I've been reading along, debating an answer. I am a bargain shopper by nature -- I love finding a good deal, and I won't spend a lot on a trendy piece that I suspect will only have a season or two before it starts looking a bit dated for my style. I am, however, willing to pay for certain pieces, items, and brands if they tick all my style boxes and they fall within my ability to comfortably pay for them. My wardrobe is a mix of high and low, and I fully recognize the privilege I have of being able to afford to buy items I love at many price points. It was not always so -- I spent many years avoiding full-price "expensive" stores unless I scoured the sale racks. I still remember what a treat it was when a lovely couple for whom I petsat many years ago gave me a Nordstrom gift certificate, and I bought a pair of full-price black boots that I wore happily for years.
I'll pay more for good fit, nice quality, etc., but mostly if the style really speaks to me and there is some unique quality of the item that can't be found at a lower price point. I don't care about labels, and in fact, I avoid any large or obvious logos or branding, but I do appreciate that certain brands have a design aesthetic that appeals to me, is unique, and yet retains some bit of timelessness. Examples: I splurged on Valentino Rockstuds many years ago and they are still my go-to dressy shoe for occasions -- they're comfortable, sexy, and well-made. I'll wear them for decades to come. Also, my teal Burberry trench -- perfect color for me, lovely quality, classic but with a twist. I'll wear it forever.
So what else will I spend a bit more on? Jeans, for one. I don't do super trendy denim, so my jeans last for years and I'm willing to pay for premium denim, up to a point. My threshold for jeans is around $200. But I wear them near daily from October into May, they are hard to fit for me, and my preferences defy trend for the most part, so I more than get my money's worth out of my denim. On the other hand, I also have $30 jeans from Gap and Old Navy, so I'm definitely a customer based on style and fit, not price or label. I'm not a big secondhand shopper, and the thrift stores around my area tend to be filled with things that hold little appeal for me.
I am more likely to pay a bit more for footwear (particularly boots, although I've learned that sandals can be a decent investment as well because I wear them so much), denim, pants, and jackets. I'm less likely to pay a lot for knits, tees, basics, and summer casual tops. And I don't really spend a lot on sneakers either. My gear is a mix of REI, Lululemon, Athleta and tends to last a long time. I've learned not to skimp on bottoms but that I can get away with cheaper tops. Cheap bottoms always end up being too short or they slip down my hips.
Another item I'm willing to pay for -- as many of you know, I've developed a fondness for Alexander McQueen scarves. The designs are unique and very "me," and I carefully choose color schemes and patterns to fit in with the outfits I'm trying to accent with those pieces. For instance, I looked for a while for a red/black/cream patterned scarf before I finally decided that the butterfly print McQueen one I originally fell in love with was worth the $$ because nothing else sparked that love -- the cheaper ones I found didn't have appealing prints and the fabrics were nowhere near as nice. I now have three McQueen scarves, and I know some folks here think it's ridiculous to spend between $150-300 on a large square of silk (I purchased two of them secondhand or on sale), but I love those scarves and will wear them happily for the rest of my life. I suspect that they will end up with a CPW of pennies. They make me happy every time I put them on. They'll fit no matter what my size or weight.
So, yes, I'll happily wear a $15 tee from TJMaxx under a Veronica Beard blazer, paired with $30 boyfriend jeans from Old Navy and $300 boots. For me, it's about the item and my particular style preferences, not a label or name. A high price makes me think more carefully and often research other options, but usually if I get that far in even considering a more expensive piece, I find that nothing quite compares to the original.
I'm glad this thread has remained respectful and nonjudgmental. I believe very strongly that each one of us has to respect our own individual priorities and situations. Like some of you, I have never had to think about clothing and feeding children (at least not full-time), and style has long been a hobby of mine, so I have a bit more freedom to consider things I never would have dreamed of buying 25 years ago. I do have times when I spend less, and times when I spend more, and my spending thresholds are well in line with our overall household budget. I would like to continue being more mindful about the quantity and usefulness of my purchases, regardless of price point.