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!

  • Casual Chic Ruched Ribbed Knit Maxi Dress

    Effortlessly elevate your everyday looks with this casual chic ribbed knit maxi dress. It features a sleeveless boat neckline, tank shoulder straps with a trendy twist-back design, ruched side seams at the waist to accentuate your curves, and a fitted A-line silhouette with a maxi-length hem to flaunt your figure. Style with hoop earrings and strappy mules.

    Fit & Features

    • Stretchy ribbed knit
    • Boat neckline
    • Tank shoulder straps, twist-back design
    • Side ruching at the waist
    • Fitted A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5834

    Category Name: Maxi Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: GRAY

    Available Size: S, M, L

    Product Badge:
  • Sultry Fave Halter Cowl Neck Floral Maxi Dress

    You'll always embody sultriness in this floral mesh maxi dress perfect for weddings or cocktail parties! The halter cowl neckline with tie adds a touch of charm, while the form-hugging silhouette highlights your curves. The maxi-length hem and floral print mesh fabric bring an elegant and romantic touch. Complete the look with rhinestone earrings and a clutch.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Halter cowl neckline with tie
    • Form-hugging silhouette
    • Maxi-length
    • Runs true to size

    Style Number/Barcode: 05101-3331

    Category Name: Maxi Dresses

    Price: $45.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS

    Product Badge:
  • Gwen Sweetheart Ruffle Floral A-Line Formal Dress

    Special Occasion

    Become a vision of love in the Gwen floral A-line formal dress perfect for bridesmaids, wedding guests, or attending a garden party! Made from an airy floral print mesh fabric, this floor-length dress will make you feel so gorgeous. With delicate ruffled adjustable spaghetti straps and a flattering sweetheart neckline, this dress will beautifully accentuate your figure with padded bra cups. The ruffled A-line silhouette and front slit add a touch of sophistication to the floor-length hem. Complete the look with dangly earrings, a bracelet, and heels.

    Fit & Features

    • Floral print, mesh fabric, woven lining, no stretch
    • Sweetheart neckline
    • Ruffled adjustable spaghetti straps
    • Padded bra cups, back zipper and hook-eye closure
    • Front slit
    • A-line ruffled silhouette
    • Runs true to size

    Style Number/Barcode: 05002-8501

    Category Name: Maxi Dresses

    Price: $109.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S

    Product Badge:
  • Catch Attention Cowl Neck Abstract Floral Maxi Dress

    Catch everyone's attention in this abstract floral maxi dress at cocktail hour! The cowl neckline adds a touch of sophistication while the adjustable spaghetti straps provide a perfect fit. The form-hugging silhouette flatters your figure and the maxi-length hem offers a chic finish. Complete the look with a clutch and heels.

    Fit & Features

    • Abstract floral print, mesh fabric lined with stretchy knit
    • Cowl neckline
    • Adjustable spaghetti straps
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05101-3323

    Category Name: Maxi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: FUCHSIA

    Available Size: XS, S, M, L

    Product Badge:
  • Mackenzie Formal Satin Floral Lace-Up Dress

    Special Occasion

    Long in reasons to love, the Mackenzie formal satin dress will have you feeling so romantic! She features a sleeveless cowl neckline, sleek spaghetti straps that lace up along the back, and a flattering A-line silhouette, high front slit, and floor-length hem. The formal dress is crafted from a silky satin fabric with a gorgeous dainty floral print and has a smooth woven lining. Complete the look with a sparkly clutch and strappy heels for an outdoor wedding or black tie soiree!

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps, lace-up back
    • Back zipper and hook-eye closure
    • A-line silhouette, high front slit, floor-length hem
    • Dainty floral print, silky satin, woven lining
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05002-7727

    Category Name: Maxi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M

    Product Badge:
  • Abbie Off-The-Shoulder Mermaid Ombre Formal Dress

    Special Occasion

    Turn heads with your significant allure in the Abbie ombre formal dress perfect for weddings or banquets! Made of ombre mesh fabric, this dress is a true work of art. Its off-the-shoulder neckline and side ruched seams flatter your figure, while the mermaid silhouette and floor-length hem give a sophisticated touch. Complete the look with sparkly rhinestone earrings, a clutch, and heels!

