Maxi Dresses
Maxi dresses are the ultimate mix of chic and effortless, perfect for everything from date night to semi-formals or fall wedding guest looks. A-line silhouettes keep it timeless, while fit and flare styles bring a flirty edge. Cowl-neck and strapless designs add allure, and fabrics like buttery soft jersey knit or printed mesh keep it fresh. With shades of brown, black, burgundy, and rust, plus florals and abstract swirl prints, these maxi dresses are the go-to for polished yet trendy style.
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Maxi Dresses
Product Recommendations
Maxi Magic for Socials
Own every social moment in a Windsor maxi dress. Bold tropical prints and pastel florals set the scene for brunch dates, beach days, and nights out, while adjustable straps and high front slits keep things easy and effortless.
Casual long dresses and maxi-length dresses deliver breezy comfort with layered ruffles and flowy silhouettes in seasonal hues like burnt orange and soft ivory. Maxi‑length floral styles shine in exclusive large‑bloom prints and vibrant patterns, making every photo op pop. Discover sundresses that feel airy and breathable, with playful shapes and flirty details to keep you cool and confident.
Formal maxi dresses and sleek maxi‑length designs in soft mesh fabrics, tiered ruffle accents, and curve‑hugging fits elevate backyard weddings and rooftop soirées—blending chic style with total comfort.
Looking for styling inspo? Dive into brunch dresses, vacation dresses, and more on the Windsor blog: Get Insta-ready In Your Maxi Dress. Shop online, in‑app, or at your nearest Windsor store to find your next social statement.
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Feeling Good Turtleneck Maxi Dress
Look and feel good in this rib knit maxi dress perfect for everyday styling! It features long sleeves, a turtleneck, a form-hugging silhouette, and a side-slit accent. Complete the look in mules for a dinner date.
Fit & Features
- Long fitted sleeves
- Turtleneck
- Form-hugging silhouette
- Side slit
- Maxi-length hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4861
Category Name: Maxi Dresses
Price: $5.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Alluring And Effortless Maxi Dress
Alluring and effortless, this sleek maxi dress will elevate your look. It features a sleeveless V-neckline, spaghetti straps, a wrap-front design at the bodice, a curve-hugging maxi-length silhouette, and a chic thigh-high front slit. Style this dress with a dainty layered necklace and heeled mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Wrap-front design at the bodice
- High waist seam, maxi-length silhouette, high front slit
- Form-hugging fit
- Smooth knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4633
Category Name: Maxi Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Fantasy Open Back Maxi Dress
Channel a floral fantasy with a maxi dress that is flowy and gorge! The dress features a pretty floral print, a sleeveless V-neckline, spaghetti straps, an open back with a floral lace panel, and a flowy maxi length silhouette. Complete look with wedges and a floppy hat.
Fit & Features
- Floral print
- Sleeveless V-neckline
- Spaghetti straps
- Floral lace back
- Maxi length silhouette
- Lined chiffon fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-1089
Category Name: Maxi Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Turn Heads Tie-Dye Open Back Maxi Dress
Serving body, back, and bold energy! This mesh maxi turns heads with a sultry cowl halter, hoop details, and a tie-dye print that does the most in the best way.
Fit & Features
- Tie-dye print, mesh fabric, stretchy knit lining
- Cowl halter neckline
- Hoop inserts, tie-back straps
- Open back
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000115
Category Name: Maxi Dresses
Price: $52.90
Availability: In Stock
Available Color: PINK
Available Size: S, M
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Trendy Muse Maxi Dress
Show off your casual and trendy style in this sleek knit maxi dress. It features a sleeveless scoop neckline, spaghetti straps that lead to a cross-back design, a ruched wrap-front creating a high slit, and a curve-hugging fit with an asymmetrical hem. Complete the look with clear mules.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps, cross-back design
- Ruched wrap-front, high slit
- Maxi-length asymmetrical hem
- Form-fitting silhouette
- Smooth knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05101-1740
Category Name: Maxi Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flatter Me Cutout Maxi Dress
You won't need anyone flattering you in this sexy maxi dress! Featuring a sleeveless, scoop neck, spaghetti straps, a cutout bodice, partial open-back, a form-fitting silhouette, and a sultry slit perfect for showcasing heels.
Fit & Features
- Sleeveless, scoop neck, spaghetti straps
- Cutout bodice
- Partial open-back
- Form-fitting silhouette
- Front slit
- Maxi-length hem
- Slinky knit fabric, moderate stretch, fits true to size
Style Number/Barcode: 05102-4603
Category Name: Maxi Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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One Night Of Chic Mesh Maxi Dress
Have your chic moment in this mesh maxi dress featuring a sultry, one-shoulder neckline, a partial open-back, side and back ruching, and an asymmetrical maxi-length hem with a side slit cutout. Complete your dressy look in sleek heels.
