$20 & Under Sale
Dive into our fabulous $20 and under sale, where affordability meets style with dresses, tops, bottoms, and shoes. Perfect for fashion-savvy shoppers, this collection allows you to create complete chic looks without straining your wallet. Whether you're updating key pieces or opting for a fresh 'fit for an upcoming event, seize the opportunity to enhance your wardrobe with our stunningly priced finds.
Home$20 & Under Sale

$20 & Under Sale
Product Recommendations
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.
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Gleaming Sterling Silver Plated Curved Hoop Earrings
These modern luxe sterling silver plated hoop earrings will have you gleaming with beauty! They feature a thin curved double hoop with an open-ended design dipped in sterling silver plating. Include a post-back closure. Style this chic pair of earrings with a layered chain necklace.
Fit & Features
- Sterling silver plating
- Thin curved double hoop
- Open-ended design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1681
Category Name: $20 & Under Sale
Price: $2.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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New Trend On The Block Shoulder Bag
This shoulder bag is currently trending! It features a large silhouette, a shoulder strap, an adjustable drawstring on the bottom to create a scrunching effect, and a zipper closure revealing a lined spacious interior with a zipper pocket and slot pockets for holding all your essentials. Complete the look in a trench coat for traveling or running errands!
Fit & Features
- Large silhouette
- Shoulder strap
- Adjustable drawstring on the bottom, scrunch effect
- Zipper closure
- Lined spacious interior, zipper pocket and slot pockets
- Smooth nylon woven material
Style Number/Barcode: 07203-1955
Category Name: $20 & Under Sale
Price: $15.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Darla Formal Satin A-Line Long Dress
Special Occasion
You'll be a divine vision of beauty in the Darla formal satin long dress perfect for wedding guests or fancy holiday parties! She features a scoop neckline with a V-wired insert, spaghetti straps, a flattering A-line silhouette, and a front slit that leads to her floor-length hem for a dramatic finish. Crafted from smooth satin fabric, the formal long dress offers a luxe sheen and minimal stretch. Complete the look with a choker and heels.
Fit & Features
- Sleeveless scoop neckline
- V-wired insert, spaghetti straps
- A-line silhouette, front slit
- Floor-length hem
- Smooth satin fabric, minimal stretch
- Strapless or sticky bra recommended
- Runs true to size
Style Number/Barcode: 05002-7313
Category Name: $20 & Under Sale
Price: $14.97 $74.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Unparalleled Chic Rhinestone Trim Cropped Blazer
Showcase an unparalleled chic style in this stunning cropped blazer! It features a lapel collar, long fitted sleeves, a button-front closure, shimmering rhinestone-embellished trims at the hems, and a fitted, cropped hem. The crepe fabric offers a moderate stretch. Complete your party outfit with the matching mini dress and metallic heels.
Shop Matching Dress: Unparalleled Chic Rhinestone Trim Mini Dress
Fit & Features
- Lapel collar
- Long fitted sleeves
- Single button-front closure
- Rhinestone-embellished trims
- Fitted cropped hem
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0423
Category Name: $20 & Under Sale
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic 'Fit Pinstripe Paperbag Dress Pants
Create an elevated and chic 'fit with these pinstripe paperbag dress pants. They feature a high-rise paperbag waist with pleated detailing, a tie-front belt to snatch your silhouette, front pockets, and a tapered skinny-leg fit. The woven fabric features a classic pinstripe pattern for a sophisticated look. Style these dressy pants with a bodysuit and mules to wear from the office to drinks with the squad!
Fit & Features
- High-rise paperbag waist, pleating
- Tie-front belt, hidden front zipper closure
- Dual front pockets
- Tapered skinny-leg fit
- Pinstripe pattern
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06402-1355
Category Name: $20 & Under Sale
Price: $21.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glimmering Beauty Gemstone Infinity Chain Belt
Glimmer with beauty with this gorgeous gemstone infinity chain belt. It features radiant marquise-shaped gemstones with a twisted rhinestone outline creating an intricate infinity design. Includes a back adjustable chain with a lobster clasp closure. Style this belt over a glitzy long formal glitter dress with metallic heels.
