Problem: I'd spend more money on clothes than I currently do, if it were easier. JackThreads is probably the best company in the space currently. Or maybe Uniqlo.
Currently, every 6-8 months or so I realize that it's been ages since I bought anything, and I go and buy a bunch of clothes at once (I don't like the experience, so I cram it into a short time frame if possible). Generally from Uniqlo+Amazon. And generally online only, now that I know my Uniqlo size I have no reason to go into any stores.
This sucks, because buying a ton of stuff at once means I project out what I'll want to wear, and I seem to be pretty bad and projecting this. A solid amount of what I buy ends up with relatively little use. And the good stuff is great, and then I overwear it (in the case of socks, quite literally).