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$20 Cabelas fleece. I bought one in late 2014 and wore it everyday for half the days out of the year ever since. It's overdue for a good replacement, though.
I also have two DE razors and for a while was intrigued by the idea of the cheapest shave. -Pennies per shave
Two pairs of black Carhartt cotton duck overalls I bought in 2010 and 2011. One knee is blown out but they are the softest most comfortable clothes I own. I still wear them once or twice a week, wash on hot, dry on hot. These, a Dickies pocket T shirt, and 15 year old 14 eye steel toe Docs are the 'uniform of the day'. Other than a few nice suits and some shorts, I'm pretty much not interested in clothing. The suits were bought for corporate recognition and I work from home otherwise.
I've got another one:
Long before COVID, I would go to a barber shop for haircuts.
The place I went to had one short, old guy who had arthritis. I'm tall, and long in the torso. When he was cutting my hair, he couldn't lower the chair enough to be able to cut my hair, so I'd have to scoot down in the chair so that I was sitting with my ass at the edge of the seat and my spine bent so my head was low enough.
When you entered the shop, you'd write your name on the board, and if you wanted someone specific to cut your hair, you'd put the barber's name next to yours. So, I started picking one of the taller, younger guys to cut my hair.
One day I was in a rush, and there was a line, so I figured I'd just take whoever was available and scoot down if I had to. The old guy skipped over me two times. When someone pointed out that I was there before him, the barber got pissy and said, "he doesn't want me cutting his hair"
One of the other barbers apologized and took me next. I gave that guy a $20 tip.
When I got home I went online and bought a Flowbee. I haven't been to a barber shop since. It does a great job, there's no line to wait in, it takes me about 10 minutes, leaves no mess behind, and I haven't paid for anything but electricity and shop vac bags ever since.
No barber visit for 7 years now. been clipping myself ever since.