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.

SHOW FILTER

SORT:

FEATURED
SIZE
COLOR
PRICE
ALL FILTERS
SORT
×
×
×
×



SEE RESULTS
Loading...
×
MAXI DRESSES
All Filters
Sort By:
FEATURED
SEE RESULTS

The Latest Maxi Dresses In Style For Fall and Winter 2024

Embrace the colder months in style with Windsor's collection of chic and versatile maxi dresses for Fall and Winter 2024! From casual to formal, our maxi dresses offer the perfect blend of comfort and sophistication, ensuring you stay warm and stylish for all your seasonal events. Whether you love turtleneck, mock neck, V-neck, or off-the-shoulder designs, we have the perfect maxi dress to elevate your cold-weather wardrobe. The best part? These dresses transition seamlessly from day to night, making them a must-have for your seasonal festivities.

Maxi dresses are the ideal casual dress to wear for everyday fall and winter outfits. Discover flowy maxi dresses with chic cutouts, long sleeves, or high slits to keep you stylish and comfortable. Layer them under your favorite faux fur coats, chunky knit cardigans, or tailored blazers for added warmth on chilly days. And when the evening arrives, switch to a sleek faux leather jacket and complete the look with heeled boots for an effortlessly edgy vibe. Create a flattering silhouette by cinching your flowy maxi dresses at the waist with a stylish belt and pairing them with ankle boots and statement earrings!

You’ll fall in love with Windsor’s maxi dresses featuring bold prints and rich textures perfect for the cooler seasons. Keep it chic in ombre or dark floral print maxi dresses at winter weddings or holiday parties. For date nights, choose curve-hugging maxi dresses in deep jewel tones like emerald, burgundy, or navy, bringing a touch of allure and sophistication. For a winter getaway, shop a trendy assortment of solid-colored maxi dresses in luxurious fabrics like velvet, satin, and knit, perfect for adding a touch of elegance to your seasonal wardrobe. If you prefer patterns, explore dresses in subtle winter florals or geometric prints that will have you feeling confident and stunning all season long!

Explore a stylish collection of maxi-length dresses in cozy, A-line, slim-fit, and bodycon silhouettes. Choose from one-shoulder or off-the-shoulder maxi dresses or long sheer-sleeved maxi dresses for a polished and warm look. Windsor offers formal dresses in maxi lengths with intricate lace, velvet, or satin details, so you can find the perfect style to match your winter vibe. Shop dresses with ruched side seams to accentuate your gorgeous curves or ruffled accents for a touch of whimsy. Our long dresses in warm fabrics like knit, satin, and chiffon will keep you comfortable and elegant through all your winter events. Formal maxi dresses are perfect for winter weddings or anniversary celebrations, with elevated fabrics that move with you, creating a romantic and enchanting vibe. For winter brides, Windsor offers a stunning selection of white long dresses, ideal for your engagement party, bridal shower, bachelorette party, or rehearsal dinner.

Get formal to casual maxi dresses with high slits, sheer layers, stylish sleeves, luxe fabrics, and soft knits at over 350 Windsor stores in the US and Canada or online here!

Can I Wear Maxi Dresses Year-Round?

Maxi dresses are a dress style you can wear year-round. Styling a maxi dress with the right accessories or pairing it with other trendy apparel will determine if your look fits the occasion. It’s common to see summer dresses in a maxi style because you can go from the pool to dinner by switching out sandals for heeled mules and adding some bling jewelry to dress up your look. Vacation maxi dresses hit all right notes regardless of the season because you can style them in multiple ways like with tie-front crop tops or short sleeve graphic tees. Maxis in floral prints or solid colors also transition effortlessly from warm weather to cooler temps when you layer knot-back sweaters, leggings or tights, and knee-high boots with a low or high heel depending on your vibe.

What is the difference between a midi and a maxi dress?

The main difference between midi and maxi dresses is the length. Midis, or mid-length dresses, hit below the knee and above the ankle. Maxi dresses are floor-length styles that typically do not show the legs unless there are slits. Both silhouettes are stunning casual and formal options for weddings, parties, dates, and graduations, or casual everyday wear!

  • 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

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bora Bora Floral Chiffon Maxi Dress

    Got vacay on the mind? This floral chiffon maxi dress is perfect for a trip to Bora Bora! Features a sleeveless, halter neck with tie-closure, ruched bust, and a cutout bodice atop a flowy, tiered maxi skirt. Complete the look in wedges and chic sunglasses. 

