10 New Ways to Style Your Over-the-Knee Boots

Fall is officially here, which means it’s time to dust off your favorite boots and bring them back into your wardrobe (or, if you’re like me, wear them every single day). But the tried and true staple is so tried and true that a little updating wouldn’t hurt. Here are some tips to help update your over-the-knee boot looks into this season. They may be a classic staple, but they’re anything but basic!


1. With a Sweater Dress in the Same Color

Source: Missguided UK


The look is instantly cooler in monochrome colors that aren’t your basic black. Not to mention the head to toe color is lengthening and insanely flattering!



2. …Or a Belted Sweater Dress

Source: Society 19


Another way to update the classic sweater dress + boots outfit is by belting the dress at the waist. Opt for a belt with cool details like western accents, add a chic crossbody bag, and you’ll look anything but basic.



3. With a Romper

Source: Who What Wear


Thanks to over-the-knee boots, you really can bring your favorite summer staple into fall! This outfit may sound tricky but it’s actually fairly foolproof — just make sure the romper is somewhat shaped (meaning a cinched waist on a baggier silhouette like on Kate Bosworth), is in colors appropriate for fall (preferably black to match the boot color), and is loose enough to look like a miniskirt or dress. Add a jacket or long cardigan for colder weather.



3. With a Midi Skirt

Source: Extra Petite


Two fall staples coming together — a midi skirt shows off the boots only at the right angle, giving the outfit a trendy and unique feel. Pair with a classic sweater and coat for the perfect and polished fall ensemble.



4. With Baggy Layers

Source: Missguided UK


A fitted high heel boot goes flawlessly with a loose silhouette like a minidress and oversized sweater. Bonus cold-weather points for furry accessories!



5. With a Cream Colored Top and Jeans

Source: Annette Haga


The most common way to wear your over-the-knees is with a good pair of skinny jeans. Update the look with a cream-colored sweater or top and contrasting black boots on bottom. If you’re really feeling bold, pair your sweater with boots in a similar color for a cohesive feel.



6. With All-Black

Source: Have a Fashion Break


All-black is nothing new, but if you couldn’t already tell, monochrome always looks trendy. Get extra style points for pairing with romantic shapes and ruffles and an on-trend fedora (all in black, of course!).



7. With Multiple Patterns

Source: Margo and Me


One of our favorite trends can be worked into fall with black over-the-knee boots, in two patterns with similar coloring, and a jacket in a solid color. Make sure both of the patterns have black in them (to match the boots), and similar colors to the jacket (like the red on Margo & Me) to ensure the look is more put-together and trendy than disorganized.



8. With a Maxi Skirt

Source: Sandra Semburg


Don’t store your summer maxi yet. Select one in a darker print or moody color and then pair it with a cropped moto for a bohemian look.



9. With a Mini Skirt

Source: @marianna_hewitt


For a cool take on a daytime look, pair your OTK boots with a leather mini skirt and ultra feminine sweater. The bottom half says party while the top half says business, ensuring your look can transition from day to night.



10. With Your Party Dress

Source: Extra Petite


We all have our favorite dresses, but when the temperature starts to drop it’s hard to feel festive with that much leg showing. Thigh high boots are the best way to keep your look chic and weather appropriate. Plus, it keeps you from having the debate about if tights really go with your look.



What’s your favorite way to wear over-the-knee boots? Which of these looks would you try?