Maxi Dresses
Your fall calendar called—it wants a maxi dress for every occasion. Go casual to formal in mesh, knit satin, silky woven satin, slinky jersey knit, or ribbed knit with long sleeves, short sleeves, mock neck, wide-neck, off the shoulder, and plunging v-necklines. Cut outs with luxe gold hardware and sheer illusion panels add an unexpected edge. Chocolate brown, burgundy, deep plums, vampy printed florals, and moody abstract swirl prints make every floor-sweeping look feel perfectly timed for the season.
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Maxi Dresses That Go Wherever the Season Takes You
Maxi dresses make an instant outfit feel anything but basic. This fall and winter, Windsor’s maxi-length dresses move from laid-back days to elevated nights with adjustable fits, flowing layers, sleek shapes, and statement details that make the look your own. Think long-sleeve styles for cooler plans, or long sundresses you can pack when winter calls for a warm-weather escape.
How Do I Wear a Maxi Dress in Colder Weather?
Layer without losing what makes the dress special. Add a cropped jacket or fitted coat over a flowy maxi, or choose long sleeves when you want more coverage built into the look. Boots give casual styles a seasonal switch, while polished outerwear can take a sleek maxi straight into a holiday dinner or evening plans. For the season’s dressier moments, explore Maxi Holiday Dresses with festive details that do more of the styling for you.
Which Maxi Dress Details Make the Biggest Statement?
Start with the feature you want people to notice. Asymmetrical hems and cutouts create unexpected shape, while stones, beads, metallic hardware, or shell accents turn simple silhouettes into conversation starters. A plunge or cowl neckline can bring drama up top, and adjustable straps or backs let you fine-tune the fit. If you want the print to lead, Maxi Floral Dresses range from moody blooms to brighter patterns perfect for a honeymoon or holiday getaway.
Can I Wear a Maxi Dress to a Wedding?
Yes—match the mood to the venue and dress code. A sleek maxi with elevated details can feel right for an evening celebration, while a softer print or flowing silhouette works beautifully for more relaxed settings. Browse maxi wedding guest dresses when you want floor-skimming options already curated with the occasion in mind.
From neutral black and creamy ivory to chocolate brown and seasonal color, the right maxi can feel relaxed, polished, or full main-character. The fun part is deciding which version of you is showing up.
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Major Fling Flutter Sleeve Maxi Dress
Fling into the spring season in this maxi dress that has an effortlessly breezy feel, while the V-neck and cutout back give it that easy, getaway-ready charm.
Fit & Features
- Airy cotton fabric, woven lining
- Flutter short sleeves
- V-neckline
- Cutout back
- Ruffled tiered flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000748
Category Name: Maxi Dresses
Price: $54.90
Availability: Out of Stock
Product Badge:- Ships Free
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Island Heat Mesh Maxi Dress
Booked, busy, and dressed like it. This tropical floral maxi dress is form-hugging with a high side slit that brings just enough drama for your next getaway or sunset dinner.
Fit & Features
- Tropical floral print, mesh fabric, brushed knit lining
- Strapless tube neckline, non-slip grip lining
- High side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000626
Category Name: Maxi Dresses
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirt Factor Floral Mesh Maxi Dress
When the invite says dress up, this is already in your hands. This flirty floral mesh maxi dress brings a sleek, curve-hugging fit with lightweight stretch that feels as good as it looks all night.
Fit & Features
- Sheer mesh fabric, full-length knit lining, high stretch
- Large floral print
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Maxi-length hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-001135
Category Name: Maxi Dresses
Price: $24.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunset Muse Ombre Mesh Cutout Maxi Dress
Serving curves, movement, and just enough drama. This ombre mesh cutout maxi dress hugs in all the right places with a fluid drape that feels effortless but looks unforgettable.
Fit & Features
- Ombre sheer mesh fabric with full-length knit lining, high stretch
- Sleeveless plunging cowl neckline, bar strap detail
- Halter tie-back straps
- Asymmetric waist cutouts leading to an open back
- Maxi-length hem, floor-length center sash accent
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-001168
Category Name: Maxi Dresses
Price: $14.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dinner Plans Sleeveless Maxi Dress
This crewneck maxi dress hugs your shape with a soft shimmer finish and adjustable side ties atop flirty slits, making it your go-to for dinner plans, vacations, or beach nights.
Fit & Features
- Lurex knit fabric
- Sleeveless crewneck
- Adjustable side ties and high slits
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05103-000854
Category Name: Maxi Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Getaway Ready Floral Print Maxi Dress
Out of office and not checking. This floral hem print maxi dress features a plunge halter neck, front slit, and a cross strap back that brings the drama from every angle. Perfect for packing with you on vacations, honeymoons, or weekend escapes!
Fit & Features
- Smooth knit stretchy fabric, knit lining
- Halter plunge neckline, hardware insert, adjustable cross back straps
- Open back design
- Cutout bosdice
- Flowy maxi-length silhouette with floral hem print
- Runs true to size
Style Number/Barcode: 05102-000576
Category Name: Maxi Dresses
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty RSVP Floral Chiffon Maxi Dress
Romantic plans pending… just add this dress. This flirty floral chiffon maxi dress hugs at the bodice and flows effortlessly, perfect for weddings, date nights, or anywhere you want compliments on repeat.
Fit & Features
- Floral printed chiffon fabric with full-length lining
- Sleeveless V-neckline
- Pleated underbust design, button closures
- Adjustable spaghetti straps, partially smocked back
- Fitted bodice, flowy silhouette
- Maxi-length hem, godet detailing
- Runs true to size
Style Number/Barcode: 05101-001316
Category Name: Maxi Dresses
Price: $49.00 $69.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: L
Product Badge:- Sale
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Undeniable Allure Plunging Cowl Neck Maxi Dress
Low cut, high impact—this maxi dress doesn’t ask for attention, it owns it. The plunging cowl neck and bodycon fit hug you in all the right places for nights when subtle just isn’t the vibe.
Fit & Features
- Sleek knit fabric with full-length knit lining, high stretch
- Sleeveless plunging cowl neckline
- Halter straps
- Open back, lower back bar strap accent
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-000682
Category Name: Maxi Dresses
Price: $20.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacation Glow Floral Satin Maxi Dress
This is the satin maxi dress that quietly steals the whole moment. Silky, draped, and barely-there in the back, this floral dress moves like you planned the entrance—even if you didn’t.
Fit & Features
- Floral print, silky satin fabric
- Cowl neckline
- Spaghetti straps
- Open cross back design
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000811
Category Name: Maxi Dresses
Price: $20.97 $45.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: XXS, XS, S, M, L
Product Badge:- Sale
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Vacation Muse Floral Halter Maxi Dress
This is the dress that makes every plan feel like a getaway. The plunging halter keeps it bold, while the floral appliqué brings that playful, standout detail.
Fit & Features
- Statement floral applique, stretch knit fabric
- Plunge halter neckline
- Open back design with tie
- Center back slit
- Form-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000446
Category Name: Maxi Dresses
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trina Abstract Animal Print Formal Dress
Special Occasion
The Trina abstract leopard print chiffon gown moves with every step and catches the light in all the right ways. Designed with a plunge V-neck with hardware, a cutout bodice, and a flowing A-line fit, it’s the kind of piece that makes the RSVP feel like your moment.
Fit & features
- Abstract animal print, chiffon-lined fabric
- Plunge V-neckline, hardware insert
- Cutout bodice with beaded strap detail
- Back zipper and hook-eye closure
- High front slit
- A-line floor-length silhouette
- Runs true to size
Where to Wear:
Prom, weddings, destination celebrations, vacations, cocktail dinner party, upscale birthday, resort evening events, engagement parties
Style Number/Barcode: 05002-001428
Category Name: Maxi Dresses
Price: $109.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Island Nights Mesh Halter Maxi Dress
Vacay booked. This tropical mesh maxi dress brings that breezy, curve-skimming fit with a trendy ruffled slit that moves with you from beach cocktails to dinner.
Fit & Features
- Tropical print, mesh fabric, soft knit lining
- Halter V-neckline with hardware insert
- Tie straps, open back
- High front ruffled slit
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000607
Category Name: Maxi Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Agenda Plunge Maxi Dress
From meetings to martinis without missing a beat. This cap sleeve maxi dress with a center drape accent and front slit keeps it polished for work hours and chic for after-hours plans.
Fit & Features
- Smooth knit stretch fabric
- Cao sleeves with shoulder pads for structure
- Plunge V-neckline
- Center front drape and slit designs
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000784
Category Name: Maxi Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Always Out Animal Open Back Maxi Dress
Walk in, and suddenly everyone’s paying attention. This cowl neck maxi dress drapes effortlessly with a bold print, open back, and high slit that was made for cocktail hour.
Fit & Features
- Animal print, mesh-lined stretchy fabric
- Cowl halter neckline, tie straps
- Open tie-back design
- High side slit
- Form-hugging maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000342
Category Name: Maxi Dresses
Price: $21.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L
Product Badge:- Sale
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Daydream Date Floral Maxi Dress
This floral maxi dress flows with every step, featuring a square neckline and tiered ruffle layers that feel light, pretty, and ready for any invite and celebration!
