Last year was my first year at doing a capsule wardrobe. I absolutely loved it but I learned a couple of things. 1) It's hard to know what are "classic" items that won't go out of style over the years (still learning). 2) Yes, I need to pick out clothing that feels like me BUT it also needs to fit into my lifestyle and the CLIMATE I live in. I loved my wardrobe last year but I didn't include enough layering products to "look good, feel good" in the outdoors. And let's be honest, I need to be ready for the outdoors in Colorado!
This year I created a style board for looks that felt like me but that included those essential looks for my lifestyle in Colorado. It started on Pinterest and Instagram (surprise!) but then got laid out into a printable sheet in photoshop. If you don't have photoshop, no worries. Use any kind of copy/paste format or be really old school and create an inspo board with magazine cutouts. Whatever it takes to have a plan so you don't just buy random, cute things when you go shopping!
Then, I go through what I currently have. I keep one storage bin under my bed with fall/winter things. The idea is to use a lot of what you currently have and supplement with a few new things.