Maxi Dresses
Maxi dresses are the definition of effortless style—perfect from casual to cocktail plans. Wear them on vacation getaways, to brunch, or as a chic wedding guest look. Bodycon shapes turn up the heat, while flowy silhouettes keep it soft. Plunging necklines, cowl neck, strapless styles, and cutouts make a statement. Choose floral, animal, tropical, or abstract swirls in printed mesh, buttery jersey knit, silky satin, chiffon, or crochet knits for a more bohemian vibe.
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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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Just Enough Drama Slit Maxi Dress
Float in, leave an impression—no extra effort needed. This maxi dress features a V-neck halter and open back with a high front wrap slit that moves effortlessly at weddings, award nights, and every dressy occasion!
Fit & Features
- Smooth knit fabric with stretch
- Halter V-neckline with tie straps
- Open back
- High front wrap slit
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001326
Category Name: Maxi Dresses
Price: $39.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
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Vacay State Of Mind Tropical Print Maxi Dress
Vacation state of mind, no passport required. This tropical print maxi dress hugs you in all the right places with a sleek bodycon fit and bold cutout details that feel both effortless and elevated.
Fit & Features
- Knit fabric with high stretch, soft knit lining
- Tropical print
- Strapless neckline
- Triple bust cutouts and oval-shaped hardware accents
- Maxi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000622
Category Name: Maxi Dresses
Price: $46.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Weekend Glow A-Line Midi Tube Dress
Sunshine, but make it wearable. This A-Line midi tube dress hugs through the ruched bodice, then flows into an effortless, breezy silhouette that’s made for everything from brunch plans to last-minute invites.
Fit & Features
- Sleek knit fabric, high stretch
- Strapless straight-across neckline
- Fitted ruched bodice
- Maxi-length flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000722
Category Name: Maxi Dresses
Price: $42.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Hot Weather Plans Strapless Maxi Dress
Serving sunshine with zero effort. This strapless bodycon dress hugs in all the right places with a bold floral moment that makes getting dressed for vacations or weekend plans easy.
Fit & Features
- Tropical floral print, stretchy knit-lined fabric
- Strapless tube neckline
- Bodycon maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000721
Category Name: Maxi Dresses
Price: $38.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L, XL
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Bold Moves Cutout Maxi Dress
She’s bold, sculpted, and not here to blend in. This cutout maxi dress hugs in all the right places with a fluid drape that moves like you mean it.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Asymmetric waist cutout
- Ruched detailing
- Maxi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-001190
Category Name: Maxi Dresses
Price: $38.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
Product Badge:- Best Seller
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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: Maxi Dresses
Price: $64.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
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Small Talk Floral Mesh Maxi Dress
Floaty, fitted, and guaranteed to get compliments before you even sit down. This floral mesh maxi dress contours through the body with ruched detailing, then flares out into a long hem made for slow dances.
Fit & Features
- Delicate floral print, airy mesh fabric, knit lining
- Strapless tube neckline, non-slip grip lining
- Ruched detail
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001167
Category Name: Maxi Dresses
Price: $46.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Blossom Blur Satin Floral Maxi Dress
This floral maxi dress was made for dressy celebrations. The body-skimming fit hugs in all the right places while the strappy tie-back design makes heads turn. Pair with heels.
Fit & Features
- Floral pattern, silky satin fabric
- Scoop neckline
- Spaghetti straps
- Strappy open tie back design
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001086
Category Name: Maxi Dresses
Price: $52.90
Availability: In Stock
Available Color: PERIWINKLE
Available Size: XS, S, M, L
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Shelly Abstract Print Mesh Ruffle Mermaid Dress
Special Occasion
The Shelly abstract print mesh mermaid dress was designed to make an impression from every angle. The strapless silhouette hugs the body in all the right places, while the cascading ruffle detail and sculptural hardware trim bring just the right amount of drama for every RSVP that calls for dressing up.
Fit & Features
- Mesh fabric with full-length knit lining, high stretch
- Abstract print
- Strapless sweetheart neckline, ruched bust, padded bra cups
- Asymmetric textured hardware accent
- Front ruffled sash
- Floor-length mermaid silhouette
- Runs true to size
Where to Wear:
Vacations, dressed-up dinners, birthday celebrations, wedding guests, rooftop parties, and glam nights out.
