$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.

  • Ribbed Knit Scoop Neck Pajama Crop Top

    Get ready to want to lounge all day, every day in this adorable ribbed knit pajama crop top! It features a comfy knit fabric and a form-hugging fit. Pair with some cute chunky sneakers for a movie marathon day.

    Shop Matching Bottoms: Ribbed Knit Pajama Micro Shorts

    Fit & Features

    • Scoop neckline
    • Tank-like shoulder straps
    • Cropped hem
    • Ribbed knit fabric
    • Matching shorts sold separately

     

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

    Style Number/Barcode: 07103-0363

    Category Name: $20 & Under Sale

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple And Sweet Pajama Crop Top

    Cozy on up in this simple and sweet pajama crop top, a perf piece to add to your loungewear wardrobe! Featuring a soft knit fabric and form-hugging fit, this top is a must-have for a movie night. Pair with some cute slides to finish off the look.

    Shop Matching Bottoms: Simple And Sweet Pajama Leggings

    Fit & Features

    • Short cap sleeves
    • Crew neckline
    • Cropped hem
    • Knit fabric
    • Matching leggings sold separately


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

    Style Number/Barcode: 07103-0358

    Category Name: $20 & Under Sale

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ribbed Knit Pajama Micro Shorts

    Get ready to want to lounge all day, every day in these adorable ribbed knit pajama micro shorts! They feature a comfy knit fabric and a form-hugging fit. Pair with some cute chunky sneakers for a movie marathon day.

    Shop Matching Top: Ribbed Knit Scoop Neck Pajama Crop Top

    Fit & Features

    • High rise banded waist
    • Short form-hugging fit
    • Ribbed knit fabric
    • Matching top sold separately

     

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

    Style Number/Barcode: 07103-0364

    Category Name: $20 & Under Sale

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple And Sweet Pajama Leggings

    Cozy on up in these simple and sweet pajama leggings, a perf piece to add to your loungewear wardrobe! Featuring a soft knit fabric and form-hugging fit, these leggings are a must-have for a movie night. Pair with some cute slides to finish off the look.

    Shop Matching Top: Simple And Sweet Pajama Crop Top

    Fit & Features

    • High rise banded waist
    • Tie front detail
    • Tapered fit
    • Knit fabric
    • Matching top sold separately

     

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

    Style Number/Barcode: 07103-0359

    Category Name: $20 & Under Sale

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild and Fierce Chunky Sneakers

    Keep it wild in sneakers that show off your fierce side! The sneakers feature a high arch, a leopard print detail, a lace-up front, and a chunky sole. Complete your look with a sleek midi dress and layer with a denim jacket

    Fit & Features

    • High arch with pull tabs at the ankles
    • Round toe
    • Lace-up front
    • Leopard print trim 
    • Chunky sole

    Style Number/Barcode: 07407-0161

    Category Name: $20 & Under Sale

    Price: $18.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam and Chic Chunky Sneakers

    Keep it glam and sporty in sneakers that bring the chicness to your look! The sneakers feature a high arch, lace-up front, a multi-tone design, and a chunky sole. Complete your look with a sleeveless mini dress and a cropped denim jacket

    Fit & Features

    • High arch with pull tabs at ankle
    • Round toe
    • Multi-tone design 
    • Lace-up front
    • Chunky sole

    Style Number/Barcode: 07407-0160

    Category Name: $20 & Under Sale

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pop of Pink Chunky Sneakers

    Keep it pretty in pink with sneakers that bring a pop of glam to your trendy streetwear look! The sneakers feature a round toe, a lace-up front, a two-tone design, and a chunky sole. Complete your look with skinny jeans and a crop top.

    Fit & Features

    • Round toe
    • Lace-up front
    • Two-tone design
    • Pull tabs at the ankle
    • Chunky sole

    Style Number/Barcode: 07407-0164

    Category Name: $20 & Under Sale

    Price: $21.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Short Sleeve Tie Waist Utility Jumpsuit

    Step out in a chic utility jumpsuit. The statement jumpsuit features a plunging V-neckline, two utility pockets, short sleeves and a tie waist belt with loops. The relaxed fit waist leads to a straight leg fit that tapers to a skinny leg fit. The jumpsuit is composed of a utility cargo knit fabric that offers a relaxed fit with a slight stretch. Complete your outfit with extra-large hoops and stiletto heels.