Fit & Features
- Delicate floral print, chiffon-lined fabric
- Square neckline, spaghetti straps
- Tie-back design
- Tiered ruffled A-line silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001029
Category Name: Maxi Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Confidence Sheer Lace Maxi Dress
A little sheer, a little bold—exactly how you like it. This lace maxi dress skims your body with a soft stretch feel, made for slipping into when the vibe calls for effortless confidence.
Fit & Features
- Textured lace fabric with a mini-length knit lining, moderate stretch
- Sleeveless V-neckline with O-ring accent at the bust
- Adjustable spaghetti straps
- Maxi-length hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000599
Category Name: Maxi Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Plans Booked Halter Slit Maxi Dress
This is the dress you slip on when you want all eyes on you! Designed with a sleek halter neckline, curve-hugging fit, and statement front slit with hardware detail, this maxi dress brings the chic drama.
Fit & Features
- Knit stretchy fabric
- Halter neckline, tie straps
- Drop waist seam
- High front slit
- Curve-hugging fit
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001180
Category Name: Maxi Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Late Dinner Plans Tube Maxi Dress
This is what you wear when the evening calls for something a little elevated. This tube maxi dress hugs through the bodice with a ruched finish, then falls into a soft shark hem that moves with every step.
Fit & Features
- Soft jersey knit fabric, stretchy lining
- Strapless tube neckline, non-slip grip lining
- Ruched fitted bodice
- Flowy curve-hugging silhouette
- Shark-cut maxi hem
- Runs true to size
Style Number/Barcode: 05102-000787
Category Name: Maxi Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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RSVP Pretty Floral Chiffon Maxi Dress
If the invite says dress up, this floral chiffon dress is ready to make an entrance. Designed to flow effortlessly with a cinched waist and airy skirt that feels just right for showers, brunches, and every dressy celebration.
Fit & Features
- Floral pattern, chiffon fabric, smooth woven lining
- Halter neckline with tie straps
- Ruched bodice detail
- Back zipper and hook-eye closure
- Flowy A-line silhouette
- Handkerchief maxi hem
- Runs true to size
Style Number/Barcode: 05101-001393
Category Name: Maxi Dresses
Price: $29.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Worth The Double Take Halter Maxi Dress
It’s the kind of dress that speaks before you do. This halter midi dress contours your shape with soft ruching and a ruffled slit that moves with you at parties, date nights, and any dressy celebration.
Fit & Features
- Slinky knit-lined stretchy fabric
- High halter neckline with tie straps
- Open back
- Ruched form-hugging silhouette
- Center front ruffled slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001400
Category Name: Maxi Dresses
Price: $38.90
Availability: In Stock
Available Color: BLACK
Available Size: L
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Wild Attraction Cowl Neck Maxi Dress
Serving curves with a side of attitude. This leopard print mesh cowl neck maxi dress drapes just right with an open back and hardware detail that makes every step feel a little extra.
Fit & Features
- Leopard print, mesh fabric, knit lining
- Plunge cowl neck halter neckline, hardware insert
- Open back
- Curve-hugging, maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000393
Category Name: Maxi Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Soft Drama Strapless Tiered Ruffle Maxi Dress
Floaty layers that do the absolute most in the best way. This strapless chiffon maxi dress brings soft movement and an easy, elevated feel for nights that turn into something a little extra.
Fit & Features
- Lined chiffon fabrication
- Strapless tube neckline
- Fitted bodice with dual cutouts
- Open back design
- Tiered ruffle silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001096
Category Name: Maxi Dresses
Price: $27.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Center Of It All Cowl Neck Maxi Dress
You don’t need an introduction in this one. This cowl neck maxi dress drapes just right with a curve-hugging fit and open back that feels both bold and effortless.
Fit & Features
- Sleek knit fabric, high stretch
- Sleeveless plunging cowl neckline
- Halter tie-back spaghetti straps
- Thin metal O-ring hardware accents
- Open back
- Maxi-length bodycon silhouette, back slit detail
- Runs true to size
Style Number/Barcode: 05101-000880
Category Name: Maxi Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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City Crush Polka Dot Lace Maxi Dress
Caught feelings… for this dress. This polka dot slip maxi dress hugs just right with a sleek silhouette that’s made for dinners, drinks, and a little lingering eye contact.
Fit & Features
- Lightweight woven knit fabrication
- Sleeveless v-neckline
- Contrast lace trim bodice
- Polka dot pattern
- Slip silhouette styled fit
- Maxi length hem
- Runs true to size
Style Number/Barcode: 05101-001218
Category Name: Maxi Dresses
Price: $49.90
Availability: In Stock
Available Color: BLUE
Available Size: S