    Fit & Features

    • Ombre print mesh fabric, stretchy soft knit lining
    • Off-the-shoulder neckline
    • Back zipper and hook-eye closure
    • Mermaid silhouette
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05002-8567

    Category Name: Maxi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: MAUVE

    Available Size: XS, S, M, L, XL

    Product Badge:
  • Set For Cuteness Twist Back Slit Rib Knit Maxi Dress

    You and this maxi dress are set for cuteness all season long! Made with rib knit fabric, this dress is both comfortable and stylish, perfect for any occasion. Featuring a square neckline and shoulder straps, this dress offers a form-hugging fit that will accentuate your curves. The twist-back design adds a trendy touch while the high side slit and maxi-length hem provide an alluring appeal. Complete the look with sandals and sunnies!

    Fit & Features

    • Stretchy rib knit fabric
    • Square neckline
    • Shoulder straps
    • Twist back design
    • High side slit
    • Form-hugging
    • Runs true to size

    Style Number/Barcode: 05102-5577

    Category Name: Maxi Dresses

    Price: $32.90

    Availability: In Stock

    Available Color: GRAY

    Available Size: S, M, L

    Product Badge:
  • Outside The Lines Tie Back Slit Marble Maxi Dress

    Color outside the lines and rock this chic marble print maxi dress for dressy showers or summer events! With a square neckline and spaghetti straps, this dress flatters your figure with a form-hugging fit. The tie-back design adds a touch of unique style while the front slit showcases your legs along the maxi-length hem. Complete the look with earrings and heels.

    Fit & Features

    • Marble print, smooth knit fabric with stretchy lining
    • Spaghetti straps
    • Square neckline
    • Tie back design
    • Form-hugging fit
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05101-3455

    Category Name: Maxi Dresses

    Price: $45.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

    Product Badge:
  • A Little Wild One-Shoulder Zebra Print Maxi Dress

    Your next night out just got a little wild in this sassy zebra print maxi dress perfect for vacation or the weekend! This form-hugging dress features a one-shoulder neckline and spaghetti strap, with a side drawstring cutout to show some skin. The high side slit and maxi-length hem add a flirty touch to this fierce and flattering piece. Complete the look with heeled sandals and earrings.

    Fit & Features

    • Zebra printed knit fabric, plenty of stretch
    • One-shoulder neckline, spaghetti strap
    • Side drawstring cutout
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5821

    Category Name: Maxi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: XS, S, M, L

    Product Badge:
  • Perfect Always Strapless Cutout Ruffle Maxi Dress

    Have all eyes on you in this strapless maxi dress boasting a sweetheart twist neckline and a cutout bodice. The smooth knit fabric hugs your curves along the form-hugging silhouette and creates a front center ruffle design. 

    Fit & Features

    • Smooth knit lined fabric, moderate stretch
    • Strapless sweetheart twist neckline
    • Cutout bodice
    • Center front ruffle design
    • Form-hugging, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3601

    Category Name: Maxi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
  • Francie Cold Shoulder Slim Floral Formal Dress

    Special Occasion

    Become a dreamy romantic vision in the Francie floral formal dress as a bridesmaid, wedding guest, or a summer banquet! The cold shoulder neckline, short-sleeve cuffs, and adjustable spaghetti straps create a flattering silhouette. The low cowl back adds a touch of sophistication, while the slim silhouette and floor-length hem exude luxury. Complete the look with rhinestone earrings and a chic clutch.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Cold shoulder neckline, short-sleeve cuffs, adjustable spaghetti straps
    • Low cowl back
    • Slim floor-length silhouette
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05002-8552

    Category Name: Maxi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M

    Product Badge:
  • Fierce Stripes Strapless Zebra Print Satin Maxi Dress

    Awaken your fierceness in this zebra print satin maxi dress for a sunset cocktail hour! Featuring a strapless neckline and a curve-hugging silhouette, this maxi-length dress is designed to make a statement. Complete the look in wedge sandals.

    Fit & Features

    • Zebra print, satin woven fabric, chiffon lining
    • Strapless neckline
    • Curve-hugging fit
    • Maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3419

    Category Name: Maxi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L

    Product Badge:
  • Serving Vibes Cutout Geometric Mesh Maxi Dress

    Serve major vibes in this geometric mesh maxi dress out by the beach this weekend or for a getaway! The square neckline, adjustable spaghetti straps, and form-hugging fit show off your curves while the cutout sides and back add a touch of sass. Complete with a center-back slit and maxi-length hem for effortless movement. Style this sleeveless dress with earrings and sandals.

