I used to only buy clothes when on sale, or second-hand. Slowly, my finances have been improving. I had problems with the sleeve length of my shirts (I have long arms for Spanish standards), so I started to buy muy shirts MTM (which implies full price; you can have nice MTM shirts of nice Italian or Swiss cotton cloth made for around USD 130 here in Spain, with your initials on the chest, which is actually very common in Spain; I almost never see that abroad, maybe it is considered to be bad taste...). Next, I started to have my suits made by a tailor (full price, of course). The next step was the shoes: it is not that I do not buy shoes on sale, but when I see some that I like, I also buy them at retail price: shoe shops can be quite exasperating during the first days of the sales period, especially when you have to try several ones before finding a pair that fits, which is often my case (I guess I have quite strange feet). I also sometimes buy jeans and other things that are strictly size-dependent at retail price, so as not to risk not finding my size, if I see a pair of jeans that I really like.
Also, it is nicer doing shopping when the shops are not so crowded.
On the other hand, things like ties, underwear, socks, pullowers, sport shoes, etc. I almost only buy when on sale.