Fit & Features
- Sleeveless, one-shoulder neckline, spaghetti strap
- Partial open-back
- Side and back ruching
- Side slit cutout
- Asymmetrical maxi-length hem
- Form-hugging fit, partial lining, mesh fabric
- Fits true to size
Style Number/Barcode: 05102-4736
Category Name: Maxi Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Timeless Twist One Shoulder Dress
Bring the allure in this one-shoulder maxi dress featuring a sleeveless bodice, a single spaghetti strap, and a form-hugging silhouette atop an asymmetrical slit hem with a timeless twist accent. Complete the look in dangly earrings and heels.
Fit & Features
- Sleeveless, one-shoulder
- Single spaghetti strap
- Form-hugging silhouette
- Twist accent and slit
- Asymmetrical maxi-length hem
- Slinky knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4714
Category Name: Maxi Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Natural Beauty Tropical Maxi Dress
Explore a tropical island looking naturally beautiful in this palm print maxi dress featuring a sleeveless, square neck, halter straps, an open back with tie, bodycon silhouette, and a front twist accent atop a sultry slit. Complete the look in a straw floppy hat.
Fit & Features
- Sleeveless, square neck, halter straps
- Open-back with tie
- Bodycon silhouette
- Front twist accent and slit
- Maxi-length hem
- Tropical palm print, knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4720
Category Name: Maxi Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sandy Toes Crochet Bodysuit Dress
The perfect long dress to walk the sandy beaches! This crochet maxi features a sleeveless, V-neck, adjustable spaghetti straps, dual front hoop inserts, and a bodysuit lining with dual-snap button closure on a cheeky bottom. Complete the look in boho earrings and a bracelet.
Fit & Features
- Sleeveless, V-neck, adjustable spaghetti straps
- Dual front hoop inserts
- Bodysuit lining, dual snap-button closure, cheeky bottom
- Form-fitting silhouette
- Maxi-length hem
- Sheer crochet fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4675
Category Name: Maxi Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Maya Long Sleeve Chiffon A-Line Dress
Special Occasion
Showcase your ethereal beauty in the gorgeous Maya chiffon dress! She features a deep V-neckline with a wrap-front design, long sheer flowy sleeves with ruffled hems, a high waist with a tie-front belt, and a floor-length A-line silhouette with a chic front slit. The sheer airy chiffon fabric includes a partial knit lining. Complete the look with cascading duster earrings and embellished heels.
Fit & Features
- Deep V-neckline, wrap-front design
- Bra-friendly
- Long sheer flowy sleeves, ruffled hems
- Back zipper, hook and eye closure
- High waist, tie-front belt
- Floor-length A-line silhouette, front slit
- Sheer chiffon fabric, partial knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05002-2171
Category Name: Maxi Dresses
Price: $14.97 $74.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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All Eyes On You High Slit Maxi Dress
Giving "I didn’t come to play, I came to slay" energy. With a draped neckline, leggy side slit, and flattering ruching—this dress is a total scene-stealer from cocktail hour to afterparty.
Fit & Features
- Soft knit fabric with stretch, full knit lining
- Draped cowl neckline with adjustable spaghetti straps
- Side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000059
Category Name: Maxi Dresses
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Sultry Spice Cutout Maxi Dress
Sultry and spicy! Make jaws drop in this sleeveless maxi dress featuring a one-shoulder neckline, waist cutout details and a form-fitting silhouette with a high-cut side slit for a show of skin. Composed of stretchy slinky knit fabric. Finish the look in lucite mules.
Fit & Features
- Sleeveless, one-shoulder neckline
- Waist cutout details
- Form-fitting silhouette
- High-cut side slit
- Maxi-length hem
- Slinky knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4528
Category Name: Maxi Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beachy Vibes Maxi Sweater Dress
Bring the beachy vibes to your summer look with this effortlessly chic maxi sweater dress. It features a sleeveless scoop neckline, spaghetti straps, an open back with a cross-back strap design, and a fitted, maxi-length silhouette with a high side slit. The sweater knit fabric features pretty crochet detailing. Style this dress with sandals.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Open back, cross-back strap design
- Fitted, maxi-length silhouette, side slit
- Sweater knit fabric, crochet detailing, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1421
Category Name: Maxi Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tropical Flower Lattice Back Dress
Look as pretty as the island flowers in this tropical maxi dress perfect for a luau dinner! It features a sleeveless, square neck, sleek spaghetti straps, an open back with lattice detailing, a sultry side slit, and a curve-hugging silhouette. Complete your vacay look in large hoop earrings.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Open-back, lattice straps
- Side slit, curve-hugging silhouette
- Maxi-length hem
- Tropical floral print, knit fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4506
Category Name: Maxi Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Paradise Ready One-Shoulder Maxi Dress
This gorgeous tropical printed maxi dress will have you looking ready for a vacay off to paradise! It features a sleeveless one-shoulder neckline, a single bungee spaghetti strap, an asymmetrical waist cutout with a chic O-ring accent, and a curve-hugging, floor-length silhouette with a front slit. The stretchy knit fabric features an all-over palm leaf print. Complete your look with slip-on sandals and your fave shades.
Fit & Features
- Sleeveless one-shoulder neckline
- Single bungee spaghetti strap
- Asymmetrical waist cutout, O-ring accent
- Maxi-length hem, form-fitting silhouette, front slit
- Tropical palm leaf print
- Knit fabric, short knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4484
Category Name: Maxi Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island Hopping Tropical Maxi Dress
Feel the island breeze in this tropical maxi dress for your next holiday in the sun! It features a sleeveless, halter neck, a sultry cutout bodice that leads to the open tie-back closure, and a flowy maxi hem with a slit. Complete your vacay look with lace-up heels.
Fit & Features
- Sleeveless, halter neck with tie
- Cutout bodice
- Open-back, tie closure
- Side slit
- Flowy maxi silhouette
- Tropical print, woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 05102-4500
Category Name: Maxi Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Desert Vacay Sleeveless Maxi Dress
Make sure to pack this effortlessly-chic maxi dress in your weekend bag for your desert vacay! It features a sleeveless plunging V-neck and back design, tank shoulder straps, a high-rise banded waist with side cutouts, and a flowy, floor-length silhouette with a front slit to show some leg. Style this dress with espadrille sandals.
Fit & Features
- Sleeveless plunging V-neck and back design
- Tank shoulder straps
- High-rise banded waist, side cutouts
- Maxi-length hem, flowy silhouette
- Front slit
- Woven gauze fabric, pleated detailing, knit skirt lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4504
Category Name: Maxi Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Summer Halter Maxi Dress
Sultry for summer. Raise the chicness in this halter maxi dress featuring a sleeveless bodice with tie-closure, o-ring inset, and a cutout accent leading to the bodycon silhouette with an asymmetrical slit hem. Complete your sultry look in espadrille wedges.
Fit & Features
- Sleeveless, halter neck, tie closure
- O-ring inset, cutout accent
- Bodycon silhouette
- Asymmetrical slit
- Maxi-length hem
- Rib-knit fabric, moderate stretch, fits true to size
Style Number/Barcode: 05102-4467
Category Name: Maxi Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Savor The Moment Halter Cutout Maxi Dress
Step into the spotlight in this halter maxi dress on vacation or for some summer fun! Featuring a striking halter neckline adorned with elegant hardware and a shimmering stone insert, this bodycon dress offers a bold cutout design that highlights your figure.
Fit & Features
- Smooth knit stretchy fabric
- Halter neckline with tie closure
- Hardware and stone insert
- Cutout accents
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000030
Category Name: Maxi Dresses
Price: $14.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gorgeous Getaway Sleeveless Maxi Dress
Get ready for a gorgeous getaway in this alluring sleeveless maxi dress! It features a V-neckline, spaghetti straps, a cross-back strap design, a fitted high waist seam, and a floor-length silhouette with a chic high front slit. The knit fabric features an all-over tropical palm leaf print. Style this dress with strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross-back strap design
- Fitted high waist seam
- Floor-length silhouette, high front slit
- Palm leaf print
- Knit fabric
- Runs true to size
Style Number/Barcode: 05102-4362
Category Name: Maxi Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Summer Style Maxi Dress
Summertime is all about showcasing that effortlessly chic style! This ribbed knit maxi dress features a sleeveless one-shoulder neckline with a single spaghetti strap, a fitted high waist seam with a knot twist design, and a curve-hugging maxi-length silhouette with a trendy high slit. Complete the look with strappy mules.
Fit & Features
- Sleeveless one-shoulder neckline, single spaghetti strap
- High waist seam, knot twist design
- Maxi-length silhouette, high slit
- Form-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4625
Category Name: Maxi Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Beauty Floral Chiffon Maxi Dress
Showcase your effortless beauty in this stunning flowy floral maxi dress! It features a sleeveless V-neckline, spaghetti straps that lead to a lace-up back design, a fitted high waist, and a floor-length silhouette with a relaxed fit. The lined chiffon fabric features an all-over floral print pattern. Style with your fave mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, lace-up back, tie closure
- High waist seam, floor-length maxi silhouette
- Floral print
- Sheer chiffon fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-1552
Category Name: Maxi Dresses
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ready Set Vacay Gauze Maxi Dress
Pack this flowy lightweight maxi dress in your carry-on as you jet set off on vacay! It features a sleeveless V-neckline, halter spaghetti straps, a smocked high waist with chic cutouts leading to an open strappy back, and a floor-length maxi silhouette with a side slit and a relaxed fit. Style with espadrille sandals.
Fit & Features
- Sleeveless V-neckline
- Halter spaghetti straps, tie at the back of the neck
- Smocked high waist, cutouts leading to open back
- Strappy back design
- Maxi-length silhouette, side slit
- Woven gauze fabric, mini skirt knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4497
Category Name: Maxi Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free