Dressy Over The Knee Boots

Dressy over the knee boots are your not-so-secret weapon for turning everyday outfits into head-turning moments. Whether you’re styling up a date night look or adding some drama to your brunch rotation, these boots know how to make an entrance. Pair them with mini dresses, sleek skirts, or your favorite oversized sweater—the options are endless, and the compliments are practically guaranteed. When you want to elevate your vibe without overthinking it, dressy over the knee boots deliver that perfect mix of polish and playful edge.

Show Filters

Sort: Recommended

Size

Color

Price

All Filters

27 results

Sort

Windsor Steppin Up Block Heel Knee High Boots in Wine

Best Seller

Windsor Steppin Up Block Heel Knee High Boots in Wine

$48.90

A knee-high boot in rich wine faux leather featuring a stacked block heel and round toe design.

Boss Moves Over-The-Knee Block Heel Boots in Black

$54.90

A sleek pair of black faux leather over-the-knee boots featuring a bold block heel and pointed toe.

Windsor Higher Standards Kitten Heel Boots in Taupe

$58.90

A pair of taupe faux suede over-the-knee boots with a pointed toe and low kitten heel.

Best Seller

Season’s Sleek Thigh-High Stiletto Boots in Black

$58.90

A dramatic pair of black faux leather thigh-high boots featuring a pointed toe and sleek stiletto heel.

Sleek Confidence Over-The-Knee Boots in Black

Best Seller

Sleek Confidence Over-The-Knee Boots in Black

$54.90

A striking pair of black over-the-knee boots combining smooth faux leather and stretch knit fabric.

Windsor Galaxy Girl Mirror Metallic Knee Boots in Silver

$68.90

A striking pair of silver mirror-chrome faux leather knee boots with a pointed toe and stiletto heel.

Windsor Major Strut Faux Leather Knee-High Stiletto Boots in Brown-2

$48.90

A knee-high brown stiletto boot crafted from patent faux leather with a pointed toe and inner zipper.

Best Seller

Gloss Effect Patent Stiletto Boots in Wine

$49.90

A glossy wine patent faux leather stiletto boot with a pointed toe and knee-high silhouette.

Icon Status Platform Knee Boots in Black

$48.90

A sleek black faux leather knee-high boot featuring a bold block heel and modern square toe design.

Fall For Me Wide Calf Knee-High Boots in Camel

$49.90

A pair of camel faux suede knee-high boots featuring a wide calf design and block heel.

Point Taken Lace-Up Stiletto Boots in Brown

Best Seller

Point Taken Lace-Up Stiletto Boots in Brown

$58.90

A bold brown faux leather stiletto boot featuring a pointed toe and lace-up foldover shaft detail.

Hot on the Heist Buckled Pocket Stiletto Boots in Snake

$59.90

A knee-length stiletto boot in snake-print faux leather with buckle accents and functional pocket detailing.

Windsor Attitude Strut Patent Stiletto Boots in Ivory

Sale

Windsor Attitude Strut Patent Stiletto Boots in Ivory

$19.97 $64.90 69% off

A pair of ivory knee-high boots featuring glossy patent faux leather and a sleek pointed toe.

Now Trending

Windsor Steppin Up Block Heel Knee High Boots in Black

$48.90

(16)

Big boot energy only—these tall babes instantly elevate any 'fit. A sleek silhouette with a comfy block heel makes them perfect for day-to-night flexing. Fit & Features3" Stacked block heel, 8" leg opening, 12" shaft height, Platform sole, Round toe, Complete inner zipper closure, Knee-length shaft, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Steppin Up Block Heel Knee High Boots in Black | Size: 7 | Leather

Totally Edgy Buckled Square Toe Boots in Black

$45.90

(15)

Step into these edgy statement faux leather boots with a buckled side accent and a calf-length fit perfect for pairing with bottoms or dresses. Fit & Feature2” in heel, 7.5” leg opening, 11.5” shaft , Square toe, Buckled side accents, Calf height shaft, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Totally Edgy Buckled Square Toe Boots in Black | Size: 8.5 | Leather

Windsor Major Strut Faux Leather Knee-High Stiletto Boots in Brown-2

$48.90

(8)

Fit & Features3" Stiletto heel, 7.5" leg opening, 13.5" shaft height, Patent faux leather material, Knee-high design, Pointed toe, Complete inner zipper closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Major Strut Faux Leather Knee-High Stiletto Boots in Brown-2 | Size: 8

Windsor Boot Scootin’ & Vibin’ Cowboy Boots in Camel

$52.90

(8)

Giddy up, but make it fashion. These cowboy boots bring rodeo realness with a side of city-girl sass—perfect for concerts, content days, or just stomping through life like it’s your personal runway. Fit & FeaturesStacked block heel, Almond toe, Western-inspired pattern, Inner zipper closure, Knee-length shaft height, Faux suede material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Boot Scootin’ & Vibin’ Cowboy Boots in Camel | Size: 7.5 | Faux Suede

Windsor Ride or Shine Studded Cowboy Boots in White

$52.90

(7)

Western, but make it glam. These faux leather cowboy boots mix classic embroidery with studded detailing and a sleek pointed toe—perfect for bachelorettes, country concerts, or costume parties. Fit & Features3.5” stacked block heel, 7.5” leg opening, 12.5” shaft, Pointed toe, side zipper closure, Studded and grommet embellishments, Western-inspired embroidery, Under-the-knee length, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Ride or Shine Studded Cowboy Boots in White | Size: 9 | Leather

Windsor Sleek Stance Faux Leather Stiletto Boots in Black

$46.90

(6)

Cold-weather dressing just got elevated. These faux leather boots bring timeless polish with a pointed toe and sleek under-the-knee cut, with a stiletto heel that pairs effortlessly with fall layers. Fit & Features3” stiletto heel, 7.5” leg opening, 15” shaft, Pointed-toe, Side zipper closure, Under-the-knee length, Sleek faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Stance Faux Leather Stiletto Boots in Black | Size: 6

Windsor Tough Love Platform Block Heel Booties in Black

$40.90

(5)

Walk tall and with edgy confidence in these faux leather booties, and elevate your outfit! They feature a platform sole for stylish height and a stacked block heel. Fit & Features3.5" Stacked block heel, Square toe, Inner zipper closure, Platform sole, Luxe fit cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Tough Love Platform Block Heel Booties in Black | Size: 8.5 | Leather

Daring Details Studded Ankle Booties in Black

$40.90

(5)

Make a bold statement with the daring details studded ankle booties. Featuring a block heel, peep toe, and criss-cross straps with metal buckles, these booties are your new go-to for standout style. Fit & FeaturesBlock heel, Ankle-length fit, Faux microsuede material, Peep toe, Criss-cross straps with metal buckles, Studded accents, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Daring Details Studded Ankle Booties in Black | Size: 10

Windsor Gloss Effect Patent Stiletto Boots in Wine

$49.90

(5)

The kind of boot that owns every room. These patent stiletto knee boots serve glossy drama with a sculpted pointed toe and sleek silhouette—made for statement looks and confident strides. Fit & Features 3.5” stiletto heel, 7.5” leg opening, 15” shaft height, Pointed-toe, Inner zipper closure, Knee-length shaft, Glossy patent faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Gloss Effect Patent Stiletto Boots in Wine | Size: 8.5 | Leather

Fringe Worthy Cowboy Knee High Boots in Brown

$52.90

(4)

Cue the country playlist—these boots were made for dancing, strutting, and stealing the spotlight. The swishy fringe and sleek western shape make every step feel like a stage walk. Fit & Features3.5” heel height, 8” leg opening, 12.5” shaft height, Pointed toe, Inner zipper closure, Fringe trim detailing, Knee-high silhouette, Faux suede material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fringe Worthy Cowboy Knee High Boots in Brown | Size: 6 | Faux Suede

Dressy Over the Knee Boots

When it comes to building a show-stopping outfit in seconds, dressy over the knee boots are the kind of piece that does all the heavy lifting—no matter what’s on your calendar. There’s just something about that extra length, that sleek silhouette, that instantly elevates everything from a sweater dress to your favorite mini skirt. Think about the scene: city lights, a little chill in the air, you’re heading out for a holiday dinner or a last-minute party invite, and you want to look put-together without overthinking it. Pull on a pair of over the knee boots and suddenly, you’re not just dressed—you’re styled. These boots don’t just keep you warm (though, let’s be real, that’s a huge perk in December); they add polish and confidence, whether you’re pairing them with cozy knits for daytime errands or slipping them on over tights for a night out. And if you’re shopping for someone else—maybe your sister who’s always borrowing your shoes, or your best friend whose birthday always sneaks up on you—dressy over the knee boots are the kind of gift that feels both thoughtful and on-trend. They’re not just an accessory; they’re a wardrobe transformer, ready to make any outfit feel intentional and fresh.

Choosing the right pair comes down to a mix of style instincts and practical know-how. Material matters—a luxe faux suede is soft and flexible, hugging your legs without slouching, while a smooth faux leather brings a little edge and structure. Heel height is another game changer: a block heel gives all-day comfort for those marathon shopping days or back-to-back holiday events, while a slim stiletto instantly turns up the glam for special occasions. Color is where you can really express your vibe, but there’s a reason classic black reigns supreme. A pair of Women's Black Over the Knee Boots is endlessly versatile—think of them as the LBD of your shoe rack, ready to anchor any look, any time. Sizing can be personal, too; some love a snug, second-skin fit that stays up all night, while others go for a slightly relaxed shaft to layer over jeans or thicker socks. Don’t forget the details: a pointed toe for a sleek finish, a subtle zipper for easy on-and-off, or a hint of metallic hardware to catch the light. These little touches make your boots feel less like a basic and more like a signature.

Over the knee boots aren’t just for the ultra-trendy or the fashion risk-takers—they’re for anyone who wants to make getting dressed feel easy and exciting, even when the temperature drops or the calendar fills up. They’re the secret weapon for those “nothing to wear” days, the finishing touch that makes you feel photo-ready even when you’re running late. Whether you’re styling them for a winter brunch, a festive night out, or just a coffee run that deserves a little extra, they’re the kind of piece that brings out your inner stylist. And if you’re wrapping them up for someone else, you’re basically giving the gift of instant confidence—because everyone deserves to step into the season feeling bold, cozy, and ready for whatever comes next.

Reset Your Password

Email Sent

Order Status

Dressy Over The Knee Boots

Home Dressy Over The Knee Boots

Now Trending

Dressy Over the Knee Boots

Related Collections