$20 & Under Sale

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.

  • Emmy Floral Cutout Formal Dress

    Special Occasion

    The Emmy dress is designed for moments when the room feels just a little brighter. Featuring a statement floral print and a sleek, floor-length mermaid silhouette, this strapless dress turns to reveal a striking cutout back with a hoop-strap insert for a modern, unforgettable finish.

    Fit & Features

    • Statement floral print, knit-lined fabric
    • Strapless neckline, non-slip grip lining
    • Hidden side zipper with hook-eye closure
    • Mermaid floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Prom, cocktail soirees, summer galas, destination celebrations, honeymoons, vacations, anniversary dinners, milestone parties, graduations

    Style Number/Barcode: 05002-000878

    Category Name: $20 & Under Sale

    Price: $19.97 $79.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M

    Product Badge:
    • Sale
  • Vintage Crush Statement Belt

    This statement belt pulls everything together with bold hardware and vintage-inspired details that instantly make denim, dresses, and basics feel styled.

    Fit & Features

    • Ornate statement buckle
    • Hoop and stud inserts
    • Medallion accents
    • Faux leather material

    Style Number/Barcode: 07301-000456

    Category Name: $20 & Under Sale

    Price: $11.97 $23.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hot Weather Favorite String Bikini Top

    Sun out, confidence on. These string 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 Bottoms: Hot Weather Favorite Bikini Bottoms

    Fit & Features

    • Smooth swim fabric with a soft stretch feel
    • Halter triangle bust design
    • Removable padding for support and shaping
    • Adjustable string ties for a customizable fit
    • Hoop inserts
    • Runs true to size

    Style Number/Barcode: 07104-000016

    Category Name: $20 & Under Sale

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Tropical Strappy Formal Dress

    Special Occasion

    The Summer dress pairs a sleek satin mermaid fit with a bold tropical floral print that feels equal parts polished and unforgettable. Mini rhinestone embellishments catch the light with every step, while the strappy back detail adds an unexpected, head-turning finish.

    Fit & Features

    • Tropical floral print, smooth-lined knit fabric with stretch
    • Mini rhinestone embellishments
    • Strapless neckline, non-slip grip lining, padded bra cups
    • Bungee strappy back with mini hoop inserts
    • Mermaid floor-length silhouette
    • Runs true to size

    Where to Wear:

    Destination weddings, honeymoons, vacations, resorts, outdoor soirees, prom

    Style Number/Barcode: 05002-001532

    Category Name: $20 & Under Sale

    Price: $19.97 $74.90

    On Sale: Yes

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS

    Product Badge:
    • Sale
  • Seaside Whisper Shell Charm Bikini Bottoms

    Make a splash in this dreamy triangle bikini top, featuring a soft flocked texture that gives effortless coastal-cool energy. Finished with a delicate shell charm at the center, it’s the prettiest little detail for your next sun-kissed moment. 

    Shop The Matching Top: Seaside Whisper Shell Charm Bikini Top
    Shop The Matching Cover Up:
    Seaside Whisper Cover Up Skirt

    Fit & Features

    • Flocked texture-lined fabric
    • Low-rise V-cut waist
    • Adjustable side ties
    • Cheeky bottom
    • Shell charm accent
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000017

    Category Name: $20 & Under Sale

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: L

    Product Badge:
    • Sale
  • Rodeo Star Studded Cowboy Hat

    This cowboy hat brings just enough western energy to feel styled without overdoing it. The star medallion and stud accents give it that extra detail moment your look has been waiting for.

    Fit & Features

    • Structured cowboy hat silhouette
    • Studded faux leather band, star medallion, studs, and colored rhinestones
    • Fringe tie-back 
    • Adjustable inner strings for a snug fit
    • Smooth faux suede material

    Style Number/Barcode: 07302-000256

    Category Name: $20 & Under Sale

    Price: $13.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Something Sweet And Chic Bow Mini Dress

    Clean, feminine, and made for milestone moments. This bow strap mini dress features a sleek A-line silhouette with delicate, cascading bow details that feel sweet—perfect for bridal events, graduations, sorority events, and birthdays worth celebrating in style.

    Fit & Features

    • Satin woven fabric, woven lining
    • Scoop neckline
    • Adjustable spaghetti straps with cascading bow details
    • A-line silhouette
    • Open back design, lower zipper and hook-eye closure
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000929

    Category Name: $20 & Under Sale

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lowkey Wild Abstract Leopard Bustier Top

    Quietly bold but absolutely intentional. This abstract leopard bustier pulls the whole look together with a snatched fit and just enough edge to pair with jeans and attitude.

    Fit & Features

    • Knit fabric with abstract leopard print
    • Structured bustier silhouette with built-in boning
    • Square neckline, adjustable spaghetti straps
    • Lace up back for a customizable fit
    • Fitted angled crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000452

    Category Name: $20 & Under Sale

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heatwave Mood Bikini Bottoms

    Bring the heat in these bikini bottoms that sit high on the hips with side ties to adjust the fit and a cheeky bottom to flaunt your curves. Pair with the matching bikini top.

    Shop Matching Top: Heatwave Mood Bikini Top

    Fit & Features

    • Sleek knit fabric, high stretch
    • Low-rise waist
    • Adjustable side ties with beaded accents
    • Cheeky bottom
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000043

    Category Name: $20 & Under Sale

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: In Stock

    Available Color: SAGE

    Available Size: L

    Product Badge:
    • Sale
  • Sweet Heat Floral Chiffon Mini Dress

    This floral mini dress is flirty, a little bold, and made for vacations, weekend plans, and showers. The halter tie and front cutout bring the drama, while the soft ruffles and A-line fit keep it balanced and feminine. 

    Fit & Features

    • Floral print, chiffon-lined fabric
    • Halter sweetheart neckline, tie straps
    • Cutout side and back
    • Ruffled detailing
    • A-line fit, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000708

    Category Name: $20 & Under Sale

    Price: $35.00 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED

    Available Size: L

    Product Badge:
    • Sale
  • Chic Bloom Flocked Floral Velvet Midi Dress

    For nights that demand something unforgettable. This flocked floral velvet midi dress hugs every curve with a sultry halter neckline and sleek, body-loving fit.

    Fit & Features

    • Sheer mesh fabric with knit lining, moderate stretch
    • Velvet flocked floral pattern
    • Sleeveless plunging neckline, U-wired design
    • Tie-back halter straps
    • Partially open back, lower zipper closure
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000758

    Category Name: $20 & Under Sale

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Out West Mood Buckle Cowboy Hat

    A little western, a lot of attitude. This cowboy hat brings that structured shape with a sleek buckle detail, that tops off your outfit for festivals, concerts, and rodeos!

    Fit & Features

    • Structured faux suede material
    • Classic cowboy hat silhouette
    • Curved brim with shaped crown
    • Adjustable inner strings for a snug fit
    • Faux leather buckle strap band

    Style Number/Barcode: 07302-000318

    Category Name: $20 & Under Sale

    Price: $12.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Outlaw Flare Studded Cowboy Hat

    Not your sweet little western moment—this one’s got edge. This studded cowboy hat brings bold attitude with a structured fit that instantly levels up any look.

    Fit & Features

    • Studded embellished trim
    • Structured cowboy hat silhouette
    • Wide brim

    Style Number/Barcode: 07302-000254

    Category Name: $20 & Under Sale

    Price: $4.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shine On Repeat Rhinestone Hand Chain Bracelet Set

    Subtle? Never heard of her. This rhinestone layered hand chain bracelet set stacks the shine with mixed chains and a draped silhouette that catches every flick of your wrist.

    Fit & Features

    • Three separate bracelets, one hand chain
    • Varying chain designs
    • Rhinestone embellishments
    • Lobster clasp closures with extenders

    Style Number/Barcode: 07003-000221

    Category Name: $20 & Under Sale

    Price: $4.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Divine Duo Layered Charm Necklace

    Shine with intention in this gorgeous layered necklace featuring a radiant cross charm paired with a classic medallion pendant. The mix of delicate chains and polished gold tones gives you that effortlessly-styled, elevated look without even trying.

    Fit & Features

    • Layered beaded chain design 
    • Gold-tone chains in varying lengths
    • Cross charm + oval medallion pendant
    • Lobster clasp closure

    Style Number/Barcode: 07002-000315

    Category Name: $20 & Under Sale

    Price: $4.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • City Crush Faux Suede Bomber Jacket

    Soft texture, bold attitude—this one knows how to show up. The faux suede bomber crop jacket delivers effortless structure with a bubble hem that makes any outfit feel styled on purpose.

    Fit & Features

    • Smooth faux suede fabric, sewn-in woven lining
    • Collar neckline
    • Long sleeves
    • Front hidden zip-up closure
    • Bubble crop hem
    • Runs true to size

    Style Number/Barcode: 06204-000113

    Category Name: $20 & Under Sale

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Crush Hoop Halter Crop Top

    When you want to bring a little chaos—in the cute way—this halter crop top steps in with all the confidence of a bold-print moment. Light, flouncy, and ready for any night you decide to turn up the charm.

    Shop The Matching Skort: Wild Crush Ruffle Mini Skort

    Fit & Features

    • Sheer mesh fabrication with animal print
    • Strapless neckline with halter strap featuring dual gold-tone O-ring hardware
    • Ruched bodice creating a fitted silhouette
    • Cropped hemline
    • Runs true to size

    Style Number/Barcode: 06001-000379

    Category Name: $20 & Under Sale

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Power Moment Sequin Velvet Hot Shorts

    The kind of hot shorts you reach for when you want your outfit to flirt a little. The velvet base and all-over sequin shimmer make every step feel like you’re walking into your next power moment.

    Fit & Features

    • Velvet fabric
    • All-over sequin embroidery
    • High-rise waist
    • Cheeky form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06503-000184

    Category Name: $20 & Under Sale

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Steffanie Floral Chiffon Formal Dress

    Special Occasion

    The Steffanie dress brings romance to every RSVP. Crafted from airy chiffon with a floral print, this flowing A-line gown features an asymmetrical neckline, cascading tiered ruffles, and a striking open-back detail that moves beautifully with every step.

    Fit & Features

    • Floral print, chiffon fabric, lined
    • One-shoulder neckline
    • Side zipper and hook-eye closure
    • Dual spaghetti straps
    • Open strappy detail
    • Tiered ruffled A-line silhouette, floor-length hem
    • Runs true to size

     

    Where to Wear:

    Outdoor weddings, bridal celebrations, baby showers, engagement photoshoots and parties, birthday brunches, garden parties, anniversaries, honeymoons, vacations, and summer galas.

    Style Number/Barcode: 05002-001663

    Category Name: $20 & Under Sale

    Price: $19.97 $139.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE, PRINT

    Available Size: XS, S

    Product Badge:
    • Sale
  • Juliet Glitter Sequin Mermaid Ball Gown

    Special Occasion

    Designed for evenings that linger in memory, the Juliet brings sculpted glamour with a confident edge. Glitter sequin mesh shapes a floor-length mermaid silhouette, featuring a strapless sweetheart neckline, subtle front bust cutouts, and a lace-up back finished with a bonded hem for a clean, fluid line.

    Fit & Features

    • Glitter sequin mesh fabric, tulle and woven linings
    • Strapless sweetheart neckline with front bust cutouts, padded bra cups
    • Back zipper and hook-eye closure
    • Lace up back
    • Mermaid floor-length silhouette with bonded hem
    • Runs true to size

     

    Where to Wear:

    Prom, big birthday events, galas, balls, luxury black tie occasions, milestone celebrations, red-carpet events

    Style Number/Barcode: 05005-000008

    Category Name: $20 & Under Sale

    Price: $49.97 $219.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stand Out At Sundown Concho Chain Belt

    This eye-catching belt features striking square concho details with sleek chain elements for the perfect Western charm and style!

    Fit & Features

    • Square concho plates
    • Chain
    • Lobster clasp closure

    Style Number/Barcode: 07301-000022

    Category Name: $20 & Under Sale

    Price: $4.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Annalise Floral Embroidered Satin Gown

    Special Occasion

    Designed for nights that call for a little drama, the Annalise satin gown glides with a polished ease that feels straight out of a red-carpet moment. Floral embroidered satin shapes this gorgeous dress, blending soft romance with a confident, formal silhouette made for unforgettable entrances.

    Fit & Features

    • Premium satin fabric with full-length woven lining, no stretch
    • Tulle lining for added volume
    • Sleeveless sweetheart neckline with V-wired center accent, padded bust
    • Corset-style bodice with flexible boning, floral embroidery with rhinestone embellishments
    • Adjustable spaghetti straps, lace-up back, lower back zipper with hook-eye closure
    • Floor-sweeping A-line silhouette, pleated detailing, hidden lined side pockets
    • Runs true to size

     

    Where to Wear:

    Prom, galas, black-tie parties, red-carpet events, and fancy soirees.

    Style Number/Barcode: 05005-000014

    Category Name: $20 & Under Sale

    Price: $49.97 $239.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Soft Curve High Slit Midi Tube Dress

    Serving soft curves with a little edge—this one knows exactly what it’s doing. The midi tube dress hugs in all the right places with a high slit that makes every step feel intentional.

    Fit & Features

    • Ribbed cotton-blend knit fabric, high stretch
    • Strapless sweetheart neckline, knot-front design
    • High-cut side slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000665

    Category Name: $20 & Under Sale

    Price: $19.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Anaya Lace Open Back Formal Dress

    Special Occasion

    The Anaya dress is pure evening romance, designed to feel timeless yet undeniably captivating as it moves with you. Delicate lace, a sweetheart neckline, and an open back with tie come together in a fitted mermaid silhouette that feels elegant, confident, and unforgettable.

    Fit & Features

    • Lace fabric with full knit lining
    • Sweetheart neckline with spaghetti strap tie, underwire bust
    • Fitted lace bodice with open back cutout, lower zipper and hook-eye closure
    • Defined waist with contoured shaping
    • Floor-length mermaid skirt
    • Runs true to size.

     

    Where to Wear:

    Weddings, evening galas, seasonal celebrations, formal dinners, upscale receptions, elegant soirees, milestone celebrations, destination vacations, honeymoons, red-carpet occasions

    Style Number/Barcode: 05002-000724

    Category Name: $20 & Under Sale

    Price: $19.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale