$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.
Now Trending
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.
-
All Eyes Strappy Rhinestone Mules
These understood the assignment—no notes. Strappy mule heels with rhinestone detailing bring just enough shine, while the sculpted heel keeps your look elevated from dinner to after plans.
Fit & Features
- Stiletto heel
- Square toe
- Rhinestone-embellished, asymmetrical straps
- Cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-000720
Category Name: $20 & Under Sale
Price: $12.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE, LIGHT, BLUE
Available Size: 10, 5.5
Product Badge:- Sale
-
Curve Cue Collar Necklace
Neckline upgrade, handled. This coil ball charm collar necklace brings a sleek sculptural shape that instantly pulls together strapless tops, plunging necklines, and dressy outfit plans.
Fit & Features
- Coil strand design
- Ball charms
- Collar necklace silhouette
- Lobster clasp closure
Style Number/Barcode: 07002-000528
Category Name: $20 & Under Sale
Price: $3.97 $14.90
On Sale: Yes
Availability: In Stock
Available Color: SILVER
Available Size: NS
Product Badge:- Sale
-
Pick Me Cherry Graphic Tank Top
The perfect pick this season. This tank top is sure to be a part of your summer rotation with a cherry graphic and polka dot trim that feels made for coffee runs, errands, and weekend fun.
Fit & Features
- Stretchy knit fabric
- Contrast trim scoop neckline and spaghetti straps
- Cherry graphic design
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06002-000632
Category Name: $20 & Under Sale
Price: $9.97 $22.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Sale
-
Spotted And Booked Polka Dot A-Line Mini Dress
Already RSVP’d and now you have the dress. This polka dot A-line mini dress hugs just right up top, then flares for that easy, flirty fit you’ll wear from dinner plans to after.
Fit & Features
- Ribbed knit fabric with knit lining, high stretch
- Polka dot print
- Sleeveless V-neckline, eyelet trim, velvet bow detail
- Adjustable thin eyelet shoulder straps
- Mini-length hem, ruffled trim
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000729
Category Name: $20 & Under Sale
Price: $22.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S
Product Badge:- Sale
-
Chic Invite Metallic Rope Box Clutch
Tiny bag, huge social calendar. This metallic rope box clutch brings the chic finishing touch your looks have been waiting for, whether you’re headed to cocktails, weddings, or dressing like the RSVP said “best dressed only.”
Fit & Features
- Oval-shaped design
- Metallic woven rope exterior
- Top metal clasp closure, metal trim
- Woven interior lining
- Attachable chain-link shoulder strap
Style Number/Barcode: 07203-000184
Category Name: $20 & Under Sale
Price: $14.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Chic On Arrival Metallic Espadrille Wedges
These metallic espadrille wedges pair a leg-lengthening platform with sleek straps, making them an easy chic pick for weddings, vacations, rooftop dinners, and every RSVP in between.
Fit & Features
- 4.5" Espadrille wedge heel
- Open round toe
- Metallic faux leather straps
- Toe strap, adjustable ankle strap with buckle closure
- Metallic faux leather footbed
- Runs true to size
Style Number/Barcode: 07406-000063
Category Name: $20 & Under Sale
Price: $12.97 $40.90
On Sale: Yes
Availability: In Stock
Available Color: GOLD
Available Size: 10, 11
Product Badge:- Sale
-
Timeless Mood Chain Link Watch
Serving polished plans only. This chain link watch features a sleek octagon face with a minimal dial that instantly pulls your whole look together, whether you’re heading to brunch or blocking off your calendar like a boss.
Fit & Features
- Polished finish
- Octagon watch face, adjustable dial
- Minimal analog dial with hour markers
- Chain link band with secure clasp
Style Number/Barcode: 07007-000083
Category Name: $20 & Under Sale
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Butterfly Kisses Mesh Tie-Front Top
Floaty, flirty, and fully saved to the outfit inspo folder. This mesh butterfly print tie-front top hugs just right and pairs perfectly with the matching bottoms.
Shop Matching Bottoms: Butterfly Kisses Mesh Maxi Skirt
Fit & Features
- Butterfly print, mesh fabric, bust lining
- Long sleeves with flared cuffs
- Tie-front neckline
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06202-000088
Category Name: $20 & Under Sale
Price: $12.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: TAUPE-2
Available Size: XS, S, M, L
Product Badge:- Sale
-
Smooth Talker Strapless Bodycon Midi Dress
Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion!
Fit & Features
- Rib knit fabric, sewn-in knit lining, moderate stretch
- Strapless neckline
- Side slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000724
Category Name: $20 & Under Sale
Price: $19.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN-2, IVORY, PLUM
Available Size: XS, S, M, L
Product Badge:- Sale
-
Love Letters Ruffle Maxi Dress
Floaty dresses just do something to the mood. This floral chiffon maxi dress features a ruffle V-neck, low back detail, and tiered ruffles that move perfectly from vacation dinners to wedding guest season.
Fit & Features
- Floral print, chiffon fabric, woven lining with slit accent
- Ruffled trim V-neckline
- Adjustable spaghetti straps
- Low-cut back
- Side zipper and hook-eye closure
- Tiered ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-001482
Category Name: $20 & Under Sale
Price: $29.97 $64.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
Product Badge:- Sale
-
Windsor x Von Dutch Tube Top
Vintage attitude with a modern edge—this Von Dutch tube top does the talking for you. It hugs in all the right places while the bold graphic gives your off-duty look that effortlessly iconic feel. Pair with the matching shorts.
Shop Matching Bottoms: Windsor x Von Dutch Shorts
Fit & Features
- Stretchy cotton-blend knit fabric
- Tube strapless neckline, no-slip strip
- Von Dutch logo graphic and stud detailing
- Pointed cropped hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06002-000496
Category Name: $20 & Under Sale
Price: $15.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L
Product Badge:- Sale
-
Floral Forecast Lace Mini Dress
This is the dress that gets the compliments before you've even ordered your drink. With cascading ruffles, a romantic floral print, and a curve-loving fit, it's made for garden parties, bridal events, and birthday brunches.
Fit & Features
- Floral print lace-lined fabric
- Ruffled trim halter V-neckline
- Open back
- Curve-hugging fit, cascading side ruffles
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001401
Category Name: $20 & Under Sale
Price: $22.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Sale
-
Flirting With Plans Puff Sleeve Skater Dress
She’s cute, collected, and already has plans you’ll want in on. This puff sleeve skater dress cinches in all the right places with a breezy fit that works for dinner reservations, summer parties, and every “I had nothing to wear” moment.
Fit & Features
- Linen-blend woven fabric
- Sweetheart neckline, bust tie detail
- Short puff sleeves
- Open tie-back design
- Short skater silhouette, ruffled hem
- Runs true to size
Style Number/Barcode: 05102-000543
Category Name: $20 & Under Sale
Price: $49.90
Availability: Out of Stock
Product Badge:- Sale
-
Contour Control Shaper Underbust Romper
This sculpting romper smooths and contours with a sleek second-skin feel, giving you a streamlined foundation that disappears under form-hugging styles.
Fit & Features
- Smooth, seamless knit fabric with stretch
- Sleeveless underbust scoop neckline
- Adjustable spaghetti straps
- Sculpting compression tummy control panel
- Body-hugging silhouette with supportive shaping
- 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: 07102-000077
Category Name: $20 & Under Sale
Price: $10.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: M, L, XL
Product Badge:- Sale
-
Play the Angle Mini Skirt
Meet your new go-to for nights out and everything after. This wrap mini skirt brings flirty movement with a soft ruffle side detail and body-hugging drape that shows off your shape in all the right ways.
Shop Matching Top: Play the Angle Crop Top
Fit & Features
- Knit stretch fabric
- High-rise waist
- Faux wrap front design
- Side ruffle accent
- Bodycon fit, mini-length hem
- Runs true to size
Style Number/Barcode: 06501-000099
Category Name: $20 & Under Sale
Price: $10.97 $26.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Sale
-
Midnight Vine Sequin Bodycon Mini Dress
A form-hugging fit gives this mini dress a sleek, streamlined profile. The bodycon silhouette follows the figure while the lightweight sequin mesh keeps the finish sparkling. Perfect for birthdays, hoco, and dressed-up plans.
Fit & Features
- Sequin mesh fabrication, knit lining, high stretch
- High halter neckline with tie straps
- Back zipper and hook-eye closure
- Bodycon fit
- Mini length hem
- Runs true to size
Style Number/Barcode: 05101-001280
Category Name: $20 & Under Sale
Price: $19.97 $52.90
On Sale: Yes
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
Product Badge:- Sale
-
Elevated Thong Platform Wedge Sandals
The effortless height your outfits have been waiting for. These thong wedge sandals add a sleek lift with a minimal strap design that pairs perfectly with your everyday looks.
Fit & Features
- Wedge heel
- Almond toe
- Wide thong strap
- Cushioned insole
- Platform sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07406-000039
Category Name: $20 & Under Sale
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Ahoy Cutie Sailor Satin Corset Top
A little sailor energy goes a long way when the styling is yours to steer. This satin corset top pairs contrast trim with a strapless silhouette for a DIY piece that can shift from cute and nautical to bolder Halloween territory. Change the extras and keep the main character—your outfit—moving.
Fit & Features
- Satin sailor corset top
- Strapless neckline, non-slip grip lining
- Hidden front hook and eye fasteners
- Contrast trim, lace-up back detail
- Corset-style silhouette, flexible boning
- Cropped length
- Runs true to size
How to style for Halloween: Pair it with a mini skirt or hot shorts, sailor-inspired accessories, and statement shoes to steer the DIY look in a cheeky nautical direction.
Style Number/Barcode: 06003-000433
Category Name: $20 & Under Sale
Price: $9.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: NAVY
Available Size: L
Product Badge:- Sale
-
Backless Behavior Halter Mini Dress
This dress definitely started a few unnecessary crushes. The bodycon fit, cowl halter neckline, and attached triangle bikini top bring serious vacation confidence, while the side ruffle sashes and open back keep every angle working overtime.
Fit & Features
- Slinky knit fabric, knit lining
- Plunge halter cowl open neckline
- Attached string triangle bikini top
- Open back
- Bodycon mini-length silhouette
- Attached side ruffles
- Runs true to size
Style Number/Barcode: 05103-001029
Category Name: $20 & Under Sale
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Talk Of The Town Denim Mini Skort
Not to be dramatic, but this denim mini skort is about to do all the heavy lifting. Designed with a form-hugging fit, studded embellishment pattern, and built-in shorts lining, it's the skort for effortless styling.
Fit & Features
- Medium wash denim fabric, non-stretch, built-in shorts lining
- Mid-rise waist
- Allover studded embellished pattern
- Form-hugging fit, mini-length hem
- Front buttons and hidden zipper closure
- Four-pocket styling
- Runs true to size
Style Number/Barcode: 06603-000202
Category Name: $20 & Under Sale
Price: $14.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: MED, DENIM
Available Size: S, M, L
Product Badge:- Sale
-
Stylish Transparency Espadrille Wedges
Step into these stylish espadrille wedges with PVC clear straps that create seamless look!
Fit & Features
- Wedge heel
- Square toe
- PVC clear straps
- Platform sole
- Espadrille material
- Runs true to size
Style Number/Barcode: 07406-000005
Category Name: $20 & Under Sale
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
On Watch Lifeguard Four-Piece Costume Set
Clock in for Halloween with a beach lifeguard look that comes together in one set. The four-piece costume includes a jacket, high-cut swimsuit, whistle, and binoculars for a clear uniform-inspired finish. Keep the styling sporty and streamlined to carry the theme through.
Fit & Features
- Four-piece beach lifeguard costume set
- Includes jacket, swimsuit, whistle, and binoculars
- Knit long-sleeve jacket with contrast trim, embroidered patches, cropped fit
- One-piece swimsuit, scoop neckline, side cutouts, high-cut design, embroidered patch
- Whistle lanyard accessory
- Binocular with strap accessory
How to style for Halloween: Complete the beach lifeguard look with heels and sleek makeup.
Style Number/Barcode: 06001-000720
Category Name: $20 & Under Sale
Price: $9.97 $72.90
On Sale: Yes
Availability: In Stock
Available Color: RED
Available Size: M/L, L/XL
Product Badge:- Sale
-
Linked Up Chain Belt
The finishing touch your outfit didn’t know it needed. This chain belt adds just enough shine and attitude to pull everything together, whether you’re layering over denim or styling up a dress.
Fit & Features
- Chain link
- Lobster clasp closure
- Interlocking circle link design
Style Number/Barcode: 07301-000388
Category Name: $20 & Under Sale
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Dreamy Glam Sequin Butterfly Back Mini Dress
Sparkle in the front, a little plot twist in the back. The sequin finish of this mini dress catches the light while the delicate straps frame a butterfly accent that makes every angle more interesting. Perfect for hoco, date nights, and dressy night-out plans.
Fit & Features
- Mesh fabric with knit lining, moderate stretch
- All-over sequin embellishment
- Sleeveless V-neckline
- Spaghetti straps
- Open strappy back with detailed butterfly accent
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-001193
Category Name: $20 & Under Sale
Price: $19.97 $54.90
On Sale: Yes
Availability: In Stock
Available Color: MINT
Available Size: XS, S, M, L, XXS
Product Badge:- Sale