I have to wear so many clothes, just so many clothes. I wear as little as possible in the summer. That's such a hassle in the winter. And real, closed shoes all the time. Hopefully my wool wildlings will be warm and I can have barefoot winter shoes.
I love getting up in the summer and just throwing on shorts and a t shirt and being ready as opposed to underwear, sox, t shirt, sweatshirt, sweatpants, slippers. I’m a crabby motherfucker all winter long
Pro tip: study how people of the past dressed. I've settled on tight-fitting wool underclothes, a fluffy mid-layer, and a simple ruana cloak ontop. This seems to keep me comfortable at least between 0°C and like -7°C
I'm not as bad about shopping for winter clothes as I used to be. I mostly wear thrift store clothes, but I do have an Aran Crafts knit wool coat that is fairly old fashioned. I got it used on Ebay, but it's still pretty magical. I need more long, warm skirts, but they can be hard to find in cute colors or designs.