Casual Dresses

Casual Dresses Made for Everyday Fall Plans

Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.

Easy Prints, Textures & Layers for the Season

Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.

What Makes a Dress Casual?

A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.

How Do You Transition a Casual Dress From Summer to Fall?

Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.

Which Fabrics Work Best for Everyday Dresses?

Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.

How Can You Style One Casual Dress for Different Plans?

Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.

  • Island Hopping Tropical Maxi Dress

    Feel the island breeze in this tropical maxi dress for your next holiday in the sun! It features a sleeveless, halter neck, a sultry cutout bodice that leads to the open tie-back closure, and a flowy maxi hem with a slit. Complete your vacay look with lace-up heels.

    Fit & Features

    • Sleeveless, halter neck with tie
    • Cutout bodice
    • Open-back, tie closure
    • Side slit
    • Flowy maxi silhouette
    • Tropical print, woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4500

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Desert Vacay Sleeveless Maxi Dress

    Make sure to pack this effortlessly-chic maxi dress in your weekend bag for your desert vacay! It features a sleeveless plunging V-neck and back design, tank shoulder straps, a high-rise banded waist with side cutouts, and a flowy, floor-length silhouette with a front slit to show some leg. Style this dress with espadrille sandals.

    Fit & Features

    • Sleeveless plunging V-neck and back design
    • Tank shoulder straps
    • High-rise banded waist, side cutouts
    • Maxi-length hem, flowy silhouette
    • Front slit
    • Woven gauze fabric, pleated detailing, knit skirt lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4504

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Under The Palms Halter Skater Dress

    Get ready to relax under the palms in this adorable printed skater dress. It features a sleeveless V-neckline with halter straps, side cutouts leading to a strappy banded back design, a smocked high waist, and a flowy skater skirt silhouette. The lightweight gauze fabric features an all-over tropical palm leaf print. Style with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Halter spaghetti straps, tie at the back of the neck
    • Side cutouts, strappy banded back design, tie closure
    • Smocked high waist, flowy skater skirt
    • Tropical palm leaf print
    • Gauze fabric, knit skirt lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4499

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Weekend Vibes Mini Dress

    This sleek satin floral dress is perfect for your weekend outings! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back lace-up design, and a mini-length, A-line silhouette. The lightweight satin fabric features an all-over dainty floral print. Style this dress with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back lace-up design, tie closure
    • Mini-length, A-line silhouette
    • Dainty floral print
    • Smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4494

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sway With Me Floral Chiffon Dress

    Sashay and sway in this adorable floral chiffon dress featuring a sleeveless, scoop neck, adjustable spaghetti straps, smocked back panel, and a flowy, ruffled tiered short hem. Complete the look in trendy sandals for your next getaway.

    Fit & Features

    • Sleeveless, scoop neck, adjustable spaghetti straps
    • Smocked back panel
    • Flowy, tiered short hem
    • Floral pattern
    • Chiffon-lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4495

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • One More Moment Sweater Dress

    Make a lasting impression leaving the pool party in this chic cover-up sweater dress! It features a sleeveless, square neck, spaghetti straps that lead to an open-back with lace-up closure, a form-fitting silhouette, and a side slit atop the midi-length hem. Complete the look in sunglasses.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Open-back, lace-up closure
    • Form-fitting silhouette
    • Slit midi-length hem
    • Sweater knit fabric, slightly sheer, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1317

    Category Name: Casual Dresses

    Price: $8.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • It-Girl Status Midi Dress

    Showcase major it-girl status in this chic lace-up midi dress. It features a sleeveless scoop neckline, tank shoulder straps, an open back with a cross-back lace-up strappy design, a midi-length hem, and a curve-hugging silhouette. Style with clear mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Open back, cross-back lace-up strappy design, tie closure
    • Midi-length hem
    • Form-fitting, bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4489

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rulebreaker Graphic Cutout Short Dress

    Break the rules in a mini dress that shows off your bold side! The mini dress features a crew neckline, short sleeves, a graphic that reads: "Breaking The Rules", an image of an eagle with checkered flags and motorcycles, cutout at the back, and a short-length hem. The dress is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties and a moto jacket. 

