How to Update Over The Knee Boot Outfits for 2025

Keeping Your Over the Knee Boot Outfits On Trend!

I think we all are familiar with the absolute CHOKEHOLD that over-the-knee (OTK) boots had on us about 10 years ago. The question is, are these thigh-high boots a forever closet staple or just an old "cheugy" millennial trend of the past? In my opinion, fashion trends have been moving so quickly, that anything goes these days. Plus, over the knee boots are a great solution for winter outfit ideas when you want to rock a shorter skirt or sweater dress and still stay warm.

So I say, don't throw your thigh high boots out just yet! However, I totally get not wanting to look outdated! So below I am sharing some great thigh-high boot outfits that look modernized and up to date with the 2025 boots trends.  

1. Over the Knee Cowboy Boots Outfit Idea

over the knee boot outfit idea with sweater dress and winter coat

One way to update this boot style: Over-the-knee cowboy boots! Adding a western and edgy flair is incredibly on trend right now, so finding a good pair of western boots that hit at or above the knee is a great way to feel on trend and still rock an OTK boot. 

KEY STYLING TIPS:

  • Pair with a graphic tee and denim midi skirt for a preppy look with a twist.

  • Add a statement coat or long coat for colder months, especially in fashion-forward cities like New York.

  • Styling tips: Go for brown leather cowboy boots to stand out in different ways.


2. Mini Sweater Dress and OTK Boots Outfit Idea

over the knee boot outfit idea with sweater dress and leather jacket

In my opinion, this look is never going to go out of style! Sweater dresses are a winter staple, and pairing them with thigh-high or over-the-knee boots creates a chic combo.

KEY STYLING TIPS:

  • Consider block heels or a slouchy sweater for a more casual look.

  • Layer with a leather jacket or a turtleneck top for an edgier vibe.

  • This look is actually perfect for date night or a night out with friends.


3. Lug Sole Over the Knee Boots Outfit Idea

The Lug sole boot trend can absolutely carry over to your OTK boots! This brings an edge to knee-high boots for a utilitarian look.

KEY STYLING TIPS:

  • Pair with leather leggings or a slouchy sweater for easy ways to look put together.

  • Finish the look with a wool coat for colder winter months.

  • Boot trends: These are a good option for those who love a mix of comfort and style.


4. Sweater, Mini Skirt, and Over the Knee Boots Outfit

I think leather skirt or really any cold weather friendly mini skirt outfits are perfect with OTK boots!

KEY STYLING TIPS:

  • Style with a looser fit sweater for a balanced, trendy outfit.

  • Add a bold look by choosing statement boots like the lug sole, block heel or western style like mentioned above.

  • Finish the look with trending elements like old money style earrings or a banana clip in your hair for a chic combo.

Your Fresh Take On OTK Boots

In 2025, over-the-knee boots are going to remain one of my favorite ways to elevate any outfit. Whether you're going for a bold, statement look with cowboy boots or keeping it casual with a cozy oversized sweater and suede boots, there are so many ways to style them for the winter months. I love how versatile OTK boots are—they can take you from a casual day out to a chic night on the town. By playing around with textures like leather, suede, and soft knits, you can easily create trendy outfits that feel fresh and modern. So don’t be afraid to try out different styles and colors this year—I promise, OTK boots will keep you looking stylish no matter the occasion!

outfit ideasKatie HennesseyComment