Q and Answer
Sam writes:
Having (relatively) recently graduated high school, I have decided that I have crossed the threshold into adulthood, and I would like to dress the part. However, for as long as I can remember, I’ve been wearing graphic t-shirts and the same five or six pairs of jeans which are covered in god-knows-what of irremovable stains.
 During what I want to say was August, a French Connection retailer was having an end of summer sale, so I grabbed a white oxford and some pinstripe slacks which I have fallen in love with and want every excuse to wear.  Now, I am at a point where I don’t know what my next purchase should be. I can’t buy an entire ensemble due to my lack of funds, but I want to make one solid purchase. Something that will be that one bridge from my adolescence pile of clothes to a gentleman’s wardrobe.
First of all, you’re still college aged.  There’s no need to be Alex P. Keaton and wear a suit to class.
I’d focus on upgrading your casual wardrobe.  Don’t wear stained clothes.  Whatever clothes you have that have stains, give them to the goodwill or use them as rags.  Get yourself something plain that fits, even if it’s some t-shirts from Target.  Get yourself a decent pair of blue jeans - Levi’s 514s or 501 shrink-to-fits are a good starting point.  Maybe a pair of slim-fitting J. Crew or Canvas chinos.  Simplify, simplify, simplify.
Pinstripe pants are incredibly difficult to wear.  For one thing, pinstripes are traditionally a business pattern.  For another, they’re traditionally limited to suits.  So pinstripe odd trousers are very limiting.
Focus your money on flexible basics.  Oxfords are great.  So are solid color t-shirts.  Good blue jeans.  Converse Jack Purcells.  Get to the other stuff once you have a foundation.

Q and Answer

Sam writes:

Having (relatively) recently graduated high school, I have decided that I have crossed the threshold into adulthood, and I would like to dress the part. However, for as long as I can remember, I’ve been wearing graphic t-shirts and the same five or six pairs of jeans which are covered in god-knows-what of irremovable stains.

During what I want to say was August, a French Connection retailer was having an end of summer sale, so I grabbed a white oxford and some pinstripe slacks which I have fallen in love with and want every excuse to wear.  Now, I am at a point where I don’t know what my next purchase should be. I can’t buy an entire ensemble due to my lack of funds, but I want to make one solid purchase. Something that will be that one bridge from my adolescence pile of clothes to a gentleman’s wardrobe.

First of all, you’re still college aged.  There’s no need to be Alex P. Keaton and wear a suit to class.

I’d focus on upgrading your casual wardrobe.  Don’t wear stained clothes.  Whatever clothes you have that have stains, give them to the goodwill or use them as rags.  Get yourself something plain that fits, even if it’s some t-shirts from Target.  Get yourself a decent pair of blue jeans - Levi’s 514s or 501 shrink-to-fits are a good starting point.  Maybe a pair of slim-fitting J. Crew or Canvas chinos.  Simplify, simplify, simplify.

Pinstripe pants are incredibly difficult to wear.  For one thing, pinstripes are traditionally a business pattern.  For another, they’re traditionally limited to suits.  So pinstripe odd trousers are very limiting.

Focus your money on flexible basics.  Oxfords are great.  So are solid color t-shirts.  Good blue jeans.  Converse Jack Purcells.  Get to the other stuff once you have a foundation.

Q&A!
Over on the MaxFunForum, woodysallen asks:
 I’m the guy who has a tendency to think he looks great walking out the door and when I arrive to class have people ask “what’s the special occasion?” or “why so dressed up?” and then I feel like an asshole. should I worry about that, or just feel proud that Im the only one who’s actually yearning to look nice/dress his age.
I don’t know exactly how old you are, woody, but this is certainly a problem for the budding style maven — and the grown-up one, for that matter.
The key issue here is that men’s dress is ceremonial, and always hinges on the occasion.  The meaning of your clothes is as much about context as it is about the clothes themselves.  This is particularly true for young people.  Why do goths wear black?  It’s not functional, it’s symbolic.  Just like when Alex P. Keaton wore a necktie.
When you’re in high school and college, most of your peers will assume you’re trying to send a message with your clothes.  “Neutrality” of style may vary depending on where you are — at my school is it was a slovenly version of indie rock style, at yours it may be an American Eagle polo and shorts.  Dress differently, and you’re sending a message, whether that’s your intent or not.
Choose your clothes based on the message you want to send, and understand that if you show up at high school in a coat and tie, people will think you are trying to send the message you’re better than them or more adult than you are.
Of course, this doesn’t mean that you can’t dress up when the occasion warrants, or that you can’t dress sharply at any level of formality.  It doesn’t even mean that you won’t, from time to time, hear “what’s the occasion?”  But when you do hear that question, you should have an answer.

Q&A!

Over on the MaxFunForum, woodysallen asks:

I’m the guy who has a tendency to think he looks great walking out the door and when I arrive to class have people ask “what’s the special occasion?” or “why so dressed up?” and then I feel like an asshole. should I worry about that, or just feel proud that Im the only one who’s actually yearning to look nice/dress his age.


I don’t know exactly how old you are, woody, but this is certainly a problem for the budding style maven — and the grown-up one, for that matter.

The key issue here is that men’s dress is ceremonial, and always hinges on the occasion.  The meaning of your clothes is as much about context as it is about the clothes themselves.  This is particularly true for young people.  Why do goths wear black?  It’s not functional, it’s symbolic.  Just like when Alex P. Keaton wore a necktie.

When you’re in high school and college, most of your peers will assume you’re trying to send a message with your clothes.  “Neutrality” of style may vary depending on where you are — at my school is it was a slovenly version of indie rock style, at yours it may be an American Eagle polo and shorts.  Dress differently, and you’re sending a message, whether that’s your intent or not.

Choose your clothes based on the message you want to send, and understand that if you show up at high school in a coat and tie, people will think you are trying to send the message you’re better than them or more adult than you are.

Of course, this doesn’t mean that you can’t dress up when the occasion warrants, or that you can’t dress sharply at any level of formality.  It doesn’t even mean that you won’t, from time to time, hear “what’s the occasion?”  But when you do hear that question, you should have an answer.