Leather High Waisted Skirts

Leather high waisted skirts are the ultimate power move for anyone who loves a look with a little edge and a lot of confidence. Instantly elevate your outfit with a silhouette that’s equal parts sleek and versatile, whether you’re headed to brunch, date night, or just out to turn some heads. Pair yours with everything from oversized knits to crisp button-downs and watch your style go from everyday to unforgettable. Whatever your vibe—bold, classic, or somewhere in between—these skirts are ready to flex with you.

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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.

Cool-Girl Vibes Faux Leather Wrap Skort in Black

$22.90

A sleek black faux leather wrap skort with a high-rise waist and pleated detailing.

Windsor Chasing The Night Bodycon Dress Mini Skort in Black

$22.90

A sleek black faux leather bodycon mini skort with a high-rise waist and stretchy knit lining.

Polished Moves Faux Leather Skort in Black

$36.90

A sleek black faux leather skort featuring a high-rise waist, front slit, and mini-length silhouette.

Slick Moves Faux Leather Pleated Skort in Black

$36.90

A sleek black faux leather skort featuring sharp pleats, a high-rise silhouette, and built-in fitted shorts.

Windsor Worth It Faux Leather Mini Skort in Black

$36.90

A sleek black faux leather mini skort with a ruched front overlay and bodycon silhouette.

Windsor Untamed Energy Animal Print Mini Skirt in Black

$42.90

A black faux leather mini skirt featuring a snakeskin animal print, wrap front, and metal buckle accents.

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Bold Agenda Pleated Skort in Brown

$9.97 $39.90 75% off

A brown faux leather pleated skort featuring a high-rise waist, belted accent, and mini silhouette.

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Windsor Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in Yellow

$34.90

(103)

This satin mini dress will be your favorite for celebrations, events, and date nights! Sleek and smooth satin shapes this off-the-shoulder dress, which features a flattering A-line silhouette perfect for styling with heels. Fit & FeaturesSmooth and sleek satin fabric, stretchy knit lining, Off-the-shoulder neckline, Short sleeve cuffs, A-line silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in Yellow | Size: XS | Knit Fabric/Satin Fabric

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Windsor Senorita Mesh Strappy Mini Dress in Light Blue

$23 $32.90
30% off

(95)

Look and feel like a sultry senorita in this mesh mini dress perfect for an chic night on the town! It features a sleeveless cowl neckline, dual adjustable spaghetti straps with a tie-neck closure, and side and back ruched seams designed to flaunt your curves along the bodycon silhouette. Complete the look with hoop earrings. Fit & FeaturesSleeveless cowl neckline, Dual adjustable spaghetti straps, tie-neck closure, Side and back ruched seams, Back zipper and hook-eye closure, Bodycon silhouette, mini-length hem, Mesh fabric, brushed soft knit stretchy lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Senorita Mesh Strappy Mini Dress in Light Blue | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric

Windsor Lucy Taffeta Bow Mini Party Dress in White

$79.90

(73)

The Lucy mini party dress is sleek and simple from the front and stunning from the back. Turn heads as you stun from the back with a flirty big bow tie with a dramatic train that glides against the floor! Fit & FeaturesTaffeta structured woven-lined fabric, slight stretch, Strapless, square neckline, non-slip grip, Hidden side zipper, hook and eye closure, Front and back pleating and ruching, Form-hugging, mini-length hem, Detachable back bow with train, Runs true to size, Where to Wear:Prom, weddings, brides, bachelorettes, big birthday events, fancy date nights, gorgeous dinner parties, cocktail soirees, rehearsal dinners, engagement photoshoots and parties Free Shipping on All Orders Over $75. | Windsor Lucy Taffeta Bow Mini Party Dress in White | Size: XS

Windsor Cute Attitude Ponte Slit Mini Skort in Black

$27.90

(70)

Bring on the cute attitude in this ponte mini skort brings featuring a flattering high-rise waist, and a skirt overlay designed with dual front slits along the form-hugging fit. Fit & FeaturesSmooth ponte knit fabric, minimal stretch, High-rise waist, Skirt overlay, dual front slits, Form-hugging silhouette, Mini-length hem, Shorts lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute Attitude Ponte Slit Mini Skort in Black | Size: L | Knit Fabric

Lena Strapless Bodycon Beaded Mesh Mini Dress in White

$84.90

(66)

Express your devotion to romance in the Lena mesh mini dress perfect for modern brides, birthday girls, or graduates! The strapless cowl neckline adds a touch of elegance, while the bodycon fit accentuates your figure. Fit & FeaturesBeaded mesh fabric, stretchy knit lining, Strapless cowl neckline, Back zipper and hook-eye closure, Bodycon fit, mini-length hem, Runs true to size, Where to Wear:Prom, date nights, bachelorettes, girl's night out, birthdays Free Shipping on All Orders Over $75. | Windsor Lena Strapless Bodycon Beaded Mesh Mini Dress in White | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric

Get Down With Basic Slit Mini Skirt in Black

$16.90

(57)

Minimal, but never boring. This sleek mini skirt brings the heat with a flirty slit and body-hugging fit made for going out or dressing up your everyday looks. Fit & FeaturesStretchy and smooth knit fabric, High-rise elasticized waistband, Mini-length hem, short front slit, Bodycon silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get Down With Basic Slit Mini Skirt in Black | Size: M | Knit Fabric

Windsor Flawless Allure Cowl Neck Bodycon Mini Dress in Black

$35.90

(49)

Show off a flawless allure in this figure-flaunting mini dress! Designed with a sleek knit fabric with a fab sheen, this mini-length dress offers plenty of stretch so you can dance all night. The sleeveless bodice is shaped with a pleated cowl neckline for a chic draped effect and spaghetti straps. The pleating across the bodycon silhouette will accentuate your stunning curves. Style with metallic heels for a club night out.Fit & FeaturesStretchy sleek knit fabric, Sleeveless pleated cowl neckline, Spaghetti straps, Pleating, Bodycon fit, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flawless Allure Cowl Neck Bodycon Mini Dress in Black | Size: M | Knit Fabric

Catalina Rhinestone And Pearl Formal Mini Dress in Yellow

$69.90

(44)

Bling on the sultry glamour with the sparkling details of the stunning Catalina formal mini dress with a bodycon silhouette that will flaunt your gorgeous figure! Fit & FeaturesSheer mesh fabric, full-length knit lining, plenty of stretch, Mini iridescent rhinestones, faux pearl embellishments, Sleeveless cowl neckline, Adjustable spaghetti straps, Mini-length hem, bodycon silhouette, Runs true to size, Where to Wear:Prom, bachelorettes, birthdays, girl's night out, date nights Free Shipping on All Orders Over $75. | Windsor Catalina Rhinestone And Pearl Formal Mini Dress in Yellow | Size: M | Knit Fabric/Rhinestone/Mesh Fabric

Paige Rhinestone Formal Bodycon Mini Dress in Red

$59.90

(27)

Capture all the attention with your sultry allure in the Paige rhinestone formal bodycon mini dress! She features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, all-over rhinestone embellishments for that total glam girl vibe, a mini-length hem, and a bodycon silhouette to hug your gorgeous curves. The slinky knit fabric offers plenty of stretch. Style this mini dress with metallic heels for your next dressy night out! Fit & FeaturesSleeveless cowl neckline, Adjustable spaghetti straps, All-over rhinestone embellishments, Mini-length hem, bodycon silhouette, Slinky knit fabric, full-length knit lining, plenty of stretch, Runs true to size, Where to Wear:School dances, date nights, bachelorettes, birthdays, cocktail parties, rooftop hotel bars, GNO, parties Free Shipping on All Orders Over $75. | Windsor Paige Rhinestone Formal Bodycon Mini Dress in Red | Size: XL | Knit Fabric/Rhinestone

Windsor Sleek Sophistication A-Line Pleated Mini Dress in Mint

$38.90

(27)

The mini dress features a sleeveless square neckline with a pleated bust, spaghetti straps, and an A-line silhouette. Complete outfit with a sleek rhinestone clutch. Fit & FeaturesSmooth knit fabrication with full knit lining, Sleeveless square neckline, Pleated bust, Spaghetti straps, A-line silhouette, Mini length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Sophistication A-Line Pleated Mini Dress in Mint | Size: L | Knit Fabric/Rhinestone

Leather High Waisted Skirts

There’s something about a high waisted leather skirt that just gets it—equal parts classic and daring, with a silhouette that works overtime for your wardrobe. March is that in-between month where you’re ready to ditch the heavy winter layers but not quite ready for bare legs and breezy sundresses, and this is exactly where leather high waisted skirts shine. Picture this: the morning chill still lingers, but you’re already dreaming of patio brunches and gallery strolls. Pull on a high waisted leather skirt, add a fitted knit or a tucked-in tee, and suddenly you’ve got that perfect balance of edge and ease. The structured waistline flatters in all the right places, giving you a confidence boost whether you’re heading into a big meeting or a last-minute night out. And let’s be real—leather (faux or genuine) always brings a little attitude to the table, but when it’s cut with a high waist, it’s more sophisticated than rebellious. It’s that rare staple that feels just as right with ankle boots as it does with strappy heels or even sneakers for an off-duty twist.

If you’re shopping for yourself, lean into the versatility—these skirts are the definition of outfit repeaters in the best way. Pair with a crisp button-down for work, then swap in a cropped sweater or a bold graphic tee for after-hours plans. The high waisted fit means you can play with proportions, layering oversized jackets or cinching with a belt for a custom vibe. And if you’re on the hunt for a gift, a high waisted leather skirt is a thoughtful pick for anyone who loves to experiment with style or needs a wardrobe refresh. It’s a go-to for the friend who’s always mixing textures, the sister who’s building her “grown-up” closet, or the roommate who borrows your favorite pieces and never wants to give them back. These skirts also make a statement without being fussy—ideal for birthdays, graduations, or just-because surprises that feel personal without the guesswork. Plus, leather is seasonless: layer over tights in early spring, go bare-legged when the sun finally sticks around, and keep it in rotation long after the clocks spring forward.

When you’re choosing your perfect high waisted leather skirt, think about length, finish, and the details that make it yours. Do you want a sleek pencil silhouette for maximum polish, or are you drawn to a flirty A-line that moves with you? Matte finishes bring a modern edge, while a subtle sheen can amp up the drama for date night or special events. Look for thoughtful touches—like statement zippers, snap closures, or unexpected colorways—that let your personality shine through. And if you’re craving something a little shorter for spring, don’t miss our collection of Leather Mini Skirts for even more ways to show off your style. However you style it, a high waisted leather skirt is the kind of piece that makes getting dressed feel less like a chore and more like a celebration—because you deserve to feel as bold and effortless as you look, every single day.

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