27+ Outfits to Wear With Over The Knee Boots

Over-the-knee boots is a trend that’s not just surviving, but thriving. These bold beauties are the perfect way to elevate your look from ordinary to extraordinary.

They elongate your legs, add a touch of drama to any outfit, and let’s be honest – they make you feel like a total boss.

Whether you’re heading to the office, meeting friends for brunch, or painting the town red, there’s an over-the-knee boot outfit waiting to become your new signature look.

Let’s break down some seriously chic outfits that will have you falling head over heels (pun intended) for these versatile boots. So, buckle up, buttercup – it’s time to boot-ify your wardrobe!

Cozy Autumn Vibes: Oversized Sweater + Pleated Skirt

@vivaia_official

An oversized brown sweater paired with a soft pleated skirt creates a cozy autumn look. The knee-high brown boots not only keep you warm but also add a stylish touch. This outfit is perfect for a day out in the crisp fall air, effortlessly combining comfort and fashion for a chic appearance.

Sleek Sophistication: Blazer + Dress + Boots

Instagram: @imnotsorrydarling

There’s something undeniably elegant about pairing a tailored blazer with a dress and over-the-knee boots. This combination exudes sophistication and is perfect for those days when you want to look polished and put-together.

The contrast between the structured blazer and the sleek boots creates a visually appealing silhouette. It’s an outfit that transitions seamlessly from day to night, making it ideal for those busy days that turn into evenings out.

Layered Luxe: Jacket + Skirt + Boots

Instagram: @stephanieleighnyc

Embrace the art of layering with this chic combination. A leather jacket paired with a mini skirt and over-the-knee boots creates a look that’s both edgy and sophisticated.

The key is to play with proportions – a fitted jacket with a flared skirt, or vice versa. This outfit is perfect for transitional weather and can be easily adjusted by adding or removing layers. It’s comfortable, stylish, and oh-so-versatile.

Chic Layering: Cardigan + Leather Mini Skirt

@iolite.lb

This outfit features a burgundy cardigan layered over a sleek leather mini skirt, complemented by knee-high black boots. The combination of textures adds depth to the look, making it suitable for both casual and semi-formal occasions. It’s a perfect example of how knee-high boots can enhance a stylish, layered outfit.

Bold Statement: Blazer + Mini Dress

@allisonbornstein6

A classic black blazer over a white mini dress creates a bold statement look. The knee-high black boots add an edgy flair, making this outfit perfect for a night out or a stylish event. This ensemble showcases the versatility of knee-high boots, proving they can be both chic and sophisticated.

Modern Classic: Brown Coat + Mini Skirt

@indianbootslover

This outfit features a tailored brown coat over a matching mini skirt, paired with knee-high boots for a modern twist. The combination is both stylish and practical, making it ideal for a day out. This look highlights how knee-high boots can seamlessly integrate into a classic wardrobe, adding a contemporary edge.

Cozy Chic: Coat + Leggings + Boots

Instagram: @aurelafashionista

A gorgeous faux fur coat paired with sleek leather leggings and those show-stopping over-the-knee boots creates the perfect blend of cozy and chic.

It’s ideal for those crisp autumn days when you want to look put-together without sacrificing comfort.

The contrast between the plush coat and the sleek boots adds visual interest and keeps you warm in style.

Trendy Textures: Leopard Print Cape + Leather Shorts

@bethgoldfarb

This outfit features a stylish leopard print cape paired with sleek leather shorts, creating a bold and trendy look. The knee-high brown boots add warmth and sophistication, making it perfect for a chic day out. This ensemble showcases how knee-high boots can enhance a fashionable outfit while providing comfort and style.

Classic Contrast: Turtleneck + Mini Skirt

@thekelsg

A cozy white turtleneck is beautifully paired with a black mini skirt, creating a classic yet modern look. The knee-high black boots elevate the outfit, adding a touch of elegance. This combination is ideal for transitional weather, demonstrating how knee-high boots can seamlessly blend with various styles for a polished appearance.

Minimalist Chic: Cropped Jacket + White Shorts

@wara_official

This outfit features a cropped cream jacket over white shorts, exuding a minimalist vibe. The knee-high beige boots add a stylish flair, making it perfect for a casual outing. This look highlights the versatility of knee-high boots, proving they can complement a range of outfits while maintaining a chic aesthetic.

Cozy Layers: Oversized Sweater + Maxi Skirt

@savers_thrift

This outfit combines a cozy burgundy sweater with a flowing white maxi skirt, creating a comfortable yet stylish look. The knee-high brown boots add a touch of sophistication, making it ideal for a casual day out. This ensemble demonstrates how knee-high boots can enhance layered outfits, providing both warmth and style.

Boss Babe: Blazer + Turtleneck + Jeans + Boots

Instagram: @felicitymbird

Channel your inner girl boss with this power combo. A sharp blazer over a turtleneck and jeans, complemented by those killer over-the-knee boots? It’s a look that screams confidence and sophistication.

Perfect for important meetings or when you need to make a lasting impression. The boots add just the right amount of edge to balance the polished blazer, creating a perfect blend of professional and trendy.

Street Style Queen: Dress + Boots

Instagram: @gabrielegz

Pair over-the-knee boots with a chic mini dress for a look that’s straight off the streets of fashion week. It’s unexpected, it’s bold, and it’s absolutely fabulous. I love how the contrast between the short dress and tall boots creates a visually striking silhouette. Add a statement bag, and you’re ready to turn the sidewalk into your personal runway.

