Maxi Dresses
Embrace versatility and style with our collection of maxi dresses, designed for every occasion. Our assortment features relaxed, breezy styles perfect for casual beach days to romantic A-line dresses for formal weddings. Our maxi dresses come in various styles, including dreamy bohemian looks with flutter sleeves, romantic off-the-shoulder designs, and elegant halter necklines. Whether you’re dressing for a laid-back afternoon or a formal evening, find a maxi dress that combines comfort with chic appeal, ensuring you look effortlessly stylish no matter the setting.
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Maxi Dresses
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Maxi Magic for Sunny Socials
Own every summer 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 summer dresses deliver breezy comfort with layered ruffles and flowy silhouettes in seasonal hues like sunset orange and soft ivory. Maxi‑length floral styles shine in exclusive large‑bloom prints and vibrant patterns, making every photo op pop. Discover lightweight 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 summer statement.
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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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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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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
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Lucilla V-Neck Tiered Mesh Dress
Special Occasion
Ooh la la, Lucilla is here! Make a dramatic entrance in this eye-catching formal dress for your next fancy gathering. She features a trendy, sleeveless, surplice V-neck, adjustable spaghetti straps, and mesh straps that lace up along her open-back design. The voluminous ruffled tiered mesh skirt is designed in an A-line silhouette that gently sweeps across the floor. Complete the look in a glam rhinestone hairpiece for a stunning updo.
Fit & Features
- Sleeveless, surplice V-neck, adjustable spaghetti straps
- Open-back, lace-up, zipper closure
- A-line silhouette, floor-length hem
- Ruffled tiered mesh skirt, stretchy knit lining
- Sticky bra or pasties recommended
- Fits true to size
Style Number/Barcode: 05002-2184
Category Name: Maxi Dresses
Price: $59.97 $139.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Veronica Formal Floral Chiffon A-Line Dress
Special Occasion
Fresh, floral, and ready for your spring formal! The Veronica chiffon a-line dress is all romance in her effortless, sleeveless bodice with delicate details everyone will be swooning for. She features a plunge v-neckline with pleating and adjustable spaghetti straps that cross in the back on the open design. Her a-line silhouette flows into a floor-length hem to elongate your figure while creating an hourglass appearance. The formal dress is composed of an airy chiffon overlay with an inner knit lining. Complete the look in an elegant hairpiece for a stunning updo.
Fit & Features
- Plunge v-neckline, pleating, adjustable spaghetti straps
- Adhesive bra recommended
- Open-back design, cross straps, zipper closure
- A-line silhouette
- Floor-length hem
- Airy floral chiffon overlay, inner lining, no stretch
- Fits true to size
Style Number/Barcode: 05002-1886
Category Name: Maxi Dresses
Price: $14.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Siesta Keys Tropical Maxi Dress
Take a vacation to Siesta Keys looking fab in this tropical maxi dress! It features a sleeveless, v-neck, spaghetti straps, and a tie-front bust atop a cutout bodice leading to the form-fitting silhouette with a sultry side slit. Complete your vacay look in a straw hat and your fave sunglasses.
Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Tie-front bust
- Cutout bodice
- Form-fitting silhouette
- Side slit, maxi hem
- Tropical print
- Fits true to size
Style Number/Barcode: 05102-4377
Category Name: Maxi Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Life Made Easy Linen Halter Maxi Dress
Look effortlessly put together in this breezy striped linen maxi dress for a Duffy boat cruise or beachside brunch! It features a sleeveless, halter v-neck with tie-closure, a partial open-back with tie, hidden side pockets, and a flowy, maxi-length silhouette with a sultry front slit. Complete the look in a straw floppy hat and sandals.
Fit & Features
- Sleeveless, halter v-neck, tie-closure
- Partial open-back with tie
- Hidden side pockets
- Flowy silhouette
- Front high-cut slit
- Maxi-length hem
- Striped linen fabric, lining, no stretch
- Fits true to size
Style Number/Barcode: 05102-4468
Category Name: Maxi Dresses
Price: $6.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Total Beauty Floral Maxi Dress
Radiate your beauty in this blooming floral printed maxi dress! It features a romantic off-the-shoulder neckline, short ruffled drape sleeves, an empire waist, and a flowy floor-length silhouette with dual high front slits. Style this dress with strappy sandals.
Fit & Features
- Off-the-shoulder neckline
- Short ruffled drape sleeves
- Empire waist
- Floor-length silhouette, flowy fit, dual front slits
- Floral print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4535
Category Name: Maxi Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Frolic Crochet Maxi Dress
Frolic around this summer in this breezy sleeveless maxi dress featuring a delicate crochet trim, a plunge v-neckline, and a flowy, tiered floor-length hem on gauze woven fabric with a knit lining and no stretch. Complete your sunny day look in a floppy straw hat.