    Fit & Features

    • Sleeveless, halter neck, tie-closure
    • Ruched bust
    • Cutout bodice
    • Flowy, tiered maxi skirt
    • Floral print
    • Airy chiffon fabric, inner lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4391

    Category Name: Maxi Dresses

    Price: $9.97

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Date Night Chic Floral Maxi Dress

    You'll be totally chic for date night in this floral maxi dress that brings the romantic vibes. It features a sleeveless cowl neckline, spaghetti straps that lead to a lace-up back design for a customized fit, and a fitted floor-length silhouette with a thigh-high front slit. Complete the look with cute mules

    Shop Midi Dress: Chic Romance Floral Midi Dress

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Open back, strappy lace-up design, tie closure
    • Floor-length fitted silhouette, high front slit
    • All-over floral print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1443

    Category Name: Maxi Dresses

    Price: $9.97

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Zaya Formal Floral Chiffon Dress

    Special Occasion 

    Let love bloom in a formal dress that brings the charm to your event! Zaya features a beautiful floral print, a sleeveless V-neckline, adjustable spaghetti straps that cross at the back, pleating throughout, and a high waist that leads to a flowy A-line silhouette. The dress is composed of a lined chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with a rhinestone bracelet and heels. 

    Fit & Features

    • Sleeveless V-neckline
    • Adhesive bra recommended
    • Adjustable spaghetti straps, cross at back 
    • Empire waist, lower back zipper
    • Floral print, pleats
    • A-line
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05002-1884

    Category Name: Maxi Dresses

    Price: $14.97

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Swept Away Floral Ruffled Maxi Dress

    Get swept up in a pretty maxi dress that brings the romance! The dress features a sleeveless sweetheart neckline, tie-up spaghetti straps, tiered ruffles, a floral print, and a maxi-length silhouette. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with sandals and butterfly earrings. 

    Fit & Features

    • Sleeveless sweetheart neckline
    • Tie-up spaghetti straps
    • Tiered ruffles
    • Floral print
    • Maxi length silhouette
    • Lined lightweight woven fabric
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05101-1101

    Category Name: Maxi Dresses

    Price: $9.97

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Geneviève Floral Chiffon Wrap Dress

    Special Occasion 

    Wrap yourself in a floral dress that brings romance to your event! Geneviève features a darling floral print, a sleeveless V-neckline, and adjustable spaghetti straps that cross at the back. Her back features a lace-up strap design and an elastic stretch at the lower back that leads to a zipper closure. Her slim-fit waist leads to a flowy wrap silhouette that is accented with a high side slit. She is composed of a lined chiffon fabric that offers a form hugging fit with minimal stretch. Complete look with wedges and a clutch for the perfect wedding guest outfit

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, lace-up back  
    • Back zipper closure
    • Floral print
    • Wrap silhouette, high side slit
    • Lined chiffon fabric 
    • Form hugging fit, minimal stretch, runs true to size 

    Style Number/Barcode: 05002-1889

    Category Name: Maxi Dresses

    Price: $19.97

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Rose Above It V-Neck Slit Maxi Dress

    Rise to a sophisticated and chic style in this rose floral maxi dress for your next dressy occasion! It features a sleeveless, v-neck, spaghetti straps that cross in the back, and a form-fitting silhouette with a sultry front slit to showcase some leg. Complete the look in heels and a clutch.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Cross back straps
    • Form-fitting silhouette
    • Front slit, maxi-length hem
    • Rose floral pattern. moderate stretch
    • Fits true to szie

    Style Number/Barcode: 05101-1509

    Category Name: Maxi Dresses

    Price: $9.97

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mailyn Chiffon Ruffled Formal Dress

    Special Occasion

    Leave them all entranced as you enter the room in the Mailyn chiffon formal dress that brings the ethereal vibes! She features a sleeveless scoop neckline, a ruffled trim overlay, adjustable spaghetti straps so you can customize the fit, an empire waist, and a flowy, floor-length silhouette. Dress her up in sparkly rhinestone heels and a matching clutch.

    Fit & Features

    • Scoop neck, adjustable spaghetti straps
    • Strapless or adhesive bra recommended
    • Ruffled trim overlay, empire waist
    • Flowy silhouette
    • Floor-length hem
    • Sheer chiffon fabric, inner knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05002-2040

    Category Name: Maxi Dresses

    Price: $9.97

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Beachside Brunch Swim Coverup Dress

    Strut down the pier looking so fab in this maxi coverup dress featuring a sleeveless V-neckline, tank straps, and a form-fitting silhouette with a sultry front slit. The coverup dress is composed of an unlined semi-sheer knit fabric that offers a form-hugging fit. Perf for layering over your bikinis, complete the look in sandals.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless V-neckline, tank straps
    • Surplice accent
    • Form-fitting silhouette
    • Front slit
    • Maxi-length hem
    • Unlined, semi-sheer sweater-knit fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06005-1250

    Category Name: Maxi Dresses

    Price: $6.97

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Catch The Bouquet Chiffon Maxi Dress

    Tis' the season for weddings! Catch the bouquet in this floral chiffon maxi dress featuring cute long peasant sleeves, ruffled shoulders, and a sweetheart neck with a built-in padded bust. The fitted bodice leads to a maxi-length hem with a sultry side slit. Complete the look in strappy mules.

    Fit & Features

    • Long peasant sleeves, ruffled shoulders
    • Sweetheart neck, built-in padded bust
    • Fitted bodice, back smocked panel
    • Side slit, maxi-length hem
    • Floral pattern
    • Chiffon-lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1521

    Category Name: Maxi Dresses

    Price: $23.97

    Availability: Out of Stock

    Product Badge:
  • Vineyard Floral Slit Maxi Dress

    Wine tasting anyone? This floral maxi is perfect for sipping on your fav red or white! It features a sleeveless, off-the-shoulder neckline, a form-fitting silhouette, and dual front slits for a sultry show of leg. Complete the look in wedges and a floppy hat.

    Fit & Features

    • Sleeveless, off-the-shoulder neckline
    • Flutter sleeve cuffs
    • Form-fitting silhouette
    • Dual front slits, maxi-length hem
    • Floral pattern
    • Stretch-knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4554

    Category Name: Maxi Dresses

    Price: $19.97

    Availability: Out of Stock

    Product Badge:
  • Zen Floral Chiffon Dress

    Special Occasion

    Bring the romance with a formal dress that shows off your sweet side at prom. Zen features a gorgeous floral print, a sleeveless square neckline, and adjustable spaghetti straps that lead to a cross-back design. Her slim-fit bodice leads to a flowy A-line silhouette accented with a stunning high side slit. She is composed of a lined chiffon fabric that offers a relaxed fit with minimal stretch. Complete your look with duster earrings.

    Fit & Features

    • Sleeveless square neckline, adjustable spaghetti straps
    • Adhesive bra friendly
    • Cross-back strap design
    • A-line silhouette, side slit
    • Floral print
    • Lined chiffon fabric 
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05002-1845

    Category Name: Maxi Dresses

    Price: $14.97

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chasing Sunsets Floral Maxi Dress

    This floral maxi dress is perfect for sunset dinners while on vacay! It features sleeveless, v-neck, sleek spaghetti straps, and a slim-fit silhouette with a front side slit to showcase some skin. Complete the look in trendy sandals.

    Fit & Features

    • Sleeveless, V-neck, sleek spaghetti straps
    • Slim-fit silhouette
    • Front side slit
    • Maxi-length hem
    • Floral pattern
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1393

    Category Name: Maxi Dresses

    Price: $9.97

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jade One Shoulder Ruched Formal Dress

    Special Occasion

    Alluring and chic, the Jade One Shoulder Ruched Formal dress never disappoints to create an eye-catching entrance on your next evening affair! She features a one-shoulder, long-sleeve bodice on a curve-hugging silhouette and a front ruching with a tie so you can customize the fit. Her sultry side slit shows some skin while elongating your figure on the floor-length hem. Composed of a slinky knit-lined fabric with plenty of stretch. Finish your look in a memorizing hairpiece.

    Fit & Features

    • One-shoulder asymmetrical neckline, single long fitted sleeve
    • Adhesive bra recommended
    • Front ruching with adjustable tie
    • Side slit, floor-length hem
    • Slinky knit-lined fabrication
    • Curve-hugging silhouette, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05002-2218

    Category Name: Maxi Dresses

    Price: $14.97

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shaylee Chiffon A-Line Slit Formal Dress

    Special Occasion

    Look ravishing in the Shaylee chiffon A-line formal dress for your next fancy soiree, wedding, or formal dance. She captivates in an alluring wrap, pleated V-neckline atop the empire waist. Shaylee features sleeveless, adjustable spaghetti straps that shape the strappy back detail. Her floor-length A-line silhouette is designed to flatter and give you a curvy appearance while the front slit shows off some leg. This formal dress is composed of an airy chiffon fabric with a full knit lining. Complete your stunning look in rhinestone stiletto heels.

    Fit & Features

    • Wrap, pleated V-neckline, adjustable spaghetti straps
    • Adhesive bra recommended
    • Strappy back, zipper and hook and eye closure, high front slit
    • Empire waist
    • Floor-length A-line silhouette
    • Sheer chiffon fabric, full knit lining
    • Flowy fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05002-1787

    Category Name: Maxi Dresses

    Price: $19.97

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Mood Ribbed Knit Midi Dress

    Keep it lowkey in a dress that brings those casual vibes! The dress features a crew neckline, short sleeves, and a sexy open back with a tie-back accent. The midi dress is composed of a lined ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with sneakers and a denim jacket for those girl next door vibes!

