It kind of depends what kind of a shopper you are. There are many approaches I've read here, but one thing seems to be that there tend to be many who fall into one of two camps.
Minimal purchases, carefully planned ahead of time to fill specific item holes in an existing cohesive wardrobe, highest quality (ergo may be on sale, but may not be). This may net you five to fifteen items for your 500$ depending on your price points. Shopping experience is online or in a well-organized store with a current season collection. Frustrations might be that you can't find the exact thing you are looking for and need to try multiple stores. If that feels about right - go for it.
Opportunistic purchasing - you go in with an idea of colors, tops/toppers/or bottoms, styles/cuts and materials you are interested in, but you are opportunistic, you try on lots of items to see what works best and are open to discovery in the moment. Often linked to shopping sales and clearance and off price retailers. Your 500$ could go much further. Frustrations - you need to be comfortable shopping in clearance environments, and disciplined in only bringing home pieces that fit your needs and are good quality (not have sale goggles). Also you still might have a wardrobe hole or two when you are done.
It's all what you have the time and tolerance for, and what meets your needs right now better.
I'll add that it is possible to do both at the same store, especially a big department store like Dillards or Macy's. The Nordstrom near me only has big discounts at the Rack which is all the way across town with no parking