I actually didn't dress that well until a year or two ago.

But to answer your question, the going out clothes in my suitcase are the following:
- Couple pairs of designer jeans
- black dress shoes from Aldo
- Three tailored Italian dress shirts. No idea what brand they are. Bought them in a shop in Amsterdam. They look like nothing in the US. Have also a plain white button down from Express
- Leather Jacket from Diesel. Limited line. $750. Looks amazing on me though.
- An amazing sweater I got from Banana Republic. Have no idea how to describe it. Very unique and edgy though (I know, I was surprised to find it there too).
- A couple scarves (no one in the US wears these), ties and a vest (rarely wear anymore)

I'm by no means the best dressed guy in the world. I still think my fashion-knowledge is mediocre. I've just found some really nice items that look good on me. In Europe, I'm average-dressed in many venues. In America, I'm anywhere from over-dressed, to ridiculously stand-out over-dressed. I've probably been approached in the US by 25+ women on my leather jacket alone in the last two years. I've had some women ask me if I'm a male model (flattering, really). Get asked if I'm gay all the time. I've even had women ask which European country I'm from. When I say I'm American, they have a hard time believing me.

Often I get lazy and just wear a T-Shirt and jeans out. Needless to say, I get NONE of the comments/approaches like mentioned above when I do. Probably get half the eye-contact as well. In fact, it took me like three years just to learn to stop wearing T-shirts at all. Figuring that out by itself and buying the jacket probably doubled the amount of eye contact and approaches I get. Granted, I'm sure getting into good shape helped a lot too.

I'm going to be back in Asia this year, and I'm thinking about picking up a number of custom-tailored suits while I'm out there and see what happens when I wear them around. I've talked to a couple guys who absolutely swear on this. Honestly, over the course of five years, I've slowly learned that it's more or less impossible to be over-dressed. It's almost never a disadvantage. So might as well take that to the next level.