Style Number/Barcode: 05002-001439
Category Name: Maxi Dresses
Price: $79.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Jasmine Halter Slit Formal Dress
Special Occasion
Made for the kind of night that starts with compliments and ends with everyone asking where you found it, the Jasmine column dress delivers a striking silhouette with effortless allure. The halter neckline, cascading hardware, and side slit create a bold yet polished look that feels made for destination soirées and RSVP moments alike.
Fit & Features
- Texture knit fabric, smooth knit stretchy lining
- Halter cutout plunge neckline with chunky hardware
- High side slit
- Column silhouette
- Long-length hem
Where to Wear:
Bridal celebrations, bachelorettes, destination weddings, beach weddings, beach clubs, vacations, honeymoons, birthday dinners, resorts, yacht parties
Style Number/Barcode: 05002-001664
Category Name: Maxi Dresses
Price: $69.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L, XL
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Double Take Paisley Print Mesh Maxi Dress
Low back, high impact. This paisley print mesh maxi dress brings the drama with a curve-skimming fit, barely-there straps, and a draped back that keeps every exit memorable.
Fit & Features
- Paisley printed mesh fabric with knit lining, high stretch
- Sleeveless deep V-neckline, bar strap detail
- Spaghetti straps
- Open cross-back strappy design with tie closure
- Lower draped back
- Maxi-length hem, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000647
Category Name: Maxi Dresses
Price: $49.90
Availability: In Stock
Available Color: RED, BROWN
Available Size: XS, S, M, L
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Flirty Chic Cutout Maxi Dress
The kind of dress that makes every plan feel a little more chic. With its flowy silhouette, flirty cutout detail, and side pockets, this maxi dress was made for vacations, weekend plans, and showers.
Fit & Features
- Gauze cotton woven fabric, woven lining
- Sweetheart neckline, spaghetti straps
- Open tie-back design
- Cutout bodice
- Hidden side pockets
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000559
Category Name: Maxi Dresses
Price: $46.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Sunkissed Stunner Halter Maxi Dress
Vacation mode called, and this maxi dress already answered. With a plunging halter neckline, bold cutout details, and a flowy front slit silhouette, this maxi dress was made for beachside brunches, sunny getaways, and weekend plans.
Fit & Features
- Artsy print, woven fabric
- Halter neckline
- Strappy cutout bodice, back zipper and hook-eye closure
- High front slit
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000645
Category Name: Maxi Dresses
Price: $59.90
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, M, L
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Extra Attention Slinky Knit Cutout Maxi Dress
The kind of dress that changes the whole mood the second you walk in. This slinky knit maxi dress hugs in all the right places with daring cutouts, gleaming hardware accents, and a plunging halter neckline made for plans that deserve a little extra attention.
Fit & Features
- Slinky knit fabric, high stretch
- Sleeveless plunging V-neckline
- Dual waist cutouts, hardware accents
- Tie-back halter straps
- Partially open back, lower zipper closure
- Maxi-length hem, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-001205
Category Name: Maxi Dresses
Price: $54.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
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Vacation Flirt Knit Cutout Maxi Dress
Serving vacation flirt and trendy vibes. This knit maxi dress hugs in all the right places with lace-up cutouts, a plunging halter neckline, and an open back that knows exactly what it’s doing.
Fit & Features
- Knit fabric with flame stitch pattern
- Sleeveless plunging V-neckline, beaded strap
- Tie-back halter straps
- Lace-up side cutouts
- Open back, lower tie-back spaghetti straps
- Back zipper and hook-eye closure
- Maxi-length bodycon silhouette, back slit accent
- Runs true to size
Style Number/Barcode: 05102-000606
Category Name: Maxi Dresses
Price: $48.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
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Daydream Detour Paisley Maxi Dress
Easy, floaty, and somehow always the prettiest thing in your closet. This floral paisley maxi dress features a flowy silhouette, lace trim details, and an open tie back that feels made for brunch, weekend markets, and sunny day plans.
