There are essentially the five stages of fashion:

1.) D&D playing dweeb who spends ten dollars a month or less on clothing. Clothing will be cheap or corny.

2.) Comfortable. Stroll through a college campus and you will see comfortably dressed guys everywhere. The clothes are typically oversized, generic, and will probably be a minor name-brand (Gap, American Eagle, etc.)

3.) Well-dressed. Clothes will be more expensive and well-matched. Best product on this is Pickup 101s “Dress to Impress”.

4.) Sexual stereotype. At this stage, the person will be a recognizeable sexual identity, e.g. prep, metrosexual, urban prep, etc. The best book on this is Brad P’s “Fashion Bible”.

5.) Peacocked. An identity which is recognizable but is even more overdone.
The Iron Law of Peacocking: You will either be the coolest guy at the club, or the biggest loser walking on God’s Green Earth. The way you can tell is the reactions you get from people. If people are laughing at you, give you bad initial reactions, or ignore you, then you look like a clown. Do not dress like Mystery! He’s a professional magician, he can get away with dressing like that because magicians go over the top. You are not, don’t do it.

Start wearing accessories, and pay attention to things like what socks you wear and what shoes you wear. This will take a long time and is one of the more expensive areas of pick-up.