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Graphic: "Breaking The Rules"
    • Image of eagle, motorcycle, checkered flags
    • Short length hem, cutout at the back 
    • Cotton knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 06002-1204

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Let's Get Brunch Skater Dress

    You'll be ready for weekend brunch with your girls in this adorable swiss dot woven skater dress. It features a sleeveless V-neckline with a twist-front design, spaghetti straps, an open back with a cute tie-back detail, a high waist seam, and a short skater-style silhouette with a ruffled hem. Style with wedges and chic shades.

    Fit & Features

    • Sleeveless V-neckline, twist-front design
    • Spaghetti straps
    • Tie-back closure
    • High waist seam, skater silhouette
    • Ruffled short-length hem
    • Swiss dot woven fabric, lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1582

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Paradise Ready One-Shoulder Maxi Dress

    This gorgeous tropical printed maxi dress will have you looking ready for a vacay off to paradise! It features a sleeveless one-shoulder neckline, a single bungee spaghetti strap, an asymmetrical waist cutout with a chic O-ring accent, and a curve-hugging, floor-length silhouette with a front slit. The stretchy knit fabric features an all-over palm leaf print. Complete your look with slip-on sandals and your fave shades.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Single bungee spaghetti strap
    • Asymmetrical waist cutout, O-ring accent
    • Maxi-length hem, form-fitting silhouette, front slit
    • Tropical palm leaf print
    • Knit fabric, short knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4484

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Perfection Sleeveless Midi Dress

    Showcase effortless perfection in this simple yet chic midi dress. It features a sleeveless scoop neckline, spaghetti straps, an open-back design, a midi-length, curve-hugging silhouette, and a high side slit. Style this dress with heeled mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Open-back design
    • Midi-length, form-fitting, bodycon silhouette
    • Side slit
    • Lined ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4485

    Category Name: Casual Dresses

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cold Brew Collared Mini Dress

    For coffee dates and everything else, you'll adore this collared v-neck mini dress designed to flatter your figure on a bodycon silhouette with a faux button-down accent and all-over ruching. Composed of sleek knit fabric with a moderate stretch. Finish the look in cute booties.

    Fit & Features

    • Sleeveless, collared v-neck
    • Faux button-down placket
    • All-over ruching
    • Bodycon silhouette
    • Mini-length hem
    • Sleek knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4482

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chain Reaction Rib Knit Dress

    This rib knit dress may cause a chain reaction of followers! It features a sleeveless square neckline, edgy chain-link straps, and a bodycon mini-length hem. Complete the look in platform heels for girl's night.

    Fit & Features

    • Sleeveless square neckline
    • Chain-link shoulder straps
    • Bodycon silhouette
    • Mini-length hem
    • Ribbed knit fabric, sewn-in knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4480

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutest Look Floral Mini Dress

    Get the cutest look for the spring season with this adorable floral mini dress! It features a sleeveless sweetheart neckline with shirring at the bust, spaghetti straps, a short, curve-hugging fit, and an all-over dainty floral print pattern. Style this dress with a cropped denim jacket and strappy sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Shirring at the bust
    • Spaghetti straps
    • Mini-length, form-fitting silhouette
    • Floral print
    • Brushed knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4612

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Sweetheart Midi Dress

    Sweet but sexy, this denim midi dress was made for you! It features a sleeveless, sweetheart neck, adjustable spaghetti straps, corset-style bodice, and a high-waist seam leading to the bodycon silhouette with a back slit accent. Complete the look in statement earrings.

    Fit & Features

    • Sleeveless, sweetheart neck, adjustable spaghetti straps
    • Corset-style bodice, back zipper closure
    • High-waist seam, back slit accent
    • Bodycon silhouette
    • Midi-length hem
    • Denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4477

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daisy Darling Sleeveless Short Dress

    Fall into a daisy daze with a short dress that brings all the feels! The dress features a sleeveless square neckline with lace trim, spaghetti straps, a pretty daisy print, and a short-length hem. The dress is composed of a brushed knit fabric with a form-hugging fit and moderate stretch. Complete the look in strappy mules.

