Overweight Slob looking to update bar attire. Need some help!

I'm an overweight guy that apparently has a bad taste in clothing. I'm a proud nerd, have lots of video game shirts and other things, does the whole button up + t-shirt thing + jeans thing. What do I need to buy in terms of footware, clothing, accessories (I don't know if this is the right male word), hats and other things? I usually go out to the bar with my friends on the weekends and I'm tired of looking like a complete slob with low self esteem.

My budget is $200 for basically what I hope is 1 or 2 outfits with things I can interchange like shirts and shoes, at a later date as I buy more and more items. I like in a moderately busy city, not the biggest, but it has lots of malls. I don't really know what kind of style I have, but hopefully with the above information I can get a little bit of help and a pick me up with some new clothes that make me look good.