Fit & Features
- Marquise-shaped gemstones
- Twisted rhinestone outline, infinity design
- Back adjustable chain, lobster clasp closure
Style Number/Barcode: 07301-0706
Category Name: $20 & Under Sale
Price: $4.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sparkle Time Rhinestone Western Ankle Booties
It's always sparkle time with these totally fab rhinestone western ankle booties! They feature an above-the-ankle height with rhinestone-adorned pull tabs, a pointed toe with a rhinestone-embellished toe cap design, a stacked block heel, and western-style seams on the sleek faux leather material. Pair these boots with a sleek clutch to complete your 'fit for a concert.
Fit & Features
- Above-the-ankle height
- Rhinestone pull tabs
- Pointed toe, rhinestone toe cap design
- Stacked block heel
- Western-style seams
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1733
Category Name: $20 & Under Sale
Price: $4.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek As Can Be Faux Leather Puffer Jacket
Stay sleek and cute as can be in this faux leather puffer jacket perfect for the chilly season! It features long sleeves, a standing collar neckline with snap-button closures for extra warmth, a hidden front zipper and snap-button closures, front pockets for keeping your hands warm, and an adjustable drawcord cropped hem. The jacket is crafted from a quilted faux leather-insulated woven fabric that helps keep you warm and protected. Complete the look in boots for holiday activities or casual hangs!
Fit & Features
- Long sleeves
- Standing collar neckline, snap-button closures
- Hidden front zipper and snap-button closures
- Front pockets
- Adjustable drawcord cropped hem
- Faux leather fabric, insulated woven lining
- Runs true to size
Style Number/Barcode: 06201-0449
Category Name: $20 & Under Sale
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gleam On Sequin Halter Tie-Waist Jumpsuit
Gleam on in this ultra-glam sequin jumpsuit, an iconic look for holiday parties and soirees! It features a sleeveless bodice with an alluring draped cowl neckline, halter straps, a sultry backless design, a high waist with a tie-front belt to create a snatched look, a hip-hugging fit, and a wide-leg silhouette. The all-over glitzy sequin embroidery on the knit fabric will gorgeously glimmer to get you all the compliments! Style this dressy jumpsuit with gold hoops and clear heels.
Fit & Features
- Sleeveless draped cowl neckline
- Halter straps, open back, back zipper closure
- High waist, tie-front belt
- Hip-hugging fit, wide-leg silhouette
- All-over sequin embroidery, sewn-in mesh lining
- Runs true to size
Style Number/Barcode: 06502-2418
Category Name: $20 & Under Sale
Price: $15.97 $76.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stay Toasty Cable Knit Beanie
This cable knit beanie has you covered with toasty warmth and style! The cable knit fabric and foldover design make this beanie a stylish addition to any winter look. Complete the look with the matching scarf for a fun winter day!
Shop Matching Scarf: Cozy Cutie Cable Knit Fringe Scarf
Fit & Features
- Cable knit material
- Foldover design
- Soft and comfortable
Style Number/Barcode: 07302-1523
Category Name: $20 & Under Sale
Price: $4.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In The Lineup Mock Neck High Slit Midi Dress
This alluring mock neck high slit midi dress needs to be in your winter lineup! It features a mock neckline, long fitted sleeves, a trendy ruched side seam with an adjustable drawstring, an asymmetric midi-length hem creating a high-cut side slit, and a form-hugging silhouette to flaunt your figure. The brushed knit fabric offers plenty of stretch. Style this midi dress with ankle booties!