    Fit & Features

    • Sleeveless square neckline, lace trim
    • Spaghetti straps
    • Daisy floral print
    • Short length hem
    • Brushed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4479

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Accents Bodycon Mini Dress

    You'll love the alluring accents of this trendy-chic bodycon mini dress. It features a sleeveless square neckline, spaghetti straps, a revealing side cutout at the waist, ruching down one side with an adjustable drawstring, and a short, curve-hugging fit. The smooth knit fabric features an all-over snake print pattern. Style this dress with clear heels.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Side cutout at the waist
    • Ruching down one side, adjustable drawstring
    • Bodycon silhouette, mini hem
    • Snake print, lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4473

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Perfect For Paradise Midi Dress

    This curve-hugging midi dress is perfect for your vacation in paradise, or to just look like you're on one! It features a sleeveless V-neckline, spaghetti straps, a midi-length asymmetrical hem to showcase some leg, and an all-over tropical floral print to match the vibe of a vacay. Style this dress with strappy mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Midi-length asymmetrical hem
    • Form-fitting silhouette
    • Tropical floral print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4474

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always On Point Ruched Mini Dress

    You'll always look on point in this trendy ruched mini dress! It features a sleeveless square neckline, bungee straps, a high waist seam, side ruched detailing with adjustable drawstrings, and a short, curve-hugging fit. Style this dress with sleek hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless square neckline
    • Bungee straps
    • High waist seam
    • Side ruching, adjustable drawstrings
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4472

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Life Made Easy Linen Halter Maxi Dress

    Look effortlessly put together in this breezy striped linen maxi dress for a Duffy boat cruise or beachside brunch! It features a sleeveless, halter v-neck with tie-closure, a partial open-back with tie, hidden side pockets, and a flowy, maxi-length silhouette with a sultry front slit. Complete the look in a straw floppy hat and sandals. 

    Fit & Features

    • Sleeveless, halter v-neck, tie-closure
    • Partial open-back with tie
    • Hidden side pockets
    • Flowy silhouette
    • Front high-cut slit
    • Maxi-length hem
    • Striped linen fabric, lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4468

    Category Name: Casual Dresses

    Price: $6.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Wild Leopard Mini Dress

    Flaunt your wild side in a leopard mesh mini dress for your next prowl! It features a sleeveless, square neck bodice with spaghetti straps and side ruched seams on a bodycon silhouette. Complete the look in heels.

    Fit & Features

    • Sleeveless bodice, square neck
    • Spaghetti straps
    • Side ruched seams
    • Mini-length bodycon silhouette
    • Leopard print pattern
    • Sheer mesh fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4470

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Summer Halter Maxi Dress

    Sultry for summer. Raise the chicness in this halter maxi dress featuring a sleeveless bodice with tie-closure, o-ring inset, and a cutout accent leading to the bodycon silhouette with an asymmetrical slit hem. Complete your sultry look in espadrille wedges.

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • O-ring inset, cutout accent
    • Bodycon silhouette
    • Asymmetrical slit
    • Maxi-length hem
    • Rib-knit fabric, moderate stretch, fits true to size

    Style Number/Barcode: 05102-4467

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spot Me In Leopard Slit Midi Dress

    You can be spotted all season in this leopard print midi dress perfect for a casual lunch or a wine night with friends! It features a sleeveless V-neckline, tank shoulder straps, and a form-hugging, slim silhouette with a flowy slit hem. Complete the look in sleek statement hoop earrings and sandals.

    Fit & Features

    • Sleeveless V-neckline, tank shoulder straps
    • Form-hugging, slim silhouette
    • Front slit
    • Midi-length flowy hem
    • Leopard print
    • Woven non-stretch fabric
    • Runs true to size

    Style Number/Barcode: 05102-4469

    Category Name: Casual Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropic Like It's Hot Halter Midi Dress

    It's vacay season and this halter midi dress is here for it! Featuring a sleeveless, high neckline with a tie closure, cutout bodice with a cinch accent, and a bodycon midi-length hem. Composed of a nylon-blend knit fabric with a moderate stretch. Finish the look with trendy mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless, high halter neckline, tie closure
    • Cutout bodice, cinch accent
    • Bodycon silhouette
    • Midi-length hem
    • Nylon-blend knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1305

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance