My strategy on buying clothing: generally hold off on shopping for clothing until I wind up in very favorable conditions for buying, and then buy a lot at once.
That means if a very good 70% or 90% off sale is happening at a high-end American store, that might be a good time to restock everything.
Failing that, I'll look to buy my clothing in China or Malaysia. Recently, I was in Istanbul where clothes were incredibly inexpensive for very high quality, perhaps the least expensive country I've seen in that regard, and foreigners taking their materials will them got all taxes refunded at the airport. It's a good deal.
So I bought a lot of clothing. For a couple hundred dollars, I've got all my casual clothing taken care of for the next couple years. I'll pick up a couple nicer items in New York City for occasions that dictate it, get tailoring done in Beijing, and be good to go.
There is a downside, though: by doing this relatively quickly, I don't agonize over every single piece. Sometimes, I buy things that don't fit so well or aren't so durable. If you look at it mathematically, you can just put into the cost of the items you do like. Quite cool casual shirts in Istanbul started as low as $3 USD (no joke) up to $25 or so. This is roughly the same quality level you'd be looking at for $25 to $70 in the United States.