The most important prerequisite of this guide is to have an open mind about what you might want to wear. Don't be afraid to try a new look.
The next most important prerequisite is money. The more you are willing to spend, the more clothes you'll be able to buy. The last time I did this, I spent a little less than $100 and bought 2 shirts and a belt. And, needless to say, I was very satisfied with my purchases.
Step 1
Call a female friend who you think dresses well and ask her if she has a good sense of fashion. She will most likely say yes.
Step 2
Use the foot-in-the-door phenomenon (Yes Ladder) and ask her if she wants to go shopping with you to help pick out some new clothes.
Step 3
Pick her up from her place and go to the mall together. Ask her what stores she would recommend checking out. If you've got a budget, be sure to tell her. She'll choose stores accordingly.
Step 4
This is the easiest part of all. You don't really have to do anything at all. Your chick friend will go around picking clothes for you. To a man, this is hard, stressful work. To a woman, however, this is fun.
Step 5
Take as many clothes as you're allowed into the fitting room and try them on one by one. Get opinions from your chick friend.
*Optional - To save time, ask your chick friend to come into the fitting room with you "as long as there's no funny business."

Step 6
Buy the clothes that you and her think are the best ones for you. Then, do something nice for your friend as a thank you such as buying her lunch or dinner.
Step 7
Look better than you did before.
-Chief