That's the key, never to pay retail so if you do flip shortly after, you won't take much of a hit (if at all).
I like to try new things for the hell of it, even if it's out of nowhere (julius, etc) and if it doesn't work oh well. In central Florida I have NOWHERE to get clothes, it only happens if I go on vacation to Miami or NYC to visit friends. and as stated, if I buy at discount it's not like I take a big hit or anything and I get to try a new designer/new type of garment, etc, etc. I think a lot of guys on here are used to a 'NYC mentality' and don't realize that there's a ton of members on here in cities where literally NOBODY has a clue what something like Dries or CdG or Ann D is. Even Margiela, one of the more mainstream fashion brands, is unheard of to 90% of people at my school/people I know. Hell, it's 'asburd' of for most guys to spend over $100 on a button up shirt. Let's not get into $500 shoes.
Pair that with the fact that I have a really hard frame to fit with broad shoulders and big quads with a small waist, it's 75% miss/25% hit. I could probably get that ratio a lot better but I'm a sucker for if something is at deep discount I'll still TRY and make it work if I really like it.
Then lastly, I buy a bunch of shit, wear it once or twice and the 'desire' for that certain garment sort of goes away so I just sell it. I'd rather do that than have it sit in my closet and wear it once every couple of months. I know a lot of guys and especially girls who are like that. Sort of silly to just have a stockpile of clothes that just sit in a closet when you can sell it to buy stuff you'll wear (even if it's just for a few times).
Just my 2c