$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.

  • On Point Lace Up Stiletto Booties

    Lace-up in chic booties to keep your look on point! Perfect for your next GNO or your next date night with bae. The booties feature a trendy lace-up front to create a customized fit, a pointed toe, and a sleek stiletto heel. Complete your look with a sweater dress and moto jacket

    Fit & Features

    • Around the ankle fit
    • Lace-up front
    • Inner zipper closure
    • Pointed toe
    • Stiletto heel 
    • Faux microsuede material 

     

    Please be advised that these booties run small. Fit model recommends sizing one size up.

    Style Number/Barcode: 07403-0318

    Category Name: $20 & Under Sale

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Moving On Faux Leather Lucite Booties

    Move on from basic to chic in booties that elevate your looks! The booties feature an around the ankle fit, an inner zipper closure, a pointed toe, and a narrow lucite block heel. Complete your look with high waist jeans and an oversized sweater

    Fit & Features

    • Around the ankle fit
    • Inner zipper closure
    • Pointed toe
    • Narrow lucite block heel
    • Faux leather material

    Style Number/Barcode: 07403-0311

    Category Name: $20 & Under Sale

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cross Charm Huggies Variety Five Pack

    Set up your look with trendy earrings that add the finishing touch to any look! The pack includes five pairs of earrings featuring a cross charm, huggies, and ear cuff design. Complete your look with a crop top and high waist jeans and you're ready to go! 

    Fit & Features

    • Includes five pairs of earrings
    • Huggie, cross charm and ear cuff design


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

    Style Number/Barcode: 07001-0411

    Category Name: $20 & Under Sale

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Special Price
  • Clearly Chic Lucite Block Heels

    Clearly stay on trend in heels that keep your looks stylish and chic. The heels feature an adjustable ankle strap, an open almond toe with clear strap, and a lucite block heel. Complete your look with a chic sweater dress and duster earrings

    Fit & Features 

    • Adjustable clear ankle strap
    • Clear strap at the heel
    • Open almond toe with clear strap
    • Lucite block heel
    • Faux patent leather sole

    Style Number/Barcode: 07401-2388

    Category Name: $20 & Under Sale

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Nikita Formal High Slit Satin Dress

    Special Occasion 

    Keep it sleek in our Nikita dress that brings the elegance to your formal evening. She features a plunging sleeveless wrap V-neckline, padded cups that eliminate the need for a bra, sleek spaghetti straps, a ruched silhouette that enhances curves, and a floor-length silhouette with a dramatic asymmetrical high slit. Complete your look with rhinestone earrings and clear heels

    Fit & Features

    • Plunging wrap V-neckline
    • Padded cups, sleek spaghetti straps
    • Ruched silhouette, asymmetrical high slit
    • High waist fit
    • Floor-length wrap silhouette
    • Stretchy satin fabric
    • Form hugging fit, moderate stretch, runs true to size 

    Style Number/Barcode: 05002-1038

    Category Name: $20 & Under Sale

    Price: $14.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish And Tapered Tie Waist Jumpsuit

    This stylish and tapered jumpsuit is just what you need to get a dressy everyday 'fit. It features a paper bag tie-front waist and a sleek form-fitting silhouette. Pair with some hoop earrings and strappy heels for a chic look you can take from the office to happy hour.

    Fit & Features

    • Adjustable spaghetti straps
    • V-neckline
    • Back zipper and hook and eye closure
    • High-rise paper bag tie-front waist
    • Front pockets
    • Tapered pant legs
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06402-0339

    Category Name: $20 & Under Sale

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pretty In Plaid Woven Mini Skirt

    Get an effortlessly pretty look in this trendy plaid woven mini skirt! With its flattering high rise waist and chic side slit, this skirt is a must for a casual date night out. Pair with a cute top and layer on a leather jacket.

    Fit & Features

    • High rise waist
    • Hidden back zipper closure
    • Small side slit
    • Short, curve-hugging fit
    • Plaid print
    • Woven fabric

    Style Number/Barcode: 06401-0251

    Category Name: $20 & Under Sale

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Clara High Rise Destructed Fringe Skinny Jeans

    Oasis by Eunina

    Give your skinny jeans an edgy update in this must-have pair! Perfect for styling with your favorite basic tops for a casual day out or dressing up with a bodysuit for a night out. The jeans feature a high rise waist, a flattering medium wash, a skinny tapered leg with light destruction, and a fringed raw edge hem.  

