Always have a choice of 3-4 outfits you can wear.
First outfit - Clubbing
Get a nice blazer (Black), Dress Shirt, T-Shirt, Vest, Graphics T-Shirt, Dress Shoes and Accessories (Chains, Bracelets, belt and Earings)
Outfit one can equal two outfits since you have a choice of going blazer or vest as well as dress shirt or graphics shirt. Get this stuff fitted so if it means spending 20-30$ for alterations do it and look after the stuff. Fitted clothing give a more comfortable feel for skinny guys and it shoes your body off well. A nice watch can go a long way and this is key wearing flashy means its appealing and attractive. Women like guys with one of three things, nice smile (Whiten those teeth), Nice shoes and a great watch. Rest is personalty you have to learn from experience and develop.
Average cost probably look at spending 200$-400$ go to any of the stores listed to buy fair priced stuff
->Aldo
->American Eagle
->The Bay
->Sears
->Calvin Klein
->Zara
->H&M
Second Outfit - Shopping/Malls
Get a casual outfit nice graphics shirt, jeans and sneakers. Basis stuff something you can keep and get it fitted again. Don't have to break the bank either this should be cheap for you nothing lavish no one breaks 500$ prada shoes to go to the mall with, do that for the clubs. Get nice accessories leather braclets, chains, a basic watch.
->American Eagle
->H&M
->Hugo Boss
->Calvin Klein
->Any graphics shirt store
Third Outfit - First Dates
One can wear their clubbing clothes but get something special or mix with the first two outfits to get a great first date outfit. Always dress to the best because this is the image she will have of you when she first meets you never under dress go overboard. She may say she doesnt like it but she does. women don't know what they want but they do know they want a man who can take charge. Go all out don't break the bank with 500$ shoes and etc., just make sure you clean yourself and groom. Wear ironed clothes and washed shirts. Put on deodryant and cologne. Don't forget to brush 3 times and shower twice
. Its idol to do this as for the second date you don't have to impress anymore she has grown around your comfort level.