/fa/ - Fashion

This should suffice.

Well the thing is that "Dressing well" does not really have anything to do with the cost of your clothes.

Dressing well connotates an amount of skill, and therefore implies that you have a good sense of coordination in your outfits and that your clothes fit properly. You can be wearing an expensive blazer, pants, shirt, and shoes, that all fit terribly and have mismatched colors/patterns/fabrics. Meanwhile you can be like JGL over here, be wearing inexpensive clothes, and still look fine, if not great.

So really, it's not cost you need to worry about. It's about fit an coordination. After all, James Dean is considered a fashion icon, and all he ever really wore were jeans, t-shirts, and occasionally a jacket.