I think a good guideline is to be willing to pay more for your personal wardrobe essentials -- whatever those are. And they are different for each person. Here's one of Angie's posts.
I have determined several categories of "essential" for my lifestyle and climate. First are the weather necessary items. In my first autumn at YLF, I therefore put my big $$ into winter coats. I'm still wearing these coats. And will probably be wearing them four years from now. Or even more. They're classic enough to go that distance.
My second winter, I bought another coat in a different style, and a really great pair of booties. Slightly pointed almond toe with a cuban heel. I got them on sale but they were still more than I had ever paid. Totally worth it for my climate and lifestyle. They will be on year three --- still going very strong. I expect to be wearing these happily for another two seasons after this year. At least.
And I bought two leather jackets that year as well. I expect to be wearing them for quite a few years.
Last year, I bought tall boots. That was a huge expense, because in order to get them to fit right, I had to buy expensive ones at full price (I'm not an easy fit in boots.)
Next we come to "life style essentials." That's the stuff you will wear almost every day. So...with that in mind.....I also invested in quite a lot of knitwear and in a few pairs of premium denim.
And I bought two dresses to wear for occasions. These were necessary (i.e. I had to have something for those occasions) and I luckily found them on sale -- but even so...it was an expensive year.
This year I bought a suit, and a beautiful, higher-end blazer. I'm stocking up on undies at the NAS! I will also buy one or two special pieces -- a sweater and possibly another jacket.
I have bought a lot of other stuff, too -- footwear, belts, tops, knits, etc. etc. etc. But most other purchases were mid to low range.
In some cases I actually paid less for the high end item than other items in my closet, because I was able to find it on sale -- but my point is, I wanted these particular items to be higher end. I knew they needed to be well made; either I'd be wearing them a lot for quite a few years, or they were important for special occasions. Or both.
You never know in advance if an item is going to work out, of course, but there are telltale signs. Construction, fabrication, the fit of it. I have not been disappointed by a single higher end item I've purchased, I don't think. And I haven't been sorry. Nor have I purged a single one of those items yet; I'm still wearing them three or two years later, and looking forward to more wears.
I have regretted some of my lower end purchases. And my consignment buys. Almost all the consignment and thrift purchases are gone, and many of my lower end items. But I do buy the lower end stuff deliberately to indulge in trends, so that makes sense.
Mid-range is the trickiest, to tell you the truth. Sometimes the stuff wears like iron and stays current, and sometimes you tire of it almost instantly or it falls apart.