$20 Skirts

$20 skirts are the secret weapon for every closet crisis—proof that style doesn’t have to come with a splurge. Whether you’re building your week-to-week rotation or just need something fresh for tonight, these picks make it easy to play with trends, experiment with color, and still have budget left over for brunch. Because let’s be honest: the best outfits are the ones that look expensive but keep your wallet happy. Ready to find your new favorite skirt? Let’s make it happen.

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Get Down With Basic Slit Mini Skirt in Black

$16.90

A black knit mini skirt with a high-rise waistband and flirty front hem slit.

Sleek Status Faux Leather Mini Skirt in Black

$19.90

A chic black mini skirt in smooth faux leather with a high-rise waist and side slit accent.

Serving Prep & Sass Bubble Mini Skirt in Light Blue

Sale

Serving Prep & Sass Bubble Mini Skirt in Light Blue

$9.97 $32.90 70% off

A playful light blue cotton mini skirt featuring a pinstriped print and flouncy bubble hem.

Trendy Match Chevron Knit Midi Skirt in Natural

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Trendy Match Chevron Knit Midi Skirt in Natural

$9.97 $39.90 75% off

A natural chevron knit midi skirt with a high-rise waist and bodycon silhouette.

Windsor Heatwave High-Rise Mini Skort in Black

$19.90

A sleek black knit mini skort featuring a high-rise waist and adjustable side drawstring for a custom fit.

Windsor Radiant Sweetie Floral Polka Dot Ruffle Skirt in Black

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Windsor Radiant Sweetie Floral Polka Dot Ruffle Skirt in Black

$9.97 $26.90 63% off

A black woven skort with a floral polka dot pattern and ruffled mini-length skirt overlay.

Windsor Small Town Girl Mid-Rise Bubble Denim Mini Skirt in White

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Windsor Small Town Girl Mid-Rise Bubble Denim Mini Skirt in White

$9.97 $39.90 75% off

A charming white denim mini skirt with a bubble hem and mid-rise waist, perfect for casual outings.

Windsor Special Moment Floral Glitter Dot Mini Skirt in Ivory

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Windsor Special Moment Floral Glitter Dot Mini Skirt in Ivory

$9.97 $39.90 75% off

An ivory floral mini skirt with glitter dots, ruffle trim, and a high-waist smocked style.

Heavenly Match Floral Slit Midi Skirt in Brown

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Heavenly Match Floral Slit Midi Skirt in Brown

$9.97 $34.90 71% off

A brown floral mesh midi skirt with a high-rise waist and sultry front slit.

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Cool Girl Casual Denim Skater Skort

$9.97 $42.90 77% off

A high-rise denim skater skort with a contrast tie-front waistband, pleating, and hidden fitted shorts.

Give Trendy Vibes High-Rise Button Mini Skort in Yellow

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Give Trendy Vibes High-Rise Button Mini Skort in Yellow

$9.97 $34.90 71% off

A yellow woven mini skort featuring a high-rise waist, side button accents, and a flirty ruffled hem.

Talk About Me Mid-Rise Pleated Denim Skort in Med Denim

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Talk About Me Mid-Rise Pleated Denim Skort in Med Denim

$9.97 $39.90 75% off

A stylish medium denim skort featuring a pleated mini skirt overlay and edgy exposed pockets.

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Windsor Wild At Heart Long Fringe Skirt in Tan

$29.90

(34)

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: S | 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

Keep A Secret Lace Slit Maxi Skirt in Black

$39.90

(9)

Make a statement in this lace slit maxi skirt. With sheer lace, ruching, and a high slit, it's your go-to for that effortlessly chic vibe. Fit & FeaturesSheer lace fabric with mini-length knit lining, plenty of stretch, High-rise waist, Ruching, High front slit, Maxi-length hem, Flowy silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Keep A Secret Lace Slit Maxi Skirt in Black | Size: M | Lace Fabric/Knit Fabric/Sheer Lace Fabric

Windsor Sleek Status Faux Leather Mini Skirt in Black

$19.90

(8)

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: L

Sale

Windsor Vacay Ready High Rise Crochet Maxi Skirt in Natural

$9.97 $32.90
70% off

(4)

Heading on vacation? Don't forget to grab this vacay ready high-rise crochet maxi skirt with a sultry high front slit that flaunts some leg. Pair with the matching top and your fave shades! Fit & FeaturesCrochet fabric, stretchy knit lining, High-rise elasticized waist, High front slit, Flowy maxi-length silhouette, Runs true to size , Shop The Matching Top: Vacay Ready Tie-Front Bandea Crochet Crop Top Free Shipping on All Orders Over $75. | Windsor Vacay Ready High Rise Crochet Maxi Skirt in Natural | Size: L | Knit Fabric

Windsor Trendy Moves Long Fringe Skirt in Black

$36.90

(3)

Make major trendy moves in this long fringe skirt featuring a high-rise waist, a flowy fringe design, and cheeky fitted shorts for coverage. Style with a crop top and boots for a country concert. Fit & FeaturesKnit fabric, high stretch, High-rise elasticized waist, Ruched side seams, Long flowy fringe design, Cheeky fitted shorts, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Trendy Moves Long Fringe Skirt in Black | Size: M

Sale

Strut It Out Abstract Zebra Maxi Skirt in Brown

$9.97 $34.90
71% off

(3)

Perfect your vibe with the strut it out abstract zebra maxi skirt. This sheer mesh beauty flaunts a zebra print and mid-rise waist for a fierce look. Pair it with the matching top for ultimate style. Fit & FeaturesSheer mesh fabrication lined with stretchy knit, Mid-rise waist, Zebra print, Maxi length hem, Runs true to size, Shop Matching Top: Strut It Out Abstract Zebra Tie-Front Top Free Shipping on All Orders Over $75. | Windsor Strut It Out Abstract Zebra Maxi Skirt in Brown | Size: L | Mesh Fabric/Sheer Mesh Fabric

Sale

Go With The Vibe Slit Midi Skirt in Rust

$9.97 $26.90
63% off

(3)

Embrace your daring side and let this midi skirt elevate your look. Its sleek high-rise waist and side slit highlight your confidence and flair, perfect for making a statement at any event. Pair with the matching top. Shop Matching Top: Go With The Vibe Halter Crop TopFit & FeaturesSlinky knit stretchy fabric, High-rise waist, Side pleated hip seam, High side slit, Form-hugging silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Go With The Vibe Slit Midi Skirt in Rust | Size: M | Knit Fabric/Stretchy Fabric

Sale

Serving Prep & Sass Bubble Mini Skirt in Light Blue

$9.97 $32.90
70% off

(2)

This skirt said “main character energy” and meant it. With a playful bubble mini hem and classic pinstripe print, she’s made for casual hangs, day dates, and being the moment. Fit & FeaturesPinstriped print, cotton woven fabric, sewn-in woven lining, High-rise waist, Side zipper and hook-eye closure, Flouncy bubble mini hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Serving Prep & Sass Bubble Mini Skirt in Light Blue | Size: L | Cotton/Woven Fabric

Windsor She's Irresistible Faux Leather A-Line Mini Skirt in Black

$39.90

(2)

A faux leather mini skirt like this will make you simply irresistible! This high-rise skirt flaunts side button details for an edgy vibe and a flirty a-line silhouette perfect for pairing with heels or boots. Fit & FeaturesSleek faux leather fabric, High-rise waist, Side snap-button and zipper closures, A-line silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor She's Irresistible Faux Leather A-Line Mini Skirt in Black | Size: L

$20 Skirts

When it comes to building a wardrobe that feels fresh, fun, and totally you, there’s something about a $20 skirt that just hits different. Maybe it’s the thrill of finding a piece that looks luxe but doesn’t make your wallet wince, or maybe it’s the freedom to experiment with trends you’ve been eyeing without the commitment of a splurge. Skirts at this price point are like the ultimate fashion playground—whether you’re curating your closet for the season, searching for that last-minute party look, or just in the mood to treat yourself (because, honestly, why not?), these styles have your back. Think of them as the unsung heroes of your wardrobe: easy to dress up or down, endlessly versatile, and always ready to step in when your jeans need a break. As November settles in and the calendar fills up with everything from Friendsgiving to family dinners, a $20 skirt is your secret weapon for looking put-together on a moment’s notice. Picture this: you’re running late for a coffee date, you reach for that go-to skirt, and suddenly your outfit is working overtime—paired with a chunky sweater and boots for daytime errands, or swapped for a sleek bodysuit and heels when the evening calls for something a little extra.

These skirts aren’t just for you, either—they make the kind of gift that feels thoughtful and fun without the pressure of getting it “just right.” Maybe you’ve got a friend who’s always down to try a new trend, a sister who’s building her college wardrobe, or a cousin who’s impossible to shop for (we all have one). A $20 skirt is the kind of present that says, “I saw this and thought of you,” without breaking the bank or feeling impersonal. And let’s be real: gifting a piece that can be styled a dozen different ways is basically handing over a season’s worth of outfit possibilities. For the friend who’s always planning group pics, a twirl-worthy skirt is a no-brainer; for the one who loves layering, it’s the perfect base for tights, boots, and oversized knits. Even if you’re just stocking up for yourself, these skirts are an easy way to refresh your rotation for fall and winter—think cozy textures, rich colors, and silhouettes that move with you, not against you. Whether you’re navigating packed schedules, unpredictable weather, or just the daily “what do I wear?” dilemma, having a few affordable skirts on hand is a game-changer.

Shopping smart doesn’t mean sacrificing style, and $20 skirts prove it every single time. The beauty is in the details: playful prints that pop under a classic coat, unexpected textures that turn a simple tee into a statement, and silhouettes that flatter every mood (and every mirror selfie). If you’re all about that capsule wardrobe life, these skirts are an easy way to add a little edge or romance without overthinking it. And if you’re the type who loves a good seasonal refresh, you’ll find that these pieces slip seamlessly into your closet, ready to mix, match, and remix with everything you already own. As the holiday deals start rolling in, don’t sleep on special collections like $20 Black Friday Skirts—it’s the perfect excuse to stock up, swap out, or surprise someone you love with a style that makes getting dressed feel easy and exciting. Skirts at this price point are more than just a bargain; they’re an invitation to play, experiment, and show up for every moment feeling like the best version of yourself.

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