Fit & Features
- Mock neckline
- Long fitted sleeves
- Ruched side seam, adjustable drawstring
- Asymmetric midi-length hem, high-cut side slit
- Form-hugging silhouette
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5404
Category Name: $20 & Under Sale
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pop Diva Status Metallic Faux Fur Crop Jacket
Layer on this metallic trucker jacket to let your inner pop diva shine! It features faux fur-lined long sleeves, a faux fur collar with satin lining, snap-button down front closures, flap satin-lined pockets, and a cropped hem. Complete the look with a chic faux leather skirt for a concert or holiday party!
Fit & Features
- Faux fur lined long sleeves
- Faux fur collar with satin lining
- Snap-button down front closures
- Flap satin-lined pockets
- Cropped hem
- Metallic fabric, faux fur lining
- Runs true to size
Style Number/Barcode: 06201-0423
Category Name: $20 & Under Sale
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Iconic Style Plaid Knit Skort
Bring an iconic style to your 'fits this season with this on-trend plaid knit skort. It features a high-rise waist, a mini-length overlay with a side slit, and fitted shorts. The knit fabric features a chic plaid print pattern that is perf for the fall and winter seasons. Complete the look with a long sleeve bodysuit and over-the-knee boots.
Fit & Features
- High-rise waist
- Mini-length overlay, side slit
- Fitted shorts
- Plaid print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-1098
Category Name: $20 & Under Sale
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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All That Bling Rhinestone Stiletto Booties
These fabulous rhinestone stiletto booties will bring that bling and gleam all night long. They feature an above-the-ankle height, an inner zipper closure for easy on-and-off wear, a trendy pointed toe, a sleek stiletto heel, and all-over baguette-shaped rhinestone embellishments for an ultra-glam sheen. Style these boots with a bodycon dress and a metallic clutch for your next GNO!
Fit & Features
- Above-the-ankle height
- Inner zipper closure
- Pointed toe
- Stiletto heel
- Baguette rhinestone embellishments
- Runs true to size
Style Number/Barcode: 07403-1670
Category Name: $20 & Under Sale
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Best For Last Floral Metallic Midi Dress
This floral midi dress gives you an excuse to arrive fashionably late! The midi-length dress is designed with a cowl neckline, spaghetti straps, a flattering bodycon silhouette, and a side ruched seam atop a high slit to reveal some leg on floral print metallic fabric. Complete the look with earrings for a celebration party!
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Bodycon silhouette
- Side ruched seam, high slit
- Midi-length hem
- Floral print, metallic knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2878
Category Name: $20 & Under Sale
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cool-Girl Confidence Contrast Waist Trouser Pants
Show off your cool-girl confidence in these contrast waist trouser pants. They feature a high-rise waist with a trendy exposed waistband design, pleated detailing at the front, dual side pockets, a single back pocket, and a straight-leg silhouette with a relaxed fit. Style these trouser pants with a crop top and ankle booties.
Fit & Features
- High-rise waist, exposed waistband
- Hidden front zipper, hook and bar closure
- Pleated front detailing
- Dual side pockets, single back pocket
- Straight-leg silhouette, relaxed fit
- Woven fabric
- Runs true to size
Style Number/Barcode: 06402-1321
Category Name: $20 & Under Sale
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Shine Tonight Sequin Marabou Mini Dress
Bring the shine tonight in this sequin mini dress ready for a good time! The mesh mini-length dress features a strapless neckline with a fab marabou trim, bodycon silhouette, and front slit accent. Complete the look with earrings for a dressy celebration party!
Fit & Features
- Strapless neckline, marabou trim
- Back zipper closure
- Bodycon silhouette
- Front slit accent
- Mini-length hem
- Sequin-embellished mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2643
Category Name: $20 & Under Sale
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bri High-Rise Destructed Flared Jeans by Windsor Denim
The Bri high-rise destructed flared jeans by Windsor Denim will step up your everyday casual 'fits for on-point looks! They feature a high-rise waist, trendy destructed detailing at the knees, and a flattering flared-leg hem. Include a front button closure and a five-pocket and belt loop design. Style these jeans with a crop top and clear heel mules!
Fit & Features
- High-rise waist
- Destructed knee design
- Flared-leg hem
- Front button and zipper closure
- Five-pocket and belt loop design
- Denim fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06602-0458
Category Name: $20 & Under Sale
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cute On Cloud Nine Hoodie Puffer Jacket
Brace the chill looking cute in this hoodie puffer jacket up on cloud nine! Layer on this jacket featuring long sleeves with rib knit cuffs, a drawstring hoodie neckline with front snap-button closures for extra warmth, a front zipper closure, front flap pockets with snap-button closures, and an adjustable drawcord crop hem. The puffer jacket is crafted from an insulated nylon-woven fabric that helps keep you warm and protected from the elements. Complete the look in a cute lounge catsuit with cozy boots for running errands or meet-ups!
Fit & Features
- Long sleeves, rib knit cuffs
- Drawstring hoodie neckline, front snap-button closures
- Front flap pockets, snap-button closures
- Adjustable drawcord crop hem
- Insulated nylon-woven fabric
- Runs true to size
Style Number/Barcode: 06201-0441
Category Name: $20 & Under Sale
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cutest Vibe Flower Print Knit Scarf
Layer on the cutest vibe with this plush flower print knit scarf! Composed of a soft knit material with a trendy dual-color design and an adorable flower pattern, this long scarf is perf for bringing some florals into the season! Style with a cropped sweater, a mini skirt, and over-the-knee boots!
Fit & Features
- Soft knit material
- Dual-color design
- Floral pattern
- Long design
Style Number/Barcode: 07305-0478
Category Name: $20 & Under Sale
Price: $4.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stomp It Up Thigh-High Lug Boots
Stomp it up in these faux leather lug boots to elevate your everyday style! They feature a round toe, inner zipper closure, a sturdy lug sole, and a thigh-high shaft with an elastic insert and tie for easier on-and-off styling. Complete the look in a basic smooth knit dress and jacket!
Fit & Features
- Round toe
- Inner zipper closure
- Sturdy lug sole
- Thigh-high shaft, elastic insert and tie
- Faux leather material
- Runs true to size
Style Number/Barcode: 07402-0984
Category Name: $20 & Under Sale
Price: $4.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cozy Stroll Colorblock Fringe Blanket Scarf
Layer on this adorable colorblock fringe blanket scarf for a cozy stroll to grab coffee! Composed of a soft fuzzy woven material with trendy fringe hems and a cute colorblock pattern, this long scarf is a stylish staple for the season. Pair with a trench coat and booties.
Fit & Features
- Soft fuzzy woven material
- Long fringe hems
- Long design
- Colorblock pattern
Style Number/Barcode: 07305-0471
Category Name: $20 & Under Sale
Price: $3.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dare To Be Chic Velvet Burnout Mini Dress
Dare to be chic on your next dressy date night in this velvet burnout mini dress. It features a plunging V-neckline, long fitted sleeves with fab flared bell sleeve hems, a mini-length hem, and a bodycon silhouette to showcase your gorgeous curves. The sheer mesh fabric features a velvet burnout scroll pattern for an alluring look. Style this mini dress with strappy stiletto heels.
Fit & Features
- Plunging V-neckline
- Long fitted sleeves, flared bell sleeve hems
- Mini-length hem
- Bodycon silhouette
- Velvet burnout scroll pattern
- Sheer mesh fabric, partial knit lining
- Runs true to size
Style Number/Barcode: 05101-2855
Category Name: $20 & Under Sale
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfectly Seasoned Plaid Crew Neck Mini Dress
Fabulous and flavor-filled, step into this plaid mini dress for the new season! The mini dress features fitted long sleeves, a classic crew neckline, and a flattering bodycon silhouette on stretchy knit fabric with a trendy plaid print. Complete the look in a moto jacket for a coffee shop hang!
Fit & Features
- Fitted long sleeves
- Crew neckline
- Bodycon silhouette
- Mini-length hem
- Plaid print
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5247
Category Name: $20 & Under Sale
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale