$20 & Under Sale

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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.

  • Drama Meets Ruffles Tie-Front Top

    Serving sleeves, ties, and ruffles—this set didn’t come to play. The long sleeve crop features a flirty lace-up front. Match the skirt up and cue the compliments.

    Shop The Matching Skirt:

    Fit & Features

    • Slinky knit double-lined stretchy fabric
    • Long fitted sleeves with ruffled cuffs
    • Tie-front design
    • Crop-length hem
    • Runs true to size

    Style Number/Barcode: 06202-000068

    Category Name: $20 & Under Sale

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Rosaline Sequin Open Back Formal Dress

    Special Occasion

    When the spotlight hits, the Rosaline dress does the rest. Designed with a geometric sequin pattern, a sculpted mermaid silhouette, and a daring front slit, this gown delivers high-impact shine with a sleek, confident edge that feels made for a grand entrance.

    Fit & Features

    • Allover geometric sequin embellishment, mesh-lined fabric
    • V-neckline with tank-style straps, padded bra cups
    • Criss-cross open back, hidden zipper with hook-eye closure
    • Fitted mermaid silhouette
    • High front slit
    • Floor length hem
    • Runs true to size

     

    Where to Wear:

    Prom, black tie gala, wedding, red carpet awards, milestone birthday party, formal celebrations, anniversaries

    Style Number/Barcode: 05002-001053

    Category Name: $20 & Under Sale

    Price: $19.97 $99.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wrapped In Shine Rhinestone Cuff Bracelet

    Minimal but make it glam—this rhinestone cuff bracelet wraps your wrist with sleek shine and a touch of sparkle. It’s the kind of piece that takes any look from simple to luxe in seconds.

    Fit & Features

    • Rhinestone-embellished trim
    • Wrapped cuff style

    Style Number/Barcode: 07003-000093

    Category Name: $20 & Under Sale

    Price: $4.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jillian Sequin Slit Long Formal Dress

    Special Occasion

    A sequin scroll pattern brings elegant sparkle to the Jillian formal long dress! She features a curve-flaunting silhouette designed with an alluring high front slit for movement and a floor-length hem for a sophisticated finish.

    This dazzling dress was made for the spotlight! Love the shimmer? Discover more sequin prom dresses or find a sophisticated look in our wedding guest dresses.

    Fit & Features

    • Sequin scroll pattern, mesh fabric, full knit stretchy lining
    • Sleeveless square neckline
    • Adjustable spaghetti straps, padded bust
    • Back zipper and hook-eye closure
    • Form-hugging silhouette, high front slit
    • Floor-length hem
    • Runs true to size

     

    Where to Wear:

    Prom, weddings, and black-tie parties.

    Style Number/Barcode: 05002-9320

    Category Name: $20 & Under Sale

    Price: $19.97 $109.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS

    Product Badge:
    • Sale
  • Gracelyn Satin Corset A-Line Gown

    Special Occasion

    Made for the kind of entrance that quiets a room, the Gracelyn dress stuns in luminous satin with a sculpted corset bodice and sweeping A-line gown silhouette. A softly draped sweetheart neckline and keyhole detail add a chic look for prom nights, galas, and every black-tie moment on your calendar.

    Fit & Features

    • Premium satin fabric, tulle and woven linings
    • Sleeveless sweetheart neckline, pleated wrap-front design, padded bra cups
    • Corset bodice with flexible boning, keyhole cutout
    • Adjustable spaghetti straps
    • Open lace-up back with tie closure, lower back zipper with hook-eye closure
    • Pleated floor-length A-line silhouette, hidden side pockets
    • Runs true to size

     

    Where to Wear:

    Prom, galas, black-tie parties, red-carpet events, and formal affairs.

    Style Number/Barcode: 05005-000020

    Category Name: $20 & Under Sale

    Price: $49.97 $219.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WINE

    Available Size: 3, 5

    Product Badge:
    • Sale
  • Ivana Satin Ball Gown With Pockets

    Special Occasion

    Graceful and effortlessly polished, the Ivana gown is made for entrances that feel timeless and intentional. Smooth satin shapes a strapless silhouette with a folded neckline, structured corset bodice, and a flowing floor-length A-line skirt finished with a V drop waist seam and discreet side pockets.

    Fit & Features

    • Premium satin fabric with tulle and woven linings
    • Strapless foldover neckline, padded bra cups
    • Lace-up back, zipper and hook-eye closure
    • Corset bodice, flexible boning
    • V-shaped drop waist seam, hidden side pockets
    • A-line floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Prom, balls, big birthday events, military balls, galas, black tie occasions, formal milestone celebrations

    Style Number/Barcode: 05005-000022

    Category Name: $20 & Under Sale

    Price: $49.97 $219.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NAVY

    Available Size: 3

    Product Badge:
    • Sale
  • Sultry Glam Cutout Halter Mini Dress

    The mini dress features a paisley burnout pattern, a sleeveless halter neckline with a draped cowl bust, halter neck ties for an adjustable fit, an asymmetrical waist cutout accented with an O-ring, and a ruffled hanky hem trim. Complete night out outfit with chrome heels. 

    Fit & Features

    • Smooth knit fabrication
    • Halter cowl neckline
    • Halter neck ties
    • Asymmetrical waist cutout with o-ring
    • Ruffled hanky trim at the hem
    • Paisley burnout pattern
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05103-5968

    Category Name: $20 & Under Sale

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hot Weather Favorite Bikini Bottoms

    Sun out, confidence on. These bikini bottoms keep it clean and flattering with a barely there fit that feels effortless from shoreline walks to all-day lounging. 

    Shop The Matching Bikini Top: Hot Weather Favorite String Bikini Top

    Fit & Features

    • Smooth swim fabric with a soft stretch feel
    • Hoop inserts
    • Minimal coverage
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000024

    Category Name: $20 & Under Sale

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dazzling Elegance Necklace And Earrings Set

    This elegant necklace and earrings set features sparkling rhinestones that capture and reflect light with brilliance while adding the perfect complement to your formal dress.

    Fit & Features

    • Necklace and earrings set
    • Rhinestone lariat necklace, lobster clasp closure
    • Rhinestone linear earrings, post-back closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07002-000029

    Category Name: $20 & Under Sale

    Price: $4.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Double Trouble Snake Chain Lariat Necklace Set

    Two chains, one goal—steal the spotlight. This snake chain lariat necklace set is your new go-to for stacking drama and drip, whether you’re out for dinner or just feelin’ yourself in selfies.

    Fit & Features

    • Two-pack necklace set
    • Short snake chain
    • Longer snake chain, triangle-shaped center accent, long lariat design
    • Back lobster clasp closures with extenders

    Style Number/Barcode: 07002-000026

    Category Name: $20 & Under Sale

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Plans Faux Leather A-Line Romper

    Plans came up and you’re already ready. This faux leather romper is smooth and fitted on top with a flirty A-line skirt that brings chic movement, perfect for nights out or last-minute invites.

    Fit & Features

    • Faux leather fabric with a smooth finish and high stretch
    • Sleeveless square neckline with tank shoulder straps
    • Side waist tie detail
    • Pleated mini skirt overlay, A-line fit
    • Romper silhouette with built-in hidden shorts
    • Runs true to size

    Style Number/Barcode: 06503-000124

    Category Name: $20 & Under Sale

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jolie Sequin Bead Mermaid Formal Dress

    Special Occasion

    Elegant with a touch of after-dark drama, The Jolie is designed for entrances that feel poised and unforgettable. Crafted in sequin beaded mesh-lined fabric, this mermaid floor length silhouette features a chiffon-lined halter-padded neckline and a fluid tie-back detail that moves beautifully through the evening.

    Fit & Features

    • Sequin beaded mesh-lined fabric
    • Chiffon-lined halter neckline with padded bra cups, tie closure
    • Chiffon tie-back detail, lower zipper and hook-eye closure
    • Mermaid floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Formal weddings, evening galas, black tie events, upscale cocktail receptions, winter formals, romantic destination celebrations, special occasions

    Style Number/Barcode: 05002-000787

    Category Name: $20 & Under Sale

    Price: $19.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Talk Chiffon Flutter Sleeve A-Line Mini Dress

    Soft, sweet, and already on your weekend mood board. This chiffon A-line mini dress features short flutter sleeves and a ruched sweetheart neckline that hugs just right—perfect for brunch, birthdays, and every RSVP that pops up last minute.

    Fit & Features

    • Sheer chiffon fabric with lining
    • Sleeveless sweetheart neckline, ruched bust
    • Short ruffled flutter sleeves, adjustable back straps
    • Open lace-up back design, tie closure
    • Mini-length hem, fitted A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000934

    Category Name: $20 & Under Sale

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Style So Sleek Long Sleeve Knit Bolero

    Get ready to slay in the style so sleek long sleeve knit bolero. With its ultra-cropped hem and open front, this stretchy knit piece is your go-to for effortless chic vibes.

    Fit & Features

    • Smooth knit stretchy fabric
    • Fitted long sleeves
    • Open front design
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-0514

    Category Name: $20 & Under Sale

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: L

    Product Badge:
    • Sale
  • Off Duty Attitude Belted Mini Skort

    Serving cool without even trying. This belted mini skort hugs in all the right places with a sleek, structured feel that’s made for going out or leveling up your everyday look. Style with the matching cropped vest top.

    Shop Matching Top: Off Duty Attitude Zip-Front Cropped Vest Top

    Fit & Features

    • Woven fabric
    • Mid-rise waist
    • Belted design
    • Back zipper closure
    • Mini-length overlay with pleating and grommet trim, A-line fit
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06403-000106

    Category Name: $20 & Under Sale

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: M

    Product Badge:
    • Sale
  • Hotter Than Ever Baseball Cap

    Say less, wear more confidence. This embroidered hat finishes off casual looks with an effortless attitude that feels intentional, not try-hard.

    Fit & Features

    • Soft cotton fabric with structured feel
    • Classic baseball cap silhouette
    • Curved brim for everyday wear
    • Front embroidered Hotter Than Ever text
    • Adjustable back strap

    Style Number/Barcode: 07302-000232

    Category Name: $20 & Under Sale

    Price: $7.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Chaos Mid-Rise Wide Leg Denim Jeans

    These distressed wide leg jeans bring a laidback attitude with ripped details and a relaxed fit. Perfect for pairing with baby tees, oversized blazers, or a little crop moment.

    Fit & Features

    • Medium denim fabric
    • Mid-rise waist
    • Distressed back accents
    • Wide-leg fit
    • Front button closures, belt loop accents
    • Five-pocket styling
    • Runs true to size

    Style Number/Barcode: 06602-000064

    Category Name: $20 & Under Sale

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: MED, DENIM

    Available Size: 11

    Product Badge:
    • Sale
  • Quinn Soutache A-Line Slit Formal Dress

    Special Occasion 

    Striking a balance between romance and refinement, The Quinn dress is designed for moments that call for quiet drama and confident presence. Delicate soutache detailing elevates the flowing A-line silhouette, while the high front slit and bonded floor-length hem create a finish that feels polished and intentional.

    Fit & Features

    • Mesh satin-lined fabric with dimensional soutache detailing
    • V-neckline with adjustable spaghetti straps, padded bra cups
    • Hidden back zipper and hook-eye closure
    • A line silhouette
    • High front slit
    • Bonded floor length hem
    • Runs true to size

     

    Where to Wear:

    Prom, black tie galas, weddings, engagement parties, milestone celebrations, big birthday events, elegant cocktail receptions, red-carpet occasions, formal balls

    Style Number/Barcode: 05002-001495

    Category Name: $20 & Under Sale

    Price: $19.97 $149.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S

    Product Badge:
    • Sale
  • Serving Cool Studded Faux Leather Mini Skirt

    Serving cool without trying too hard. This studded faux leather mini skirt hugs in all the right places with a trendy belted waist and just enough attitude for nights out, rooftop plans, or that last-minute “I need a look” text. Style with the matching vest top.

    Shop Matching Top: Serving Cool Studded Zip-Front Faux Leather Vest Top

    Fit & Features

    • Distressed faux leather fabric
    • Mid-rise waist
    • Asymmetric belted design
    • Back zipper closure
    • Studded trim
    • Mini-length hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06401-000040

    Category Name: $20 & Under Sale

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: CHARCOAL

    Available Size: L

    Product Badge:
    • Sale
  • Go To Denim Wrap Skort

    This denim wrap skort gives mini skirt energy with built-in shorts and a tie detail that keeps it playful and easy with a cute top and sandals.

    Fit & Features

    • Medium denim fabric
    • Mid-rise waist
    • Front pockets
    • Wrap-around adjustable tie design
    • Built-in shorts
    • Form-hugging fit, mini-length hem
    • Runs true to size

    Style Number/Barcode: 06603-000133

    Category Name: $20 & Under Sale

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: MED, DENIM

    Available Size: M, L

    Product Badge:
    • Sale
  • Sapphire Shine Necklace And Earrings Set

    A little sparkle, a lot of drama. This rhinestone necklace and earring set stuns with blue gemstones framed by radiant rhinestone trim—made to shine under the lights.

    Fit & Features

    • Necklace and earrings set
    • Rhinestone trim
    • Colored gemstone insets
    • Necklace has a lobster clasp closure
    • Earrings have a post-back closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07002-000244

    Category Name: $20 & Under Sale

    Price: $4.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Edgy Stunner Grommet Trim Mini Skort

    Unleash your inner fashionista in this faux leather skort for a day or a night out! The high-rise waist flatters your figure while the bodycon fit showcases your curves while the grommet trim along the mini-length hem adds that edgy touch you've been craving.

    Fit & Features

    • Faux leather fabric, shorts lining
    • High-rise waist, belt loop accents
    • Hidden front hook-eye and zipper closure
    • Bodycon silhouette
    • Grommet trim mini-length hem
    • Runs true to size

    Style Number/Barcode: 06403-000016

    Category Name: $20 & Under Sale

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetly Sculpted Floral Mesh Midi Dress

    A dress that knows how to flirt back—soft mesh, blooming prints, and a cowl neckline that moves with a little drama. The wrap detail and curve-hugging skirt follow your shape just right, making this your go-to for nights when you want a look that feels effortless yet unforgettable.

    Fit & Features

    • Floral print, mesh-lined fabric, moderate stretch
    • Cowl neckline, padded bra cups
    • Spaghetti straps
    • Wrap cinched bodice accent
    • Curve-hugging silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000770

    Category Name: $20 & Under Sale

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet On You Strapless Mini Dress

    She’s sweet, sleek, and totally crush-worthy. With its smooth satin-like finish and flirty A-line fit, this strapless mini dress is your go-to for first impressions that last.

    Fit & Features

    • Smooth satin-like knit fabric, bust lining, high stretch
    • Strapless wrap neckline
    • Curve-hugging A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000248

    Category Name: $20 & Under Sale

    Price: $36.90

    Availability: In Stock

    Available Color: LIGHT, BLUE, PINK, MINT

    Available Size: XS, S, M, L

    Product Badge:
    • Sale