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my main advice to you would be to just spend twice the money on half the clothes. You'll feel better, they'll stay in place, and they will last a lot longer. Just like with women, you want to go for the quality over the quantity if you can help it.
I've never thought about this. I used to be what the UK calls a chav... basically means I used to walk around in tracksuits and hats lol. Tracksuits used to cost me around £120... but now I dress a lot smarter, and my clothes are 1/2 the price. I'm wearing a T shirt today that cost me £5 (about $9)
I'm also wearing skinny jeans that cost me £15 ($45) and I feel quite smart...
I've had French Connection shirts that have looked shit after a couple times in the wash.
I'll say one thing though: I've found that expensive tops generally fit better.
I think an expensive jacket and shoes are all that you really need. You can get high quality jeans at low prices, if you know what to look for... a plain, slim fit T shirt doesn't need to be expensive.
I agree with feeling a lot better though. Which in turn makes you feel and look a lot more confident, and motivates you to take better care of other things such as your hair and whatever. If you've got the money for the expensive clothes, then go for it... but not to the point that you'll be struggling to afford things.
Another tip that I found on a site called SoSuave or something, was to dress like you're going on a date every single day. Apparently this changes your whole life lol... I've been slacking on this, but I have randomly dressed my best for no reason for a week or 2 before... and I felt a lot better about myself.