There are shoes, and then there are shoes. Rachel Comey footwear falls into the second category. Yes, they have a $300+ price tag, but that’s because they’re high-quality in terms of materials, construction, and even aesthetic. At Penelope’s, we’re all about her boots for fall. The cult Mars ankle boot, which she’s made for years and which almost all our employees own; the newer, shorter, low-heeled Dorsey ankle boot; and a classic knee-high version called the Rubie boot. Constructed from thick, supple leathers in deep browns and blacks, these boots elevate every outfit. Suddenly, jeans and a tee or a simple dress look cool, smart, and sophisticated. The bottom line? Rachel Comey’s fall collection is most definitely worth an investment. Grab a pair in store or online!

And a little advice: her style’s run narrow, so be prepared to size up. Also, the leather stretches, so that painfully tight fit will expand with just a week of wear. You do want them to be a little snug, initially.