Over-the-Knee Boots: How to Wear Them Now, and How to Find a Pair That Stays Up

The short answer: wear over-the-knee boots with a hem that meets them, a midi skirt, a knee-length coat, a dress with a slit, so only a little leg shows, and pick stretch leather if you want them to stay up without a tie. Keep the toe pointed and the heel slim for evening, and the rest of the outfit simple. The pair we recommend is the Khaite Valerie Over-the-Knee Boot in Black, cut in Italy from stretch-infused lambskin. Shop all designer boots, the full shoes edit and every Khaite piece at Coveti.

Over-the-knee boots carry more baggage than any other shoe, from Pretty Woman to the 2010s street style shot. The modern version is quieter. Leather that fits like a second skin, a pointed toe, a curved heel, and an outfit that treats the boot as a long, dark line rather than a statement. Khaite is the New York label Catherine Holstein founded in 2016. It won the CFDA American Womenswear Designer of the Year award in 2022 and again in 2023, and it is known for reworked wardrobe essentials: cashmere knitwear, denim, leather and a very particular kind of evening dress.

Stretch vs structured: which over-the-knee boot?

How to wear over-the-knee boots

• With a midi skirt: the hem should cover the top of the boot, so the leg reads as one line.
• With a slip dress: the slit reveals the boot as you walk. Add a long coat.
• With a long coat and a short dress: the classic evening proportion, almost no skin showing.
• With jeans: only with a slim jean tucked in, and with a longer sweater over the top.

Our picks

1. Valerie Over-the-Knee Boot in Black

Stretch-infused lambskin, an elongated pointed toe etched with fine lines, and a curved heel integrated into the leather sole. The side zip reaches to mid calf, so it pulls on smoothly and sits close without slipping.

2. Petra Knee-High Boot in Ebano Suede

If over-the-knee is a step too far, the knee-high Petra has a tubular suede shaft, a square toe and a stacked block heel. Made for the working week.

What to wear with the Valerie

Try the silk Ophelia Skirt in Black and the Juniper Sweater in Charcoal for a long dark line by day, then the Scarla Dress in Black Velvet and the Sonti Coat in Charcoal at night. For more boot styles see our Khaite boots guide.

Frequently asked questions

How do I keep over-the-knee boots from falling down?

Buy stretch leather that fits close at the thigh, and make sure the calf fits too. A boot that is loose at the calf will slide whatever the shaft is made of.

Are over-the-knee boots in style in 2026?

Yes, in a sleeker form: stretch leather, pointed toes and slim heels, worn under midi hems rather than with mini skirts.

Can you wear over-the-knee boots with a dress?

Yes. A knee-length dress with a slit, a slip dress and a velvet mini all work. Keep the top half covered and simple.

Do Khaite boots run true to size?

Khaite sizes its boots in Italian (EU) sizes. Check the fit note on each product page, where Coveti repeats any guidance the brand gives.