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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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
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Weekend Away Strapless Maxi Dress
This chevron maxi dress hugs in all the right places with a sleek strapless neckline and leg-baring side slit that was practically made for resort dinners, sunset cocktails, and strolling the beachside town.
Fit & Features
- Chevron pattern, crochet fabric, smooth knit lining
- Strapless neckline
- Side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000595
Category Name: Maxi Dresses
Price: $46.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
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Midnight Coast Halter Maxi Dress
This dress makes every head turn. The sleek halter neckline, hardware detail, and curve-skimming silhouette bring allure to weddings, cocktail parties, and dressy date nights.
Fit & Features
- Slinky knit fabric, smooth knit lining
- Halter neckline, tie straps, hardware insert, cutout accent
- Partial open back
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-001469
Category Name: Maxi Dresses
Price: $54.90
Availability: In Stock
Available Color: NAVY-2
Available Size: XS, S, M, L, XL
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Rynlee Strapless Mermaid Formal Dress
Special Occasion
Made for the kind of evening that lingers long after the last dance, Rynlee slinky knit mermaid gown blends sleek glamour with striking detail. The strapless neckline, wooden hoop insert cutout bust, and flowing center front sash create a sculpted silhouette that feels equal parts polished and unforgettable.
Fit & Features
- Slinky knit fabric, knit lining
- Strapless neckline
- Wooden hoop insert, cutout, center front sash
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, engagement parties, vacations, honeymoons, resort getaways, cocktail parties, date nights, birthday dinners, formal celebrations
Style Number/Barcode: 05002-001603
Category Name: Maxi Dresses
Price: $69.90
Availability: In Stock
Available Color: SAGE
Available Size: XS, S, M, L, XL
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Rooftop In Santorini Maxi Dress
The dress equivalent of a first class upgrade. With a plunging halter neckline, statement bead details, and a low open back, this maxi dress was made for resort dinners, oceanfront cocktails, and making every entrance feel a little more unforgettable.
Fit & Features
- Mesh fabric, knit lining
- Plunge halter neckline
- Open back design, lower zipper and hook-eye closure
- Front colored stone button accents
- Ruched drop waist panel
- Side slit
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001163
Category Name: Maxi Dresses
Price: $48.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Make Them Stare Mesh Slit Maxi Dress
This is the dress that captures all the attention on vacations and weekend escapes. Featuring a bold floral print, curve-hugging fit, and a leg-baring side slit, it's equal parts sultry and unforgettable.
Fit & Features
- Statement floral print, mesh-lined fabric
- Strapless tube neckline
- High side slit
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001170
Category Name: Maxi Dresses
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
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Valerie Polka Dot Ruffle Formal Dress
Special Occasion
Made for that slow-turn, stop-and-stare moment, the Valerie polka dot mermaid gown moves with every step like it knows it’s being watched. The strapless sweetheart neckline, ruched bodice, and cascading ruffle tiers bring a playful kind of drama that feels equal parts polished and unforgettable.
Fit & Features
- Polka dot print, organza woven fabric with full-length lining
- Strapless sweetheart neckline, keyhole cutout at the bust, padded bra cups, non-slip grip lining
- Lace-up back with tie closure, lower back cutout detail, zipper and hook-eye closure
- Sculpted ruffled design
- Floor-length mermaid silhouette with a bonded hem
- Runs true to size
Where to Wear:
Prom, garden parties, galas, upscale birthday events, formal milestone celebrations, fancy brunches, tea parties, race days, derby days, and black-tie occasions.
Style Number/Barcode: 05002-001396
Category Name: Maxi Dresses
Price: $129.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Center Of Attention Floral Maxi Dress
This is the dress that gets the double-take. Designed with a curve-hugging mermaid silhouette and oversized floral print, it brings major romance with a little bit of drama.
Fit & Features
- Statement floral print, lined mesh fabric, high stretch
- Strapless tube neckline
- Curve-hugging, mermaid fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000593
Category Name: Maxi Dresses
Price: $42.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
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Coconut Coast Cutout Maxi Dress
Booked the trip and packed this tropical maxi dress that brings vacay vibes with a smocked fit, breezy skirt, and just the right amount of skin-baring detail. Pair with sandals and sunnies.
Fit & Features
- Tropical palm print, gauze-woven fabric
- Strapless sweetheart neckline
- Ruched drawstring tie-front bodice
- Cutout accent
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000601
Category Name: Maxi Dresses
Price: $59.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Rare Find Animal Print Maxi Dress
A little wild, a little glamorous, and impossible to scroll past. This animal print mesh maxi dress pairs a sweetheart neckline, cutout details, hardware accents, and a dramatic front sash for the kind of entrance people remember.
Fit & Features
- Multi-animal print, lined mesh fabric
- Strapless sweetheart neckline
- Hardware bust insert with cascading sash
- Cutout bodice
- Curve-hugging, maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000803
Category Name: Maxi Dresses
Price: $54.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Sleek Hardware Cutout Halter Maxi Dress
Consider this your shortcut to a sharper going-out look. Metallic ring accents and angled front openings give this body-skimming dress a sculpted finish made for dressy occasions.
Fit & Features
- Lined smooth stretch knit fabric
- Halter tie neckline
- Front cutouts with metal hardware accents
- Body-skimming fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000807
Category Name: Maxi Dresses
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival