$20 & Under Sale

Home$20 & Under Sale
Loading...

Now Trending

Unveil the Magic of Windsor's $20 and Under Sale – Hot Deals on Must-Have Dresses & Clothing!

Looking to elevate your wardrobe affordably? Search no further than Windsor's spectacular $20 and under sale, where chic meets affordability! This fashion sale is the perfect opportunity to update your wardrobe with stylish pieces that won't break the bank. Discover a curated selection of $20 sale clothing that includes affordable dresses for any occasion, from weddings and cocktail hours to summer parties.

Featured $20 and Under Deals:

Elegant Dresses: Find the perfect dress for formals, birthdays, or date nights without overspending. Our collection features stunning styles that make a statement.

Summer Party Dresses: Stay cool and fashionable with our range of dresses designed for summer parties and casual gatherings. Light, breezy, and effortlessly chic!

Versatile Wardrobe Staples: Whether you're dressing up or down, our affordable tops and bottoms offer versatility and style for any event.

Why You'll Love Our $20 Deals

  • Capture unbeatable prices on current trends featuring high-quality, fashionable pieces at prices you’ll adore.
  • Brag about getting something new with fresh updates and how you always have exciting pieces to discover that won't break the bank.
  • Come back to get limited-time offers: These hot deals won’t last long – make sure you snag your favorites before they're gone!

At Windsor, we believe that everyone deserves to look and feel fabulous without overspending. Our $20 and under sale is designed to bring you the best in trendy fashions at incredible prices. From elegant wedding guest dresses to fun and flirty summer party outfits, you'll find everything you need to stay stylish this season. Capture more savings and shop the full collection of affordable women's apparel!

Don’t miss out on these unbeatable $20 deals. With new styles added regularly, there's always a fresh find waiting for you. Shop now and discover the joy of Windsor fashion sale – stylish, affordable, and simply irresistible.

  • Call Me When You're Sober Tee

    Let this sassy graphic tee speak for itself! It features a crew neckline, short sleeves, a cropped fit with an asymmetrical front hem you can tie into a knot, and a center script that reads "Call me when you're sober" with butterfly graphics. Style this cotton-blend tee with distressed denim.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Cropped fit, asymmetrical front hem
    • Script that reads "Call me when you're sober"
    • Butterfly graphics
    • Cotton-blend fabric, moderate stretch, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06002-1266

    Category Name: $20 & Under Sale

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ally High-Rise Denim Mini Skirt by Windsor Denim

    Style up your everyday casual looks with the Ally denim mini skirt by Windsor Denim! Featuring a high-rise waist, destructed detailing, and a mini-length frayed hem, this jean skirt is a cute wardrobe staple. It is composed of a light wash denim fabric that offers a moderate stretch. Pair with your fave crop tops.

    Fit & Features

    • High-rise waist
    • Distressed accents, fitted silhouette
    • Mini-length, frayed hem
    • Five-pocket and belt loop design
    • Front button, hidden zipper closure
    • Light wash denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06601-0051

    Category Name: $20 & Under Sale

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Born To Ride Jersey Graphic Tee

    You were obviously born to ride! Hop on your hot rod in this edgy jersey knit tee featuring a crew neck, short sleeves, adjustable drawstring hem, and a front graphic with a script that reads, "Born To Ride Forever". Complete the look in a sleek faux leather mini.

    Fit & Features

    • Short sleeves
    • Crew neck
    • Adjustable drawstring hem
    • Front graphic and script that reads, "Born To Ride Forever"
    • Jersey knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1248

    Category Name: $20 & Under Sale

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Poolside Vibe Mesh Coverup

    Showcase only chic vibes as you lounge poolside in this sultry mesh coverup dress! It features a sleeveless scoop neckline, spaghetti straps, ruching down one side, and a fitted maxi-length silhouette with a high side slit. The sheer mesh fabric offers a moderate stretch and an airy, lightweight feel. Style this coverup over your fave bikini with cat-eye sunglasses.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Ruched side detailing, high side slit
    • Fitted maxi-length silhouette
    • Sheer mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4187

    Category Name: $20 & Under Sale

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • All It Takes Linen Halter Jumpsuit

    This halter linen jumpsuit is all it takes to look chic on the go! It features a sleeveless, plunge v-neckline, a front hoop inset, a form-fitting silhouette, and an open-back with dual tie closures. Complete your vacay look in sleek hoop earrings.

    Fit & Features

    • Sleeveless, halter plunge v-neckline
    • Front hoop inset
    • Form-fitting silhouette
    • Open-back, dual tie closures, zipper closure
    • Partially lined linen fabric
    • Fits true to size

    Style Number/Barcode: 06302-0622

    Category Name: $20 & Under Sale

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Remy High-Rise Cutoff Denim Shorts by Windsor Denim

    Every girl needs that classic pair of cutoff jean shorts! The Remy high-rise shorts by Windsor denim are perfect for creating cute and casual summer 'fits. They feature subtle distressing, an on-trend frayed cutoff hem, and a form-hugging fit. The medium wash denim fabric offers a moderate stretch for comfortable wear. Style with your fave graphic tee.

    Fit & Features

    • High-rise waist
    • Destructed detailing, frayed cutoff hem
    • Five-pocket and belt loop design
    • Front button, hidden zipper closure
    • Medium wash denim fabric, moderate stretch
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-0233

    Category Name: $20 & Under Sale

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Life's A Breeze High Rise Shorts

    Life's a breeze under the palm trees in paradise! Create an effortless vacay vibe in this breezy short featuring a high-rise waist and flowy silhouette on palm print fabric. Complete the look in the matching top.

    Shop Matching Top: Life's A Breeze Kimono Tie-Front Top

    Fit & Features

    • High-rise waist
    • Flowy silhouette
    • Palm leaf print woven fabric
    • Runs true to size

    Style Number/Barcode: 06303-0152

    Category Name: $20 & Under Sale

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Life's A Breeze Kimono Tie-Front Top

    Life's a breeze under the palm trees in paradise! Create an effortless vacay vibe in this breezy crop top featuring 3/4 length kimono sleeves, a plunge V-neckline, and a tie-front closure on palm print fabric. Complete the look in the matching shorts.

    Shop Matching Shorts: Life's A Breeze High Rise Shorts

    Fit & Features

    • 3/4 length kimono sleeves
    • Plunge V-neckline
    • Tie-front closure
    • Cropped hem
    • Palm leaf print woven fabric
    • Runs true to size

    Style Number/Barcode: 06204-1146

    Category Name: $20 & Under Sale

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Major Flirt Ruched Chiffon Blouse

    Bring on the flirty vibes with a blouse that is made for romance! The blouse features a plunging V-neckline, flutter cap sleeves, a hook and eye closure, ruching at the hem, and a smocked back. The top is composed of a semi-sheer chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with mom jeans and mules. 

    Fit & Features

    • Plunging V-neckline
    • Flutter cap sleeves
    • Hook and eye front closure
    • Ruching
    • Smocked back
    • Chiffon fabric
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-1805

    Category Name: $20 & Under Sale

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Strappy Open-Back Knit Bodysuit

    Swap out your basic bodysuit for this sassy strappy back style! It features a sleeveless square neckline, bungee spaghetti straps, an open back with a dual bungee strap design, and a fitted silhouette with a thong bottom. Pair this bodysuit with faux leather pants and clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Open back, dual bungee strap design
    • Form-hugging fit
    • Thong bottom, dual snap button closure
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4224

    Category Name: $20 & Under Sale

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picnic Date Eyelet Lace V-Neck Dress

    The cutest picnic date dress ever! Make an adorable impression in this eyelet lace dress featuring a sleeveless V-neck, ruffled straps, and a pencil silhouette on a short hem. Complete the look in wedges.

    Fit & Features

    • Sleeveless, V-neck, ruffled straps
    • Pencil silhouette
    • Short-length hem
    • Back zipper, hook and eye closure
    • Eyelet lace fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4386

    Category Name: $20 & Under Sale

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shorebird Crochet Woven Kimono

    Chill along the shore looking so trendy in this crochet woven kimono featuring flowy, long sleeves with cuffs and a sheer longline design. Complete the look in a bikini top and denim shorts.

    Fit & Features

    • Flowy long sleeves with cuffs
    • Open-front
    • Sheer longline design
    • Crochet woven fabric

    Style Number/Barcode: 06204-1320

    Category Name: $20 & Under Sale

    Price: $16.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feel The Sun Halter Sweetheart Skater Dress

    Bare your shoulders in this cute skater dress on a sunny day! Its easy, breezy design features a halter sweetheart neck, tie-back closure, a ruched bust, and a flowy silhouette and back zipper closure. Composed of seersucker woven fabric with an inner knit lining. Finish the look in lace-up sandals.

    Fit & Features

    • Sleeveless, halter sweetheart neck, tie-back closure
    • Ruched bust
    • Flowy skater silhouette
    • Above the knee length
    • Back zipper closure
    • Seersucker woven fabric, no stretch, inner knit lining
    • Runs true to size

    Style Number/Barcode: 05101-1537

    Category Name: $20 & Under Sale

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Contemporary Shine Hoop Earrings

    Embrace the simple things in life. Finish your look with these gold metal hoops featuring a two-row design with an omega-back closure. Style with an oversized denim jacket.

    Fit & Features

    • Gold metal hoops
    • Two-row design
    • Omega-back closure

     

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-1207

    Category Name: $20 & Under Sale

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Glam Statement Chain Belt

    Accessorize your trendy summer looks with this boho glam statement belt. It features a chain-link design with a rhinestone embellished square buckle to add some sparkle. Style with cutoff denim shorts.

    Fit & Features

    • Three-row chain-link design
    • Square buckle
    • Rhinestone embellishment

    Style Number/Barcode: 07301-0445

    Category Name: $20 & Under Sale

    Price: $2.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Howdy Cow Print Pajama Shorts

    Howdy, comfy, and cute cow print PJ shorts! They feature a trendy high-rise elasticized waistband, tie-front closure, and a form-fitting silhouette. Complete the cozy look in the matching top.

    Shop The Matching Top: Howdy Cow Print Pajama Top

    Fit & Features

    • High-rise elasticized waistband
    • Tie-front closure
    • Form-fitting silhouette
    • Cow print design
    • Soft and comfortable
    • Fits true to size

    Style Number/Barcode: 07103-0787

    Category Name: $20 & Under Sale

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Howdy Cow Print Pajama Top

    Say howdy to this comfy and cute cow print pajama top! It features a sleeveless, square neck, tank-style straps, and a fitted crop hem. Complete the cozy look in the matching bottoms.

    Shop The Matching Bottoms: Howdy Cow Print Pajama Shorts

    Fit & Features

    • Sleeveless, square neck, tank-style straps
    • Form-fitting
    • Cropped hem
    • Cow print design
    • Soft and comfortable
    • Fits true to size

    Style Number/Barcode: 07103-0786

    Category Name: $20 & Under Sale

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jill Formal Cowl Back A-Line Dress

    Special Occasion

    Style and grace come hand-in-hand in the Jill formal dress sure to be the hit of the night! She features a sleeveless surplice v-neck bodice with a cowl back accent, spaghetti straps, side ruched seams, a form-fitting a-line silhouette, and a high-cut side slit along her floor-length hem. Jill is composed of a slinky and sleek knit fabric that contours to your figure. Complete the look in rhinestone earrings and statement heels. 

    Fit & Features

    • Sleeveless, surplice v-neck bodice, spaghetti straps
    • Adhesive bra recommended
    • Side ruched seams, cowl back accent, form-fitting
    • A-line silhouette
    • High-cut side slit, floor-length hem
    • Slinky and sleek knit fabric
    • Fits true to size

    Style Number/Barcode: 05002-2304

    Category Name: $20 & Under Sale

    Price: $29.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Carly Formal Sequin V-Neck Dress

    Special Occasion

    Turn heads in the Carly formal sequin dress sure to leave every room dazzled! She features a sleek, sleeveless, V-neck, bungee spaghetti straps, and a form-fitting silhouette on a mid-length hem. The formal dress is composed of a mesh-lined fabric with minimal stretch. Complete the look in chic hoop earrings and lucite heels.

    Fit & Features

    • Sleeveless V-neck, bungee spaghetti straps
    • Form-fitting silhouette, midi-length hem
    • Back zipper closure
    • Sequin embroidery
    • Mesh-lined fabric, minimal stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1011

    Category Name: $20 & Under Sale

    Price: $29.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Funky Chic Tube Bikini Top

    Funk it up under the sun! Create a retro beachy vibe in this tube bikini top featuring a strapless neckline, removable padding, a center front square ring, and a texture-knit lined fabric with a moderate stretch. Complete the look in the matching bikini bottoms.

    Shop The Matching Bikini Bottoms: Funky Chic Bikini Bottoms

    Fit & Features

    • Strapless neckline
    • Removable padding
    • Center front square ring insert
    • Textured knit-lined fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 07104-0623

    Category Name: $20 & Under Sale

    Price: $4.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Funky Chic Bikini Bottoms

    Funk it up under the sun! Create a retro beachy vibe in this bikini bottom featuring a high-rise waist, cheeky fit, side square ring insets, and a texture-knit lined fabric with a moderate stretch. Complete the look in the matching bikini bottoms.

    Shop The Matching Bikini Top: Funky Chic Tube Bikini Top

    Fit & Features

    • High-rise waist
    • Cheeky fit
    • Side square ring inserts
    • Textured knit-lined fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 07105-0770

    Category Name: $20 & Under Sale

    Price: $4.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Carefree Summer Days Woven Shorts

    These lightweight woven shorts were made for those carefree summer days! They feature a high-rise paper bag waist, a cute tie-front belt, and chic pleated detailing. Style these shorts with a basic bodysuit and slip-on sandals.

    Fit & Features

    • High-rise elasticized paper bag waist
    • Tie-front belt
    • Pleated silhouette
    • Airy gauze fabric, woven inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06303-0165

    Category Name: $20 & Under Sale

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cali Palms Tropical Slit Maxi Skirt

    Embrace the sunshine in this palm tropical skirt perfect for your next adventure! It features a high-rise waist, form-fitting silhouette, and a sexy front slit along the maxi-length hem. Complete your vacay look in espadrille wedges.

    Fit & Features

    • High-rise elasticized waist
    • Form-fitting silhouette
    • Front slit
    • Maxi-length hem
    • Palm tropical print
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06501-0569

    Category Name: $20 & Under Sale

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunday's Best Floral Cutout Dress

    Create a cute look for Sunday brunch in this floral chiffon a-line dress featuring a sleeveless, v-neck, adjustable spaghetti straps, ruffled trim, cutout bodice, and a flowy, short-length hem. Complete the look in heels and a purse.

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Ruffled trimming, back zipper closure
    • Cutout bodice
    • A-line silhouette
    • Flowy, short-length hem
    • Floral chiffon-lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1384

    Category Name: $20 & Under Sale

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale