I buy a lot of my clothes at thrift stores, with mixed results. But if I screw up and don't like something, I'm only out $5 - $7. Not bad at all.
Yeah, as has been mentioned earlier, I generallyreally dislike shopping. But when I'm in the mood, I'd vastly prefer to go to a thrift store:
1. No environmental footprint
2. Cheap, if they have something I like, and
3. I'm not about to be naked -- if they don't have anything I like/need, I don't have to purchase anything.
4. If it's not perfect -- Meh, it was $3 - $10. I HATEHATEHATE shopping for jeans, because they never fit properly. I'd much rather buy a couple of pairs of $10 jeans that don't fit properly then .. what are they now, $80 - $100 if you don't want the POS jeans from old Navy or wherever? I have a used pair of those, and they stretch out so far after a single wearing that I have to start wearing a belt with them.
5. I've discovered I'm more likely to buy and wear really nice stuff if the cost to me is low. Thus, I have a winter wardrobe of cashmere sweaters that I wear (and basically wash) like fleece pullovers. It's as if I'm all fancy and s&*t. Seriously, it's plain luxurious to get to wear cashmere and silk and treat it like T-shirts and sweatshirts. And if I spill on something? It was $5, so if the stain doesn't come out, I just send it back and keep an eye out for another.
I do buy shoes new, but I buy rather expensive pairs and have them re-soled on the regular. Also, the pair that wears out fastest are my biking shoes (with recessed cleats) because I generally ride most places most days. Ride = Go Out Back Door = Biking Shoes. (Walk = Front Door = more shoe options.)