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.
But if you do this way and go quickly, you have to accept that some items are a write-off.
One thing in particular is hard for me, but I try to remain disciplined: jeans that are good all the way around, but have shallow pockets.
About every two years or so, I make the mistake of trying to keep jeans or trousers where the pockets are cut awkwardly or shallow. Inevitably, a phone, money, or wallet falls out of my pocket. Sometimes I see it in time and grab the item; sometimes not.
It's especially hard to just throw out a new pair of jeans, but I've started doing so. It's an error to wear clothing that makes you likely to lose your phone, money, or wallet. It feels wasteful, but it is what it is.
And yet, even knowing this intellectually, it's hard for me to do. I keep saying, "Ah, but, that's wasteful... I could perhaps..."
— nothing good comes of this. It's allowing a sort of "leak in the bucket" of one's life, almost literally in this case. And it's always hard to say, "Well, okay, I got four pairs of jeans I like, three of them are good for the next few years most likely, this one I erred on and should go in the trash so I don't wear it."
Last time I violated this rule, I lost about around $100 USD of Taiwanese money (3 blue 1000 NTD bills) that fell out of a shallow pair of pockets.
I didn't even realize it; I thought I'd set the money aside or something, I was confused when I didn't have it later. Then, another time wearing the same jeans, a Taiwanese guy on his motorcycle flagged me down and pointed out that another bill had come out of my pocket and landed on the ground.
Well, those jeans go in the trash. They're a liability. In theory, you could build some better structure around wearing them only around the house or something, but in practice eventually one would make an error and go outside, and having clothing that is dangerous to wear in terms of losing your personal articles is a bad idea.
So it's hard, but you throw it out.
Of course, this post isn't about jeans. It's about things in life that seem almost workable but have some fatal flaw that make them dangerous to keep around. It's hard to get rid of them, eh? But the alternative is your money falling out of your pocket, and most people aren't so nice to pick it up for you.