$20 & Under Sale

Loading...

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.

  • Polished Edge Ruffle Bouclé Skort

    This bouclé lurex mini skort serves polished-but-playful energy — sparkly woven texture, gold button details, and a flirty ruffle hem that ties the whole “effortlessly chic” vibe together. It’s giving a holiday party, a gallery opening, and any night you want to look expensive without even trying. 

    Shop The Matching Jacket: Polished Edge Crop Bouclé Jacket

    Fit & Features

    • Bouclé lurex woven fabrication, sewn-in lining
    • Mini skort silhouette with flounce ruffle hem
    • Decorative button and pocket detailing
    • Hidden shorts for comfort
    • Back zipper and hook-eye closure
    • Runs true to size

    Style Number/Barcode: 06403-000083

    Category Name: $20 & Under Sale

    Price: $18.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serve It Up Long Sleeve Crop Top

    Low effort, high payoff. This long sleeve top brings sultry vibes without even trying. Made from smooth, stretchy fabric that hugs just right, it’s perfect for layering or stealing the spotlight.

    Fit & Features

    • Smooth knit stretch fabric
    • Plunge V-neckline
    • Fitted long sleeves
    • Cutout square back design
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000482

    Category Name: $20 & Under Sale

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt First Strapless Lace Tiered Mini Dress

    Sweet at first glance, bold once you turn around. This strapless lace mini dress hugs through the bodice and finishes with playful tiered ruffles—made for nights that start casual and end unforgettable.

    Fit & Features

    • Stretch lace-lined fabric with a soft, floral texture
    • Strapless neckline
    • Drop waist silhouette
    • Tiered ruffle skirt
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05102-000557

    Category Name: $20 & Under Sale

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romantic Rebel Lace Cross Choker

    A little romantic, a little rebellious—this lace choker knows how to set the tone. The delicate lace band paired with a cross charm adds instant edge, whether you’re styling it for nights out or layering it into your everyday look.

    Fit & Features

    • Delicate sheer lace
    • Cross charm
    • Lobster clasp closure

    Style Number/Barcode: 07002-000421

    Category Name: $20 & Under Sale

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All The Angles Textured Hoop Earrings

    Minimal effort, maximum polish. These textured hoop earrings add just enough shine and detail to make your everyday fit feel styled in seconds.

    Fit & Features

    • Polished construction
    • Medium hoop silhouette
    • Textured etched front detail
    • Post back closure

     

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

    Style Number/Barcode: 07001-000332

    Category Name: $20 & Under Sale

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love Notes Rose Mesh Maxi Skirt

    Soft, romantic, and impossible to ignore—this skirt feels like a handwritten note you keep rereading. The rose print and fluid maxi length skim your curves for date night.

    Shop Matching Top: Love Notes Rose Strapless Mesh Corset

    Fit & Features

    • Sheer mesh fabrication, knit lining
    • Mid-rise waist
    • Contrasting rose pattern
    • Fitted bodycon silhouette
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 06501-000109

    Category Name: $20 & Under Sale

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Classic Americana Crochet Sweater

    Cue the backyard invites and rooftop sunsets. This Americana crochet sweater brings that laidback cool with its airy knit and American flag graphic—perfect for tossing over denim cutoffs or a bikini when the night cools down.

    Fit & Features

    • Open crochet knit fabric
    • Wide crew neckline
    • Long sleeves
    • Front American flag graphic
    • Mid-length hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06005-000347

    Category Name: $20 & Under Sale

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Spur Floral Cowboy Hat

    Western, but make it flirty. This tea-stained straw cowboy hat features a feminine floral band with soft embroidery detailing for the perfect mix of rugged and romantic. Top off your look for festivals, concerts, and bachelorettes!

    Fit & Features

    • Straw material
    • Wide curved brim with floral embroidery, tea-stained finish
    • Floral embroidered band and beaded designs
    • Tea-stained finish top

    Style Number/Barcode: 07302-000310

    Category Name: $20 & Under Sale

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Seaside Rodeo Shell Cowboy Hat

    Coastal cowgirl is calling. This woven straw cowboy hat features a shell-trim band with subtle rope detail, giving beachy energy with a western twist—perfect for vacations, festivals, or sunny day styling.

    Fit & Features 

    • Seashell trimmed band with string tie
    • Wide curved brim
    • Classic cowboy hat silhouette
    • Straw material

    Style Number/Barcode: 07302-000313

    Category Name: $20 & Under Sale

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Escape Straw Cowboy Hat

    Easy, effortless, and made for sun-soaked days. This woven straw cowboy hat features a breezy open weave and a braided tie with fringe detail for that laid-back western vibe that goes from beach to festival without missing a beat.

    Fit & Features

    • Straw material
    • Structured cowboy hat silhouette
    • Open weave design
    • Braided tie detail with fringe ends
    • Curved wide brim
    • Adjustable inner strings for a snug fit

    Style Number/Barcode: 07302-000311

    Category Name: $20 & Under Sale

    Price: $12.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tania Sequin Bodycon Mini Dress

    Special Occasion

    Bring the shine and dazzle on the dance floor in the Tania sequin bodycon mini dress. She features a sleeveless scoop neckline, bungee spaghetti straps, a short, curve-hugging silhouette, and all-over sequin embroidery in a chic scroll pattern that will catch the light. The sheer mesh fabric features a full knit lining. Style with strappy stilettos for the perfect prom look.

    Fit & Features

    • Sleeveless scoop neckline
    • Strapless or adhesive bra recommended
    • Bungee spaghetti straps
    • Mini-length hem, fitted bodycon silhouette
    • Sequin embroidery, scroll pattern
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05001-1096

    Category Name: $20 & Under Sale

    Price: $29.97 $66.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Layne Square Neck Slim Mesh Formal Dress

    Special Occasion

    Sultry and sophisticated, the Layne mesh formal dress is a stunning option for bridesmaids, wedding guests, or attending a banquet! Featuring a sleeveless square neckline and shoulder straps, this dress is designed to flatter your figure with flexible boning and side-ruched seams. The slim silhouette and high side slit add a touch of sophistication, while the long length hem and mesh-lined fabric exude chic. Complete the look with earrings and block heels.

    Fit & Features

    • Mesh fabric, stretchy knit lining
    • Square neckline, shoulder straps
    • Back zipper and hook-eye closure
    • Flexible boning
    • High side slit
    • Slim silhouette
    • Runs true to size

    Style Number/Barcode: 05002-8519

    Category Name: $20 & Under Sale

    Price: $19.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Confidence Slinky Knit Halter Mini Dress

    Neckline doing the most, effort doing the least. This slinky knit halter mini dress drapes effortlessly up top and sculpts through the body, giving you that sleek, pulled-together feel for nights out.

    Fit & Features

    • Slinky knit fabric with knit lining, high stretch
    • Sleeveless plunging cowl neckline, grommet trim
    • Halter strap, elastic back detail
    • Open back, lower tie-back spaghetti straps
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000793

    Category Name: $20 & Under Sale

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RUST

    Available Size: XS

    Product Badge:
    • Sale
  • Kara Formal Floral High-Slit Mermaid Dress

    Special Occasion

    For the evening when elegance feels instinctive, The Kara stuns in floral lace with a sculpted mermaid silhouette and a striking front slit that reveals just the right amount of movement. Beaded sequins shimmer across the V-neck bodice and delicate straps, creating a look that feels refined, romantic, and unforgettable from ceremony to last dance.

    Fit & Features

    • Floral lace fabric with a smooth knit lining
    • Sleeveless V-neckline with adjustable spaghetti straps
    • Padded bra cups
    • Lace-up back with lower zipper and hook-eye closure
    • High front-slit
    • Fitted mermaid silhouette
    • Runs true to size

     

    Where to Wear:

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

    Style Number/Barcode: 05002-001512

    Category Name: $20 & Under Sale

    Price: $19.97 $129.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE, PRINT

    Available Size: XS

    Product Badge:
    • Sale
  • Hallie Rosette Lace-Up Skater Dress

    Special Occasion

    The Hallie formal skater dress is for the nights that feel straight out of a fairy tale. With a flouncy rosette mesh design and playful skater silhouette, this lace-up-back dress was made for twirling, flirting, and making unforgettable entrances.

    Fit & Features

    • Sheer mesh fabric with all-over rosette appliques
    • Layered tulle and stretchy knit linings
    • Sleeveless square neckline, no-slip strip, padded bust
    • Adjustable spaghetti straps
    • Open lace-up back design, hidden lower back zipper with hook-eye closure
    • Mini-length hem, fit-and-flare skater silhouette
    • Runs true to size

     

    Where to Wear:

    Homecoming, birthday celebrations, garden parties, bridal showers, and bachelorette parties.

    Style Number/Barcode: 05001-000046

    Category Name: $20 & Under Sale

    Price: $39.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alanna Ruffled Lace Corset Mermaid Dress

    Special Occasion

    Showcase your romantic flair in the Alanna formal mermaid dress that features a sleeveless sweetheart neckline with a built-in padded bust, a chic corset bodice, and adjustable spaghetti straps detailed with cascading ruffled accents. The floor-length mermaid silhouette will hug your stunning curves. Complete your look with dainty duster earrings.

    This dress is all about movement and flair. Want more standout designs? Discover our eye-catching ruffle prom dresses or embrace an elevated style with our guest dresses.

    Fit & Features

    • Sheer floral lace fabric with knit lining, moderate stretch
    • Sweetheart neckline with padded bust, no-slip strip
    • Corset bodice, angled high waist seam
    • Back zipper with hook-eye closure
    • Adjustable spaghetti straps, ruffled accents
    • Floor-length mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05002-8737

    Category Name: $20 & Under Sale

    Price: $19.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ruby Floral Sequin Halter Mini Dress

    Special Occasion

    Flirt with the spotlight in the Ruby dress—a mini that shimmers with floral sequin detail and soft draping at the halter cowl neckline. The bodycon fit sculpts and shines, made for the kind of night that lingers.

    Fit & Features

    • Floral sequin pattern, mesh fabric lined with stretchy knit
    • Cowl halter neckline, padded bra cups
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Bodycon fit, mini-length hem
    • Runs true to size

     

    Where to Wear:

    Homecoming, birthdays, milestone events, Vegas, bachelorettes, glam parties, date nights

    Style Number/Barcode: 05001-000333

    Category Name: $20 & Under Sale

    Price: $59.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crystal Sequin Rose Tie Mini Dress

    Special Occasion

    Every detail catches the light in the Crystal mini dress, adorned with a shimmering sequin rose pattern. A flattering V-neckline meets a soft chiffon tie-back, blending sultry allure with a touch of romantic ease.

    Fit & Features

    • Rose sequin pattern, mesh fabric, stretch knit lining
    • V-neckline, padded bra cups
    • Adjustable spaghetti straps
    • Chiffon tie back, zipper and hook-eye closure
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

     

    Where to Wear:

    Homecoming, birthdays, weddings, milestone celebrations, date nights, rooftop hotel bars, red carpet events, fancy brunches

    Style Number/Barcode: 05001-000307

    Category Name: $20 & Under Sale

    Price: $29.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sydney Sequin Bead Lace-Up Mini Dress

    Special Occasion

    Shimmer with every step in the Sydney sequin bead mini dress that pairs a sleek, fitted silhouette with a striking lace-up back. Designed to catch the light and highlight your shape, it’s a true showstopper from every angle.

    Fit & Features

    • Sequin, beaded, embellished, mesh-lined fabric
    • Square neckline
    • Adjustable spaghetti straps
    • Lace-up back, zipper and hook-eye closure
    • Bodycon fit, mini-length hem
    • Runs true to size

     

    Where to Wear:

    Homecoming, birthdays, milestone celebrations, date nights, bachelorettes, bridal showers, fancy brunches, rooftop hotel bars, parties

    Style Number/Barcode: 05001-000308

    Category Name: $20 & Under Sale

    Price: $39.97 $89.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mildred Flocked Velvet Strappy Mermaid Formal Dress

    Special Occasion

    Romantic meets refined in the Mildred formal dress—a figure-skimming gown that feels equal parts timeless and daring. Crafted from floral flocked mesh with a sweetheart neckline and delicate straps, its lace-up open back adds a sultry twist, while the mermaid silhouette moves with effortless elegance from every angle.

    Fit & Features

    • Flocked velvet mesh-lined fabric
    • Sweetheart neckline
    • Adjustable spaghetti straps
    • Lace-up open back for a custom fit, lower zipper and hook-eye closure
    • Mermaid silhouette
    • Floor-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, formal galas, upscale dinner parties, engagement parties, red-carpet nights, anniversaries, fancy milestone celebrations

    Style Number/Barcode: 05002-000574

    Category Name: $20 & Under Sale

    Price: $19.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ashlynn Open Back Ruched Mermaid Formal Dress

    Special Occasion

    Have everyone swooning over you in the Ashlynn mermaid formal dress as a stunning bridesmaid or wedding guest! Made from a mesh fabric lined with stretchy knit, this formal dress is perfect for any fancy occasion. With a flattering square neckline, shoulder straps, and a pleated bodice, this dress enhances your figure. The open back with a tie closure adds a touch of allure while the front ruched seam, high slit, and mermaid silhouette add a modern twist.

    Fit & Features

    • Mesh fabric lined with stretchy knit
    • Square neckline, shoulder straps, padded bra cups
    • Pleated bodice
    • Open back with tie closure
    • Front high slit
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05002-8604

    Category Name: $20 & Under Sale

    Price: $29.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Kaylie V-Neck Bodycon Sequin Bead Formal Dress

    Special Occasion

    Designed to dazzle, the Kaylie sequin bead formal dress is ultra glamorous and ready to have a picture taken! Strut looking fabulous in the flattering bodycon silhouette that effortlessly flares into a floor-length hem for drama.

    Fit & Features

    • Sequin bead embellishments, mesh fabric, stretch knit lining
    • V-neckline, padded bra cups
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Floor-length hem
    • Runs true to size

     

    Where to Wear:

    Prom, weddings, black tie galas, big birthday events, red-carpet functions, fancy dinner parties

    Style Number/Barcode: 05002-9589

    Category Name: $20 & Under Sale

    Price: $69.97 $159.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Arie Strapless Rhinestone A-Line Party Dress

    Special Occasion

    This strapless party dress features a flattering A-line silhouette with a ruffled short-length hem for a flirtatious allure. The glitter rhinestone embellished mesh fabric offers a sparkling look at the school dance or birthday party.

    Fit & Features

    • Glitter rhinestone mesh fabric lined with stretchy knit
    • Strapless neckline, padded bra cups
    • Back zipper and hook-eye closure
    • Flexible boning
    • A-line ruffled short-length silhouette
    • Runs true to size

    Style Number/Barcode: 05001-2348

    Category Name: $20 & Under Sale

    Price: $29.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Nyssa Strapless Slit Mermaid Formal Dress

    Special Occasion

    Designed to steal the spotlight, the Nyssa strapless gown features a ruched bust, mermaid fit, and a daring thigh-high slit. Equal parts sultry and sophisticated, it’s a look that guarantees unforgettable entrances.

    Fit & Features

    • Foil sheen knit fabric, stretchy knit lining
    • Strapless neckline, padded bra cups, ruched bust
    • High front slit
    • Mermaid silhouette
    • Floor-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, black tie galas, cocktail parties, red-carpet events, romantic dinner dates, formal celebrations, engagement parties, rehearsal dinners, anniversaries

    Style Number/Barcode: 05002-000266

    Category Name: $20 & Under Sale

    Price: $19.97 $59.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S

    Product Badge:
    • Sale