The reason that the rich were so rich, Vimes reasoned, was because they managed to spend less money. Take boots, for example. ... A man who could afford fifty dollars had a pair of boots that'd still be keeping his feet dry in ten years' time, while a poor man who could only afford cheap boots would have spent a hundred dollars on boots in the same time and would still have wet feet.
A cute little passage from Terry Pratchett, but it holds very true if you ever need boots.
Paying for quality boot work, especially the kind that can be re-soled, is worth it for anyone who has to wear boots with any regularity.
When I first got a job that needed boots I was using an old secondhand pair. It was hell. Eventually I saved up for a quality pair and was totally worth it. I've not underspent on boots since.
As for suggestions as to what brand to go with these days for that... I'm less sure on that because I'm researching new brands myself since Red Wings are a joke compared to what they used to be. Danner still seems pretty all right these days.
I dropped a semi truck lift gate on my toes one time, and didn’t even notice until I went to walk away and realized I was pinned down. Red Wing doesn’t fuck around with their safety toe boots.
I always walk my dog after I finish work in my steel capped work boots. The times that I actually do walk in my sneakers is so weird, like I’m not used to not having weights on my feet while I walk.
Redwing still makes some good stuff, but they also make some "fashion" stuff that looks similar. Unfortunately happens with a lot of quality workwear.
Rose Anvil on YouTube cuts boots and shoes in half and explains how and why they are designed the way they are, and where corners are cut, and what to look out for. He's a good resource for checking out a boot you are interested in.
Most of your "good" brands still have some crappy stuff in their lineup, but you might not be able to spot it by just looking at a web page.
Wearing a 16 year old pair of Redwings as I'm typing this. I haven't even looked after them properly (e.g. greasing them frequently) and they're still in good shape. Gave them a new sole a few years back.
I wear a similarly old pair of Chippewa's that have also been poorly treated, and they are still good (though I don't have a job that would beat them up anymore)
I second boots. I went through 3 cheap pairs of hiking boots (between £40 - £70) all promising the world and dry feet. In the end, sacked it off and bought all leather boots with a vibram sole. Requires maintenance of waxing them but they've had many miles in them now and just as good as day 1.
Upvote for discworld quotes. Pratchett was full of good advice. Some of that advice may have required living in a world full of magic and dragons but it was good advice all the same!
Clothes in general. Sure, you can get and Old Navy T-shirt for ~$3-4, but they break down quickly. However, even a mid-level shirt from someplace like Land's End or Eddie Bauer on sale can last year after year. Same with pants, jeans, coats, jackets, belts and other clothing. It's also why it sucks to be poor. Needs need to be met immediately, but since you're needing to keep food on the table and a roof over your head, so you buy what you can afford, even knowing that it's more expensive in the long term.
Generally, don't skimp on anything that goes between you and the ground. Shoes, mattresses, tyres... your future you will hate you for cheaping out on those.