Nowadays I mostly buy Levi's 550 or 505 for cheap (40 canadian $, so like 30US$) and plain white/black tees and longsleeve tees (my gf loves the plain tees for some reason) and I buy a couple pieces from skateshops when I find something I like.
That being said, like others have said, most of my wardrobe is Dime, Polar and other skate brands I've bought over the years. They stay in good shape bc I wash them with cold water and never put them in the dryer.
Shoes from my local skateshop, mostly NB and Last Resorts, but I do have some pairs of vans I got for cheap and still have an old pair of dunks (NBA nuggets *Edit: Cavs* highs) from back when I bought them at 40% off, before all the hype.
Bunch of hats, both from my local shop and sports team hats.
I have too much clothes, shoes and hats tbh. Like waaaay too much.
If you have a shop around that supports the local skate scene, I personally try to support them as much as possible. Otherwise, cheap shit that fits.