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.

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Steppin Up Block Heel Knee High Boots in Wine

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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 inner zipper closure.

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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

$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 Black

$48.90

A sleek black patent faux leather knee-high boot featuring a pointed toe and 3" stiletto heel.

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.

Windsor Hot on the Heist Buckled Pocket Stiletto Boots in Snake

$59.90

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

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Steppin Up Block Heel Knee High Boots in Wine

$48.90

(25)

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, Luxe fit cushioned insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Steppin Up Block Heel Knee High Boots in Wine | Size: 8.5 | Leather

Totally Edgy Buckled Square Toe Boots in Black

$45.90

(16)

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 Ride or Shine Studded Cowboy Boots in White

$52.90

(16)

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

Sleek Stance Faux Leather Stiletto Boots in Black

$46.90

(12)

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: 7.5

Retro Rise Knee High Platform Boots in Brown

$48.90

(11)

A little vintage, a little modern—these knee-high boots are the ultimate outfit maker. With a smooth faux leather finish, a sturdy block heel, and a platform sole perfect for elevating any outfit. Fit & FeaturesBlock heel, Square toe, Side zipper closure, Knee-high shaft, Side zipper closure, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Retro Rise Knee High Platform Boots in Brown | Size: 8.5 | Leather

Windsor Cuffed Up Faux Fur Booties in Brown

$42.90

(10)

Your fall-to-winter uniform starts here. These faux fur booties keep things snug and stylish with a soft faux fur lining and a wear-everywhere flat sole. Perfect for morning coffee runs, lazy Sundays, or that “I just look effortlessly cute” vibe. Fit & Features7” leg opening, 8” shaft height, Round toe, Above-the-ankle length, Allover faux fur material, Soft fuzzy faux fur lining, Flat sole, traction bottom, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cuffed Up Faux Fur Booties in Brown | Size: 11

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

$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 | Size: 5.5

Windsor Drama Queen Faux Fur Boots in Ivory

$42.90

(6)

Go big, go fuzzy, go bold—these faux fur boots bring all the drama your outfit’s been waiting for. Perfect for stepping out, staying cozy, or just making every entrance feel like a moment. Fit & FeaturesPlush faux fur fabrication, Below-the-knee length, Round toe, Flat insole, Slip-on design, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Drama Queen Faux Fur Boots in Ivory | Size: 9

Windsor Point Taken Lace-Up Stiletto Boots in Brown

$58.90

(5)

Equal parts bold and refined. These foldover stiletto boots serve a major edge with a pointed toe, sleek faux leather finish, and lace-up back detail that ties the look together—literally. Perfect for taking your outfit from casual to captivating in one step. Fit & Features4” Stiletto heel, 7" leg opening, 16" shaft height, Pointed-toe, Foldover shaft with lace-up placket, Inner side zipper closure, Sleek faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Point Taken Lace-Up Stiletto Boots in Brown | Size: 8 | Leather

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

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.

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