I think you first need to figure out what you like and what makes you feel good. Go to a store (thrift stores are great for this) and try on lots of different things—dresses and skirts of all cuts and lengths, all types of pants, some pretty blouses and louche tees, whatever catches your eye.
You may have to try on a million things to find something that really makes you feel good, but you’ll find it. When you do, buy it. That’s your starting point.
Again, lots of this depends on lifestyle—how much money you have to spend, how much time you can invest in it, where you’ll be wearing your clothes, etc.—so change this advice as you see fit.
If there’s something you’re wearing all the time but that doesn’t make you feel great, figure out why. If you’re wearing it a lot, it’s either:
-easy to match.
All of these positive things are also available in clothes that make you feel good—I promise. You just have to work a bit. I’d say about 80% of what’s in stores won’t fit 80% of body types well, if only because fit models are so standard and traditionally proportional in their measurements, and normal people aren’t.
A good start for you would be to take whatever you’re currently wearing the most and figure out why you’re wearing it (those three reasons above should give you a good start). Then, compare it with why you like the garment you found on your shopping excursion (or really any garment you have that makes you feel fantastic).
There should be some middle ground there, and that’s what you need to look for. Do you want comfy but fancy? Convenient but sexy? Easy to match but androgynous?
Don’t be afraid of a uniform, either—ifblack jeans, a colorful top, and some kicks make you feel good, wear that all the time! If maxi dresses are your flow, find 20 (they’re all over thrift stores).
Take your next few days off for yourself and build a starter wardrobe based only on pieces you absolutely love. You don’t to dress like the other people at your high school or office or college. Wear what makes you glow and don’t feel bad about donating anything that makes you self-conscious every time you wear it.