Fit & Features
- Sleeveless, plunge v-neckline, wide straps
- Empire waistline
- Back zipper closure
- Flowy, tiered maxi-length hem
- Crochet trim throughout
- Gauze woven fabric, knit lining, no stretch
- Fits true to size
Style Number/Barcode: 05101-1573
Category Name: Maxi Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Rosalynn Formal Sweetheart Dress
Special Occasion
Have yourself a renaissance romance in the Rosalynn formal dress sure to sweep your date off their feet. She features a sweetheart neckline, long bishop sleeves with button closures, and a twisted bodice with sultry cutout accents that lead to her floor-length a-line silhouette. The formal dress is composed of flowy chiffon fabric with lining. Complete the look in statement earrings for a touch of glam.
Fit & Features
- Sweetheart neckline, long bishop sleeves, button closure
- Padded cups
- Twisted bodice, cutout accents
- A-line silhouette, floor-length hem
- Back zipper closure
- Flowy chiffon fabric, lining
- Fits true to size
Style Number/Barcode: 05002-2077
Category Name: Maxi Dresses
Price: $19.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tie Dye For One Shoulder Dress
This maxi dress is totally tie-dye for your next beach day or vacay! Featuring a sleeveless, one-shoulder neck, tank-style strap, high waist seam, and a form-fitting silhouette with a side knot accent atop an asymmetrical hem. Complete the look in cute wedges and shades.
Fit & Features
- Sleeveless, one-shoulder neck, tank-style strap
- High waist seam
- Form-fitting silhouette
- Side knot accent
- Asymmetrical maxi-length hem
- Tie-dye print, brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4622
Category Name: Maxi Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Kris Formal Floral Chiffon Dress
Special Occasion
Romance the room in the Kris floral chiffon dress is perfect for a summertime soiree. She features a sleeveless, V-neck, adjustable spaghetti straps, and a delicately pleated bust atop an empire waist. Create a lovely look in her tiered A-line silhouette that gracefully sweeps along the floor with each step. The formal dress is composed of airy chiffon with an inner lining and no stretch. Complete your dressy look in chandelier earrings.
Fit & Features
- Sleeveless, V-neck, adjustable spaghetti straps
- Strapless bra recommended
- Pleated bust, empire waist, smocked back
- Tiered A-line silhouette
- Floor-length hem
- Floral chiffon fabric, inner lining, no stretch
- Runs true to size
Style Number/Barcode: 05002-2185
Category Name: Maxi Dresses
Price: $19.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Rue Formal Floral Wrap Dress
Special Occasion
Lace up in a formal dress that brings the romance! Rue features a pretty floral pattern, a sleeveless square neckline with padded cups, spaghetti straps that lead to a cross-back, and a lace-up back. Her slim fit bodice leads to a flowy wrap silhouette with a high side slit that is accented with a ruffled trim. The dress is composed of a lined of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges and a straw hat.
Fit & Features
- Sleeveless square neckline
- Padded cups
- Spaghetti straps, cross-back
- Lace-up back
- High side slit, ruffled trim
- Floral pattern
- Lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05002-2078
Category Name: Maxi Dresses
Price: $14.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sonia Formal Halter Cutout Chiffon Long Dress
Special Occasion
Show some skin! Feel so sultry in the Sonia Formal Halter Cutout Chiffon Long dress for your next evening out. She features an alluring, sleeveless halter neck with tie-back closure, a ruched cutout bust, and a pleated empire waist. Her airy silhouette leads to a floor-length hem with a high-cut front slit for a sexy show of leg. The formal dress is composed of a flowy chiffon texture-lined fabric with no stretch. Finish the look in stiletto heels.
Fit & Features
- Halter neck with tie-back closure
- Disposable pasties recommended
- Ruched cutout bust, pleated empire waist
- Airy silhouette, floor-length hem
- High-cut front slit
- Chiffon texture lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 05002-2101
Category Name: Maxi Dresses
Price: $14.97 $79.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Boho Breeze Crochet Maxi Dress
Look and feel like a daydream in this boho maxi dress designed in a breezy, silhouette featuring a sleeveless, crochet lace v-neck bodice, spaghetti straps, and a sultry open-back with a tie closure that leads to the flowy long hem. Complete the look in strappy sandals.
Fit & Features
- Sleeveless, crochet lace v-neck bodice, spaghetti straps
- Open-back, tie closure
- Flowy maxi silhouette
- Long-length hem
- Partially lined woven fabric
- Fits true to size
Style Number/Barcode: 05102-4449
Category Name: Maxi Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale