For me, it was a pair of merrell shoes on sale. They have lasted 3+ years, have great grip in the snow and ice, and so comfortable, my feet don’t hurt after wearing all day.
Never cheap out on anything that comes between you and the ground; shoes, tires, a bed.
What have been some of your good purchases under $100?
Love my Merrels, I wear the mocs which I got because they have a rounded heel (good for driving) and I was always in and out of them getting in and out of the bunk of the truck. They fit really well despite being slip ons.
A good penlight, streamlight makes some decent models, much better than a phone flashlight and comfortably fits in the pockets of loose fitting mens clothing to carry everywhere. usually more useful in the winter if you aren’t a night owl.
A decent pocket knife, nothing fancy, but something heavier duty than a little Victorinox is nice to have though those are also great to carry! CRKT , Civivi, and Kershaw make a lot of nice models under $40 that will last you a lifetime if you take care of them. 8Cr13v is bargain bin steel by modern standards but it has some nice qualities, easy to sharpen and mildly rust resistant, holds a much better edge than a 316 “surgical grade” stainless knife from the dollar store for sure. I have found countless uses for a pocketknife over the years and I’m sure you will too!