Ask Our Style Techs | Styling Over-the-Knee Boots

Q: Do you have ideas for how I can wear my over-the-knee flat boots? -Shelby B.

A: That’s a great question. Often times this style is negatively associated with being “too much” or “too young” which doesn’t have to be the case. At MSL, the over-the-knee (OTK) boot is one of our “go-to” styles during the fall/winter season. It truly is a classic look – one of our favorite OTK boots, the Stuart Weitzman 50/50, just celebrated its 20^th anniversary.

Here are a few great ways to wear this look that aren’t scary or too scandalous.

1. With a flowy dress that has a good amount of coverage. Perhaps something with a drop waist, long-sleeved, that comes to the knee or just above it. 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 under it or boyfriend cardigan over it for fall. If the dress is on the shorter side, add opaque tights.

2. Over skinny jeans. If your jeans are fitted enough to fit into the shaft of the boot, that’s a great way to wear this look. Make sure your top isn’t fitted and on the longer side. Balance is key.

3. Over leggings. A great trend this season is the mixed media leather/cotton legging. It will make your look appear more expensive and goes well with all types of shoes. An OTK boot is a good compliment to leggings and generally very flattering.

Keep in mind that this look isn’t for everyone. If you don’t have the pieces to go with the boots, it can often look like you’re trying to rock something that really isn’t your style. It’s all about feeling comfortable and wearing what you feel most confident in!