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.

  • Trendsetting Cutie Cable Knit Lace-Up Dress

    Step out as a trendsetting cutie in this cable knit midi dress perfect for daytime strolls! It features a sleeveless square neck, thin shoulder straps that create the lace-up back design, a tie-waist belt, a bodycon silhouette, a side slit, and a midi-length hem. Complete the look in flat sandals and sunglasses.

    Fit & Features

    • Sleeveless square neck, thin shoulder straps
    • Lace-up back design
    • Tie-waist belt
    • Bodycon silhouette
    • Side slit, midi-length hem
    • Cable knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5155

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Refresh One-Shoulder Bodycon Mini Dress

    This chic bodycon mini dress is the summer style refresh you need! It features an asymmetric one-shoulder neckline with an O-ring accent, a thin braided shoulder strap, a mini-length hem, and a curve-hugging silhouette. The double-lined brushed knit fabric offers plenty of stretch. Complete the look with strappy sandals.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • O-ring accent, thin braided shoulder strap
    • Mini-length hem
    • Bodycon fit
    • Double-lined brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5151

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ready For Sun Rib Knit Mini Dress

    Ready for some sun? Let this rib knit mini dress cue the sunshine! It features a sleeveless scoop neckline, a flirty bust tie with a keyhole accent, spaghetti straps, and a bodycon silhouette. Complete the look in trendy flat sandals for a backyard bbq!

    Fit & Features

    • Sleeveless scoop neckline
    • Bust tie, keyhole accent
    • Spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5149

    Category Name: Casual Dresses

    Price: $6.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Appeal Mock Neck Bodycon Mini Dress

    A must-have basic for the upcoming season! This dress features fitted long sleeves, a mock neck, a flattering bodycon silhouette, and a mini-length hem. It's composed of a cotton-blend knit fabric with a moderate stretch for comfort. Complete the look in strappy heels for a birthday brunch!

    Fit & Features

    • Fitted long sleeves
    • Mock neck
    • Bodycon silhouette
    • Mini-length hem
    • Cotton-blend knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5153

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Next Level Lace-Up Slit Maxi Dress

    A next-level maxi dress to elevate your look for upcoming parties or date nights! It features a sleeveless square neckline, spaghetti straps that form the lace-up back with tie closure, a side ruched seam to show off your figure, a bodycon silhouette, and a sexy side slit on smooth knit stretchy fabric. Complete the look with fringe rhinestone earrings for a touch of glamour!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Lace-up back, tie closure
    • Side ruched seam, bodycon silhouette
    • High side slit, maxi-length hem
    • Smooth knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 05102-5147

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Details Basic Ruched Midi Dress

    The true style of this basic midi dress lies in the detail! Features a sleeveless square neckline, sleek bungee spaghetti straps, ruched seams down the sides to accentuate your curves, and a flattering bodycon silhouette. The dress is composed of a brushed soft knit fabric with a full-length lining. Complete the look with a chic handbag for a dinner date.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruched side seams
    • Bodycon silhouette
    • Midi-length hem
    • Brushed soft knit fabric, lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5146

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Strappy And Stunning Rib Knit Midi Dress

    Step out looking stunning in this rib knit midi dress for a casual beach day with friends or a date! It features a sleeveless V-neckline, spaghetti straps, a head-turning strappy open back, a bodycon silhouette, a side slit cut out, and a midi-length hem. Complete the look in trendy flat sandals and sunglasses!

    Fit & Features

    • Sleeveless V-neckline, spaghetti straps
    • Strappy open back
    • Bodycon silhouette
    • Side slit cut out
    • Midi-length hem
    • Rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5144

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Refresh Ruched Bodycon Mini Dress

    Update your dress collection with this ruched bodycon mini dress that will be a chic refresh! It features a sleeveless crew neckline, tank shoulder straps, a partially open back with a cross-back strap design for a trendy detail, ruching down the side seams, and a mini-length hem with a bodycon silhouette that will hug your natural curves. The lined ribbed knit fabric offers plenty of stretch. Style with clear lucite heels for happy hour.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Open back, cross-back strap design
    • Ruched side seams
    • Mini-length hem, bodycon fit
    • Ribbed knit fabric, smooth sewn-in knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5143

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Moments A-Line Mini Dress

    This gorgeous mini dress was made for sunset dates! It features a sleeveless cowl neckline, spaghetti straps, an open back with a cross-back strap design and a low back draped accent, and a mini-length hem with an A-line silhouette. Style this short dress with a dainty necklace and espadrille wedges.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Open back, cross-back strap design
    • Low back draped accent
    • Mini-length hem, A-line silhouette
    • Lightweight woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5325

    Category Name: Casual Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Taking Care Of Business Collar Tank Mini Dress

    Take care of business in preppy style! This sleeveless mini dress features a trendy collared V-neckline, a bodycon silhouette, and a fitted mini-length hem on stretchy rib knit fabric. Complete the look with a dainty bracelet for a coffee shop hang!

    Fit & Features

    • Sleeveless collared V-neckline
    • Bodycon silhouette
    • Fitted mini-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5139

    Category Name: Casual Dresses

    Price: $13.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tag You're Knit Bodycon Midi Dress

    Tag you're it to rock this casually cute midi dress all over town! It features a sleeveless scoop neck, spaghetti straps, a flirty bust tie, and a figure-hugging bodycon silhouette with a side slit accent on stretchy rib knit fabric. Complete the look in sparkly teardrop earrings for an outdoor dinner party.

    Fit & Features

    • Sleeveless scoop neck
    • Bust tie, spaghetti straps
    • Bodycon silhouette
    • Side slit accent
    • Midi-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5138

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dial B For Basics Square Neck Mini Dress

    Dial B for this basic mini dress that'll inspire all your fashion-forward looks! It features a sleeveless square neckline, sleek bungee spaghetti straps, a form-hugging silhouette, and a mini-length hem. The double-line buttery knit fabric offers a seamless design and plenty of stretch. Style with a minimalistic necklace and earrings to inspire your day or night outfit! 

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Form-hugging silhouette
    • Mini-length hem
    • Double-lined buttery knit fabric, moderate stretch
    • Seamless design
    • Runs true to size

    Style Number/Barcode: 05102-5134

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Passport To Paradise Tropical Print Ruched Midi Dress

    Whether you're headed on a weekend getaway or a plane ride to paradise, pack this tropical print midi dress for a gorgeous glow! It features a sleeveless cowl neckline, spaghetti straps, ruching down one side seam, an asymmetric midi-length hem creating a thigh-high side slit, and a curve-hugging silhouette. The smooth and stretchy knit fabric features an all-over tropical palm leaf print. Style with espadrille sandals.

    Fit & Features

    • Sleeveless cowl neckline, spaghetti straps
    • Ruched side seam
    • Asymmetric midi-length hem, high side slit
    • Bodycon fit
    • Tropical palm leaf print
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5136

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heat Things Up Cutout Mini Dress

    Heat things up in this showstopping bodycon mini dress on vacation or at a summer party! It features a sweetheart neckline, spaghetti straps that crisscross in the back, dual front center O-ring inserts and cutout accents, side ruched seams, and a fitted hem. Complete the look with geo-shaped earrings and a layered necklace.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps, crisscross back
    • Dual front center O-ring inserts, cutout accents
    • Bodycon silhouette, side ruched seams
    • Mini-length fitted hem
    • Double-lined brushed knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 05102-5137

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Allure Polka Dot Mesh Mini Dress

    Show off a flirty allure in this adorable polka dot mesh mini dress. It features a square neckline, short puff sleeves with ruffled trims, an open back with a chic bow tie-back design, ruching down the side seams, a mini-length hem, and a curve-hugging silhouette. The sheer mesh polka dot patterned fabric includes a partial knit lining. Style with platform heels for a fresh date look!

    Fit & Features

    • Square neckline
    • Short puff sleeves, ruffled trims, elasticized hems
    • Open back, bow tie-back design
    • Ruched side seams, lower back zipper, hook and eye closure
    • Mini-length hem, bodycon fit
    • Sheer mesh fabric, polka dot pattern, partial knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5133

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mix And Mingle Square Neck Mini Dress

    Ready to mix and mingle? This chic little black mini dress will have you looking so stunning at cocktail mixers and dates! It features classic cap sleeves, a square neckline, a bodycon silhouette, a side slit accent, and a mini-length hem on smooth and stretchy rib knit fabric. Complete the look with an embellished clutch and simple block heels.

    Fit & Features

    • Cap sleeves
    • Square neckline
    • Bodycon silhouette
    • Side slit accent
    • Mini-length hem
    • Smooth and stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5132

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Follow The Sun Sweetheart Mini Dress

    Dare to bare some skin on a sunny day in this flirty casual mini dress for hanging by the beach or downtown! It features a sleeveless sweetheart neckline, spaghetti straps, a bust tie with a keyhole accent, and flattering side ruched seams that accentuate your curves along the bodycon fit. Complete the look with cute sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Bust tie, keyhole accent
    • Side ruched seams, bodycon fit
    • Mini-length hem
    • Brushed knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 05102-5127

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sippin' On Sultry Off The Shoulder Maxi Dress

    Strut your sultry self in this off-the-shoulder maxi dress for sipping on cocktails at sunset! It features a strapless neckline, fitted long sleeves, a bodycon silhouette, and a high-side slit along the hem. The dress is composed of a slinky knit and stretchy fabric. Complete the look with block heels.

    Fit & Features

    • Strapless neckline
    • Off-the-shoulder
    • Fitted long sleeves
    • High-side slit
    • Maxi-length hem
    • Slinky knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5124

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Dream Ditsy Floral Mini Dress

    Create a dreamy summer vibe in this adorable floral mini dress perf for sunny weekends! It features a sleeveless V-neckline with ruching at the center of the bust, spaghetti straps, a mini-length hem, and a form-hugging silhouette. The ditsy floral printed brushed knit fabric offers plenty of stretch. Style with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline, ruching at the bust
    • Spaghetti straps
    • Mini-length hem
    • Form-hugging fit
    • Ditsy floral print
    • Brushed knit fabric, full lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5122

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Leaving Impressions Strapless Ribbed Knit Midi Dress

    You'll be leaving chic impressions in this ribbed knit midi dress! It features a strapless neckline, a flirty cutout waist with contrast trim, a flattering bodycon silhouette, and a side slit accent on stretchy rib knit fabric. Complete the look in this mid-length dress with simple hoop earrings for a birthday dinner!

    Fit & Features

    • Strapless neckline
    • Cutout waist, contrast trim
    • Bodycon silhouette, side slit accent
    • Midi-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-2042

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Perfection Cutout Midi Dress

    This chic cutout midi dress is elevated perfection! It features a sleeveless subtle sweetheart neckline with a knot detail at the center of the bust, an alluring keyhole cutout under the bust, spaghetti straps, a high waist seam to create a figure-flattering look, a midi-length hem with a thigh-high side slit, and a bodycon silhouette that will hug your curves. The ribbed knit fabric offers plenty of stretch. Style with a pair of strappy stilettos.

    Fit & Features

    • Sleeveless sweetheart neckline, center knot detail
    • Keyhole cutout under the bust
    • Spaghetti straps
    • High waist seam, midi-length hem, high side slit
    • Bodycon silhouette
    • Ribbed knit fabric, smooth knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5121

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fierce And Fine Satin Leopard Midi Dress

    Fierce, fine, and looking flawless in this satin leopard midi dress! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a knotted bust, and a relaxed slim silhouette. Complete the look with a dainty bracelet and strappy heels for a birthday lunch!

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Knotted bust
    • Relaxed slim silhouette
    • Midi-length hem
    • Leopard print, smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5120

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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