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.

  • Vacay Happy Hour Tropical Print Maxi Dress

    This tropical print maxi dress was made for sippin' margaritas and enjoying the ocean breeze! It features a sleeveless V-neckline with the cutest tie-front design, adjustable spaghetti straps, a stretchy smocked back panel, a high waist seam, and a flowy floor-length hem with a thigh-high front slit. The lightweight gauze fabric features an all-over palm leaf print to capture those vacay vibes. Style with slip-on sandals.

    Fit & Features

    • Sleeveless V-neckline, tie-front
    • Adjustable spaghetti straps, stretchy smocked back
    • High waist seam
    • Flowy floor-length hem, high front slit
    • Tropical palm leaf print
    • Gauze fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5117

    Category Name: Casual Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dressing For Sunshine Eyelet Lace Mini Dress

    The perfect eyelet lace mini dress for sunny days! It features adorable puff short sleeves, a sweetheart neckline, a front bust ruched drawstring, and a bodycon silhouette. The eyelet lace fabric includes a knit lining and offers moderate stretch. Complete the look in this mini dress with cute sandals.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neckline
    • Front bust ruched drawstring
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet lace fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5118

    Category Name: Casual Dresses

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Marvelous Style Marble Print Maxi Dress

    Showcase a marvelous style in this trendy marble print maxi dress! It features a sleeveless square neckline, spaghetti straps, an asymmetric side cutout at the waist to add a sultry vibe, ruching down one side seam with an adjustable drawstring, an asymmetric maxi-length hem creating a thigh-high side slit, and a curve-hugging silhouette. The all-over eye-catching marble print pattern on the smooth and stretchy knit fabric will draw all the attention to you! Complete your summer party look with clear heels.

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Asymmetric side cutout at the waist
    • Ruching down one side seam, adjustable drawstring
    • Asymmetric maxi-length hem, high side slit, curve-hugging fit
    • Marble print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5119

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Love Eyelet Knit Mini Dress

    You'll fall in love with the effortless summer vibes of this eyelet knit mini dress! It features a sleeveless square neckline, spaghetti straps, a mini-length hem, a form-hugging fit, and a pretty floral eyelet pattern. The lined knit fabric offers plenty of stretch for comfortable wear. Style with strappy sandals.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Mini-length hem
    • Form-hugging fit
    • Floral eyelet pattern, knit fabric, knit lining
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5113

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ticket To Flirty Ditsy Floral Mini Dress

    Your ticket to looking fun and flirty is this ditsy floral mini dress perfect for a staycation or weekend getaway! It features a sleeveless sweetheart neckline, spaghetti straps, a front bust tie with a keyhole accent, and a bodycon silhouette. The soft brushed knit fabric offers plenty of stretch. Complete the look in heeled sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Front bust tie, keyhole accent
    • Bodycon silhouette, mini-length hem
    • Ditsy floral print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5115

    Category Name: Casual Dresses

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Mood Ditsy Floral Mini Dress

    This adorable ditsy floral mini dress will have you in the mood for easy summer days! It features a sleeveless scoop neckline, a small bust cutout with a tie-front detail, spaghetti straps, a mini-length hem, and a form-hugging silhouette. The ditsy floral printed ribbed knit fabric offers plenty of stretch. Style with hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless scoop neckline
    • Small bust cutout, tie-front detail
    • Spaghetti straps
    • Mini-length hem, form-hugging fit
    • Ditsy floral print
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5114

    Category Name: Casual Dresses

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Twisted Up Long Sleeve Rib Knit Midi Dress

    Get twisted up in this stylish midi dress! The rib knit dress features fitted long sleeves, a V-neckline, a twisted bust accent, and a bodycon silhouette with flattering side ruched seams and a midi-length hem perfect for styling with your favorite booties or heels. Complete the look in best-selling shoes to make a fabulous statement this season! 

    Fit & Features

    • Fitted long sleeves
    • V-neckline
    • Twisted bust accent
    • Bodycon silhouette, side ruched seams
    • Midi-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5112

    Category Name: Casual Dresses

    Price: $5.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Love Tropical Print Maxi Dress

    Fall in love with the island you're vacationing on in this breezy tropical maxi dress perfect for sunset cocktails and dinners! It features a sleeveless V-neckline, adjustable spaghetti straps, a stretchy smocked bust, and a flowy maxi-length silhouette with a flirty front slit. Complete the look in wedge sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Stretchy smocked bust
    • Flowy maxi-length hem
    • Front slit
    • Tropical palm leaf print, airy woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5111

    Category Name: Casual Dresses

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Looking Marvelous One Shoulder Midi Dress

