High Waist Maxi Skirts

High waist maxi skirts are the ultimate style statement for our Windsor girl who wants to twirl through life with confidence and flair. These skirts effortlessly blend elegance and comfort, making them the perfect go-to for any occasion where you want to feel like a bohemian goddess or a chic city dweller. Whether you're headed to brunch with the squad or a spontaneous road trip, these skirts have got your back, offering endless possibilities to mix and match with your favorite tops and accessories. So get ready to strut your stuff and make every sidewalk your runway!

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Windsor Wild At Heart Long Fringe Skirt in Tan

Best Seller

Windsor Wild At Heart Long Fringe Skirt in Tan

$29.90

A tan faux suede skirt with a high-rise waist and ankle-length fringe for a festival vibe.

Windsor Vacay Bloom Floral Mesh Maxi Skirt in Light Blue

Best Seller

Windsor Vacay Bloom Floral Mesh Maxi Skirt in Light Blue

$36.90

A light blue floral mesh maxi skirt featuring a high-rise waist, ruching, and a high-cut side slit.

Sweet Like Summer Crochet Maxi Skirt in Ivory

Best Seller

Sweet Like Summer Crochet Maxi Skirt in Ivory

$46.90

An ivory crochet maxi skirt featuring a high-rise waist, scalloped trim, and a thigh-high side slit.

Windsor Shake It Up Fringe Maxi Skirt in Tan

Best Seller

Windsor Shake It Up Fringe Maxi Skirt in Tan

$29.90

A tan faux suede maxi skirt featuring a high-rise waist and dramatic fringe silhouette for festival flair.

Cool Confidence Animal Print Mesh Maxi Dress Skirt in Rust

Best Seller

Cool Confidence Animal Print Mesh Maxi Dress Skirt in Rust

$36.90

A rust-colored mesh maxi skirt featuring an abstract animal print, high-rise waist, and form-hugging fit.

Cool Girl O-Ring High-Rise Maxi Dress Skirt in Black

$29.90

A sleek black knit maxi skirt featuring a high-rise waist, O-ring detail, and a high side slit.

Windsor Night Out Muse Abstract Print Mesh Maxi Skirt

$34.90

A multi-color abstract print mesh maxi skirt with a sheer overlay and form-hugging silhouette.

Windsor Bloom Babe Abstract Floral Mesh Maxi Dress Skirt in Pink

$34.90

A pink mesh maxi skirt featuring an abstract floral print, ruched detailing, and a form-hugging silhouette.

Edgy Glam High-Rise Buckle Maxi Skirt in Black

$54.90

A black faux leather maxi skirt featuring a high-rise waist, dual front buckles, and a dramatic front slit.

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Wild At Heart Long Fringe Skirt in Tan

$29.90

(35)

Channel your western side with this trendy-chic skirt that will level up your festival look! It features a high-rise waist, an asymmetric mini-length hem with a form-hugging fit, and long fringe detailing that cascades to your ankles. The stylish fringe design will dance with you to your favorite band! Complete your 'fit with a cropped graphic tee and cowboy boots. Fit & FeaturesHigh-rise waist, Back zipper, hook and eye closure, Asymmetric mini-length hem, Form-hugging fit, Long fringe design, ankle-length hem, Faux suede fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Wild At Heart Long Fringe Skirt in Tan | Size: XS | Faux Suede

Bold Staple Ruched Asymmetrical Midi Skirt in Black

$26.90

(14)

Fit & FeaturesStretchy smooth knit-lined fabrication, High-rise fit, Ruching, Asymmetrical high-side slit, Midi length hem, Runs true to size, Shop Matching Crop Top: Bold Staple Long Sleeve Crop Top Free Shipping on All Orders Over $75. | Windsor Bold Staple Ruched Asymmetrical Midi Skirt in Black | Size: XS

Sleek Status Faux Leather Mini Skirt in Black

$19.90

(9)

Level up your sleek status with this chic mini skirt made with smooth faux leather fabric to elevate your casual 'fits. It features a high-rise waist, a side slit accent at the hem, and a form-hugging silhouette to highlight your stunning curves. Fit & FeaturesFaux leather fabric, plenty of stretch, High-rise elasticized waist, Side slit, Mini-length hem, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Status Faux Leather Mini Skirt in Black | Size: XS

Windsor Vacay Bloom Floral Mesh Maxi Skirt in Light Blue

$36.90

(5)

A maxi skirt that feels like slipping into vacation mode without even trying. The soft floral print mesh hugs just right, giving you that effortless “I’m ready for whatever” confidence—day plans or date nights included. Shop Matching Top: Vacay Bloom Floral Mesh Halter TopFit & FeaturesSheer mesh fabric with knit lining, high stretch, Large floral print, High-rise waist, Ruching, High-cut side slit, Maxi-length hem, form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Vacay Bloom Floral Mesh Maxi Skirt in Light Blue | Size: L | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric

Throwback Cool Denim Cargo Mini Skirt

$39.90

(5)

Low-rise nostalgia meets modern street style—this denim cargo mini skirt is made for layering with baby tees, tanks, or oversized fits. The pocket detail gives it that effortless “just stepped out of an early 2000s music video” energy. Fit & FeaturesDenim fabric with color fade effect, Mid-rise waist, Cargo-style front and side pockets, Fitted mini-length hem, Front button closure, belt loop accents, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Throwback Cool Denim Cargo Mini Skirt | Size: XL

Life Of The Party Lace-Up Mini Skirt in Brown

$42.90

(4)

This faux leather skirt gives life to the party vibes! It has lace-up sides that demand attention, a high-rise waist, and a flattering form-hugging fit that shows off your figure. Fit & FeaturesFaux leather fabric, High-rise waist, Back zipper closure, Side lace-ups , Form-hugging fit, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Life Of The Party Lace-Up Mini Skirt in Brown | Size: M | Leather

Windsor After Dark Flutter Mini Skirt in Black

$29.90

(4)

Sleek with a little edge, this mini skirt is made for plans that don’t end early. The smooth knit finish and subtle butterfly detail bring just enough intrigue, while the side slit keeps things flirty without trying too hard. Fit & FeaturesSmooth knit fabric with stretch, Low-rise waist, High front slit with subtle butterfly detailing, Form-hugging fit, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor After Dark Flutter Mini Skirt in Black | Size: M | Knit Fabric

Chic Confidence High Slit Mesh Midi Skirt in Black

$26.90

(4)

When subtle isn’t the move, this mesh midi skirt delivers. With a thigh-high slit and ruched waist, it’s the kind of style that owns the night and brings the confidence. Fit & FeaturesSheer mesh fabric with knit lining, high stretch, High-rise waist, ruching, Ultra-high front slit, Asymmetric midi-length hem, Flowy fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Confidence High Slit Mesh Midi Skirt in Black | Size: S | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric

Going Somewhere Wrap Slit Maxi Skirt in Black

$29.90

(3)

Easy confidence, built in. This high-rise skirt hugs smoothly with a slinky double-lined knit and a front wrap slit that brings just enough drama for day or night plans. Fit & FeaturesSlinky double-lined knit fabric with stretch, High-rise waist, Body-skimming silhouette, High front wrap slit for movement, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Going Somewhere Wrap Slit Maxi Skirt in Black | Size: M | Knit Fabric

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Windsor Velvet Crush Denim Mini Skirt in Navy Blue

$9.97 $36.90
73% off

(2)

Classic with a soft twist. This flocked velvet denim mini skirt combines luxurious texture with everyday ease, featuring a mid-rise fit, pockets, and a perfectly flirty mini length. Perfect for styling with a sweater and boots! Fit & FeaturesFlocked velvet denim fabric, Mid-rise waist, Form-hugging fit, Mini-length hem, Front button closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Velvet Crush Denim Mini Skirt in Navy Blue | Size: S

High Waist Maxi Skirts

When it comes to building a wardrobe that actually works for real life—not just Pinterest boards—high waisted maxi skirts are the kind of style staple that quietly does the most. Whether you’re navigating the last chilly weeks of winter or daydreaming about those first not-quite-warm-enough spring afternoons, these skirts are the definition of adaptable. High waisted long skirts bring instant polish to a basic tee and sneakers, but they’ll also play nicely with chunky knits, cropped jackets, or a sleek bodysuit when you’re headed out after dark. There’s something about the way a high waist maxi skirt skims the body and floats just so that makes you feel equal parts put-together and free—like you could hop on a train, stroll through a gallery, or linger over coffee with friends and never feel out of place. The high waist silhouette does wonders for your shape, creating that coveted cinched effect while letting you move with total ease. And if you’re the type who’s always thinking about comfort (but refuses to sacrifice style), high waisted long flowy skirts are basically a sartorial cheat code: breezy, forgiving, and endlessly versatile.

Gifting a high rise long skirt is a move that says you actually know her style—not just her size. It’s thoughtful, practical, and a little bit luxe, whether you’re shopping for a birthday, a “just because” pick-me-up, or a treat-yourself moment that doesn’t require an occasion. These skirts suit everyone from your bestie who’s always on the go to your sister who swears by vintage vibes, and even your mom who secretly loves to make an entrance. They’re especially great for transitional seasons, when layering is key and you want options that work with boots now and sandals later. If you’re curating a closet that can handle spontaneous weekend plans, brunch invites, or even a last-minute date night, a high waist maxi skirt is the piece you’ll reach for over and over. Think of it as your personal style chameleon: dress it up, dress it down, mix in bold prints or classic solids, and let it reflect whatever mood you’re in. And don’t underestimate the power of a great black skirt—timeless, flattering, and always in season. If you’re looking to expand your collection, you’ll want to check out the range of Black High Waist Skirts for those days when nothing but classic will do.

Shopping for the right high waisted maxi skirt comes down to a few key considerations: fabric, fit, and the little details that make it feel personal. Lightweight, flowy materials are your best friend for movement and all-day comfort, while a structured option can give you that ultra-sleek, editorial vibe. Pay attention to length—some love a true floor-sweeping maxi, while others prefer a slightly shorter cut that shows off a killer pair of shoes. Look for thoughtful touches like side slits, subtle pleats, or a playful print to keep things interesting. And if you ever find yourself in the “I have nothing to wear” spiral, remember: high waisted long skirts are the ultimate reset button. They’re the piece you can throw on without overthinking and somehow always look like you’ve got it all figured out. That’s the magic of a great skirt—effortless, confidence-boosting, and always ready for whatever the day brings.

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