    Fit & Features

    • Geometric print, mesh fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Square neckline
    • Cutout sides and back
    • Form-hugging fit
    • Center back slit
    • Runs true to size

    Style Number/Barcode: 05102-5759

    Category Name: Maxi Dresses

    Price: $35.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
  • Madalyn One-Shoulder High Slit Formal Dress

    Special Occasion

    The sleek and sultry style of the Madalyn formal dress makes it the perfect option for parties, weddings, or fancy date nights! She features a sleeveless asymmetric one-shoulder neckline with a single spaghetti strap, a high waist seam, ruching down one side seam leading to a thigh-high slit, a floor-length hem, and a slim-fit silhouette. The smooth knit fabric offers plenty of stretch. Complete the look with strappy stilettos.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline, spaghetti strap
    • High waist seam, ruched side seam
    • Thigh-high side slit
    • Floor-length hem, slim-fit silhouette
    • Knit fabric, lined bust, plenty of stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05002-7214

    Category Name: Maxi Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M, L, XL

    Product Badge:
  • Out Of Office One Shoulder Tropical Maxi Dress

    This tropical maxi dress says it's time for vacation! Switch your email to out of office and enjoy a sunny destination in this sleeveless dress featuring a one-shoulder neckline adorned with a knotted shoulder strap, a flattering mermaid silhouette, and a maxi-length hem. Complete the look with sunglasses and a cocktail in hand!

    Fit & Features

    • Tropical palm leaf print, stretchy knit fabric
    • One-shoulder neckline
    • Knotted shoulder strap
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5695

    Category Name: Maxi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M

    Product Badge:
  • Sensational Sultry One-Shoulder Floral Satin Maxi Dress

    Make sure all eyes are on you stepping on the scene in this floral satin maxi dress at cocktail parties! The one-shoulder neckline and strappy open back exude sultriness, while the form-hugging fit and maxi-length hem create a flattering silhouette on the floral satin fabric. Complete the look in stiletto heels.

    Fit & Features

    • Floral print, satin fabric
    • One-shoulder neckline
    • Adjustable spaghetti strap
    • Strappy open back
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05101-3397

    Category Name: Maxi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S

    Product Badge:
  • Stunning Favorite Strapless Cutout Floral Maxi Dress

    Create a stunning aurora in this floral maxi dress for summer cocktail hours! The strapless neckline and side cutout provide a flattering silhouette, while the form-hugging fit accentuates your curves, and the high side slit offers a show of leg. Complete the look in strappy stiletto heels.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Strapless neckline
    • Side cutout
    • Form-hugging fit
    • High side slit
    • Runs true to size

    Style Number/Barcode: 05101-3278

    Category Name: Maxi Dresses

    Price: $49.90

    Availability: Out of Stock

    Product Badge:
  • Perfect Style Cowl Neck Slit Paisley Maxi Dress

    Bask in the aesthetic perfection of this paisley mesh maxi dress whether you're on vacation or having a sunset dinner with friends! This form-hugging dress features a cowl neckline and spaghetti straps, highlighting your figure in all the right ways. The high-side slit and sheer maxi-length hem add a touch of allure to this must-have dress! Complete the look with a necklace and earrings.

    Fit & Features

    • Paisley print, partially lined mesh fabric
    • Cowl neckline
    • Spaghetti straps
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5694

    Category Name: Maxi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S

    Product Badge:
  • Floral Perfection One-Shoulder Chiffon Maxi Dress

    Create a picture-perfect look for weddings in this gorgeous floral chiffon maxi dress! The airy and breezy sheer chiffon fabric is detailed with a blooming floral print and includes a full-length lining for coverage. The maxi-length dress is shaped with a sleeveless one-shoulder neckline with a tank strap, leading to fitted high waist seams with the cutest tie-front design. The dress flows out with a pleated A-line silhouette for that effortlessly chic look. Style this long dress with clear heels to be the best-dressed guest!

