Everyone’s needs are different. Use what you have instead of purchasing a new wardrobe. Many women recommend athletic wear, specific brands of shoes, jackets, and sleeping bags.
My body core is rather hot and I wear tanks all year. As well as a new brand to me, Lularoe. I wash this and hang it to dry, by the next morning it is dry. I was jeans and tank girl before, now I am tanks and leggings or maxis. An upside, if you gain/lose weight they still fit unlike a pair of jeans. The clothes are a bit pricey but this gal gives excellent service and your 11th pair is free. https://www.facebook.com/LuLaRoeAmberCorkhill
As for shoes, I do the dreaded flip flops, along with Mukluks and boots. Keens are generally my shoe-choice. I require a wide toe box. Camp shoes are a must. I prefer Uggs (or similar) and Crocs.
Winterwear I have two beautiful long, sweater coats to use on the east coast and my winter coat is a Columbia. My winter coat I have not worn yet. Three hats, a felt and a straw along with a toboggan that matches my one long scarf. I know many also add vests to their wardrobe, I haven’t at this time.
PJ’s include fleece capri and a tank in case of the dreaded knock and for areas where I’m sure the knock won’t come I have cotton jammies. Many opt for merino wool for winter.
Daily makeup includes a tinted sunscreen moisturizer and Vaseline lip balm. I don’t color my hair. It is mid-back in length. Favorite styles include a bun, braid, ponytail or wind-blown free. As a nomad, my clothes are about function and easy care. Life on the road is so much easier when you weren’t on a perpetual vacation of sorts <wink>
My suggestion is to pack for two weeks if you are in a van, then one set of winter wear/summer wear. Thrift stores are open all year so you could purchase seasonally and give back when you need a new season. For me that doesn’t work, when I find something that works for me I want to keep it until it is worn out. Your first year will show you what you need, want, and can release.