    Fit & Features 

    • Plunging v-neckline
    • Short sleeves
    • Utility pockets
    • Tie waist belt with loops
    • Skinny leg fit
    • Cargo knit fabric 

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

    Style Number/Barcode: 06302-0100

    Category Name: $20 & Under Sale

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feelin' Sassy Leopard Print Pajama Shorts

    Get a sassy sweet vibe in these adorable leopard print pajama shorts! They feature a high rise banded waist and an all over pastel-hued leopard print. Pair with some comfy slides for the perfect stay at home look.

    Shop Matching Top: Feelin' Sassy Leopard Print Pajama Tank Top

    Fit & Features

    • High rise banded waist
    • Form-fitting style
    • All over leopard print

     

    Model is 5'6.5" with a 32" bust,  23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 07103-0380

    Category Name: $20 & Under Sale

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Radiant Rhinestone Tube Hoop Earrings

    You'll be the center of attention in these gorgeous rhinestone tube hoop earrings! Featuring a rhinestone-encrusted hoop, these will sparkle and make you all the more radiant. Pair with a sleek mini dress for date night.

    Fit & Features

    • Tube hoop design
    • Mini rhinestone embellishments
    • Omega closure

     

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

    Style Number/Barcode: 07001-0583

    Category Name: $20 & Under Sale

    Price: $3.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tie Dye Thermal Knit Pajama Shorts

    Add a pop of color to your loungewear outfits with these trendy shorts. The pajama shorts feature a fab tie-dye print, a drawstring waist, and composed of a cozy thermal knit fabric. Complete your loungewear outfit with the matching top and cozy slides

    Shop Matching Top: Tie Dye Thermal Knit Pajama Top

    Fit & Features

    • Tie-dye print
    • High rise waist
    • Drawstring
    • Cheeky fit
    • Matching top sold separately 

     

    Model is 5'7" with a 32.5" bust,  24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 07103-0376

    Category Name: $20 & Under Sale

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tie Dye Thermal Knit Pajama Top

    Add a pop of color to your loungewear outfits with this trendy top. The pajama top features a fab tie-dye print, v-neckline, and composed of a cozy thermal knit fabric. Complete your loungewear outfit with the matching shorts and cozy slides

    Shop Matching Pajama Shorts: Tie Dye Thermal Knit Pajama Shorts

    Fit & Features 

    • Tie-dye print
    • V-neckline
    • Cap sleeves
    • Thermal knit fabric
    • Matching shorts sold separately 

     

    Model is 5'7" with a 32.5" bust,  24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 07103-0375

    Category Name: $20 & Under Sale

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Sassy Leopard Print Pajama Tank Top

    Get a sassy sweet vibe in this adorable leopard print pajama tank top! It features a form-fitting cropped hem and an all over pastel-hued leopard print. Pair with some comfy slides for the perfect stay at home look.

    Shop Matching Bottoms: Feelin' Sassy Leopard Print Pajama Shorts

    Fit & Features

    • Adjustable spaghetti straps
    • Rounded neckline
    • Cropped hem
    • Form-fitting style
    • All over leopard print

     

    Model is 5'6.5" with a 32" bust,  23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 07103-0379

    Category Name: $20 & Under Sale

    Price: $15.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Chic Wrap Front Crop Top

    Wrap yourself in this simply chic crop top for the perfect everyday 'fit! It features a flattering V neckline and a wrap front with a side tie detail. The ribbed knit fabric provides plenty of stretch for comfortable wear. Pair this trendy basic with distressed denim for a go-to look.

    Fit & Features

    • V neckline
    • Long fitted sleeves
    • Wrap front with side tie detail
    • Cropped
    • Ribbed knit fabric with plenty of stretch
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06001-2792

    Category Name: $20 & Under Sale

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Purrfect Style Halloween Face Mask

    Stay safe while also getting that purrfect style in this adorable face mask! Perfect for pairing with your Halloween costume, this mask is a must-have. Mask features a cute cat face graphic with earloops for a comfortable fit.

    Fit & Features

    • Cat face graphic
    • Earloops
    • Wash before and after use is recommended
    • Not a medical-grade mask
    • Final Sale

     

    Halloween Costumes are excluded from Promotions.

    Style Number/Barcode: 07305-0185

    Category Name: $20 & Under Sale

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Sweet Puff Sleeve Mini Dress

    Keep your look sweet and stylish in this adorable puff sleeve mini dress! It features a tie front detail and a short, curve-hugging fit. Pair this cute dress with some strappy heels and a chic mini handbag for a brunch date with your squad.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline
    • Tie front detail
    • Back zipper closure
    • Short, form-hugging fit
    • Woven fabric
    • Runs true to size

    Style Number/Barcode: 05102-1011

    Category Name: $20 & Under Sale

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • All About Knit Mock Neck Mini Dress

    You'll be totally all about this chic mock neck mini dress! Featuring long fitted sleeves and a curve-hugging fit, this dress is perfect for the fall season. Pair with gold hoop earrings and chunky sneakers for that fab everyday 'fit.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Short, form-hugging fit
    • Knit fabric

    Style Number/Barcode: 05102-0855

    Category Name: $20 & Under Sale

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bite Me Graphic Cropped Tee

    Keep it fierce in fangs with a crop top that reveals your mysterious side this season! The top features a bitten red lip graphic with exposed vampy fangs and a cropped hem. Complete your vampire-inspired Halloween outfit with a high waist skirt and face gems to create the perfect DIY costume. 

    Fit & Features

    • Round neckline
    • Short sleeves
    • Bitten lip graphic with exposed fangs
    • Cropped hem
    • Cotton knit fabric
    • Relaxed fit, moderate stretch 

     

    Model is 5'8" with a 32" bust,  23" waist and 35" hips. She is wearing a size small. 

    Halloween Costumes are excluded from Promotions.

    Style Number/Barcode: 06002-0584

    Category Name: $20 & Under Sale

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • V In Satin Mini Dress

    Look like an absolute stunner in satin and work it in this mini dress! It features a sleeveless bodice with spaghetti straps, a deep V neckline, a low open back, and a short, form-hugging fit. Pair this dress with strappy heels and a faux leather jacket for a night out.

    Fits & Features

    • Spaghetti straps
    • Plunging V neckline with princess seam details
    • Low open back
    • Mini length silhouette
    • Satin-like fabric
    • Curve-hugging fit
    • Zipper not featured

    Style Number/Barcode: 05103-0657

    Category Name: $20 & Under Sale

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bohemian Vibes Cropped Ruffled Sleeve Top

    Go boho chic in a crop top that brings the good vibes. The crop top features a surplice neckline, kimono-style ruffled sleeves, and a cropped hem. Complete your look with high waist skinny jeans and mules.

    Fit & Features

    • Surplice neckline
    • Long kimono-styled ruffled sleeves
    • Cropped hem
    • Lightweight woven fabric
    • Relaxed fit 
    • Minimal stretch 

    Style Number/Barcode: 06003-0823

    Category Name: $20 & Under Sale

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Glam It Up Rhinestone Hoop Earrings

    Glam up your look and make it luxe with these gorg rhinestone hoop earrings! They feature an extra-large hoop earring design with rhinestone embellishment inside and out of the hoop. Pair with a basic mini dress and some chunky sneakers for a casual-chic vibe.

    Fit & Features

    • Extra-large hoop earring design
    • All over rhinestone embellishment

     

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-0595

    Category Name: $20 & Under Sale

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Totally Grounded Two-Strap Sandal

    Equal parts versatile and vibrant, these summer sandals make a statement, and the statement is chill, down to earth, boho babe.

    • Round toe
    • Double buckle design
    • Slide on 
    • Cork + lug sole
    • Silver hardware

    Style Number/Barcode: 07404-0530

    Category Name: $20 & Under Sale

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Is Better Face Mask

    Sometimes, basic is better, like with this adorable face mask! Stay safe and keep it cute in this face mask that features earloops for a comfortable fit. Pair with a loungewear set for a casual chic look.

    Shop Matching Top: Ready To Lounge Triangle Bralette

    Shop Matching Bottoms: Ready To Lounge Tulip Pajama Shorts

    Fit & Features

    • Earloops
    • Wash before and after use is recommended
    • Not a medical-grade mask
    • Final Sale

    Style Number/Barcode: 07305-0151

    Category Name: $20 & Under Sale

    Price: $2.97 $6.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Dreams Striped Pajama Shorts

    Have only the sweetest of dreams in these adorable striped pajama shorts! They feature a high rise waist with a cute merrow edge trim at the hem. Pair with some slides for a cozy night in look!

    Shop Matching Top: Sweet Dreams Striped Pajama Top

    Fit & Features

    • High rise waist
    • Fitted shorts
    • Cheeky
    • Merrow edge trim

     

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

    Style Number/Barcode: 07103-0374

    Category Name: $20 & Under Sale

    Price: $13.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale