The best thing you can do for yourself is get rid of things.
No, hear me out. I've gotten rid of the majority of my clothes over the last year and I would honestly rather die than to have the closet that I used to have. It's really refreshing to be able to look in your closet and throw on one of the five dresses you have, and the only decision you have to make is which of the three pairs of sandals you own that would go best.
You see it in the media every day: the wonders of the girls with the walk-in closets, shoe shelves piled up to the ceiling and at least four purses that match every pair of shoes.
I own four purses, and they're all brown and black, which match everything. They all were expensive enough that I can rationalize using them for years to come, and I have for years past (well, minus my new one).
I'm working on pairing down my shoes, but things get tricky because the weather changes so much on the upper east coast that I can't rationalize getting rid of my old beat-up Timberlands, because they go great with three or four outfits that I cycle through throughout winter.
Now, clothing: I really don't own the amount that I used to. Granted, I'm a girl: I still have quite a bit of clothes, but they're for certain occasions, from work to sorority meetings to lazy days to just throwing things on. It all depends. But at the end of the day, everything fits perfectly. There's nothing that I let enter my wardrobe that I don't absolutely love.
I can't rationalize the point of spending money on things that I don't ever intend on wearing. The most detrimental thing you can do to yourself is say "I'll wear this when I lose twenty pounds", or "I'll find something to match this some day". It'll sit in your closet and waste your money over nothing, but I can honestly say that it is exactly what I used to do. There's not point in it; when you love everything you have, life gets easier. I swear.