How to Wear It: Over-the-Knee Boots

Over-the-knee boots

Let me start out by saying that I’ve had these boots for ages. But you wouldn’t know it, because they hide out at the back of my closet, neglected, whispering ‘pick us! pick us!’ every time I reach for a pair of shoes. For all their beauty, all their sumptuous, buttery soft goatskin goodness, they’ve always remained something of a mystery for me in terms of how to actually wear them. Short ankle booties seem effortlessly to complement every outfit, while over-the-knees can feel either pretentiously high fashion or suspiciously lady-of-the-night-ish. So in the interest of avoiding weird looks or wolf whistles, I go for the ankle booties every time.

Sweater and boots for fall

However, it’s absurd to have an item this lovely in your wardrobe and let it go to waste, and these boots were long past due for some attention. I told myself I’d either find a few great outfits to wear with these babies, or I’d sell them at consignment—and there was NO way I wanted to part with them. So I dragged all my clothes from the closet, sampled myriad combinations in front of my full-length mirror, and I’m happy to report that I’ve found a way to sport over-the-knee boots that feels stylish yet comfortable at the same time.

Chunky knit + skirt

As it turns out, the lynchpin for making these boots work is the frowsy mom sweater. This season’s wave of oversized, shapeless knits are the perfect foil to the boots’ provacative silhouette. Once I realized I could balance out the powerful presence of the boots with a boxy, chunky sweater, it was like the fashion clouds parted and a bright ray of extremely chic light cast its warm glow upon me. From the short A-line skirt here to the cardigan/shirt dress pairing I’m also loving, it is possible to wear a thigh high boot without feeling like your goods are on full display!

P.S. Funny story: I shot these photos in 105 degree heat and my legs swelled up so much that I could barely get the boots on, and then REALLY couldn’t get them off. I have a whole new appreciation for the episode of ‘Friends’ with Ross and the leather pants! Outfit details: Boots, Chloe (similar over-the-knee boots). Oversized Sweater, Vince. Skirt, Etoile by Isabelle Marant (similar full mini skirt). Bag, 3.1 Phillip Lim (similar black mini bag). Necklace, Alexis Russell. Glasses, Rowley Eyewear