Knee-High Boots Are the Most Versatile Shoes I Own—8 Looks That Back Me Up

In a season where ankle boots reign supreme, a classic pair of knee-highs often gets overlooked. And while they seem less versatile in theory, my real-life rotation of outfits styled with them says otherwise. As my most-worn boots, I genuinely couldn’t get by without them—they’re the hero piece that instantly takes my fall essentials to new heights (literally). If you ask me, no fall wardrobe is complete without a great pair of knee-high boots.

That wasn’t always the case, though. When skinny jeans left the chat, my knee-high boots quietly exited with them. I couldn’t figure out how to style them in the era of baggy denim, so my once most-worn shoes ended up on the back burner. Then last year, my husband gifted me the highly coveted Staud Wally Boots, and everything changed. I was reminded just how adaptable knee-high boots really are. Contrary to popular belief, they work with just about any outfit—not just dresses and skirts—and these eight looks prove it.

How to Style Knee-High Boots

1. With wide-leg pants

Skinny jeans are back in rotation, but that doesn’t mean styling knee-high boots with other denim silhouettes is out of the question. The shift toward baggier styles once disrupted the tucked-in formula we relied on, but pairing knee-highs underneath relaxed denim is just as chic. Sure, you won’t see the full boot—but I take comfort in knowing I’m getting more mileage out of mine.

2. With mini skirts

The most tried-and-true way to style knee-high boots is, without question, with a skirt. When I reach for a mini, I like to balance the look with an oversized chunky sweater—and as temps drop, I’ll add a pair of tights for extra warmth. The next time you try the skirt-and-knee-high combo, play with the proportions of your top. My rule of thumb: choose a silhouette that contrasts your skirt. Think a long, chunky knit with a mini, or a fitted turtleneck with a midi.

3. With shorts

My most-complimented outfit combo as of late is a pair of suede shorts styled with knee-high boots. It’s an unexpected pairing that lets you stretch your warm-weather staples well into the cooler months, and it’s a seamless stand-in for a mini skirt when you want something that feels a bit more out of the box.

4. With leggings

Perhaps the most underrated cold-weather combo of all is leggings and knee-high boots. (Please don’t try this with booties—been there, done that, it was not good.) To balance out the slimmer profile of leggings, pair them with a top that brings some volume. A crisp button-down topped with a long wool coat or a heavy, oversized jacket creates the perfect proportion play.

5. With midi skirts

Styling a midi skirt with ankle boots is usually a no-go, as the gap between the hem and the boot shaft tends to break up the line of the leg. In this case, reach for knee-high boots instead. They eliminate that pesky gap and instantly help lengthen the legs. No matter the material or silhouette of the skirt—leather, cashmere, pleated, or ribbed—a knee-high boot is almost always the easier, more flattering option. I personally prefer a sleek, pointed-toe kitten heel over a chunky round toe. This will create a more streamlined shape.

6. With double denim

Without fail, double denim is my go-to outfit formula on the days I have no idea what to wear. What started as a no-brainer look has become one of my most–asked about outfits to date. I like to think it’s the juxtaposition of rugged, casual denim with the sleekness of a black leather knee-high boot. The coordinating black belt ties it all together and brings a bit of chicness to the all-denim moment up top. And of course, a fabulous statement coat never hurts either.

7. With straight-leg jeans

OK, so maybe all hope isn’t lost when it comes to tucking your denim into a pair of knee-high boots. When styled with a straight-leg jean that has a slimmer fit, the tuck actually works—bringing an effortless cool factor that’s hard to top. This look could’ve easily ended with the double-layered knits and wool coat, but finishing it with a baseball cap gives it that “I didn’t try too hard” vibe (even if, yes, I absolutely spent 10 minutes tucking these jeans into my boots).

8. With culottes

I bet you haven’t heard the word “culotte” in a while. But they’ve quickly become one of my favorite wardrobe pieces of the moment. Are they pants? Is it a skirt? Honestly, they’re the best of both worlds—and an unexpected surprise in the chicest way possible. I reach for them when I want to feel a little dressed up but still stay ultra functional and comfortable. And the best part? They’re the perfect width to slip a pair of knee-high boots underneath.

The Best Knee-High Boots to Shop Now

Sam Edelman

Sylvia Knee-High Boots

10+ colors available
also come in wide and extra wide calf

Shop now

Dolce Vita

Black Leather Gyra Boots

4 colors available
also come in wide and extra wide calf

Shop now

Sézane

Garrett Boots

2 colors available

Shop now

Steve Madden

Riggs Banana Leather Boots

7 styles available
also come in wide calf

Shop now

Vagabond

Blanca Tall Boots

2 colors available

Shop now

Madewell

Emilie Tall Boots

3 colors available

Shop now

Schutz

Raffaela Up Suede Boots

6 styles available

Shop now

Franco Sarto

Gisella Wide Calf Knee High Boot

2 colors available
also come in medium calf

Shop now

Lifestride

Brinley Wide Calf Tall Boot

4 colors available
also come in medium calf

Shop now

J.Crew

Stevie Leather Knee-High Boots

2 styles available
also come in wide calf

Shop now

Circus NY

Yulia Knee-High Boots

4 colors available

Shop now

Anthropologie

Cheetah Kitten-Heel Boots

2 colors available

Shop now

Jeffrey Campbell

Checkmate Boots

10 colors available

Shop now

Alohas

Nicky Leather Boots

Shop now

Madewell

Suede Lexie Tall Boots

Shop now

Sam Edelman

Wyatt Black Boots

3 colors available
also come in wide calf

Shop now

STAUD

Western Wally Boots

Shop now

Free People

Kiki Kitten-Heel Boots

Shop now

ABOUT THE AUTHOR

Tinsley Crisp, Fashion & Beauty Staff Writer

Tinsley Crisp is a Fashion & Beauty Staff Writer at The Everygirl and specializes in reporting on the season’s latest trends and hottest products. As a New York City-based stylist, she’s committed to injecting joy into the art of getting dressed and delivering attainable yet aspirational content to our readers.

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