It's an interesting question, and I appreciate hearing everyone's take on it from different backgrounds and areas around the world. My parents were bargain hunters par excellence and a lot of my shopping behavior comes from those habits I learned as a kid. Part of me does enjoy 'the hunt' and feeling like I got a good deal. But it's a trade-off that you make, because you spend more time looking, and you may have to settle for a color or silhouette you wouldn't have picked if you didn't care as much about prices and sales.
Angie remarked about the constant sales cycle as a fairly new and American thing. I sew and Joann's, the chain fabric store, is notorious for sales practically every week. If you wait a month, the brand of pattern you want will be on sale for 30% of its usual price, and there are regular fabric and notion sales as well. Basically, if you are paying 'list' price for anything you're getting taken advantage of. Now, is it all a head-game? Probably. Joann's has to know what the 'real price' that most customers are paying is, and I'm sure that their margins are still there even at the sale price, or they wouldn't stay in business. If any of you shop at Kohl's you'll know they're very similar. I think on any given day, it would be hard to find something at Kohl's that's not on some sort of discount sale. It's a psychological play, like gas prices with the hidden .9 cents at the end.
I would be OK, I think, with a more European model where sales are less frequent and you could feel all right spending full price on something most of the time, because the prices are pretty stable. But the way it is in my local stores, I would feel foolish paying full price because there are so many sales and discounts.
I kinda wish I had had the experience of a more expensive item being "worth it" as far as quality and longevity goes, but generally I haven't. Take shoes, for example - I can tell the difference between a $20 shoe and a $50 shoe, sure, and I will be more likely to buy the latter because the former will tend to be less comfortable and fall apart faster. But I have not found any notable difference between a $50 shoe and a $100 shoe - my $50 shoes are often more comfortable and durable than my splurge shoes. Maybe my amounts just aren't high enough - if I tried $300 shoes and $200 jeans perhaps I would find them that much nicer than my normal price range items.
I know that throwing thrift/secondhand in there muddies the waters because then you're talking about items that may have been pricey on the first go-round but now are inexpensive to purchase. But that's where a lot of my purchases come from, which allows me the best of both sides - quality and low price. The trade-off is that I have to spend more time looking and I may not find what I want.
I think about this a lot, actually, because there are a lot of wealthy people where I live, and they are able to not even worry about how much they spend on clothes. Then there are people that are barely scraping by and thrift shop because they can't even afford Target and Walmart prices. Most of us are somewhere in-between, and we have to decide what we do with our income, and implicitly with our time. It's easy to say that you want to shop in line with your values and priorities, but it's hard to figure out what exactly that means. Do I want to optimize my time so I can do other things? Do I want to limit my budget so I don't have to work as much or work in a job I don't like but that pays well? Do I want to prioritize a hobby or traveling over clothes, or clothes over other things? The questions can go on and on (just like I am, so I'll stop).