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How should I be dressing?

post #1 of 15
Thread Starter 
Another basic question from yours truly. I am 28 years old. Recently I've decided to upgrade my dress style. The past few weeks I've worn mostly button-up shirts with a sports coat, and slacks. Sometimes I trade the button-up for a polo or other more casual shirt (though most of the time still with coat), and sometimes I trade the slacks for jeans.

I've had many people make comments along the lines of: 'Why are you so dressed up?' As a 28 year old going through my daily business, such as going to the grocery store or visiting friends, is this over dressed?

Thank you,
J
post #2 of 15
According to today's sad standards: Yes.

Now a more important question: Do you care?

If you feel comfortable and like how you look, keep at it. Life is full of too many forced compromises without having to voluntarily make others.
post #3 of 15
Quote:
Originally Posted by gorgekko View Post
According to today's sad standards: Yes.

Now a more important question: Do you care?

If you feel comfortable and like how you look, keep at it. Life is full of too many forced compromises without having to voluntarily make others.
+1
post #4 of 15
Quote:
Originally Posted by dj-jd View Post
Another basic question from yours truly. I am 28 years old. Recently I've decided to upgrade my dress style. The past few weeks I've worn mostly button-up shirts with a sports coat, and slacks. Sometimes I trade the button-up for a polo or other more casual shirt (though most of the time still with coat), and sometimes I trade the slacks for jeans.

I've had many people make comments along the lines of: 'Why are you so dressed up?' As a 28 year old going through my daily business, such as going to the grocery store or visiting friends, is this over dressed?

Thank you,
J

Sounds fine. I feel that if you're going to be out and about, you should at least be presentable. I understand being comfortable but I think it's ridiculous that if someone sees a guy in dirty sweat pants with a ratty t-shirt they don't question it but they see someone in a suit and it's odd.
post #5 of 15
Quote:
Originally Posted by Lel View Post
I think it's ridiculous that if someone sees a guy in dirty sweat pants with a ratty t-shirt they don't question it but they see someone in a suit and it's odd.

+1
post #6 of 15
You said you just switched up your style, so part of it is probably that people are not used to seeing you in said clothing so they figure something must be going on (and obviously the fact that most people are slobs).

Another thing (and I am not saying this is you), is that some people put on dress clothes and it is apparent that it is not 'them' - as in the clothes are wearing them, not the other way around. People who wear dressier clothing but seem completely natural look great.
post #7 of 15
I've been asked the same question when I'm wearing an oxford and broken-in chinos.
post #8 of 15
It's better to be overdressed then under dressed. You'll have more confidence knowing your clothing is impeccable when approaching a female than if you just threw on whatever(random t shirt and jeans)
post #9 of 15
Ask them back, 'why are you so underdressed?'
post #10 of 15
Quote:
Originally Posted by Lel View Post
Sounds fine. I feel that if you're going to be out and about, you should at least be presentable. I understand being comfortable but I think it's ridiculous that if someone sees a guy in dirty sweat pants with a ratty t-shirt they don't question it but they see someone in a suit and it's odd.

I don't understand this either. I guess they think everyone should dress down to their level. I have, thankfully, never heard the question posed the other way 'Why are you dressed like a slob?' I suppose if someone was crude enough to ask that, the answer would have to do with comfort as if dressing in a sloppy manner was more comfortable.

Cheers, Jim.
post #11 of 15
At 26, I get much the same response, but only from people I don't know. Friends and family understand that I dress well because I like to and because I think it's respectful to those around me. That said, I will dress 'more my age' (think streetwear and denim, not what the mall kids are wearing) during the day while I tend to go 'dressed up' in the evenings. I also take into account where I will be and with whom. This is a strategy that has worked well for me for the past couple of years, and most likely I will move to more jackets and suits as I age.
post #12 of 15
Quote:
Originally Posted by acidicboy View Post
Ask them back, 'why are you so underdressed?'

+1

I get the dressed up question all of the time, at least once a week, and surprisingly usually when I have a BD Oxford shirt tucked into khakis with boat shoes on the weekends. I always feel comfortable when I go out, and not the least dandyish when in the aforementioned outfit. But I do think it's reasonable to counter with "Why are you so underdressed?"
post #13 of 15
I was thinking about buying a pair of blue chinos this week, but when my gf saw them, she said: you're not 60 yet (I'm 32). Stick to jeans. So that put a temporary stop to my attempt of dressing up. Apart from that: I don't have to dress up.
post #14 of 15
Sounds like you're doing fine; 28 is certainly old enough to start looking like a productive member of society, and after all, I assume you're wearing trendy jeans (or whatever) on the weekends, etc.

Tell your friends that they're idiots and to get back to mowing your lawn.
post #15 of 15
Quote:
If you feel comfortable and like how you look, keep at it.

Agreed. If the comments make you uncomfortable, maybe you could switch to more fitted, youthful jackets and fashion-forward shoes. That would still look dressed-up in public, but presumably the comments aren't from total strangers.
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