I'm more in the middle to be honest with you I do a lot of yard work and mess around outside a lot so practical but good clothing is what I prefer but I also like looking good so I buy more expensive but classy clothes as well. Luckily my family is full of classy guys with lots of clothes they don't wear anymore so I have a wealth of dress pants, nice shirts, suit, sports coats, formal wear and the like.
I do find buying high end brand name clothes to be kind of silly though as you are mostly just paying for the name and that's it.
Both. Actually I try to buy some stuff cheap so I can pay more money on stuff that actually matter. I buy cheap T-shirts and pants, so I can save for a pair of leather ankle boots, a pretty dress or sunglasses.
I do both. With tshirts I bulk buy them when they're cheap. Underwear and bras I buy them bulk when they are expensive as I've started to like Victoria Secret underwear. Buying bulk from there is cheaper then just buying one.
It doesn't have to be name brand or anything but expensive clothes do tend to look better and hold up longer. I like just focusing on one outfit when I decide to shop. So I'll pick out either a dress or a top/bottom, shoes, and accessories. It builds up over time.