I’m going to warn you upfront: There are a lot of Chelsea-boots outfits in this story. I’m honestly surprised my chunky oxfords didn’t make more appearances because, between the two, I hardly wear any other shoe style outside of the summer months. There are many who will assert the false notion that California doesn’t have seasons, but I’m here to tell you that once October hits, there is a certain je ne sais quoi to California’s crisp air that you know if you’re from here. It’s unmistakable, and when it comes, so do my tried-and-true outfits. I love layering mock necks, turtlenecks, and sweaters, whether they have sleeves or not, and tucking them into high-waisted jeans and skirts of all lengths. Then I reach for my Chelseas or oxfords, and my outfit is set. I hardly need to accessorize, especially if I’m feeling lazy, and because I’m in L.A., the layers keep me cozy throughout the day. But I assure you, add an on-trend workwear jacket or leather trench to any of these outfits, and you’re set for all sorts of weather.