I'm the same. I'm wearing a non-brand polo shirt and jeans most days. Honestly, I'd go to a good mens clothing store and talk to them about your goals. Don't b

I'm the same. I'm wearing a non-brand polo shirt and jeans most days. Honestly, I'd go to a good mens clothing store and talk to them about your goals. Don't buy too much at once, try to stay fairly classic/timeless at first until you figure out what you like. I can't do it because I'm too much of a tightwad to spend $180+ on a shirt, or $1,000 on a blazer, which is what the average is at the store I'm thinking of. But they will work with you, get your measurements, and do alterations so that the stuff you buy really fits well (which is a big part of what makes an outfit look really good -- it's more than just the right combination of colors).