[Blarg]

Wait until the day after Christmas, and then shop early. You will get a lot of stuff for half off, some even cheaper, as they try to dump their stock. This will make your $500 go much, much further. This is almost the only time I shop for clothes.

P.S. At good department stores with non-[censored] staff, if you find something you really like but the color or size is just a bit off, you can ask them to phone other branches and reserve you the size you want, and either hold it for pick-up for you for a day or two in the other branch or send it to the branch you're at, which might take a few days to a week to get there.

Someone mentioned striped button down shirts. I'd pass on the stripes and get solid colors. They match more easily with a lot of stuff and tend to keep in style more.

Also, don't hesitate to get two of your favorite thing, just like you've been doing with your t-shirts. Sometimes it's hard to find things that are really cool, or what you have gets damaged or eventually a little frayed or whatnot, so two copies of the same shirt if you really like it. As well as the same one in different colors.

As you're starting from scratch, get some very basic colors first that go with lots of things, like a few ordinary blues that aren't "funky" or weird off-color blues, and some other colors the same -- a regular red or green rather than a weird looking one.

Final advice -- girls dig shoes. I mean they REALLY dig them. And not at all just on themselves. I've heard them countless times saying they judge a man by his shoes and that it's a good idea. In all seriousness. It's the kind of "last detail" that proves to some of them that you're "really" classy or rich or hip or whatever the code words are for it these days. (Along with a good belt, to a far lesser extent.)

Get yourself a nice pair of shoes or two, even though it's costly. Then women, even ones you'd think would know better, will think you're the real deal when it comes to, uh, class.