Fit & Features
- Floral paisley print, woven fabric, short woven lining
- V-neckline, spaghetti straps
- Open tie-back
- Center front button-up closures
- Flowy maxi silhouette, sheer lace trim
- Runs true to size
Style Number/Barcode: 05102-000592
Category Name: Maxi Dresses
Price: $54.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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Postcard From Paradise Maxi Dress
Mentally already sipping something fruity by the water. This flowy maxi dress brings vacation dressing to life with a citrus postcard print, flirty front tie detail, and lace-up back that looks good from every angle.
Fit & Features
- Multi-printed design, woven fabric
- V-neckline with trim and tie bust
- Spaghetti straps
- Lace-up tassel back
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000572
Category Name: Maxi Dresses
Price: $49.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Brown Sugar Breeze Cutout Maxi Dress
This strapless maxi dress brings the kind of effortless allure that looks good from beach strolls to walks back to the hotel. The smocked fit, soft cutout detail, and flowy skirt keep it stylish with a pair of sandals.
Fit & Features
- Gauze woven fabric
- Strapless sweetheart neckline
- Stretchy smocked bodice with cutout
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000602
Category Name: Maxi Dresses
Price: $56.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Table For Two Lace Maxi Dress
The kind of dress that keeps the compliments coming before you’ve even made it to dinner. This lace maxi dress hugs in all the right places with a curve-skimming fit and strappy open back that feels equal parts effortless and unforgettable.
Fit & Features
- Lace fabric, knit lining
- Sweetheart neckline
- Spaghetti straps
- Open strappy back
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001131
Category Name: Maxi Dresses
Price: $49.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Vacay Romance Floral Maxi Dress
This is the dress that turns dinner plans into an occasion. Featuring a draped cowl neckline, open back, and oversized florals, it hugs in all the right places while serving effortless looks on vacations, weekend getaways, or date nights.
Fit & Features
- Floral tropical print, knit stretchy fabric with lining
- Cowl halter neckline, tie straps
- Open back
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-001148
Category Name: Maxi Dresses
Price: $44.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L, XL
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Coast To Cocktails Striped Maxi Dress
The dress that belongs in your vacation photo dump. With a plunging halter neckline, textured striped knit, and an open tie-back design, this maxi dress was made for ocean views, dinner reservations, and weekend escapes.
Fit & Features
- Striped pattern, sheer texture crochet knit fabric
- Halter neckline, tie straps
- Open tie-back
- High side slit
- Curve-hugging, long hem
- Runs true to size
Style Number/Barcode: 05102-000591
Category Name: Maxi Dresses
Price: $39.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
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Vacation Booked Tropical Floral Cutout Maxi Dress
This deserves a spot in your vacation photo dump. This tropical floral cutout maxi dress pairs a bodycon fit with a striking waist cutout, statement hardware detail, and a sweeping silhouette made for unforgettable entrances.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Large tropical floral print
- Sleeveless sweetheart neckline, metal hardware accent
- Adjustable spaghetti straps, partially open back
- Front waist cutout
- Maxi-length hem with high-cut side slit, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000673
Category Name: Maxi Dresses
Price: $44.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
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Kristie Pleated Satin A-Line Formal Dress
Special Occasion
The Kristie formal dress pairs pleated satin woven fabric with a luminous sheen and effortless movement. A plunge halter neckline framed by a snake chain strap, open back, and underbust tie front detail creates a striking look, while the flowy A-line floor-length silhouette glides with every step.
Fit & Features
- Pleated satin woven fabric with sheen, woven lining
- Plunge halter neckline, snake chain strap
- Underbust tie-front detail
- Open back
- Flowy A-line silhouette
- Floor-length hem
- Runs true to size
Where to Wear:
Black tie weddings, galas, destination celebrations, birthday events, cocktail soirees, date nights, anniversaries, red carpet events, fancy dinner parties
Style Number/Barcode: 05002-001716
Category Name: Maxi Dresses
Price: $69.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
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Worth The Wait Chain Detail Maxi Dress
The kind of dress that changes the whole plan. This abstract print maxi dress combines a plunging cowl neckline, draped chain detail, and an open-back silhouette for a look that's both art exhibit and dinner reservation.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Abstract print
- Sleeveless plunging cowl neckline, triple chain strap accents
- Tie-back halter straps, open back
- Maxi-length hem, high-cut back slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000370
Category Name: Maxi Dresses
Price: $48.90
Availability: In Stock
Available Color: PLUM
Available Size: XS, S, M, L