I am most certainly on a budget myself. Just yesterday, I had $20 to my name! Thank God for paychecks.
I've been trying to get out of the money hole for a while and am just now starting to get back up beginning with this paycheck and the next one, but I'm afraid that Christmas is going to suck it all back out of me again. I bought my first stuff back in early October, and it's been nearly 2 months since then and I haven't been able to buy a single thing. All I can say is, if you really want to do this, just be patient and don't worry about the money too much. You don't have to get it all at once, you can spread it out as you have money to spend.
I was caught by my parents as I was starting, they were very disapproving and as far as they know I have stopped (obviously, I haven't). I'm now living in a dorm room with a guy I met in August and I still manage to do some dressing. Just have to pick the right times to get your fix, when you know you're going to be alone, like at night.
The best I can tell you is, if you really feel strongly about this, don't be afraid to start. If you're afraid of what others will think, don't worry, we've all been there. Just take your time and try to be comfortable with yourself. If you can't accept who you are, you can't expect anyone else to.
Wish you all the best, and good luck.