Romantic Rebel: Coat + Dress + Boots

Instagram: @newyorkersinthecity

Soft meets edgy in this irresistible combination. A flowing mini dress gets a cold-weather makeover when paired with a long coat and over-the-knee boots. It’s the perfect outfit for a date night or a day out in the city, striking that delicate balance between feminine and fierce. The contrast in lengths between the dress and coat creates visual interest, while the boots tie the whole look together.

Sophisticated Layers: Knitted Top + Suede Skirt

@stuartweitzman

This outfit features a fitted knitted top paired with a chic suede skirt, creating a sophisticated look. The knee-high black boots add a stylish edge, making it perfect for a day out in the city. This ensemble highlights how knee-high boots can elevate a simple outfit, blending comfort with elegance.

Fashion-Forward: Cropped Sweater + High-Slit Denim Skirt

@stylewithgen

A cropped ribbed sweater is paired with a high-slit denim skirt, creating a bold and fashion-forward look. The knee-high brown boots enhance the outfit, adding a touch of sophistication. This combination is perfect for those who want to make a statement while showcasing the versatility of knee-high boots in modern fashion.

Elegant Night Out: Off-Shoulder Dress + Statement Boots

@chlobellexx

This outfit features a sleek off-shoulder black dress, complemented by knee-high black boots for a chic night out. The combination creates a striking silhouette, perfect for evening events. This look demonstrates how knee-high boots can add a touch of glamour to any outfit, making it a go-to choice for stylish occasions.

Casual Chic: Oversized Sweater + Mini Skirt

@heycarmen

An oversized cream sweater paired with a black mini skirt creates a cozy yet chic look. The knee-high black boots add a stylish flair, making it ideal for a casual day out. This ensemble showcases how knee-high boots can enhance a relaxed outfit while maintaining a fashionable edge.

Trendy Contrast: Denim Shirt + Leather Mini Skirt

@lifewithmegz

This outfit combines a classic denim shirt with a sleek leather mini skirt, creating a trendy contrast. The knee-high brown boots complete the look, adding sophistication and style. This ensemble highlights the versatility of knee-high boots, proving they can seamlessly integrate into various outfits for a polished appearance.

Monochrome Magic: Blazer + Mini Skirt + Boots

Instagram: @_fashionessa

When in doubt, go monochrome. A black blazer, paired with matching shorts and over-the-knee boots create a sleek, elongating silhouette that’s both timeless and modern.

It’s a look that works for any occasion, from gallery openings to dinner with friends. The key is to play with textures – think a smooth blazer with pleated skirt and suede boots. It’s simple, yet so impactful.

Casual Cool: Sweater + Boots

Instagram: @lojsanwallin

Pair an oversized sweater with your over-the-knee boots for a look that’s both comfortable and stylish.

This outfit is perfect for those lazy weekends or casual outings. The boots elevate the simple sweater, adding a touch of glamour to an otherwise relaxed look. It’s a playful yet polished ensemble that works for brunch, shopping, or even a casual Friday at the office.

Edgy Elegance: Oversized Shirt + Denim Shorts

@karicassandra

An oversized white shirt paired with distressed denim shorts creates a relaxed yet edgy look. The knee-high black boots add a bold statement, making this outfit perfect for a night out. This ensemble showcases how knee-high boots can transform a simple outfit into a fashion-forward statement.

Cozy Glamour: Cardigan + Dress + Boots

Instagram: @lisadnyc

When comfort meets style, magic happens. A soft, figure-hugging dress paired with a cozy cardigan and over-the-knee boots is the epitome of effortless glamour.

I absolutely love how the layering adds depth to the outfit, while the boots provide a sleek finish. It’s an outfit that feels like you’re wrapped in a warm hug but looks like you’ve stepped off a fashion magazine cover.

Denim Darling: Coat + Jeans + Boots

Instagram: @brooklynblonde1

Never underestimate the power of a great pair of jeans. Combine your favorite denim with a statement coat and over-the-knee boots for a look that’s both classic and contemporary.

This outfit works wonders for casual outings, weekend errands, or even a relaxed date night. The boots add an element of surprise to an otherwise casual ensemble, elevating it to street-style worthy status. It’s proof that sometimes, the simplest combinations can be the most impactful.

Effortless Elegance: Light Blue Shirt + Embellished Shorts

@ilasalsabilla

This outfit combines a light blue oversized shirt with embellished shorts, creating a chic yet relaxed vibe. The knee-high white boots add a striking contrast, making it perfect for a casual outing. This look is ideal for those who want to blend comfort with style, showcasing how knee-high boots can elevate any ensemble.

Edgy Elegance: Jacket + Skirt + Boots

Instagram: @lolariostyle

For those who like to walk on the wild side, try pairing a leather bomber jacket with a sleek skirt and over-the-knee boots.

This combination is the perfect blend of edgy and elegant. The contrast between the tough leather and the feminine skirt creates a dynamic look that’s sure to turn heads. It’s ideal for a night out, a rock concert, or anytime you want to channel your inner rebel while maintaining a touch of sophistication.

Office Chic: Button Down + Leggings + Boots

Instagram: @lovisabarkman

Take your work wardrobe up a notch by pairing a crisp button-down shirt with leather leggings and over-the-knee boots. This look is professional enough for the office but stylish enough for after-work drinks. The boots add a touch of drama to an otherwise classic outfit, while the leggings keep things comfortable.

It’s a perfect balance of business and pleasure that will have you feeling confident from 9 to 5 and beyond.

In short, over-the-knee boots are truly a wardrobe powerhouse.

They are more than just a trend; they’re a statement of confidence and style. They elongate your legs, add drama to simple outfits, and have the power to make you feel like the best version of yourself. So go ahead, step into those boots and step up your style game. After all, life’s too short for boring shoes!