    Fit & Features

    • Floral-printed sheer chiffon fabric with knit lining, minimal stretch
    • Sleeveless one-shoulder neckline with tank strap
    • High waist seams with tie-front design
    • Hidden side zipper with hook and eye closure
    • Pleated A-line silhouette
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05101-3334

    Category Name: Maxi Dresses

    Price: $54.90

    Availability: In Stock

    Available Color: PINK

    Available Size: S, M, L, XS

    Product Badge:
  • Never A Dull Moment Strapless Cutout Maxi Dress

    Bring a stunning look in this strapless maxi dress for your look-back-it moment! The strapless neckline and cutout bust add a touch of allure, while the strappy back and form-hugging fit emphasize your figure. With a center-back slit, you'll be able to move in style. Complete the look with earrings and a clutch!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Cutout bust, strappy back
    • Form-hugging fit
    • Center back slit
    • Runs true to size

    Style Number/Barcode: 05102-5766

    Category Name: Maxi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

    Product Badge:
  • Stunning One Halter V-Neck Ruffle Floral Maxi Dress

    You'll take every vacation or summer party by storm when you have this floral maxi dress! This stunning maxi dress features a halter V-neckline with spaghetti strap tassel ties, a stretchy smocked bodice accentuating your figure, and hidden side pockets for added convenience. The flowy ruffled silhouette and floor-length hem add a stylish finish. Complete the look in sandals and sunglasses!

    Fit & Features

    • Floral print, woven fabric with lining, no stretch
    • Halter V-neckline
    • Spaghetti strap tassel ties
    • Stretchy smocked bodice
    • Flowy ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5776

    Category Name: Maxi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: RUST

    Available Size: S, M

    Product Badge:
  • Coastal Dream Lace-Up Ruffled Maxi Dress

    A dreamy sleeveless maxi dress perfect for styling for beach city days or coastal vacations! The scoop neckline and bust tie accentuate your figure, while adjustable spaghetti straps provide the perfect fit. The lace-up back adds a touch of charm, while the flowy ruffled silhouette and maxi-length hem exude effortless chicness! Complete the look with strappy sandals and sunglasses.

    Fit & Features

    • Woven fabric, short knit stretchy lining
    • Scoop neckline with bust tie
    • Adjustable spaghetti straps
    • Lace-up back
    • Flowy tiered ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5565

    Category Name: Maxi Dresses

    Price: $56.90

    Availability: Out of Stock

    Product Badge:
  • Pretty In Paradise One-Shoulder Tropical Maxi Dress

    You'll be looking so pretty as you stroll the beach in paradise in this tropical maxi dress! The smooth stretchy knit fabric showcases a bold tropical print perfect for an island vacay. The long dress is shaped with a sleeveless asymmetric one-shoulder neckline with a single spaghetti strap. The sultry ruched cutout at the waist features an adjustable drawstring for a customized look. Reveal some leg with the sexy high-cut side slit on the maxi-length silhouette. Style this slim-fit dress with espadrille wedges.

    Fit & Features

    • Stretchy knit fabric, knit lining at the bust
    • Tropical print
    • Asymmetric one-shoulder neckline, spaghetti strap
    • Ruched side cutout, adjustable drawstring
    • High side slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5542

    Category Name: Maxi Dresses

    Price: $45.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: S

    Product Badge:
  • Marylou Lace Mesh Plunge Neck Formal Dress

    Special Occasion

    Bring the romantic allure to the evening affair in the Marylou lace mesh plunge formal dress! She embodies flirtatious style in a sleeveless plunge V-neckline with a built-in padded bust and adjustable spaghetti straps on her empire waist bodice. The sparkly embroidered lace mesh fabric effortlessly flows into a floor-length silhouette with a high-side slit to showcase some legs. She also features a curve-conscious silhouette to flaunt your stunning figure! Complete the look in an elegant hair clip.

    Fit & Features

    • Plunge V-neckline, adjustable spaghetti straps
    • Adhesive bra recommended, built-in padded bust
    • High side slit, back zipper, hook and eye closure
    • Empire waist, form-fitting silhouette
    • Floor-length hem
    • Sparkly embroidered lace mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05002-1852

    Category Name: Maxi Dresses

    Price: $69.90

    Availability: In Stock

    Available Color: DENIM, BLACK

    Available Size: XS, S, M, L

    Product Badge: