$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.

  • Fab Icon Butterfly Rhinestone Stiletto Heels

    A showstopping stiletto heel adorned with a whimsical rhinestone butterfly accent on sleek metallic that turns heads! 

    Fit & Features

    • Stiletto heel
    • Square toe
    • Rhinestone-embellished twist toe straps
    • Rhinestone-embellished ankle support strap
    • Adjustable ankle strap, buckle closure, rhinestone butterfly accent
    • Metallic faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000181

    Category Name: $20 & Under Sale

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Star Cheerleader Four-Piece Costume Set

    Serve squad glamour and bring the star cheerleader look together with a four-piece set made for Halloween. The tie-front top, cropped vest, belt, and shorts create a cute blue-and-white uniform-inspired look with star details and fringe trim.

    Fit & Features

    • Four-piece costume set
    • Smooth knit top with collared V-neckline, tie-front design, long sleeves with tapered hems, and fitted ultra-cropped hem
    • Smooth knit vest with embroidered star patches, fringe trim, and cropped hem
    • Smooth knit hot shorts with low-rise waist, belt loops, and cheeky, form-hugging fit
    • Woven belt with embroidered star patches, buckle, and grommet details
    • Runs true to size
    • Please note the pom-poms and boots are not included

     

    How to style for Halloween: Complete the star cheerleader costume with the metallic pom-poms and knee-high cowboy boots for a look that slays.

    Style Number/Barcode: 06503-000068

    Category Name: $20 & Under Sale

    Price: $9.97 $79.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: L/XL

    Product Badge:
    • Sale
  • Point Made Buckle Strap Sling-Back Pumps

    When your shoes do all the talking—you just strut. These sling-back pumps feature a glossy finish and block heel that serve just-right drama for dressing up your everyday.

    Fit & Features

    • Block heel
    • Patent faux leather material
    • Closed pointed toe
    • Thin adjustable strap with buckle
    • Thin sling-back strap with buckle
    • Runs true to size

    Style Number/Barcode: 07401-000197

    Category Name: $20 & Under Sale

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alayna Satin V-Neck Mermaid Formal Dress

    Special Occasion

    Elegantly effortless, the Alayna drapes in satin with a refined V-neckline that sets the tone for a beautifully fluid moment. The open strappy back and mermaid floor-length silhouette bring soft drama and movement, creating a look designed for polished, unforgettable celebrations.

    Fit & Features

    • Satin fabric with smooth, fluid drape
    • V-neckline with slim adjustable straps
    • Open strappy back with sleek cowl drape
    • Mermaid floor length silhouette
    • Runs true to size

     

    Where to Wear:

    Weddings, formal holiday soirees, black tie galas, anniversaries, luxe date nights, dressy birthday events, engagement parties, rehearsal dinners, winter formals, red-carpet nights, opera or theatre nights, destination celebrations, resort dinners

    Style Number/Barcode: 05002-000779

    Category Name: $20 & Under Sale

    Price: $29.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Sparkle Glitter Tube Mini Dress

    All eyes, all on you. This glitter strapless mini hugs every curve and stuns with an open draped back—made for nights that start with champagne and end on the dance floor.

    Fit & Features:

    • Stretch glitter knit fabric, knit lining
    • Strapless tube neckline
    • Bodycon silhouette
    • Open back with bar detail, lower ruched seam
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000421

    Category Name: $20 & Under Sale

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED, LIGHT, BLUE

    Available Size: L, XS, S, M

    Product Badge:
    • Sale
  • Checking In Chiffon Mini Dress

    This ruffle chiffon mini dress was made for resorts, celebrations, and every vacation photo that somehow becomes your favorite. Just add sandals and oversized sunnies.

    Fit & Features

    • Chiffon fabric, smooth lining
    • Square neckline
    • Adjustable spaghetti straps
    • Ruffled A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001178

    Category Name: $20 & Under Sale

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Cut to the Chase Ruched Tube Mini Dress

    Serving just the right amount of sass, this strapless mini dress knows how to work a room. With a flirty cutout and curve-hugging ruching, it’s basically your secret weapon for any night out.

    Fit & Features

    • Smooth knit fabric with stretch, knit lining
    • Tube neckline with center cutout
    • Knot detail at bust
    • Bodycon ruched silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000389

    Category Name: $20 & Under Sale

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Brittany Satin Column Formal Dress

    Special Occasion

    The Brittany satin column gown moves with sleek, sculpted ease and just the right hint of drama. Featuring a high halter neckline with statement gem rhinestone straps, an open back, and dual high slits, it’s the kind of look that makes an entrance without trying too hard.

    Fit & Features

    • Premium satin fabric, knit stretchy lining
    • High halter neckline
    • Statement gem rhinestone chain, adjustable spaghetti straps
    • Open back design, lower hidden zipper and hook-eye closure
    • Dual high slits
    • Column long-length silhouette
    • Runs true to size

     

    Where to Wear:

    Prom, black tie occasions, weddings, galas, upscale cocktail parties, birthday dinners, graduations, formal celebration parties, rehearsal dinners, engagement parties, elegant bridal showers, garden parties

    Style Number/Barcode: 05002-001020

    Category Name: $20 & Under Sale

    Price: $29.97 $69.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M

    Product Badge:
    • Sale
  • Sleek Trendy Buckle Strap Slingback Kitten Heels

    Sleek and so on-trend, these slingback kitten heels will level up your 'fits with the closed pointed toe and bold buckle strap design.

    Fit & Features

    • 2" Stiletto kitten heel
    • Closed pointed toe
    • Buckle strap design
    • Slingback strap
    • Cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-000193

    Category Name: $20 & Under Sale

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alexa Rhinestone And Pearl Lace-Up Mini Dress

    Special Occasion

    Sparkle with every step—the Alexa rhinestone and pearl mini dress brings instant glam with its curve-skimming silhouette and delicate lace-up back. Designed to dazzle, it’s the perfect look for nights that call for shine.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Rhinestone and faux pearl embellishments, diamond pattern
    • Sleeveless V-neckline, padded bust
    • Adjustable spaghetti straps
    • Open lace-up back design, tie closure
    • Mini-length bodycon silhouette
    • Runs true to size

     

    Where to Wear:

    Homecoming, birthday celebrations, bachelorette parties, dressed-up dinners, and glam nights out.

    Style Number/Barcode: 05001-000429

    Category Name: $20 & Under Sale

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Poolside Pretty Butterfly Belly Chain

    This delicate layered belly chain features dainty butterfly charms that catch the light with every step, adding an effortless finishing touch to swimsuits, low-rise denim, and vacation-ready looks.

    Fit & Features

    • Dainty butterfly charms
    • Layered design
    • Lobster clasp closure

    Style Number/Barcode: 07002-000407

    Category Name: $20 & Under Sale

    Price: $3.97 $12.90

    On Sale: Yes

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

    Product Badge:
    • Sale
  • Too Chic To Quit Sling-Back Pumps

    She’s giving vintage chic with a modern twist. These patent faux leather sling-back pumps are all about that buckle detail, block heel, and padded insole comfort you’ll want from day to night.

    Fit & Features

    • Block heel
    • Patent faux leather material
    • Closed pointed toe
    • Thin adjustable strap across the foot, buckle detail
    • Thin adjustable sling-back strap, buckle detail
    • Padded insole
    • Runs true to size

    Style Number/Barcode: 07401-000198

    Category Name: $20 & Under Sale

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shine Bright Metallic Thong Kitten Heels

    Shine loud without saying a word—these heels were made for the spotlight. The square toe and delicate straps give flirty vibes with just the right touch of glam.

    Fit & Features

    • 3" Kitten heel
    • Square toe
    • Strappy thong silhouette
    • Cushioned insole
    • Metallic faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000545

    Category Name: $20 & Under Sale

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Mood Metal Oval Sunglasses

    Small frames, big attitude. These oval sunglasses deliver a sleek retro vibe while blocking 100% UV, making them the effortless finishing touch for sunny day fits.

    Fit & Features

    • Metal trim oval frames
    • Tinted lenses
    • Rubber nose supports
    • 100% UV protection

    Style Number/Barcode: 07008-000116

    Category Name: $20 & Under Sale

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Kaida Sleeveless Slit Mermaid Formal Dress

    Special Occasion

    Sleek and striking, the Kaida long formal dress offers a simply chic style with a flattering mermaid silhouette and high front slit giving effortless flair!

    Channel elegance in this stunning dress. Loving rich hues? Explore our bold green prom dresses or make a statement in our elevated formal dresses.

    Fit & Features

    • Stretch knit fabric lined with knit
    • Square neckline, padded bra cups
    • Adjustable spaghetti straps, back zipper and hook-eye closure
    • High front slit
    • Mermaid silhouette
    • Floor-length hem
    • Runs true to size

     

    Where to Wear:

    Prom, weddings, bridesmaids, dinner parties, milestone celebrations, cocktail soirees

    Style Number/Barcode: 05002-9211

    Category Name: $20 & Under Sale

    Price: $39.97 $79.90

    On Sale: Yes

    Availability: In Stock

    Available Color: GREEN

    Available Size: XS, S

    Product Badge:
    • Sale
  • Out Of Office Gradient Oversized Sunglasses

    These sunnies say “catch me on a yacht”—even if it’s just brunch. With oversized gradient lenses and glam hardware, these sunglasses are made for low-effort luxe and spontaneous selfies.

    Fit & Features

    • Rimless square-shaped oversized design
    • Metal chain-link detail on the arms
    • Flexible nose pads
    • Gradient-tinted lenses

    Style Number/Barcode: 07008-000058

    Category Name: $20 & Under Sale

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Talk Removable Faux Fur Cardigan

    Soft girl meets it-girl. This zip-up crop cardigan is cozy with a twist—removable faux fur trim gives you two vibes in one: polished for brunch, playful for after hours. Basically, it’s the definition of cute versatility.

    Fit & Features

    • Soft rib knit stretchy fabric
    • Removable faux fur collar neckline
    • Fitted long sleeves with removable faux fur cuffs
    • Front zip-up closure
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06202-000053

    Category Name: $20 & Under Sale

    Price: $21.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floating Moment Pleated Palazzo Pants

    Float through the day in these effortless pleated palazzo pants. The lightweight chiffon fabric creates soft movement with every step, while the relaxed silhouette keeps your look easy and polished. Perfect for dressing up with heels or keeping it breezy with sandals.

    Fit & Features

    • Chiffon-lined fabric
    • High-rise waist
    • Flowy wide-leg silhouette
    • Pleated design
    • Runs true to size

    Style Number/Barcode: 06402-000031

    Category Name: $20 & Under Sale

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: M, L

    Product Badge:
    • Sale
  • Sweet Talk Lace Tie Back Mini Dress

    Sweet, but not subtle. This lace trim mini dress with a flirty tie back and smooth fit keeps things soft up front and unforgettable from behind.

    Fit & Features

    • Smooth knit fabric
    • Lace-trimmed bust
    • V-neckline, spaghetti straps
    • Strappy tie-back design
    • A-line mini silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001112

    Category Name: $20 & Under Sale

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PINK

    Available Size: M, L

    Product Badge:
    • Sale
  • Chic Rush Tortoise Watch

    Serving polished with a side of chic, this tortoise watch pulls your whole look together in seconds. It’s that effortless mix of classic and trendy you’ll reach for on repeat.

    Fit & Features

    • Polished finish with tortoise band
    • Analog watch face with adjustable side dial
    • Hinge style

    Style Number/Barcode: 07007-000073

    Category Name: $20 & Under Sale

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shine Bright Strapless Sequin Mini Dress

    Bring the sparkle, babe—this strapless sequin mini is pure magic. With a fitted silhouette and flirty ruffle hem, it’s the ultimate pick for party nights and standout moments.

    Fit & Features

    • Sequin mesh-lined fabric
    • Strapless neckline
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Tiered ruffle mini hem
    • Runs true to size

    Style Number/Barcode: 05101-001598

    Category Name: $20 & Under Sale

    Price: $59.90

    Availability: In Stock

    Available Color: LAVENDER

    Available Size: XS, S, M, L, XXS

    Product Badge:
    • Sale
  • Ruffle With It Ruffle Mini Dress

    A little ruching, a little ruffle, and a whole lot of cute—this dress was made for playful nights and picture-perfect brunches. The bodycon fit keeps it flirty while the flounce hem adds that extra twirl factor.

    Fit & Features

    • Smooth knit stretch fabric
    • Surplice V-neckline
    • Spaghetti straps
    • Bodycon fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000475

    Category Name: $20 & Under Sale

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Windsor x Von Dutch Logo Mid-Rise Denim Jeans

    Y2K nostalgia just clocked back in. These Windsor x Von Dutch straight-leg jeans feature a bold Von Dutch logo graphic, patches, and contrast stitching for that effortlessly cool, thrifted-but-better vibe you’ll keep reaching for.

    Fit & Features

    • Vintage-inspired medium wash denim fabric
    • Mid-rise waist
    • Front, side, and back Von Dutch logo graphics and patches
    • Straight-leg fit
    • Front button and hidden zipper closure, belt loops
    • Five-pocket styling
    • Runs true to size

    Style Number/Barcode: 06602-000105

    Category Name: $20 & Under Sale

    Price: $39.97 $94.00

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty And Playful Floral Tie-Back Mini Dress

    Flirty from every angle—this strapless floral mini dress shows off a fitted bodice up front and a dramatic bow in the back. Lightweight, twirl-worthy, and perfect for any RSVP that calls for pretty but playful.

    Fit & Features

    • Floral brocade pattern, woven fabric, knit and tulle linings
    • Strapless neckline, no-slip strip
    • Pleated bodice
    • Back zipper with hook-eye closure, tie-back design
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000336

    Category Name: $20 & Under Sale

    Price: $24.97 $59.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: L

    Product Badge:
    • Sale