Without a doubt, boots are my number-one fall and winter staple. My favorite style are riding boots; they’re a bit more classic and look great with dresses, skirts, and denim. I own two pairs, both in brown and black, and I wear them nonstop once the weather cools down. My big tip for buying riding boots? Be prepared to invest. Spending a bit more on a pair of leather (rather than manmade-material) riding boots will pay off in the long run. My first pair of leather riding boots lasted four years before the soles gave out, and the leather looked better and more supple with age. The boots you see in the above pictures are ones I bought as replacements last fall from Sole Society for less than $100, and you can find this year’s version here in black, brown and gray.