Happy Birthday!!
Do you have a really trusted, fashion-concious female (or male) friend? Try on the outfit for them, and get their honest, uncensored opinion. I use my mom; she has great fashion sense and will honestly tell me when something looks great or like poo. She'll encourage me to wear things that I don't think a "fat girl should wear," that in my head make me look like 2 pounds of sausage in a 1 pound casing. But it's ALL IN MY HEAD!! In reality I may look awesome.
I tend to frump/sloppy it up when I'm feeling bad about myself/my body, and for me, this is a vicious circle. I feel ugly -> I dress ugly -> I feel uglier. You get the point.
To solve this problem, I've had to revamp my wardrobe. I get to wear sweats when I'm working out, sleeping, and on my one day off a week. The rest of the time, I dress up. Not too dressy, but nice jeans/khakis/skirt with a nicer top (usually fitted). My big T-shirts, once an almost daily wear have been banished to my workout/sleep drawer. I choose things that are still comfortable, but are also pretty and sexy. For me, it's helped a lot.
Quote:
It's like I'm more comfortable looking sloppy & unstylish so that others won't notice me.
IMHO, when you dress sloppy and unstylish, you draw more attention to yourself. And not the good kind either!