$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.

  • Denim Darling Cropped Bustier

    Keep it cute in a denim bustier fit for trendsetter like you! The bustier features a sweetheart neckline, corset-like seams, piping detail, removable spaghetti straps, and a cropped hem. Complete your look with a high waist skirt and sunnies

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps 
    • Corset-like seams
    • Hook and eye closure
    • Piping detail
    • Cropped hem 
    • Denim knit fabric

     

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0682

    Category Name: $20 & Under Sale

    Price: $4.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Crushing On You Long Puff Sleeve Crop Top

    We're totally crushing on this crop top, perfect for that upcoming BBQ with the squad. The crop top features plunging v-neckline, long puff sleeves, tie front ties, and a cropped hem. Complete your casually cute look with high waist jeans and sunnies

    Fit & Features

    • Plunging v-neckline
    • Tie-front ties at center of the bodice
    • Long puff sleeves
    • Cropped hem 

     

    Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0943

    Category Name: $20 & Under Sale

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cropped Ruched Tie Front Top

    Stay on-trend in a ruched crop top. The top features a plunging sweetheart neckline, a tie-front accent, ruched side seams, spaghetti straps, and a cropped hem. The top is composed of a smooth knit fabric that offers a relaxed fit with a moderate stretch. Complete your look with the matching skirt and heels

    Shop Matching Skirt: High Waist Ruched Pencil Skirt

    Fit & Features

    • Sweetheart neckline, spaghetti straps
    • Tie-front accent 
    • Ruched side seam
    • Cropped hem 
    • Smooth-knit stretch fabric
    • Runs true to size

    Style Number/Barcode: 06001-2674

    Category Name: $20 & Under Sale

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Rise Tie Waist Tapered Pants

    Give your office look a chic vibe in these high rise tie waist tapered pants! Pair with your fave blouse and some open toe block heels.

    Fit & Features

    • High rise waist
    • Tie front belt
    • Hidden back zipper
    • Tapered pant legs
    • Woven fabric, no stretch

    Style Number/Barcode: 06402-0209

    Category Name: $20 & Under Sale

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Waist Ruched Pencil Skirt

    Stay on-trend in a ruched pencil skirt. The must-have skirt features a high-rise waist, ruched side seams that flatter curves, and a pencil skirt silhouette. The skirt is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete outfit with matching top and heels.

    Shop Matching Top: Cropped Ruched Tie Front Top

    Fit & Features 

    • High-rise waist
    • Ruched side seams
    • Pencil silhouette
    • Smooth knit fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0279

    Category Name: $20 & Under Sale

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Button Up Ribbed Mini Dress

    Button up in this classic ribbed dress to channel a cool chick vibe! Step out for a girl's night out or for a casual date night out with bae. The dress features a sleeveless bodice, a trendy square neckline, bungee straps for a secure fit, and a button-down center to create a customized look. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit and a moderate stretch. Pair this baby with your favorite heels to create a standout look and finish off with statement earrings

    Fit & Features

    • Square neckline
    • Bungee spaghetti straps 
    • Button-down center closure 
    • Lined ribbed fabric 
    • Form hugging fit 
    • Moderate stretch 

     

    Olive Dress: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Black Dress: Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06002-0402

    Category Name: $20 & Under Sale

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sassy Smocked Mini Skirt

    Ooo girl, you'll be lookin' sassy in this smocked mini skirt! Pair with the matching crop top for the perf look for a sunny day out!

    Shop Matching Top: Sassy Smocked Crop Top

    Fit & Features

    • High rise elastic banded waist
    • Short, form hugging fit
    • Merrow edge hem
    • Stretchy smocked knit fabric
    • Knit lining

    Style Number/Barcode: 06501-0224

    Category Name: $20 & Under Sale

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ribbed Scallop Trim Bodysuit

    Stay simply chic in this basic bodysuit. This must-have staple piece that be used for a date night in features a trendy square neckline, and scalloped tank-like straps to add that extra detail. Rock your look with heels and gold accessories for a flawless look.

    Fits & Features

    • Sleeveless bodice
    • Square neckline
    • Scalloped trim straps
    • Square neckline
    • Ribbed fabric
    • Form-hugging, moderate stretch 

     

    Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06001-2693

    Category Name: $20 & Under Sale

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic One Shoulder Neckline Sweatshirt Top

    Give your basic sweatshirt a fab twist in this top! This must-have top features a one-shoulder neckline, an oversized long sleeve with a ribbed cuff, and a cropped hem with ribbed trim. The top is composed of soft to the touch terry knit fabric that offers a relaxed fit with a moderate stretch. Complete your look with a pair of high waist jeans and hoops to keep a minimal vibe. 

