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.