So after finally finding myself a job (I can put up with being called "miss" and stuff because terrible job where you have to present yourself as female is better than no job imo.) I finally have the money to start my wardrobe! For some extra info, I'm something of a bigger guy. (As in, I've got the hourglass figure going on because I'm kinda chubs. Even with my binder, I've still got those big ol' obvious hips n' thighs. I've been losing weight, but it's taking time. I guess my problem is, how do I disguise this figure? And how do I be confident in buying clothes? This post is all kind of a mess, but it's late here..
Okay, so I'm not familiar with what guys like in general, or what you like, but if it's the confidence you need, then here's something. Do a quick shop in a charity store, bring home some clothes, and for the people who you're confident with put on a show for them. They could rate what kind of style they like and compare it to what you like. Then once you've got the style then go shop in some mainstream stores, or again in charity if that's what you like, and have fun. Oh, I like your Narnia reference, I came up with something similar.