For what it's worth, I discovered thrift stores when my first baby was born. I realized with amazement that babies and children grow out of many of their clothes faster than they can wear them out, and I was able to buy better quality clothes second-hand than new clothes first-hand, given the budget I had. (We happen to have excellent second-hand stores where I live.)
I also discovered that a child's outfit in good condition that you buy second-hand looks like a new outfit that has been worn five or six times. How often do children wear their clothes? We're probably talking about a month's wear, at most, for the high-priced clothing to look used!
Now I have grandchildren, and they're all fine about wearing hand-me-downs... so on their birthdays and at Christmas, I like to give them an outfit that nobody else has ever worn, because that's a real treat. But I still look for a good sale on it.
I don't do the coupon thing, because coupons say, "Buy THIS!" when maybe THIS is not the best thing. But if you can find the coupons for what you really need, do it!
Poor quality is never a bargain.
My bags are second-hand, too, but I discovered that I like leather bags so much I'm willing to use them practically forever. Years and years ago I found a Coach bag with a damaged clasp for $20, sent it to the Coach people (who fixed the clasp for free), and still have the bag.
I understand what you're saying about your own clothes. The only thing I consistently spend big money on for myself is good running shoes (and socks to go with them). I love to look in the stores but... there's just no way. I try to keep aware of changes in style and do the best I can, but I'll never be "second-glanced" for any complimentary reason. Oh well. I'd LOVE to look artsy, though!