    Fit & Features

    • One-shoulder ribbed neckline
    • Long sleeve, ribbed cuff
    • Cropped hem 
    • Terry-knit fabric 
    • Relaxed fit
    • Moderate stretch 

    Style Number/Barcode: 06002-0516

    Category Name: $20 & Under Sale

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Something More High Waist Ponte Pencil Skirt

    Create the perfect polished look in a high-waist pencil skirt. From the office to happy hour this bodycon midi skirt is the fashion essential for every wardrobe. This high-waist silhouette is made of double-lined Ponte knit fabric with minimal stretch for a sleek and structured look. Pair this pencil skirt with a bodysuit blouse and blazer for an office-ready ensemble or style it with a corset top for a flirty date night look.

    Fit & Features

    • High-rise waist
    • Form-hugging fit
    • Knee-length hem
    • Pull-on/off styling
    • Double ponte-lined fabric
    • Minimal stretch
    • Runs true to size 

    Style Number/Barcode: 06501-2105

    Category Name: $20 & Under Sale

    Price: $9.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Puff Sleeve Ruched Knit Mini Dress

    Keep on trend in a puff sleeve dress. This must-have dress features a sweetheart neckline with ruched detailing, puff sleeves, and a mini length silhouette. The dress is composed of a knit fabric that offers a form hugging fit with a slight stretch. Complete look with a pair of pumps and earrings

    Fit & Features 

    • Sweetheart neckline 
    • Ruched detailing at the bust 
    • Short puff sleeves 
    • Knit fabric 
    • Form hugging fit 
    • Moderate stretch 

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0733

    Category Name: $20 & Under Sale

    Price: $10.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sultry Chiffon Pleated Mini Dress

    Keep that sultry vibe going when you step out in this stunning chiffon mini dress! Style with mini hoops and your go-to strappy heels!

    Fit & Features

    • V-neckline | Long sheer sleeves
    • Pleated hip detailing | Ruffled hemline
    • Lined at the skirt & front of bodice
    • Lower back zipper + ruched bottom
    • Button detailing center back
    • Composed of chiffon with glitter threading
    • Non-stretchy

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.  

    Style Number/Barcode: 05101-0629

    Category Name: $20 & Under Sale

    Price: $19.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Off The Shoulder Ribbed Top

    Show off a little shoulder action with this essential basic ribbed top! It features an off the shoulder neckline and a button-down front. Add this staple piece to your closet to pair with your favorite denim and chunky sneakers to wear to a coffee date with your squad.

    Fit & Features 

    • Off the shoulder neckline
    • Button-down front
    • Long sleeves
    • Smocked back and a lettuce-edge trim
    • Ribbed knit fabric 
    • Relaxed fit
    • Moderate stretch 

     

    Black Top: Model is 5'4" with a 32" bust, 23" waist and 38" hips. She is wearing a size small. 

    Taupe Top: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

    White Top: Model is 5'8" with a 30" bust, 23" waist and 35" hips. She is wearing a size small.

    Mint Top: Model is 5'8" with a 34" bust,  24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06001-2635

    Category Name: $20 & Under Sale

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stuck on Floral Maxi Dress

    Have a floral moment in this flowy maxi dress! Style it with hoops and wedges for the perfect day date look.

    Fit & Features

    • Off the Shoulder
    • Double Front Slits
    • Maxi Length

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0632

    Category Name: $20 & Under Sale

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Take a Trip Tropical Mini Dress

    You’ll be ready for date night on the beach in this tropical print mini dress. Style it with clear heels and hoops for an effortless look.

    Fits & Features

    • V-Neckline
    • Spaghetti Straps
    • Asymmetrical Hem

    Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0440

    Category Name: $20 & Under Sale

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruffled Eyelet Puff Sleeve Mini Dress

    Keep it chic in an eyelet mini dress. This season-ready dress features a sweetheart neckline, a tie front accent, short puff sleeves, and ruched vertical seams that highlight and enhance curves. The relaxed waist leads to a ruffled hem. The dress is composed of a lightweight knit fabric with an eyelet pattern. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete your look with wedges and fringe earrings

    Fit & Features

    • Sweetheart neckline
    • Tie front accent 
    • Short puff sleeves
    • Vertical seams
    • Eyelet design
    • Ruffled hem 
    • Lightweight woven fabric, relaxed fit 

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0734

    Category Name: $20 & Under Sale

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simple Perfection Bodysuit

    Your beauty is effortless! This cute bodysuit loves to show off your natural perfection with an endearing off-the-shoulder neckline paired with short ruched sleeves and a stylish cross-over detail. The bodysuit is composed of a simple smooth knit fabric that offers a moderate stretch for a fitted look and includes a thong bottom with dual snap button closures. Complete your outfit with high-rise denim and clear mules.

    Fit & Features

    • Off-the-shoulder neckline
    • Short ruched sleeves
    • Cross-over detail
    • Thong bottom with dual snap button closures
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4834

    Category Name: $20 & Under Sale

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sassy Smocked Crop Top

    Ooo girl, you'll be lookin' sassy in this smocked crop top! Pair with the matching mini skirt for the perf look for a sunny day out!

    Shop Matching Bottoms: Sassy Smocked Mini Skirt

    Fit & Features

    • Spaghetti straps
    • V neckline
    • Cropped merrow edge hem
    • Smocked knit fabric

    Style Number/Barcode: 06001-2423

    Category Name: $20 & Under Sale

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Floral Eyelet Mini Dress

    We’re always in the mood for a little floral print! Pair this mini dress with sandals and layered dainty jewelry.

    Fit & Features

    • All Over Eyelet Design
    • Ditsy Floral Print
    • Mini Length

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0709

    Category Name: $20 & Under Sale

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleeveless Cut Out O-Ring Ribbed Mini Dress

    Step up in a sleeveless ribbed mini dress with sexy cutout details this season. The curve-hugging ribbed dress features a flattering crew neck that leads to a chic O-Ring at the mid-drift accented with waist cut outs for a subtle hint of skin. The back reveals a matching lower back cut out to impress from all angles. The ribbed knit embraces curves while offering a moderate stretch to easily move. Complete this date-night ready look with daring hoops and strappy stilettos

    Fit & Features

    • Sleeveless
    • Crew neckline
    • O-Ring at the center, waist cut outs
    • Lower back cut out
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 05102-0723

    Category Name: $20 & Under Sale

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tropical Getaway Sleeveless Asymmetrical Ruched Midi Dress

    Head to the tropics in this midi dress that brings a tropical burst of color. This vacation-ready dress features a sleeveless bodice, a plunging V-neckline and adjustable spaghetti straps that lead to an X-back design. The relaxed fit waist leads to a midi length silhouette with a ruched side seam and an asymmetrical high slit to show off a hint of skin. The all-over tropical print features bright hues that perfectly complement the neutral background. The dress is composed of a smooth knit fabric that offers a form-hugging fit. Complete your look with a pair of heels and golden hoop earrings

    Fit & Features

    • Plunging V-neckline
    • Adjustable spaghetti straps
    • X-back 
    • Midi length silhouette 
    • Tropical print
    • Asymmetrical high side slit
    • Form hugging fit

    Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0579

    Category Name: $20 & Under Sale

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Show 'Em Off Shoulder Smocked Mini Dress

    Show off those shoulders in this cute mini dress! For a cute daytime look, pair it with your fave denim jacket and some white sneakers! 

    Fits & Features

    • Off-shoulder neckline, short sleeves
    • Keyhole opening with self-ties at front
    • Mini length silhouette 
    • Woven textured fabric, smocked back, ruffle trim detail
    • Curve hugging fit, plenty of stretch 

    Style Number/Barcode: 05102-0472

    Category Name: $20 & Under Sale

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Small Town Girl Eyelet Mini Dress

    Whether you're a small town girl, or a city babe, this sweet mini dress is a day out go-to! Slip on and head out to brunch babe!

    Fit & Features

    • Square neckline
    • Adjustable Spaghetti straps | Sleeveless
    • Mini hemline
    • Zipper closure center back
    • Eyelet linen material
    • Minimal stretch
     Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0213

    Category Name: $20 & Under Sale

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Oh So Dainty Ruffle Trim Off Shoulder Ruched Mini Dress

    Step right into sunnier days with this charming mini dress! Opt for block heels and a cute mini purse for an eyecatching ensemble! 

    Fits & Features

    • Ruffle Trim Off Shoulder Design 
    • Tie Front 
    • Ruching Throughout
    • Mini Length Hem I Full Knit Lining
    • Form Hugging Fit I Plenty Of Stretch 

    Model is 5'7" with a 34" bust,  24" waist and 34" hips. She is wearing a size small.  

    Style Number/Barcode: 05102-0657

    Category Name: $20 & Under Sale

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance