$20 & Under Sale

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.

  • Twice As Nice Halter Ruffle Mini Dress

    Date night just found its favorite dress. This halter mini dress serves a plunging neckline and a tiered ruffle skirt that moves with you from cocktails to the dancefloor.

    Fit & Features

    • Lace-lined fabric
    • Plunge halter neckline
    • Open back
    • Form-hugging fit
    • Tiered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000816

    Category Name: $20 & Under Sale

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Favorite Girl Two-Tone Baseball Cap

    For the days you want your outfit to speak first, this cap handles the intro. The structured two-tone design and bold "Favorite Girl" embroidery make it the easiest confidence boost you can throw on.

    Fit & Features

    • Structured two-tone design
    • Bold “Favorite Girl” front embroidery
    • Classic six-panel construction with stitched eyelets
    • Curved brim
    • Adjustable snapback closure for a customizable fit

    Style Number/Barcode: 07302-000216

    Category Name: $20 & Under Sale

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bare Minimum Drama Sequin Crochet Fringe Poncho

    Sheer, shimmery, and not here to blend in. This sequin crochet fringe poncho is the ultimate layer when your bikini top or bralette deserves a little extra attention, but you still want that effortless, thrown on and thriving vibe.

    Fit & Features

    • Lightweight sheer crochet fabric
    • Sequin embellishments
    • Relaxed poncho silhouette
    • Open neckline with easy slip-on design
    • Fringe hem
    • Runs true to size

    Style Number/Barcode: 06005-000288

    Category Name: $20 & Under Sale

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Little Tie-Back Skater Dress

    The kind of dress that makes plans for you. This chiffon skater dress with a sweetheart neckline, lace trim, and tie-back detail feels light, flirty, and ready for any plans.

    Fit & Features

    • Swiss dot chiffon fabric, smooth woven lining
    • Sweetheart lace trim neckline
    • Adjustable spaghetti straps
    • Open tie-back design, stretchy smocked panel
    • Sheer lace trim waist insert
    • Skater silhouette, lace trim ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000779

    Category Name: $20 & Under Sale

    Price: $42.00 $59.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Match Point Mid-Rise Denim Skort

    This denim skort keeps it casual-cool with contrast stitching and a form-hugging fit—perfect for everyday styling or weekend plans.

    Shop The Matching Jacket: Match Point Oversized Denim Jacket

    Fit & Features

    • Denim fabric, no stretch, shorts lining
    • Mid-rise waist
    • Form-hugging fit
    • Four-pocket styling, belt loop accents
    • Front button closure
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06603-000097

    Category Name: $20 & Under Sale

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cool Girl Classic Cowboy Hat

    Throw it on and suddenly the outfit feels intentional. This cowboy hat adds that effortless western edge, whether you’re heading to a concert or just building a look that hits a little harder.

    Fit & Features

    • Classic cowboy hat silhouette
    • Curved brim design
    • Faux leather band with metal buckle accents
    • Adjustable inner strings for a snug fit

    Style Number/Barcode: 07302-000317

    Category Name: $20 & Under Sale

    Price: $12.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Laced-Up And Bold Low-Rise Shorts

    These shorts are here to make an entrance. Serving a serious attitude with lace-up details on the front and sides, this low-rise mini moment was made for nights when subtlety is not the assignment. Pair them with tights, boots, or a slinky top—either way, you’re instantly the hottest plot twist in the room.

    Fit & Features

    • Denim fabric
    • Low-rise waist
    • Lace-up detail on front and sides
    • Hardware eyelets
    • Body-hugging fit and cheeky hem
    • Runs true to size

    Style Number/Barcode: 06603-000124

    Category Name: $20 & Under Sale

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smooth Talk Ruffle Mini Skort

    Meet your next going-out favorite—the ruffle mini skort that knows how to flatter every curve. Soft, smooth, and fitted, it moves with you for that effortless mix of sleek and sexy. Style with the matching halter top.

    Shop Matching Top: Smooth Talk Plunge Halter Top

    Fit & Features

    • Smooth knit fabric, high stretch
    • Mid-rise waist
    • Tiered ruffled design
    • Ruffled side trim
    • Mini-length overlay, fitted A-line silhouette
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000186

    Category Name: $20 & Under Sale

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: In Stock

    Available Color: HUNTER

    Available Size: S

    Product Badge:
    • Sale
  • Gallery After Hours Cowl Neck Midi Dress

    It’s giving art opening energy, but make it wearable. This artsy abstract print midi dress features a draped cowl neckline, delicate spaghetti straps, and a front slit on a form-hugging silhouette that feels equal parts effortless and elevated.

    Fit & Features

    • Abstract print, knit-lined stretch fabric
    • Cowl neckline, Adjustable spaghetti straps
    • Front slit
    • Form-hugging fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000661

    Category Name: $20 & Under Sale

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Vibe Rhinestone Floral Halter Top

    Subtle shine, modern silhouette. Exactly what you want when basics feel boring. This abstract print halter top features rhinestones in a floral pattern for a trendy vibe. Style with the matching mini skirt.

    Shop Matching Bottoms: Trendy Vibe Rhinestone Floral Mini Skirt

    Fit & Features

    • Halter neckline with adjustable tie-back closure
    • Open back design with lower tie-back straps
    • All-over abstract print
    • Rhinestone floral embellishment
    • Mesh fabric with knit lining, high stretch
    • Runs true to size

    Style Number/Barcode: 06001-000401

    Category Name: $20 & Under Sale

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Eyelet Ruffle Mini Dress

    This sweet eyelet dress brings soft romance with a playful twist. The square neckline, puff sleeves, and tiered ruffle skirt create a flattering A-line silhouette that feels effortlessly feminine. Perfect for brunch dates, garden parties, or sunny day plans.

    Fit & Features

    • Eyelet fabric, knit lining
    • Square neckline
    • Short puff sleeves
    • Fitted bodice
    • Drop waist A-line silhouette
    • Tiered ruffle mini hem
    • Runs true to size

    Style Number/Barcode: 05102-000493

    Category Name: $20 & Under Sale

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: L

    Product Badge:
    • Sale
  • Picnic Plans Floral Puff Sleeve Dress

    Soft plans, cute dress, zero hesitation. This floral print skater dress features short puff sleeves, a bust tie, and a strappy lace-up open back that keeps things sweet in the front and unforgettable on the way out.

    Fit & Features

    • Linen-like fabric with floral print, woven lining
    • Sweetheart neckline with adjustable bust tie
    • Short puff sleeves
    • Strappy lace-up open back detail
    • Short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000906

    Category Name: $20 & Under Sale

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Windsor x Von Dutch Cowboy Hat

    A little country, a lot of attitude. This Von Dutch cowboy hat tops off your look with that confident, don’t-mess-with-me energy that pulls everything together instantly.

    Fit & Features

    • Classic cowboy hat silhouette
    • Woven straw material with a structured feel
    • Curved brim with pinched crown
    • Von Dutch embroidered logo patch

    Style Number/Barcode: 07302-000302

    Category Name: $20 & Under Sale

    Price: $43.97 $88.00

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cabana Crush Chevron Bikini Bottoms

    Booked the cabana before you even finished packing. These bikini bottoms bring major resort mood with its retro-inspired chevron print, hoop inserts, and matching pieces that was made for poolside photos.

    Shop The Matching Top: Cabana Crush Chevron Bikini Top
    Shop The Matching Sarang: Cabana Crush Chevron Sarong Wrap

    Fit & Features

    • Chevron print, sleek knit-lined fabric
    • Hoop insert waist detail
    • Cheeky cut
    • Runs true to size 
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000047

    Category Name: $20 & Under Sale

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Whisper Soft Mesh Balconette Bra

    Soft, subtle, and a little unforgettable. This sheer mesh balconette bra is designed with a delicate eyelash lace trim and underwire that shapes and lifts, while the delicate details keep it effortlessly alluring.

    Fit & Features

    • Sheer mesh fabric
    • Eyelash lace trim balconette neckline
    • Adjustable spaghetti straps
    • Underwire bust for support
    • Multiple back hook and eye closures
    • Runs true to size 

     

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07107-000003

    Category Name: $20 & Under Sale

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Kicked A Goal Soccer Rhinestone Bag

    Game night, but make it fashion. This rhinestone soccer ball wristlet clutch bag brings the sparkle with a statement sphere shape that’s impossible to ignore, from dinner plans to stadium selfies.

    Fit & Features

    • Soccer ball pattern
    • Rhinestone-embellished
    • Rhinestone trim handle
    • Push-lock closure
    • Satin-lined spacious interior
    • Detachable chain strap

    Style Number/Barcode: 07203-000175

    Category Name: $20 & Under Sale

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Radiant Shine Tube Mini Dress

    Like sunshine you can wear. This glitter mesh tube mini dress features a soft A-line shape that gives a flattering, flirty fit while the subtle shimmer catches the light for brunch plans, vacations, and warm night outings.

    Fit & Features

    • Glitter mesh fabric, soft knit lining
    • Strapless tube neckline
    • A-line mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000732

    Category Name: $20 & Under Sale

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love Spell Lace Skater Dress

    Flirty with a touch of vintage romance. This lace corset mini flatters every curve with a sweetheart neckline and flared skater skirt—made for date nights, parties, or whenever you want all eyes on you.

    Fit & Features

    • Lace-lined fabric, flocked velvet trims, attached panty lining
    • Strapless sweetheart neckline, bust lining
    • Corset-inspired sheer bodice, flexible boning
    • Back zipper and hook-eye closure
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000263

    Category Name: $20 & Under Sale

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunday In Bloom Strapless Midi Dress

    This midi dress feels like a soft yes to every pretty plan on your calendar. The delicate floral print, smocked bodice, and flowy silhouette make it perfect for vacations, brunch, or any sunny day plans.

    Fit & Features

    • Floral borderprint, cotton woven fabric, smooth woven lining
    • Strapless smocked bodice with stretch
    • Back zipper and hook-eye closure
    • Flowy A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000798

    Category Name: $20 & Under Sale

    Price: $51.00 $72.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLUE

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Studded With Attitude Tank Top

    A little attitude goes a long way. This grommet-studded tank top hugs in all the right places with high-stretch cotton fabric and statement hardware that gives any outfit an instant edge.

    Fit & Features

    • Cotton fabric, high stretch
    • Front grommet-studded design
    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Mid-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06002-000485

    Category Name: $20 & Under Sale

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heart On Lock Statement Necklace

    Bold chain, zero overthinking. This hammered ring necklace brings major cool factor with oversized links and heart details that make even your simplest top feel styled.

    Fit & Features

    • Chunky chain silhouette
    • Hammered circle and heart link details
    • Statement front design
    • Lobster clasp closure

    Style Number/Barcode: 07002-000427

    Category Name: $20 & Under Sale

    Price: $3.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Crush Ruffle Mini Skort

    When you want to bring a little chaos—in the cute way—this ruffle skort steps in with all the confidence of a bold-print moment. Light, flouncy, and ready for any night you decide to turn up the charm.

    Shop The Matching Top: Wild Crush Hoop Halter Crop Top

    Fit & Features

    • Sheer mesh fabrication with animal print
    • High-rise waistband with soft stretch
    • Ruched sides
    • Tiered ruffle overlay forming an asymmetrical mini skort silhouette
    • Built-in shorts lining for coverage
    • Runs true to size

    Style Number/Barcode: 06503-000210

    Category Name: $20 & Under Sale

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hayden Floral Satin A-Line Formal Dress

    Special Occasion

    A study in effortless elegance, the Hayden floral satin A-line gown is made for the kind of entrance that lingers. Designed with a softly ruched bodice and fluid skirt, it moves with you—polished, poised, and undeniably captivating.

    Fit & Features

    • Floral pattern, satin fabric, knit lining
    • Sweetheart strapless neckline, padded bra cups
    • Tie-back detail, lower zipper and hook-eye closure
    • High front slit
    • A-line floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Prom, graduations, bridal celebrations, galas, upscale birthday events, fancy brunches, vacations, formal milestone parties, anniversaries, fashion-forward soirees

    Style Number/Barcode: 05002-001379

    Category Name: $20 & Under Sale

    Price: $19.97 $99.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Instant Upgrade Concho Chain Belt

    Instant 'fit upgrade—this concho chain belt does all the talking. The engraved oval details and adjustable chain fit make it your go-to for denim days, festival looks, or leveling up a simple dress.

    Fit & Features

    • Chain-link design
    • Oval-shaped concho designs, engraved detailing
    • Lobster clasp closure with extender
    • Adjustable fit

    Style Number/Barcode: 07301-000458

    Category Name: $20 & Under Sale

    Price: $7.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale