[M2d]

Jared,
there's lots of good advice suite-wise here. I was in the same boat as you, fashion wise, and, over the years i've ended up with a couple of classic suits (one lt brown burberry and one black ungaro) that I picked up cheap at off 5th (saks fifth discount outlet for last year's models). since the suits I got were last year's cuts, they were heavily discounted, but since they were basic, they don't look dated. I also got a navy blazer and a bunch of slacks and nicer khakis.

for basic office wear, check out the banana republic outlet at waikele the next time you're in hawaii. for some reason, they stock the same styles as banana stores/outlets on the mainland, but, since it's honolulu, they have a lot more sweaters and pants (since no one buys them there) on hand. they also have an off fifth there, but i'm not sure if they carry suits. if they do, it'll probably be easy pickings to get something nice for a good price since so few people in hawaii wear them.