Basically like this:

Imagine every article of clothing you own is clean, pressed, and ready to be worn. In that situation, there are a small number of items you will always reach for first. Keep those.

Then there are some articles of clothing that the only time you would ever wear them is if nothing else was clean. Get rid of those.

Since I lost 50# in the last year, one of the associated chores was completely replacing my wardrobe. Given the opportunity to start from scratch, I'm trying really hard to avoid chasing sales and ending up with a bunch of clothes I almost, but don't quite, like. If I have to spend a little more to get stuff I really like, fits right, looks good, and will last, that's better than buying five cheaper items you don't really like.

Of course sometimes, cheap is just fine. I still haven't found a pair of jeans I like more than a pair of $15-21 Wranglers. I've never understood spending $50-300 on jeans.

Regardless, the end result is my wardrobe is A LOT smaller than it used to be. I'm also really quick on the draw to get rid of something if I decide I don't like it and don't wear it.