Maxi Dresses

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.

  • Save the Date Lace Halter Ruffle Maxi Dress

    This is the kind of entrance people remember. The lace halter maxi dress balances sheer moments and soft ruffles with a sweetheart neckline that feels elevated, confident, and ready for RSVP occasions and dressed-up date nights.

    Fit & Features

    • Chiffon-lined fabric with sheer lace paneling
    • Fitted bodice with a flowy maxi skirt
    • Sweetheart neckline with a halter strap, padded bra cups
    • Side zipper and hook-eye closure
    • Lace inset at the waist for a subtle peek effect
    • Tiered ruffle detailing through the skirt
    • Runs true to size

    Style Number/Barcode: 05101-000828

    Category Name: Maxi Dresses

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Bold Confidence Floral Print Cowl Neck Maxi Dress

    Soft drape, bold confidence. This floral print maxi dress hugs in all the right places with a plunging cowl neckline that feels effortless and a mermaid silhouette that turns heads.

    Fit & Features

    • Knit fabric with high stretch
    • Large-scale floral print
    • Halter neckline with plunging cowl front, bar strap detail
    • Open back with adjustable tie closures
    • Fitted bodice with mermaid silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000830

    Category Name: Maxi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Weekend Wandering Open Back Maxi Dress

    Light, airy, and made for unhurried afternoons that turn into early evenings. This gauze maxi drapes effortlessly, skims the body just right, perfect for shower celebrations, vacation, or a brunch.

    Fit & Features

    • Soft gauze fabric with lightweight drape, knit lining
    • V-neckline with cutout detail
    • Spaghetti straps
    • Open back with tie, zipper and hook-eye closure
    • Fitted waist flowing into a relaxed maxi skirt
    • Runs true to size

    Style Number/Barcode: 05102-000416

    Category Name: Maxi Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Unforgettable Entrance Plunge Neck Maxi Dress

    This maxi dress doesn’t blend in—it arrives. This plunging cowl neck maxi dress drapes smoothly through the body with a halter neckline that feels bold, polished, and intentionally striking. Pair with heels for date night, dressy celebrations, or a sultry vacation look.

    Fit & Features

    • Smooth knit-lined fabric with high stretch
    • Halter neckline with plunging cowl front
    • Open back with adjustable tie closure
    • Fitted bodice that skims the waist and hips
    • High side slit for movement
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000736

    Category Name: Maxi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Getaway Mood Tropical Floral Halter Maxi Dress

    Lightweight, curve-loving, and made to move with you. The airy sheer mesh fabric and tropical floral print bring a bold edge that feels right for nights out and getaway moods.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Tropical floral print
    • Sleeveless V-neckline
    • Metal flower hardware accent, keyhole cutout
    • Tie-back halter spaghetti straps, partially open back
    • Maxi-length hem, form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000464

    Category Name: Maxi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Vacation Mode Abstract Open Back Maxi Dress

    This dreamy mesh maxi dress was made for golden hour plans, tropical cocktails, and dancing 'til dinner. Designed in an abstract print that brings the ocean and desert sky together, this halter dress features a draped cowl neckline, hardware straps, and open tie-back.

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Plunge cowl halter neckline with hardware
    • Open tie-back design
    • High side slit
    • Form-hugging maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000409

    Category Name: Maxi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Garden After Dark Plunge Halter Maxi Dress

    This is the kind of entrance that doesn’t need explaining. With a plunging neckline, open back, and butterfly chain detail, this floral maxi dress is equal parts romance and edge—made for date nights and rooftop hotel bars.

    Fit & Features

    • Floral abstract print, mesh-lined fabric
    • Plunge halter V-neckline with tie closure
    • Butterfly hardware with draped chain accent
    • Open back with adjustable strappy detail
    • Form-hugging floor-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000568

    Category Name: Maxi Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Golden Hour Groove Crochet Halter Maxi Dress

    Vacation energy, locked in. This striped texture crochet knit maxi dress features a plunge halter neckline with wooden hoop inserts and an open back that feels equal parts effortless and elevated. Pair with strappy sandals for your upcoming getaway.

    Fit & Features

    • Crochet striped texture knit, smooth knit lining
    • Plunge halter neckline with wood hoop inserts, tie closure
    • Open back
    • Side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000461

    Category Name: Maxi Dresses

    Price: $21.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, L

    Product Badge:
    • Sale
  • Wild Bloom Cowl Halter Maxi Dress

    Bold print, barely-there feel perfect for vacations. This maxi dress blends leopard and tropical florals with a plunging cowl halter and open back, finished with a statement floral hardware that stands out.

    Fit & Features

    • Tropical floral and leopard print
    • Sheer mesh fabric, soft knit short lining
    • Plunge cowl halter neckline
    • Open back, lower ruched seam
    • Front tropical floral hardware piece
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000401

    Category Name: Maxi Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Bloom Floral Open Back Maxi Dress

    Floaty, fitted, and impossible to ignore. This floral mesh maxi skims the body with a draped cowl neckline and an open tie-back design perfect for serving dreamy looks on vacations, sunset cocktails, and date nights.

    Fit & Features

    • Floral bloom print, mesh-lined fabric
    • Cowl halter neckline
    • Spaghetti strap tie-back closure
    • Open back with lower ruched seam
    • Curve-hugging silhouette
    • Floor-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000845

    Category Name: Maxi Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • All Eyes On Me Floral Open Back Maxi Dress

    This floral mesh maxi dress features a plunging cowl halter neckline and an open back that feels equal parts romantic and intentional—made for weddings, date nights, and birthday cocktails.

    Fit & Features

    • Sheer mesh fabric with full-length knit lining, high stretch
    • Floral garden print
    • Sleeveless plunge cowl neckline
    • Tie-back halter straps, open back design
    • Curve-hugging silhouette
    • Flared floor-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000677

    Category Name: Maxi Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Late Arrival Abstract Maxi Dress

    Moody, sculpted, and impossible to ignore. This maxi dress hugs in all the right places with a plunging neckline and statement ring detail that feels made for vacations, sunset dinners, and GNOs!

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Strapless neckline with cutout and hardware inserts
    • Form-hugging silhouette
    • Maxi-length hemline
    • Runs true to size

    Style Number/Barcode: 05102-000348

    Category Name: Maxi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Made for the Moment Floral Maxi Dress

    Floaty, romantic, and made to move. This floral midi dress features cascading ruffles and a front slit that brings just enough drama while still feeling light, polished, and wearable for dressed-up plans.

    Fit & Features

    • Lightweight chiffon fabric with floral pattern
    • Slim-fit sweetheart bodice with spaghetti straps
    • Adjustable tie-back detail for customizable fit
    • Front slit with cascading ruffle trim
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000951

    Category Name: Maxi Dresses

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Pretty Agenda Floral Woven Ruffle Maxi Dress

    Soft, flowy, and ready for every RSVP on your calendar. This pretty floral woven maxi dress brings effortless drama with tiered ruffles and a flattering sweetheart neckline that looks just as good in photos as it does in motion.

    Fit & Features:

    • Lightweight woven fabric with full-length stretchy knit lining
    • All-over floral print
    • Sleeveless sweetheart neckline with ruched bust, adjustable tank straps
    • Open back with self-tie detail, lower back zipper with hook-eye closure
    • Tiered ruffled design
    • Maxi-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000876

    Category Name: Maxi Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Plans Chevron Crochet Maxi Dress

    This chevron crochet knit maxi dress features a flattering V-neck and lace-up back that feels equal parts stylish and unforgettable—perfect for beachside restaurants or warm nights out.

    Fit & Features

    • Chevron striped pattern
    • Crochet knit lined fabric
    • V-neck, spaghetti straps
    • Lace-up back
    • Maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000418

    Category Name: Maxi Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Lace Obsession Cutout Maxi Dress

    All eyes, all night. This lace halter maxi dress brings sultry sophistication with a deep V-neckline, corset-seamed bodice, and side cutouts that contour your shape. Perfect for flaunting at cocktail parties or a date night.

    Fit & Features

    • Lace-lined fabric with stretch
    • Halter V-neckline, tie closure
    • Corset-seam bodice, side cutouts
    • Back zipper and hook-eye closure
    • Form-hugging silhouette
    • Center back slit, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000463

    Category Name: Maxi Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Soft Focus Florals Mesh Maxi Dress

    Soft-focus florals, but make it a statement. This floral mesh maxi dress hugs just right with a sleek, fitted silhouette that’s ready for weddings, date nights, and every dressed-up plan on your calendar.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Large floral print
    • Sleeveless scoop neckline
    • Adjustable spaghetti straps
    • Fitted silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000363

    Category Name: Maxi Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love in Layers Ruffle Chiffon Maxi Dress

    Floaty, feminine, and made for golden-hour plans. This chiffon maxi dress brings effortless romance with soft movement and a breezy silhouette that feels perfect for bridal events, dressy brunches, and spring celebrations.

    Fit & Features

    • Airy chiffon fabric, sewn-in lining
    • Square neckline, adjustable spaghetti straps
    • Stretch smocked bodice, tie waist belt
    • Tiered ruffled maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000921

    Category Name: Maxi Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Blossom Beauty Floral Lace Maxi Dress

    Romance is fully in bloom with this floral maxi dress that knows how to make an entrance. The sculpting mesh fit, delicate lace bust, and side slit give it that dressed-up, spring-event energy perfect for brunches, garden parties, and shower celebrations!

    Fit & Features

    • Floral print, mesh-lined fabric
    • Lace sweetheart bust with wide straps
    • Cutout front and back accent
    • High side slit
    • Form-hugging, maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000656

    Category Name: Maxi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Postcard Pretty Halter Cutout Maxi Dress

    Booked the dinner, ordered the spritz, now you need the dress. This halter maxi dress brings the drama with a rose detail, front cutout, and tiered skirt that moves like you planned this all along.

    Fit & Features

    • Lightweight woven fabric with abstract print
    • Halter neckline with rosette detail
    • Front cutout with twist front bodice
    • Smocked back for stretch
    • Tiered ruffled maxi skirt
    • Runs true to size

    Style Number/Barcode: 05102-000411

    Category Name: Maxi Dresses

    Price: $28.97 $62.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Wildly Fierce Leopard Floral Maxi Dress

    Warning: this dress doesn’t do low profile. The leopard floral mesh print fabric and plunge halter neckline with bead inset sculpt a form-hugging maxi silhouette that’s made for vacations, birthday dinners, and any plan that deserves a little drama.

    Fit & Features

    • Floral, leopard print mesh-lined fabric
    • Plunge halter neckline with tie and bead
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000365

    Category Name: Maxi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Out Of Office Abstract Maxi Dress

    Booked, busy, and dressed for it. This abstract mesh strapless tube maxi dress hugs your curves with a sleek fit and side slit that brings just enough drama for vacations and sunset dinners with a view.

    Fit & Features

    • Abstract print, knit fabric
    • Strapless neckline
    • High side slit
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000305

    Category Name: Maxi Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Island After Hours One Shoulder Maxi Dress

    This is what you pack when the itinerary says “sunset drinks,” and you plan on being the view. The one-shoulder neckline with hardware detail gives elevates the look, while the tropical floral print and front slit keep it flowy, flirty, and very camera-ready.

    Fit & Features

    • Tropical floral print knit fabric
    • One-shoulder neckline
    • Statement hardware strap detail
    • Front slit with ruffle accent
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05102-000419

    Category Name: Maxi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Bloom Agenda Floral Mesh Halter Maxi Dress

    RSVP secured and outfit handled. This floral mesh halter maxi dress sculpts with high-stretch comfort, features a statement flower hardware accent, and serves a partially open back that’s perfect for photo ops.

    Fit & Features

    • Sheer mesh fabric with full-length knit lining, high stretch
    • Large floral print
    • Sleeveless halter neckline, tie-back design
    • Metal flower hardware accent
    • Partially open back
    • Maxi-length form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000881

    Category Name: Maxi Dresses

    Price: $54.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free