[citanul]

Clayton,

Don't buy clothes online that you haven't tried on.

Here's what I'd suggest:

1) pick up a few staples at banana republic (or j crew, or american apparel, or all of them). colored tshirts, khakis or linen pants, maybe some other form of pant.

2) head to nordstrom. even if you don't decide to buy anything (or much) there, just walk around and get some ideas. I picked up a few Penguin polos there, and was happy with those. They have enough youth to them that I don't feel like a douche, but enough class that I feel I can wear them to work. (in general, I'm a pretty big fan of polo short sleeves, but that's just me.)

At Nordstrom you'll also see a huge selection of button up shirts. Pick a few you like and just buy them.

If you don't have great jeans already, buy yourself 2 or 3 pair, somewhere. Ask the advice/help of the store people selling jeans, and remember they should be tight when you buy them. Your first few pairs of jeans, don't buy anything that you would only wear "when you go to a club" or whatever.

3) Pick up a suit, or a sportcoat, or both, if you don't have ones you like already. The Nordstrom half yearly men's sale is good for this.

Go through you closet and really honestly look at everything you've got right now and evaluate it. If you've got stuff that just sits in the closet and you never ever wear it, get rid of it. If you've got stuff that you wear sometimes, but don't like the fit, get rid of it. Etc.

I wear a pretty similar look, I think. A few good pairs of jeans, a few shirts you like, and some non jeans pants are a great way to start. But don't skimp on the basics. Gap t shirts are t shirts, but the fit is terrible on almost anyone (especially anyone close to skinny). Pay a little more elsewhere and get something that fits.

Hope some of that helps.