My freshman year of college I bought a pair of tall Frye riding boots that quickly became the star of my fall and winter wardrobe for the next six years. I wore them so often that I had to have them resoled twice. But when I pulled them out of the back of my closet recently during a major wardrobe overhaul, I found myself wondering if I could still pull off my once beloved knee-high boots without looking dated. So, to Pinterest I headed to find all the knee-high boot outfits a gal could dream of that are also fresh, modern and 2023-level chic. Below, ten gorgeous ensembles that are easy and fashion forward, all featuring our favorite knee-high style—plus two combos that are, unfortunately, too dated to be cool in 2023.
10 Knee-High Boot Outfits That Are Supremely Chic for 2023 (Plus 2 That Are, Sadly, Outdated)
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1. Wear Sock-Fit Boots with Cozy Sweater Dresses
Amplify the comfy vibes of a sock-like boot by wearing it with an equally comfy knit dress. You can sport just about any length you like, but we’re partial to styles that hit somewhere between mid-shin and just under the knee for maximum coziness.
Shop similar styles: ASOS Knit Midi Dress ($50); Staud Bean Bag ($195); Vince Camuto Arendie Boots (
2. Wear Riding Boots with Jeans and an Oversize Blazer
Lean into the preppy nature of this equestrian style by tucking in some high-waist skinny jeans and layering a structured blazer on top. Be sure to choose a jacket that hits at or below your hips, not above; a cropped cut will throw off your proportions in an unflattering way.
Shop similar styles: Everlane Oversize Blazer ($228); J.Crew Scalloped Hem Blouse (
$118; $90); AG Farrah Skinny Jeans ($198); Sam Edelman Drina Boots ( $250; $113)
3. Wear Snakeskin Boots with Denim on Denim
There are certainly ways to make this exotic print work with other printed pieces, but we prefer letting it stand out against a backdrop of dark-wash denim. Pro tip: Try buttoning up a denim jacket to wear as a top in place of a chambray shirt, like Coterie member Babba Canales.
Shop similar styles: Boden Double-Breasted Coat (
$370; $259); Levi’s Original Trucker Jacket ( $98; $59) and 311 Skinny Jeans ($70); Schutz Analeah Boots ($258)
4. Wear Black Boots with Matching Leggings
Create the illusion of miles-long legs by slipping black leggings into a pair of tall black boots. As for your top, feel free to play around with brightly-hued sweatshirts, puff-sleeve blouses, longline blazers or whatever current trend your heart desires. (Although, similar to the note above, try to avoid cropped styles as they’ll end up making your torso looking weirdly short.)
Shop similar styles: Nike Oversize Sweatshirt (
$60; $42); lululemon Everywhere Belt Bag ($38); Aerie Crossover-Waist Leggings ( $45; $32); Aerosoles Micah Boots ($140)
5. Wear Slouchy Boots with a Posh Midi Skirt
Contrast the boho feel of slouchy suede boots with a pleated midi skirt or tailored pencil skirt. So long as they have some colors in common—in this case, a rich caramel brown—they’ll look like they were meant to be, and not a random pairing. Finish the look with a ladylike bag and sleek turtleneck.
Shop similar styles: Nuuds Crewneck Sweatshirt ($98); Everlane Pima Micro-Rib Turtleneck ($50); Proenza Schouler Plaid Skirt ($395); Hereu Bauza Woven Shoulder Bag ($575); Michael Kors Leigh Suede Boots ($275)
6. Wear Roomy Styles with a Fitted Sweater Dress
We’re not talking about slouchy boots, but the ones that fit slightly wider than your calf and are stiff enough to hold their own shape rather than conform to your leg. Pair these with a cozy knit dress that ends at the top of your boots, but not above.
Shop similar styles: Eleven Six Caroline Stripe Dress (
$498; $249); ALDO Celestica Bag ( $65; $50); Steve Madden Kathleen Boots ($200)
7. Wear Croc-Embossed Boots with Posh Staples
The theme of the hour is opposites attract, and that’s exactly what’s happening in this chic mix. Black croc can feel super edgy, especially when paired with something like faux-leather leggings. But for an easier, everyday look, try wearing them with more classic pieces instead. For example, a gingham overcoat or wool mini skirt and tights.
Shop similar styles: River Island Houndstooth Coat (
$204; $133); Boden Button Mini Dress ($180); Swedish Stockings Premium Tights ($50); Chinese Laundry Krafty Boots ($160)
8. Wear Flat Boots with a Mini Skirt
One of the best fashion tips we’ve learned over the years is: The shorter your hemline, the lower your heel. So, as you might expect, the shortest hem of all warrants no heel at all, no matter what style of shoes you prefer. As for tall boots, we love combining a preppier mini with some tougher black Wellies.
Shop similar styles: ALO Heavyweight Sweatshirt ($128); Lulus Mireya Faux-Leather Skirt (
$66; $49); JW Pei Carly Saddle Bag ($109); Schutz Maryana Boots ($258)
9. Wear Any Style with Pencil Skirts
Knee-high boots and pencil skirts are a classic duo we just can’t get enough of. And while we like this combo best with heeled boots and a straight-fitting or A-line skirt (as opposed to one that clings to every curve), you can make it work for just about any style boot from equestrian to snakeskin to clingy suede.
Shop similar styles: ASOS boots ($64); Schutz boots ($238); Mango skirt ($60; $40); Blank NYC skirt ($98)
10. Wear Any Style with Monochrome Separates
When in doubt, pick one color or color family and stick to it. Any of the above outfits will look brilliantly chic done up in shades of a single hue. Feel free to play with textures and fabrics too, to add extra depth to your look.
Shop similar styles: J.Crew Rollneck Sweater (
$98; $60); Mare Mare x Anthropologie Faux-Leather Skirt ($148); Journee Collection Therese Boots ( $110; $80)
11. Don’t Wear Them with Baggy or Loose Pants
No matter what style tall boots you own, never wear them with trousers that don’t tuck neatly or create puckering or billowing at your thighs. You’ll end up looking like a 15th century swashbuckling pirate. Opt for slim-fit bottoms, like skinny jeans or leggings, to create a more streamlined silhouette.
12. Don’t Wear Them with Shorts and Tights
It may have worked for the cast of Gossip Girl back in 2010, but at this point the combination looks dated and juvenile—two things we try to avoid outside of Halloween dressing. If you really love the look, try a minidress instead to bring things back to present day.