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Open back 
    • Tie-back accent
    • Midi-length, high side slit
    • Lined ribbed knit fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4526

    Category Name: Maxi Dresses

    Price: $9.97

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Silvia Chiffon A-Line Formal Dress

    Special Occasion

    Look and feel enchanting in a long prom dress that captivates from the moment you enter the room. The Silvia formal prom dress features a delicate, sleeveless pleat v-neckline that draws the eye to the fitted empire waist. Her high-cut slit gracefully flows into an a-line silhouette that kisses the floor. The dress is composed of chiffon-lined fabric with no stretch. Complete your look with a statement bracelet.

    Fit & Features

    • Sleeveless, pleat v-neckline
    • Adjustable spaghetti straps
    • Fitted empire waist
    • High-cut slit, a-line silhouette
    • Zipper closure
    • Chiffon-lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 05002-1649

    Category Name: Maxi Dresses

    Price: $19.97

    Availability: Out of Stock

    Product Badge:
  • Erika Floral Chiffon Wrap A-Line Formal Dress

    Special Occasion

    Effortless beauty perfectly describes the Erika formal dress in all her floral glory. Charm the room in her sleeveless, surplice v-neck design with a wrap front tie on a fitted empire waist and criss-cross back straps. She features a flattering a-line silhouette with a high-cut slit on a floor-length hem perfect for twirling the evening away! The formal dress is composed of a chiffon-lined fabric with no stretch. Complete your stunning look with sparkly duster earrings.

    Fit & Features

    • Sleeveless, adjustable spaghetti straps
    • Padded v-neckline, surplice accent
    • Wrap tie-front, empire waist, criss-cross back straps
    • A-line silhouette, high-cut slit
    • Floor-length hem, zipper closure
    • Floral chiffon-lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 05002-1474

    Category Name: Maxi Dresses

    Price: $29.97

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Haylee Sequin Rose Mermaid Formal Dress

    Special Occasion

    Will you accept this rose sequin dress? Fall for the Haylee formal dress and her elegant allure! She features a one-shoulder design with strappy detail, built-in bust support, an empire waist, and a high-cut front slit on her mermaid silhouette. Zipper closure on the back. Complete the look in lace-up heels and dangly earrings. 

    Fit & Features

    • One-shoulder design, strappy detail, built-in bust support
    • Empire waist, high-cut slit
    • Mermaid silhouette, zipper closure
    • Sequin rose knit-lined fabric
    • Minimal stretch
    • Fits true to size

    Style Number/Barcode: 05002-2115

    Category Name: Maxi Dresses

    Price: $14.97

    Availability: Out of Stock

    Product Badge:
  • Lizzy Velvet Corset Mermaid Formal Dress

    Special Occasion 

    Sophisticated and modern, the Lizzy formal dress is a chic choice for any event. She features long sleeves, a mock neck on a fitted corset-mesh bodice with flexible boning. Her high-cut slit shows some skin and shapes the elegant mermaid, floor-length silhouette. The dress is composed of a luxe velvet-lined fabric with a moderate stretch. Complete your look in stiletto heels.

    Fit & Features

    • Long sleeves, mock neck
    • Corset-mesh bodice, flexible boning
    • High-cut slit, mermaid silhouette
    • Luxe velvet-lined fabric, moderate stretch
    • Zipper closure
    • Runs true to size

    Style Number/Barcode: 05002-1733

    Category Name: Maxi Dresses

    Price: $19.97

    Availability: Out of Stock

    Product Badge:
  • Shakira Cowl Neck Lace Mermaid Formal Dress

    Special Occasion 

    The Shakira formal dress is destined to make a grand entrance at your next event! She features a sleeveless cowl neckline with a display of delicate lace to add a romantic touch to her mermaid silhouette. The dress is composed of a smooth silk-like fabric that effortlessly hugs your curves into a floor-length mermaid silhouette. Complete your look with a rhinestone necklace and earrings. 

    Fit & Features

    • Sleeveless, cowl neckline
    • Lace insert with padded cups
    • Spaghetti straps
    • High waist
    • Mermaid silhouette 
    • Smooth silk fabric
    • Form hugging fit, minimal stretch, runs true to size

    Style Number/Barcode: 05002-1393

    Category Name: Maxi Dresses

    Price: $14.97

    Availability: Out of Stock

    Product Badge: