a hoodie just ditching that hood part to make it look a little bit less casual. But then again, I love wearing a hood.
• 2:19
  Chat: Fair. A nice sweater is like the diplomatic solution. It's comfortable, but it looks intentional. Sounds like you've kind of found your balance there.
• 2:32
  Edward: It's definitely true. And also, like, as someone who doesn't have an infinite closet, I wish I had a walk in closet. I don't have that many options of clothes where I could, you know, have 20 different shirts for 20 different occasions and whatnot. If my style is more laid back, it's represented in everything that I wear and everything that I do.
• 2:53
  Chat: Right. Maybe it's less about being underdressed and more about being consistently you. Like, having a personal uniform that still shows you care.
• 3:05
  Edward: Yeah. If someone's personality was to be overdressed all the time and they would always wear a button down shirt and slacks wherever they go, I'd be like, oh, that's you. That's you. That's who you are. And maybe for them being overdressed would always be the answer.
• 3:23
  But for me, weirdly enough, I love I love being underdressed.
• 3:27
  Chat: That makes sense. And, honestly, if it feels authentic and you're comfortable, it breeds as confident. And that's what people clock first anyway, not, oh, that person skipped the blazer.
• 3:42
  Edward: Mhmm. Though, I mean, to be fair, I'm not going to a wedding and being underdressed there. I think there are some scenarios where, you know, you're at a wedding, you're at a black tie event. I think you go into those scenarios knowing that you gotta be dressed up. So if you're underdressed in those occasions, then I'd say, oh, this may be a problem.
• 3:58
  But let's say a birthday party or gathering with family. Those those moments, I think it's okay to wear whatever you want, even if you're bit underdressed.
• 4:07
  Chat: Knowing when the moment really calls for stepping it up is part of the style too.
• 4:12
  Edward: Mhmm. What would be your go to outfit if I were to say to you, okay, we're going out tonight at a at a restaurant, nothing extremely fancy, just like a nice restaurant, a good restaurant, what would your outfit of choice be?
• 4:26
  Chat: Honestly, probably something easy but put together. Doc jeans or chinos, a clean sweater, casual button down, decent shoes, nothing stiff, but thought about. Not fussy.
• 4:40
  Edward: Okay. But, Chat, you're you're on a phone like you don't have a body to put that outfit on.
• 4:45
  Chat: Ah, fair point. I don't have a closet. But if I did, I'd still vote for simple and intentional.
• 4:54
  Edward: I get that. I'm more of a, you know, pants and a shirt. May... I guess, a sweater in that context, but if I could get away with a hoodie, I probably would.
• 5:05
  Chat: That's fair. Comfort matters too. If you feel good, that energy shows up louder than a collar.
• 5:12
  Edward: My laugh and my personality makes up for whatever I'm wearing, I'm sure.
• 5:16
  Chat: Exactly.
• 5:17
  Edward: Are are there moments you think that it's good to be overdressed or underdressed?
• 5:21
  Chat: Maybe when you really wanna show you respect the moment, like a first meeting, an interview, or like a close friends milestone, a touch of extra effort there says you matter.
• 5:39
  Edward: As someone who has had to hire people in the past, though, sometimes I've I've gone into interviews and people were way overdressed, and that sort of gave me a small But I don't know if that's a me thing.
• 5:49
  Chat: Maybe it feels like someone is trying too hard, not reading the room. So
• 5:56
  Edward: because there's there's something about up
• 5:58
  Chat: or down. It's beating the vibe?
• 6:00
  Edward: Exactly. There... There's something about being overdressed that almost feels like you're overcompensating in those moments where it's like, okay, what are you hiding behind the fact that you're you're wearing an expensive jacket or an expensive, like, shirt or you're like, a bit too formal, you know? Mhmm.
• 6:17
  Chat: Yeah. I hear you. So it's less a dress code and more of a subtext thing, like signaling ease and awareness rather than a shield.
• 6:29
  Edward: Mhmm. Like, let's say, for example, and you've got to go back to... Let's say it's university. Is it better on your first day of class to be overdressed and look as if you're trying too hard or underdressed and just be like, I'm blending in or like school is school, but I'm me.
• 6:50
  Chat: First day of class, I lean just slightly polished, clean, intentional, but not formal. Like, I showed up and I'm comfortable, not judge me.
• 7:02
  Edward: You see, but for me, if someone is overdressed, and, of course, there are different degrees of being overdressed. But if someone is really overdressed, I... I'm like, oh, someone's trying too hard. Someone's trying to be a bit more like mister and missus popular. Whereas if you're just being yourself and you're just taking it easy on your your first day or first week of classes, I'd vibe with that a bit more.
• 7:25
  Chat: Sounds like for you, authenticity beats polish almost every time, with the obvious exceptions like weddings.
• 7:33
  Edward: Mhmm. Someone who's authentic, I find is way more attractive. Like, not attractive in a I wanna be with this person in bed type of way, but attractive in the sense of is an alluring energy. I'd rather someone who has that than someone who overcompensates by dressing up a bit too fancier or by wearing, like, really expensive clothes or whatnot.
• 7:56
  Chat: That sounds like a solid same policy.
• 8:00
  Edward: Mhmm. And how about underdressed? Are there any scenarios where, okay, I want or I'm trying my hardest to be underdressed? Because I feel a lot of times people would say, oh, being overdressed is probably better than being underdressed. I'm the advocate of the opposite.
• 8:16
  I don't know why. But I'm wondering because most people, they'll easily say, be overdressed, and it's good. But I'm like, be underdressed. But are there any situations where being underdressed is actually a good thing?
• 8:29
  Chat: I'd say maybe some super casual hangouts, like close friends game night or a quick run to a corner store, places where closeness beats any sort of polish. In those spaces, the I've relaxed with you can feel warm and not dismissive.
• 8:51
  Edward: And I guess it comes back to the fact that I cherish a bit more those type of relationships where closeness and intimacy and security for me is probably what I'm searching more than showing off. So I don't even place myself in those situations where being overdressed is the answer.
• 9:14
  Chat: That makes sense. I mean, style follows your values. If that's front and center in your life, your clothes will tell that story naturally.
• 9:22
  Edward: And of course, there's a difference between being underdressed and just looking like straight up garbage. If your clothes are literally falling apart, they're stained, they're not, they're ill fitting, then that's a different situation. For me, underdressed is really just casual, but still put together. And so, Chat, again, I know you don't have a body, so you can't wear or you don't even have a wardrobe, so you can't even wear clothes. But again, if you did in this hypothetical situation wear an outfit, what would be your ideal laid back look?
• 9:58
  Chat: If I had a closet to call my own, I would say the ideal look for a laid back vibe is, well, soft tee, well fitting jeans or comfy chinos, clean sneakers, maybe a light sweater on hand. Easy, but got sloppy.
• 10:16
  Edward: Okay. Okay. And more importantly, what's the color story? Like, what's the color of your outfit?
• 10:25
  Chat: I would say navy, gray, maybe an olive or muted earth tone. Those are calming and low key. So nothing shouts.
• 10:34
  Edward: I I I like the vision. I like the vision. I like where it's going. You got style.
• 10:38
  Chat: Thank you. Coming from Yim, that means a lot.
• 10:42
  Edward: How about how do you even know I have style? You don't even know what I... You don't even know what I'm wearing right now.
• 10:47
  Chat: Fair point. But from what you've said about valuing comfort, authenticity, that is a style. Low key is still a choice, and that's stylish.
• 10:58
  Edward: Mhmm. So you can't see me, but if you were to guess what I'm wearing right now, what would you guess?
• 11:05
  Chat: Just a guess? Yeah. I'd say maybe a comfy tee or a hoodie, some relaxed pants, maybe sneakers. Simple. Comfortable.
• 11:15
  Edward: Yeah. You're you're close. I'm filming inside, so I'm actually wearing shorts, but a comfy tee, some shorts, no shoes and a hat because I need to get a haircut.
• 11:28
  Chat: That's on brand comfortable and true to you.
• 11:32
  Edward: It do be. It do be. If we were to go back to the initial question, so is it better to be overdressed or underdressed? My opinion, which again, my opinion is fact. My opinion is it's better to be underdressed as long as you're not at a wedding, as long as you're not at a really important event.
• 11:52
  Where do you stand, Chat, after a discussion?
• 11:54
  Chat: After talking me through, I'd say it's better to fit the vibe. Sometimes that means a touch up, sometimes relaxed, but always clean and intentional. It's less about up versus down and more does this feel like me without ignoring the moment.
• 12:16
  Edward: Lovely. Beautiful. I love everything about that. You're always right, chat, or almost always right.
• 12:24
  Chat: I'll take almost. And, hey, I love how clear you ended up being about your own take. Comfort and connection. That's a solid compass.
• 12:34
  Edward: Yeah. Do you have any last words for our audience?
• 12:37
  Chat: Just this. Wear for the moment, but don't lose yourself in it. If you feel like you, people notice. Mhmm.
• 12:47
  Edward: So don't stop being yourself. Like Chad said
• 12:50
  Chat: That's right.
• 12:51
  Edward: Be you. I'll see you guys next time. Have a beautiful day. Don't forget to like, subscribe, rate, leave a comment, whatever it is that you do on these platforms. And we'll see you next time.
• 13:02
  Bye.
• 13:04
  Chat: Bye.