    Fit & Features

    • High rise waist
    • Single-button and zipper closure
    • Traditional five-pocket with belt loop design
    • Light-medium wash denim fabric
    • Light destructed detailing fringe raw-edge hem 
    • Skinny tapered leg
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 06602-0179

    Category Name: $20 & Under Sale

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ribbed Knit Crew Neck Maxi Dress

    This simple yet stunning ribbed knit maxi dress is a must for your fab fall look. Featuring a high crew neckline and a flattering curve-hugging silhouette, this dress can easily be dressed up with some strappy heels or down with a pair of chunky sneakers. Wear on a casual date night with bae.

    Fit & Features

    • High crew neckline
    • Tank-like shoulder straps
    • Form-hugging fit
    • Side slit
    • Maxi length
    • Ribbed knit fabric

     

     

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

    Style Number/Barcode: 05102-0870

    Category Name: $20 & Under Sale

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feelin' Trendy Tie Dye Midi Dress

    This trendy tie dye knit midi dress is ready for you to style up! Featuring a sleeveless high neckline and a curve-hugging mid-length silhouette, you can easily take this dress from day to night. Layer on a denim jacket and some chunky sneakers for a casual-chic date look.

    Fit & Features

    • High rounded neckline
    • Mid-length silhouette
    • Form-hugging fit
    • Tie dye print
    • Knit fabric

     

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

    Style Number/Barcode: 05102-0866

    Category Name: $20 & Under Sale

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Wrap Around Bishop Sleeve Crop Top

    Bring on the chic vibes in this must-have wrap around crop top! It features trendy long bishop style sleeves and a tie front detail to pull your 'fit together. Pair with mom jeans and strappy mules for a go-to brunch look.

    Fit & Features

    • Long bishop style sleeves with cinched hems
    • Wrap front
    • V neckline
    • Tie front detail
    • Cropped
    • Ribbed knit fabric

     

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

    Style Number/Barcode: 06001-2786

    Category Name: $20 & Under Sale

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirty Floral Polka Dot Mini Dress

    Create a flirty first impression in this pretty floral polka dot mini dress! It features a cowl neckline, a flowy mini length silhouette, and a fun floral print on a polka dot woven fabric. For a cute day date look, layer on a denim jacket and pair with some clear heels.

    Fit & Features

    • Adjustable spaghetti straps
    • Cowl neckline
    • Flowy mini length fit
    • Floral print
    • Polka dot woven fabric

     

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

    Style Number/Barcode: 05102-0914

    Category Name: $20 & Under Sale

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Flair Woven Midi Dress

    You'll have that total floral flair in this stunning woven midi dress! Featuring a V neckline and a flowy mid-length silhouette, this dress would be perfect for a fall date night. Pair with some clear heels and accessorize with gold hoops to let the dress make the statement.

    Fit & Features

    • Adjustable spaghetti straps
    • V neckline
    • Back zipper closure
    • Flowy mid-length fit
    • Ditsy floral print
    • Woven fabric


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

    Style Number/Barcode: 05102-0915

    Category Name: $20 & Under Sale

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ribbed Off The Shoulder Fold-Over Top

    A fall staple for sure, this ribbed off the shoulder top will pair with all of your 'fits. Featuring a fold-over neckline and long fitted sleeves, this top would look so cute with a mini skirt or high rise skinny jeans. Take it from a shopping trip to dinner afterward!

    Fit & Features

    • Off the shoulder square neckline
    • Fold-over detail
    • Long fitted sleeves
    • Mid-length form-hugging fit
    • Ribbed knit fabric

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

    Style Number/Barcode: 06001-2958

    Category Name: $20 & Under Sale

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fall For Floral Woven Midi Dress

    Fall head over heels for this adorable ditsy floral midi dress! Featuring a trendy cowl neckline and a flowy mid-length silhouette, this dress would pair perfectly with some simple gold hoops and clear mules. Wear to your next brunch with your girls and you'll receive all the compliments.

    Fit & Features

    • Adjustable spaghetti straps
    • Cowl neckline
    • Flowy mid-length fit
    • Ditsy floral print
    • Woven fabric

     

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

    Style Number/Barcode: 05102-0882

    Category Name: $20 & Under Sale

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simple And Sleek Tie Shoulder Slip Dress

    Simple and sleek, this slip dress is a gorgeous piece you need to have in your closet. Featuring tie shoulder straps and a flowy mid-length silhouette, it can so easily be dressed up with some clear mules or down with chunky sneaks. Wear to your next date with bae and you'll leave a lasting impression.

    Fit & Features

    • Tie shoulder straps
    • Slight V neckline
    • Square back
    • Flowy mid-length fit
    • Woven fabric

     

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

    Style Number/Barcode: 05101-0895

    Category Name: $20 & Under Sale

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Falling For You Floral Mini Skirt

    They will be falling for you hard when you step out in this smocked mini skirt. Don’t forget to pick up the matching crop top to complete the look!

    Shop the Matching Top: Falling For You Floral Crop Top

    Fits & Features

    • Ditsy Floral Print
    • Smocked
    • Ruffle Hem

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

    Style Number/Barcode: 06301-0040

    Category Name: $20 & Under Sale

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tropical Palm Leaf High Slit Maxi Skirt

    Get set for the tropics in this skirt that will transport you to an island fantasy. The skirt features a high rise waist, a tropical palm-leaf print, and a maxi silhouette with a dramatic high slit to show off a hint of leg. Complete look with matching top and statement earrings.

    Shop Matching Crop Top: Tropical Palm Leaf Tube Top

    Fit & Features

    • High rise waist
    • Tropical floral print
    • Maxi length silhouette
    • High side slit
    • Matching top sold separately 

     

    Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small. 

    Style Number/Barcode: 06501-0225

    Category Name: $20 & Under Sale

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bella Super High-Rise Destructed Skinny Jeans

    Oasis by Eunina

    The Bella Super High-Rise Destructed Skinny Jeans are a must-have in your closet! They feature a very high waist with destructed detailing at the front, a skinny leg fit, and a medium wash denim fabric with a faded design. Style this trendy pair of denim with a crop top and clear heels for that it-girl vibe.

    Fit & Features

    • Super high waist
    • Destructed detailing
    • Skinny leg fit, form-hugging
    • Five-pocket and belt loop design
    • Front button and hidden zipper closure
    • Medium wash denim fabric, faded design, moderate stretch
    • Runs true to size

      Style Number/Barcode: 06602-0120

      Category Name: $20 & Under Sale

      Price: $18.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Double Row Tie Front Ribbed Crop Top

      Stand out babe in this chic crop top. Head out for a beach day in this trendsetting crop top that features a plunging V-neckline, a double-row tie front accent to create a customized fit, and a cropped hem. Complete your look with your favorite high waist jeans and stunning sunglasses.

      Fit & Features

      • Plunging v-neckline
      • Spaghetti straps
      • Double-row tie front accent
      • Cropped hem 
      • Ribbed knit fabric
      • Relaxed fit

       

      Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

      Style Number/Barcode: 06001-2685

      Category Name: $20 & Under Sale

      Price: $9.97 $19.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Falling For You Floral Crop Top

      They will be falling for you hard when you step out in this smocked crop top. Don’t forget to pick up the matching skirt to complete the look!

      Shop the Matching Bottoms: Falling For You Floral Mini Skirt

      Fits & Features

      • Ditsy Floral Print
      • Smocked
      • Spaghetti Straps

      Style Number/Barcode: 06003-0531

      Category Name: $20 & Under Sale

      Price: $6.97 $18.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Basic High Waist Twill Joggers

      Keep it basic and stylish in joggers that can be used to dress up or dress down in comfort! The joggers feature an elastic high rise waist, a drawstring waist, slant pockets and a tapered straight leg with elastic cuff. Complete outfit with a basic crop top and strappy mules

      Fit & Features

      • Elastic high rise waist
      • Drawstring waist
      • Slant pockets
      • Faux back pockets
      • Straight leg fit
      • Tapered elastic cuff
      • Twill knit fabric, relaxed fit 

       

      Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

      Style Number/Barcode: 06302-0164

      Category Name: $20 & Under Sale

      Price: $6.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Only The Basics Cami Top

      We love a basic cami, perfect for layering or wearing on its own with a sleek pair of pants and slingback heels! This cami top features a sleeveless square neckline that naturally flatters, and bungee spaghetti straps to create a sleek look along the cropped hem. The cami top is composed of a double-lined knit fabric that provides coverage to avoid fashion faux-pas. 

      Fit & Features 

      • Square neckline
      • Bungee spaghetti straps
      • Cropped hem
      • Double-lined knit fabric
      • Moderate stretch 
      • Fits true to size

      Style Number/Barcode: 06001-2309

      Category Name: $20 & Under Sale

      Price: $9.97 $16.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Clara High Rise Destructed Skinny Crop Jeans

      Oasis by Eunina

      Elevate your denim game in jeans that keep you on-trend. The jeans feature a high rise waist, a single button with zipper closure, distressed detailing and a skinny leg fit with a cropped hem. Complete your look with a statement bodysuit and clear heels

      Fit & Features

      • High rise waist
      • Single-button with zipper closure 
      • Traditional five-pocket with belt loop design
      • Distressed detailing
      • Skinny leg fit, tapered hem
      • Medium wash denim fabric 
      • Form hugging fit, moderate stretch   

       

      Model is 5'8" with a 32" bust,  25" waist and 35" hips. She is wearing a size three.  

      Style Number/Barcode: 06602-0064

      Category Name: $20 & Under Sale

      Price: $6.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance