$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.

  • Casual-Chic Style Muse High Slit Maxi Dress

    Show off your elevated casual-chic style in this high slit maxi dress. Featuring a sleeveless crew neckline with tank shoulder straps, trendy side cutouts at the waist, a maxi-length hem, and a thigh-high side slit, this dress will get you major compliments. The ribbed knit fabric offers plenty of stretch. Complete the look with sleek hoops and strappy heels.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Dual side cutouts at the waist
    • Maxi-length hem
    • High side slit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4866

    Category Name: $20 & Under Sale

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blaire Formal Satin Corset Slim Long Dress

    Special Occasion

    The Blaire formal satin dress is ready for debut at award ceremonies and banquets! She features a sleeveless sweetheart neckline, adjustable spaghetti straps, a corset bodice with a padded underwire bust, flexible boning, and stitch detailing. Her slim curve-hugging silhouette is designed with a high side slit to show some skin and a long hem. The formal dress is composed of a luxe satin fabric with a stretchy knit lining. Complete the look in platform heels.

    Fit & Features

    • Sleeveless sweetheart neckline, adjustable spaghetti straps, draped pleat
    • Corset bodice, padded underwire bust, flexible boning
    • Back zipper and hook-eye closure
    • Slim curve-hugging silhouette, high side slit, long hem
    • Luxe satin, stretchy knit lining
    • No bra required
    • Runs true to size

    Style Number/Barcode: 05002-7251

    Category Name: $20 & Under Sale

    Price: $19.97 $99.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stand In Command Cargo Denim Midi Skirt

    Everyone will rise when you stand in stylish command! This denim midi skirt features a flattering high-rise waist, hip-hugging fit, dual cargo flap pockets on each side, and a center front slit. The cotton-blend denim fabric offers minimal stretch. Complete the look in a basic tee and your favorite sneakers for an on-trend style!

    Fit & Features

    • High-rise waist
    • Hip-hugging fit
    • Dual cargo flap pockets on each side
    • Center front slit, midi-length hem
    • Classic two-pocket styling, front button, hidden zipper closure, belt loops
    • Cotton-blend denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06601-0131

    Category Name: $20 & Under Sale

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simple And Sultry Cutout Midi Dress

    Simple and sultry, this cutout midi dress will make a chic impression. It features a sleeveless V-neckline with ruching and a center O-ring accent, spaghetti straps, a front waist cutout, a midi-length hem with a thigh-high front slit, and a curve-hugging silhouette. The smooth knit fabric offers plenty of stretch. Style with lace-up heels.

    Fit & Features

    • Sleeveless V-neckline, ruched, center metal O-ring accent
    • Spaghetti straps
    • Front waist cutout, high waist
    • Midi-length hem, high front slit
    • Curve-hugging fit
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-2298

    Category Name: $20 & Under Sale

    Price: $5.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Space Glam Coated Faux Leather Cargo Pants

    These fabulous faux leather cargo pants will give off major space glam vibes! They feature a high-rise waist, a front zipper and button closure, front and back pockets, a straight-leg silhouette, and are composed of a coated faux leather fabric with a metallic sheen. Style with a basic crop top and clear mules.

    Fit & Features

    • High-rise waist, belt loops
    • Hidden front zipper, button closure
    • Dual front and back pockets
    • Straight-leg silhouette
    • Coated faux leather fabric, metallic sheen
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 06402-1305

    Category Name: $20 & Under Sale

    Price: $22.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Hangout Straight-Leg Cargo Pants

    These trendy straight-leg cargo pants are perfect for a casual hangout with your squad. They feature a mid-rise waist with a back elastic waistband, front and back pockets, large cargo-style side pockets with button closures, a relaxed fit, and an edgy-washed effect creating a faded look on the woven fabric. Style with a crop top and sneakers, or a corset top and mules!

    Fit & Features

    • Mid-rise waist, back elastic waistband, belt loops
    • Hidden front zipper, button closure
    • Dual front and back pockets, button closures
    • Dual large cargo-style side pockets, button closures
    • Straight-leg silhouette, back strap accents by the hem, relaxed fit
    • Washed effect, woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0774

    Category Name: $20 & Under Sale

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dreamy Island Vibes Floral Strapless Jumpsuit

    Bring those dreamy island vibes to your summer vacay look with this floral jumpsuit. It features a strapless straight-across neckline, a stretchy smocked bodice, a high waist seam with a braided tie-front belt, a wide-leg silhouette, and an all-over abstract floral and palm leaf print. The smooth knit fabric offers a moderate stretch. Style with slip-on sandals and sleek shades.

    Fit & Features

    • Strapless straight-across neckline
    • Stretchy smocked bodice
    • High waist seam, braided tie-front belt
    • Wide-leg silhouette
    • Abstract floral and palm leaf print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-2375

    Category Name: $20 & Under Sale

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Artsy Allure Abstract Print Skater Romper

    Show off an artsy allure in this chic abstract print skater romper. It features a sleeveless plunging V-neckline, adjustable spaghetti straps that lead to an open back with a cross-back strap design, a high waist with a tie-front belt, a short skater skirt overlay with a flowy fit and a scalloped hem, and fitted shorts. The sheer chiffon fabric features an all-over abstract multi-print pattern and includes a full knit lining. Style with lace-up heels.

    Fit & Features

    • Sleeveless plunging V-neckline
    • Adjustable spaghetti straps, open back, cross-back straps
    • High waist, tie-front belt, lower back zipper, hook and eye closure
    • Short pleated skater skirt overlay, flowy fit, scalloped hem, fitted shorts
    • Abstract multi-print pattern
    • Sheer pleated chiffon fabric, full knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0336

    Category Name: $20 & Under Sale

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Codi High-Rise Dad Jeans by Windsor Denim

    Your best silhouette yet is to be experienced in the Codi dad jeans by Windsor Denim! They feature a flattering ultra-high-rise waist, a slim hip-hugging fit, front distressed accents for a trendy look, and split sides along the hem. The dad jeans are crafted from a premium medium wash denim fabric with a color fading and slight stretch. Complete the look in a sleeveless bodysuit for a casual backyard dinner!

    Fit & Features

    • Ultra high-rise waist
    • Slim curve-hugging fit, dad-style leg
    • Front distressed accents, split sides along hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Medium wash denim fabric, color fading, slight stretch
    • Runs true to size

    Style Number/Barcode: 06602-0419

    Category Name: $20 & Under Sale

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feelin' Artsy Abstract Print Cutout Jumpsuit

    You'll be feelin' artsy and chic in this alluring abstract print jumpsuit. It features a sleeveless plunging V-neckline with a padded bust, halter spaghetti straps with a tie-back design, and a small center cutout with a metal accent under the bust. The waist has dual cutouts on each side with chunky chain-link accents connected to straps for a bold vibe, an open back with dual tie-back straps, and a wide-leg silhouette with a relaxed fit. The woven fabric showcases an all-over multi-colored abstract print pattern that will catch everyone's eye. Style with espadrille sandals.

    Fit & Features

    • Sleeveless plunging V-neckline, padded bust
    • Halter spaghetti straps, tie-back design
    • Small center cutout under the bust, metal accent
    • Dual waist cutouts, chain-link accents connected to straps
    • Open back, dual tie-back straps, lower back zipper, hook and eye closure
    • Wide-leg silhouette, relaxed fit
    • Multi-colored abstract print, woven fabric, knit lining at the bust, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06402-1326

    Category Name: $20 & Under Sale

    Price: $6.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Everyday Basic Seamless Mock Neck Halter Top

    This everyday basic seamless ribbed knit crop top needs to be in your lineup! It features a sleeveless mock neckline with a halter design, a partially open back, and a fitted, banded, cropped hem. The lightweight knit fabric offers plenty of stretch for comfortable wear. Style with sculpting biker shorts.

    Fit & Features

    • Sleeveless mock neckline
    • Halter design
    • Partially open back
    • Fitted, banded, cropped hem
    • Seamless ribbed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 07107-0919

    Category Name: $20 & Under Sale

    Price: $4.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Weekend Plans Wide-Leg Pants

    These airy and chic wide-leg pants are perf for your casual weekend plans. They feature a high-rise elasticized waist, a faux front drawstring, dual front pockets, and a relaxed fit with a wide-leg silhouette. The lightweight gauze fabric has no stretch. Style with a crop top and sandals for a breakfast date.

    Fit & Features

    • High-rise elasticized waist
    • Faux front drawstring
    • Dual front pockets
    • Relaxed fit, wide-leg silhouette
    • Gauze fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0778

    Category Name: $20 & Under Sale

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunkissed Beauty Tropical Print Cutout Maxi Dress

    You'll be a stunning sunkissed beauty in this tropical print maxi dress that will give off alluring energy. It features a sleeveless asymmetric one-shoulder neckline with a single bungee spaghetti strap, a bold asymmetric side cutout at the waist with a chic O-ring accent, a hip-hugging fit, a sultry thigh-high side slit, and a floor-length hem. The smooth and stretchy knit fabric features an all-over tropical palm leaf print. Style with strappy sandals.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Single bungee spaghetti strap
    • Asymmetric side cutout at the waist, O-ring accent
    • Hip-hugging fit, high side slit, floor-length hem
    • Tropical palm leaf print
    • Knit fabric, mini-length lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5091

    Category Name: $20 & Under Sale

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Instant Fave Disty Floral Short Sleeve Midi Dress

    This adorable disty floral midi dress will be an instant fave of yours for the summer season. It features a crew neckline, short fitted sleeves, a small top keyhole cutout at the back with a button closure, a larger lower back cutout, a high waist seam, a midi-length hem with a high front slit, and a form-hugging silhouette. The floral printed brushed knit fabric offers plenty of stretch. Style with espadrille sandals.

    Fit & Features

    • Crew neckline, short sleeves
    • Small back keyhole cutout, button closure
    • Larger lower back cutout, high waist seam
    • Midi-length hem, front slit, form-hugging fit
    • Ditsy floral print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5184

    Category Name: $20 & Under Sale

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Touch Of Sexy Slim-Fit High Slit Maxi Dress

    Add a touch of sexy to your evening out in this sleeveless maxi dress! It features a sweetheart neckline with cowl draping, spaghetti straps, a slim curve-hugging silhouette, a high side slit, and a long-length hem on smooth knit fabric. Complete the look in statement heels.

    Fit & Features

    • Sleeveless sweetheart neckline, cowl draping
    • Spaghetti straps
    • Slim curve-hugging silhouette
    • High side slit
    • Long-length maxi hem
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2436

    Category Name: $20 & Under Sale

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Passport To Paradise Tropical Print Ruched Midi Dress

    Whether you're headed on a weekend getaway or a plane ride to paradise, pack this tropical print midi dress for a gorgeous glow! It features a sleeveless cowl neckline, spaghetti straps, ruching down one side seam, an asymmetric midi-length hem creating a thigh-high side slit, and a curve-hugging silhouette. The smooth and stretchy knit fabric features an all-over tropical palm leaf print. Style with espadrille sandals.

    Fit & Features

    • Sleeveless cowl neckline, spaghetti straps
    • Ruched side seam
    • Asymmetric midi-length hem, high side slit
    • Bodycon fit
    • Tropical palm leaf print
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5136

    Category Name: $20 & Under Sale

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirtatious Charm Cutout Midi Dress

    Say hello to this adorable cutout midi dress that will bring those cute and fun vibes! This midi dress features an off-the-shoulder sweetheart neckline and short fitted sleeves. The center knot detail at the bust with a tie-front adds a charming touch, while the dual waist cutouts add a hint of playfulness. The midi-length hem with a high side slit showcases your legs for a sassy look. With its form-hugging silhouette and ribbed knit fabric offering plenty of stretch, this dress ensures both comfort and style. Complete your outfit with a pair of sandals to bring that flirtatious charm!

    Fit & Features

    • Off-the-shoulder sweetheart neckline
    • Center knot detail at the bust, tie-front design
    • Dual waist cutouts
    • Midi-length hem, high side slit
    • Form-hugging fit
    • Ribbed knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4992

    Category Name: $20 & Under Sale

    Price: $6.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Things Regal Flocked Velvet Mini Dress

    If you adore all things regal this flocked velvet mini dress is perfect for you! It features a sleeveless sweetheart neckline, sleek bungee spaghetti straps, a padded bust, and a bodycon silhouette. Style with door-knocker earrings for a rehearsal dinner!

    Fit & Features

    • Sleeveless sweetheart neckline
    • Bungee spaghetti straps
    • Padded bust
    • Bodycon silhouette
    • Mini-length hem
    • Flocked velvet pattern, mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2413

    Category Name: $20 & Under Sale

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous And Chic Floral Satin Midi Dress

    Gorgeous and chic will be your vibe in this floral silky satin midi dress. It features a sleeveless cowl neckline, adjustable spaghetti straps, a slim-fit bodice that leads to a midi-length flowy slip silhouette, a high front slit, and an all-over blooming floral print pattern. Style this mid-length dress with rhinestone earrings and an envelope clutch for a stunning wedding guest look.

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Slim-fit bodice, midi-length slip silhouette
    • High front slit
    • Floral print
    • Satin woven fabric, lined bust, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2385

    Category Name: $20 & Under Sale

    Price: $7.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cut Out The Drama Plunge Neck Mini Dress

    You're not here for the drama only to stand out in this chic mini dress at upcoming parties and mixers! It features long peasant sleeves, a plunge neckline with a flirty underbust cutout, and a bodycon silhouette on smooth knit-lined fabric. Complete the look with door-knocker earrings.

    Fit & Features

    • Peasant long sleeves
    • Plunge neckline
    • Underbust cutout
    • Bodycon silhouette
    • Mini-length hem
    • Smooth knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2509

    Category Name: $20 & Under Sale

    Price: $5.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Status One-Shoulder Mini Dress

    Level up your sultry status in this alluring mesh mini dress! It features a one-shoulder neckline with a tank strap with knotted details, a bold front cutout above the bust, a wired bust to provide structure, and a ruched corset-designed bodice with flexible boning. The high waist seam leads to a ruched skirt with a mini-length hem and a bodycon silhouette that will hug your curves. The lined mesh fabric offers a moderate stretch. Complete your night-out look with platform heels.

    Fit & Features

    • One-shoulder neckline, tank strap, knotted details
    • Asymmetric front cutout above the bust, wired bust
    • Ruched corset-designed bodice, flexible boning
    • High waist seam, back zipper, hook and eye closure
    • Mini-length hem, ruched detailing, bodycon fit
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-4759

    Category Name: $20 & Under Sale

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Best In Town Crepe Sweetheart Midi Dress

    You'll be best dressed all over town in this crepe midi dress perfect for wearing on rotation! It features a sleeveless sweetheart neck with a padded bust, sleek spaghetti straps, a curve-hugging silhouette, and a flirty front slit along the flowy hem. Complete the look with a pop of gold jewelry. 

    Fit & Features

    • Sleeveless sweetheart neck, padded bust
    • Spaghetti straps
    • Curve-hugging silhouette
    • Front slit, flowy midi-length hem
    • Crepe fabric, bust lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2046

    Category Name: $20 & Under Sale

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bohemian Girl High Rise Flare Pants

    Unleash your inner bohemian girl in these flare pants at festivals and concerts this season! Featuring a flattering high-rise waist, hip-hugging fit, and a flared hem. The pants are designed with a boho-inspired print on brushed stretchy knit fabric. Complete the look with the matching top.

    Shop Matching Top: Bohemian Girl Halter Tie Crop Top

    Fit & Features

    • High-rise waist
    • Hip-hugging fit
    • Flared hem
    • Boho print
    • Brushed stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2338

    Category Name: $20 & Under Sale

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bohemian Girl Halter Tie Crop Top

    Unleash your inner bohemian girl in this halter crop top at festivals and concerts this season! Featuring a sleeveless plunge halter V-neckline, dual front ties with a cutout accent, an open back, and a fitted crop hem. The top is designed with a boho-inspired multi-print on brushed stretchy knit fabric. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Bohemian Girl High Rise Flare Pants

    Fit & Features

    • Sleeveless plunge halter V-neckline
    • Dual front ties, cutout accent
    • Open back
    • Fitted crop hem
    • Boho multi-print
    • Brushed knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 06001-4874

    Category Name: $20 & Under Sale

    Price: $4.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale