Pick a look you are comfortable with (urban, indie, prep, etc.
Invest in a trusty pair of denim jeans.
Denim is the most versatile piece of clothing you own, and you should own at least ONE pair that you just cannot part with. It is imperative they fit you impeccably (make sure they meet the top of your shoe when sitting). Check out brands such as Lucky, Guess, Rock and Republic, True Religion
, and (if you don't want to spend as much!) Levi's like the 514's or BDG's for tried and true bargain buys. Avoid plain denim jeans!; look for either colors (black, white, brown) or denim that has a good wash or fade to give it a dynamic look. Skinny guys look great in slim fit jeans, and boot cut jeans are popular as well these days. Buy girl jeans only if they completely pass as guy jeans or you are having a midlife crisis. Rips are also cool this fall too, along with these very dark colored ones.
Shoes - they are sweet but don't go too overboard.
For instance, Bapes or Bathing Apes are sick but they do not match with anything! They are a collector's item, not for daily wear. Wear-ability is a must; get a color scheme that matches with what you have! Get something a little unique. Try a new style of Nike's SB's or AF1's, or try a new scheme of Onitsuka Tigers! Cop a pair of Gourmet's. Nice adult Jordan-esque designs but much more laid back and simple. Very easy to match, and no one else will have them.
Colors - they have to match your skin.
And get a variety! Verify color schemes with a trusty girl you trust yourself to trust. Trust ... trust trust trust ... trust me on this one! A person with light colored hair and light colored eyes will look better in the lighter colors while the more ethnic looking people will look the best in basic browns, grays, blacks, and other tones.
If you wear glasses, choose the kind with a thicker, more manly frame--not a wimpy one.
Rimless glasses are good too but they may bust. Go to a reputable place and have a saleswoman help you pick out a flattering pair. NOT, she wants your money. Once again bring that girl from before along to help pick a pair, or ask if you would just look better with contacts. Tell her you will tab the beer for her party and you will get unforeseen benefits from being friends.
Don't wear camouflage unless you get more action than Wilt Chamberlain.
(Look him up) or you are some redneck.
Do not go sleeveless unless you are at home, the pool/beach or the gym.
Jersey's can look great if you've got the guns ... dude. Same with tanks, which can look good in the summer. Check out Urban Outfitters or American Apparel for tank tops.
If your pants are baggy, wear a tighter shirt.
WRONG This will make you look out of proportion! The proportion should be 1:1. Equally baggy (or non baggy) shirts with equally baggy (or non baggy) pants. You don't see indie kids with baggy shirts along with their tight pants. Tight to tight, baggy to baggy! Make
Dress for the occasion.
Common sense. If you are in doubt, get your fly-est outfit (collar if above 20 years old, no matter if you are under 20) and go with it. So what if the night turns sour and you end up playing Jenga with your study buddies on a Friday. You have a washing machine, even if you don't have a life.