    Step out looking marvelous in this one-shoulder midi dress for brunch or a family party! Featuring a sleeveless one-shoulder neckline with a tank shoulder strap, a flirty side ruched drawstring cutout with tie, a bodycon silhouette, and a flattering high side slit. The dress is designed with an eye-catching marble print on stretchy knit fabric. Complete the look with strappy stiletto heels.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Tank shoulder strap
    • Side ruched drawstring cutout with tie
    • Bodycon silhouette
    • High side slit, midi-length hem
    • Marble print, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5108

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Love, Wear, Repeat Short Sleeve Maxi Dress

    Love, wear, and repeat. You'll adore this maxi dress for all of your styling needs this season! It features short sleeves, a V-neckline, a form-hugging slim silhouette, and a floor-length hem on stretchy rib knit fabric. Complete the look in rhinestone hoop earrings for a dinner date.

    Fit & Features

    • Short sleeves
    • V-neckline
    • Form-hugging, slim silhouette
    • Floor-length maxi hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5107

    Category Name: Casual Dresses

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beauty So Effortless V-Neck Slit Maxi Dress

    Envoke an effortless beauty by slipping into this maxi dress perfect for cocktail hour and dressy dinner dates! The dress features a sleeveless V-neck, dual spaghetti straps that format the caged low-back design, side ruched seams to accentuate your curves, a slim and curve-hugging fit, and a sultry high side slit and long hem. Complete the look with a glitter clutch and heels.

    Fit & Features

    • Sleeveless V-neck, dual spaghetti straps
    • Caged low-back design
    • Side ruched seams
    • Slim and curve-hugging fit
    • High-side slit, maxi-length hem
    • Slinky knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2407

    Category Name: Casual Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cute And Casual Moment High Slit Maxi Dress

    Have a cute and casual moment in this high slit maxi dress that will give you a streamlined bodycon silhouette. It features a sleeveless square neckline, bungee spaghetti straps, an asymmetric maxi-length hem creating a trendy thigh-high side slit, and a curve-hugging fit. The smooth knit fabric includes a full lining and offers plenty of stretch. Style with a crossbody bag and clear mules for dinner with the girls.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Asymmetric maxi-length hem
    • High side slit
    • Bodycon fit
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5105

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All The Attention Collared Cargo Mini Dress

    Capture all the attention in this structured and chic cargo mini dress! It features a sleeveless collared neckline, a complete zip-front design creating a V-neckline, a faux belted waist, large cargo-style side pockets, a mini-length hem, and a streamlined form-hugging fit. The woven fabric offers minimal stretch. Style this mini dress with hoop earrings and clear heels.

    Fit & Features

    • Sleeveless collared neckline
    • Complete zip-front, V-neckline
    • Faux belted waist, large cargo side pockets
    • Mini-length hem
    • Form-hugging fit
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5103

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sergeant Of Style Cargo Pocket Mini Dress

    Elevate your status to sergeant of style in this edgy mini dress perfect for casual plans! Featuring a sleeveless square neckline, adjustable spaghetti straps, a lightly padded bust, an underbust seam, cargo-style flap side pockets, and a short bodycon silhouette. Style with strappy clear strap heels.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Lightly padded bust, underbust seam
    • Back zipper and hook-eye closure
    • Bodycon silhouette, mini-length hem
    • Twill woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5104

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Beauty Abstract Cutout Maxi Dress

    Embrace your vacation looking like beauty in this abstract print maxi dress destined for sunset dinners and cocktails by the pool! It features a sleeveless square neck, sleek bungee spaghetti straps, a sassy cutout waist with a hoop insert, a slim form-hugging silhouette, and a high front slit on lined smooth knit and stretchy fabric. Complete the look in cute sandals and earrings.

    Fit & Features

    • Sleeveless square neck
    • Bungee spaghetti straps
    • Cutout waist, hoop insert
    • Slim form-hugging silhouette
    • High front slit, maxi-length hem
    • Abstract print, smooth knit fabric, short knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5101

    Category Name: Casual Dresses

    Price: $5.97 $43.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Perfection Striped Tank Mini Dress

    This adorable striped tank mini dress is the perfect casual style for a subtly elevated look! It features a sleeveless crew neckline, tank shoulder straps, a mini-length subtle curved hem, and a bodycon silhouette that offers a form-hugging fit. The striped ribbed knit fabric has plenty of stretch. Pair with strappy sandals.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Mini-length subtle curved hem
    • Bodycon silhouette
    • Striped print
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5102

    Category Name: Casual Dresses

    Price: $19.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mesh Well Square Neck Mini Dress

    You and this mini dress will mesh well together! It features adorable sheer puff short sleeves with ruffle trim, a square neckline, a ruched bust and side seams, and a flattering bodycon silhouette. Complete the look with a statement choker for a family party!

    Fit & Features

    • Sheer puff short sleeves, ruffle trim
    • Square neckline
    • Ruched bust and side seams
    • Bodycon silhouette
    • Mini-length hem
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5098

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Thing Off-The-Shoulder Mini Dress

    Show your sweet side in this must-have mini dress for a stylish look at every event! It features an off-the-shoulder neckline, short sleeve cuffs, all-over ruching with an adjustable front drawstring, and a bodycon silhouette. The lined mesh fabric offers plenty of stretch. Complete the look in platform sandals.

    Fit & Features

    • Off-the-shoulder neckline
    • Sheer short sleeve cuffs
    • All-over ruching, adjustable front drawstring
    • Bodycon silhouette
    • Mini-length hem
    • Sheer mesh fabric, knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-2399

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Girl Style Turtleneck Midi Dress

    Elevate your fall wardrobe and show off a chic girl style with this bodycon midi dress! It features a sleeveless bodice, a turtleneck, a midi-length hem with a thigh-high side slit, and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a layered chain necklace and ankle booties!

    Fit & Features

    • Sleeveless bodice
    • Turtleneck
    • Midi-length hem
    • High side slit
    • Bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5096

    Category Name: Casual Dresses

    Price: $17.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Easy Decision V-Neck Cutout Maxi Dress

    A maxi dress you can style up or down? That's an easy decision! It features a sleeveless V-neckline, spaghetti straps, a knotted bust with cutout sides and back, and a hip-hugging slim silhouette with a sultry high-side slit on stretchy rib knit fabric. Complete the look in trendy sandals for a beach club or vacation!

    Fit & Features

    • Sleeveless V-neckline, knotted bust, spaghetti straps
    • Side and back cutouts
    • Hip-hugging, slim silhouette
    • High side slit
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5094

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Showstopper Lace-Up Midi Dress

    This midi dress is a casual showstopper! Make heads turn in this alluring dress featuring a sleeveless square neck, spaghetti straps that lace up in the back, a bodycon silhouette, and a fitted hem with a back-slit accent. Complete the look in dainty stiletto heels for a daytime celebration.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Lace-up back, lower zipper and hook-eye closure
    • Bodycon silhouette
    • Fitted midi-length hem, back slit
    • Texture knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5095

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Basic Revamp Zip-Front Mini Dress

    This trendy zip-front mini dress will revamp your basic looks! It features a sleeveless mock neckline with a front zipper to style into a V-neckline, tank shoulder straps, a mini-length hem, and a bodycon silhouette that will hug your curves. The soft brushed knit fabric offers plenty of stretch. Style this mini dress with sneakers to keep it casual or mules for an elevated vibe!

    Fit & Features

    • Sleeveless mock neckline
    • Zip-front design
    • Tank shoulder straps
    • Mini-length hem
    • Bodycon fit
    • Brushed knit fabric, full lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5092

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunkissed Beauty Tropical Print Cutout Maxi Dress

    You'll be a stunning sunkissed beauty in this tropical print maxi dress that will give off alluring energy. It features a sleeveless asymmetric one-shoulder neckline with a single bungee spaghetti strap, a bold asymmetric side cutout at the waist with a chic O-ring accent, a hip-hugging fit, a sultry thigh-high side slit, and a floor-length hem. The smooth and stretchy knit fabric features an all-over tropical palm leaf print. Style with strappy sandals.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Single bungee spaghetti strap
    • Asymmetric side cutout at the waist, O-ring accent
    • Hip-hugging fit, high side slit, floor-length hem
    • Tropical palm leaf print
    • Knit fabric, mini-length lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5091

    Category Name: Casual Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Miami Mood Tropical Print Cutout Maxi Dress

    This alluring tropical print maxi dress is an iconic pick for a summer vacay to Miami! It features a sleeveless halter neckline with cross-front straps, a sultry center bust cutout followed by a chic O-ring accent, dual waist cutouts on each side, a backless design with dual tie-back straps, a floor-length hem with dual thigh-high front slits, and a flowy A-line silhouette. The lightweight woven fabric showcases an all-over tropical palm leaf pattern. Style with hoop earrings and clear mules.

    Fit & Features

    • Sleeveless halter neckline, cross-front straps, tie-back design
    • Center bust cutout, O-ring accent, dual waist cutouts
    • Backless design, dual tie-back straps, elasticized back waistband
    • Floor-length hem, dual high front slits, A-line silhouette
    • Tropical palm leaf print
    • Woven fabric, lined bust, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5087

    Category Name: Casual Dresses

    Price: $5.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale