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
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.
