Ch^H^H...Train of Thought

"I'd like to order 5 of these"?

About 2 years ago, I was told by Tanya and Jess, that I need some better fitting clothes. So they took me shopping, and we picked out some shirts and one pair of pants that look pretty good on me. But it's a dress shirt and black pants. Which isn't typically what I'd wear on a day to day basis being an engineer in Silicon Valley. Nevertheless, it's one of my favorite outfits.

Recently, a few other people at dance tell me I need to find "clothes that don't make me look like an old man," pointing out that the pleats on my khakis make me look fat, and that my shirt is one size too large. Given the shopping experience above, I understood. My teacher tells me, "you know, you have a pretty good figure. It's just you don't wear any clothes that show it off."

So I went through my wardrobe recently and started looking for all the clothes I have, and it seems the majority of stuff I have is all too big.

I went to Valley Fair this weekend, and bought myself a pair of khakis at Express Men... but here's the problem: I need to basically flush out the majority of my wardrobe, but the idea of going to buy more than one pair of the same pants seems strange to me. Is it okay to open up a closet and see like, say 4 pairs of identical pants? I'd feel uncreative or something.