Ask MSL | 3 Ways to Wear Over-the-Knee Boots

Q: I’m 45 and want your take on the best way to wear my over-the-knee boots? — Ellen P.

A: This is one of the most popular questions we get at MSL — from how to wear over-the-knee (OTK) boots to am I too old to wear them? OTK boots that hit just over the knee have become a classic look as they continue to only grow in popularity. In the past, this style has been associated with being “too much” or “too young” but we say, no way! If OTK boots fit with your style and personality, you can wear them at any age. Our tried-and-true favorite continues to be the Stuart Weitzman 50/50 boot pictured above. You simply can’t go wrong.

Now, the halfway-up-the-thigh, over-the-knee boots should be styled more carefully. This is definitely a more trendy, sexy look, especially if the heel is high. A flat or low, block heel is easier to wear. If you love the thigh-high style, we recommend a more classic skirt or dress that covers the top of the boot. No plunging necklines and cutouts or you run the risk of channeling Julia Roberts in “Pretty Woman.” Ugh.

Here are a few great ways to wear your OTK boots.

1. With a dress that has coverage. A tailored or flowy, long-sleeved style that comes to at least the knee would be a good choice. If you’re wearing a very fitted OTK boot, it’s good to balance it with some volume on top. If the dress is sleeveless, add a chambray shirt underneath or jacket over it for fall. If the dress is on the shorter side, add opaque tights — the tights will give you a longer, leaner line.

Dress, Isabel Marant // Boots, Gianvito Rossi // Handbag, See by Chloe

2. Over skinny jeans. Be sure your jeans fit into the shaft of the boot. Make sure to wear a more voluminous top (not fitted) that hangs at least to your hip. Or you might opt to tuck your shirt into your jeans on one side (aka the varsity tuck) or in the middle (aka the half tuck). Remember with this look, balance is key.

Sweater, Michael Kors // Jeans, Frame // Boots, Mia // Earrings

3. Over leggings. OTK boots are the perfect compliment to leggings and generally very flattering, especially if the leggings are the same color as the boots, such as black on black. Be sure to pair with a longer tunic sweater, blazer or jacket to cover your backside, thus you avoid having your leggings look like yoga pants.

Blazer, Simon Miller // Tee, Bella Freud // Leggings, Vince (these fit SO good!) // Boots, Stuart Weitzman // Handbag, Christian Louboutin // Earrings, Baublebar

Remember, as we always say here at MSL — Wear only what makes you feel comfortable and confident!