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.

  • Cute As A Button V-Neck Midi Dress

    You're cute as can be in this v-neck midi dress perfect for a day date! It features long sleeves, a button-down front, midi length hem on a form-fitting silhouette. The rib-knit fabric offers a moderate stretch. Style with chic heels.

    Fit & Features

    • Long sleeves, v-neckline
    • Button-down front
    • Midi length hem
    • Form-fitting silhouette
    • Rib knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4257

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Thinking About Knit Cutout Midi Dress

    You've got knit on the mind, show off in a midi dress that stuns! The dress features a crew neckline, short sleeves, a knot accent at the center with dual cutouts at the waist, and a midi-length silhouette that is accented with a high side slit. The dress is composed of a cotton knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and a clutch.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Twist knot accent
    • Dual cutouts at the waist
    • Midi-length silhouette, high side slit
    • Cotton knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4261

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stay Cozy Cable Knit Mini Dress

    Keep it cozy with a mini dress that is perf for a casual date night! The dress features a wrap V-neckline, long balloon sleeves with ribbed cuffs, a cinching tie waist with belt loops, and a mini-length silhouette. The dress is composed of cable knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with ankle booties.

    Fit & Features

    • Wrap V-neckline
    • Long balloon sleeves, ribbed cuffed hems
    • Tie-waist belt with belt loops
    • Mini-length silhouette
    • Cable knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4250

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy And Cute Cable Knit Mini Dress

    Get a cozy and cute look this season in this adorable cable knit mini dress! It features a wrap front and back design with a deep V-neckline, long loose sleeves with tapered hems, a tie-front waist, and a short, curve-hugging fit. Pair this dress with thigh-high boots for a date night.

    Fit & Features

    • Wrap front and back
    • V-neckline
    • Long sleeves
    • Tie-front waist
    • Mini-length silhouette, form-hugging fit
    • Cable knit fabric with moderate stretch
    • Runs true to size

      Style Number/Barcode: 05102-4251

      Category Name: Casual Dresses

      Price: $9.97 $48.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Denim Spirit Tie-Back Mini Dress

      Cute, casual, with the spirit of denim in a sleek bodycon mini dress! Features a sleeveless, square neck, spaghetti straps, and a tie-back closure on a sultry open-back design. Complete the look in strappy mules for a day date.

      Fit & Features

      • Sleeveless, square neck, spaghetti straps
      • Bodycon silhouette
      • Mini-length hem
      • Open tie-back, zipper closure
      • Moderate stretch
      • Fits true to size

      Style Number/Barcode: 05102-4248

      Category Name: Casual Dresses

      Price: $4.97 $35.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Cool Girl Vibes Tie-Dye Mini Dress

      Bring those effortless cool girl vibes in this fab tie-dye mini dress. It features a square neckline, short sleeves, and a short, curve-hugging silhouette. Style this knit dress with sneakers to keep it casual or clear heels for an elevated glam look.

      Fit & Features

      • Square neckline
      • Short sleeves
      • Mini-length, form-hugging fit
      • Tie-dye print
      • Knit fabric
      • Runs true to size

      Style Number/Barcode: 05102-4249

      Category Name: Casual Dresses

      Price: $9.97 $28.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Feelin' Wild Sleeveless Slip Dress

      Showcase a chic wild style in this sleeveless slip dress! It features a lined V-neckline, spaghetti straps, a cute tie-back detail, and a flirty short silhouette with a subtle flared-out hem. The lightweight woven fabric has a trendy all-over animal print. Complete the look with strappy mules.

      Fit & Features

      • Sleeveless lined V-neckline
      • Spaghetti straps
      • Tie-back detail
      • Mini-length silhouette
      • Woven fabric, no stretch, animal print
      • Runs true to size

      Style Number/Barcode: 05102-4245

      Category Name: Casual Dresses

      Price: $6.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Sweetest Frame Long Sleeve Midi Dress

      Bring the sweetness in this long sleeve midi dress featured in a sweetheart neck, bodycon silhouette, and midi-length hem. The dress is composed of a rib-knit fabric offering a moderate stretch. Complete the look with chic booties.

      Fit & Features

      • Long sleeves
      • Sweetheart neckline
      • Bodycon silhouette
      • Midi-length hem
      • Rib-knit fabric, moderate stretch
      • Fits true to size

      Style Number/Barcode: 06005-1179

      Category Name: Casual Dresses

      Price: $16.97 $39.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Strut And Snap Ribbed Knit Midi Dress

      Strut it out in a knit midi dress that is perf for every day! Designed with a ribbed knit fabric, this dress offers a form-hugging fit with a moderate stretch. It features a sleeveless square neckline, tank shoulder straps, a high side slit accented with glossy metal buttons, and a midi-length hem. Complete the look with mules.

      Shop More Sweater Dresses: Sweater Dress Collection

      Fit & Features

      • Ribbed knit fabric with moderate stretch
      • Square neckline
      • Tank shoulder straps
      • Metal button accents
      • Side slit
      • Form-hugging fit
      • Runs true to size

      Style Number/Barcode: 06005-1167

      Category Name: Casual Dresses

      Price: $16.97 $39.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Basic Ribbed Knit High Slit Midi Dress

      Channel effortless style while looking chic in a knit dress! The dress features a mock neck, long sleeves, an asymmetrical high side slit, and a midi-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with ankle booties and a moto jacket.

      Fit & Features

      • Mock neck 
      • Long fitted sleeves
      • Asymmetrical high side slit
      • Midi-length silhouette
      • Ribbed knit fabric
      • Form-hugging fit, moderate stretch 
      • Runs true to size 

      Style Number/Barcode: 06005-1174

      Category Name: Casual Dresses

      Price: $16.97 $39.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Effortlessly Stylish Linen Dress

      You'll look effortlessly stylish this season in this lightweight and flowy linen dress! Designed with a breezy woven fabric, this short dress is perfect for your summer parties. The bodice is shaped with a square neckline with ruching at the bust and long balloon sleeves. The fitted waistband creates a cinched silhouette, flowing out to a short ruffled hem with an A-line fit for a pretty flair. Complete the look with clear heels.

      Fit & Features

      • Linen woven fabric, no stretch
      • Square neckline, ruched bust
      • Long balloon sleeves, elastic cinched hems
      • Front waistband, back zipper closure
      • Ruffled hem
      • A-line silhouette
      • Runs true to size

      Style Number/Barcode: 05102-4246

      Category Name: Casual Dresses

      Price: $9.97 $48.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Bad To The Bone Halloween Mini Dress

      Get a bad-to-the-bone spooky look with this mini dress that brings the ghoul factor to your costume! The mini dress features a mock neck, short sleeves, a skeleton graphic, and a mini-length silhouette. The dress is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with over-the-knee boots and adhesive face gems.

      Fit & Features

      • Mock neck
      • Short sleeves
      • Skeleton graphic
      • Mini length silhouette
      • Cotton knit fabric
      • Form hugging fit, moderate stretch
      • Runs true to size

      Halloween Costumes are considered final sale merchandise. FINAL SALE merchandise may not be returned or exchanged.

      Style Number/Barcode: 05102-4247

      Category Name: Casual Dresses

      Price: $9.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • For The Thrill Of Knit Mini Dress

      Keep it stunning with a mini dress that wows! The dress features a sleeveless scoop neckline, spaghetti straps, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules. 

      Fit & Features

      • Sleeveless scoop neckline
      • Spaghetti straps
      • Mini length silhouette
      • Ribbed knit fabric 
      • Form hugging fit, moderate stretch 
      • Runs true to size

      Style Number/Barcode: 06005-1154

      Category Name: Casual Dresses

      Price: $4.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Casual-Chic Sweater Knit Dress

      Casual and chic, this sweater knit dress is perf for a weekend getaway. It features a sleeveless crew neckline, tank shoulder straps that lead to a cross-back design, and a curve-hugging longline silhouette. Style this dress with a floppy hat and cute sunnies.

      Fit & Features

      • Sleeveless crew neckline
      • Tank shoulder straps
      • Cross-back design
      • Form-fitting longline silhouette
      • Ribbed sweater knit fabric
      • Runs true to size

      Style Number/Barcode: 06005-1150

      Category Name: Casual Dresses

      Price: $4.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Button Up In Style Midi Dress

      Button up in a stylish midi dress! The dress features a sleeveless crew neckline, a midi length silhouette, and a mini side slit with multi-button-up closure. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and hoops. 

      Fit & Features

      • Sleeveless crew neckline
      • Mini side slit
      • Button-up closure 
      • Midi length silhouette
      • Ribbed knit fabric 
      • Form hugging fit, moderate stretch 
      • Runs true to size

      Style Number/Barcode: 06005-1151

      Category Name: Casual Dresses

      Price: $39.90

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Ruched Ribbed Knit Cutout Mini Dress

      Keep it casually chic with a mini dress that stuns with stylish details! The dress features a crew neckline, long sleeves, a cutout at the midriff with criss-cross straps, ruched drawstrings, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and statement earrings. 

      Fit & Features 

      • Crew neckline
      • Long sleeves
      • Cutout at the midriff
      • Criss-cross straps, ruched drawstrings
      • Mini length silhouette
      • Ribbed knit fabric
      • Form hugging fit, moderate stretch, runs true to size

      Style Number/Barcode: 05102-4242

      Category Name: Casual Dresses

      Price: $9.97 $33.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Preppy Trendsetter Plaid Mini Dress

      Keep your everyday look on-trend in this preppy plaid mini dress! It features a collared V-neckline, short sleeves, a short, form-hugging silhouette, and is composed of a knit fabric with a moderate stretch. Style this dress with a denim jacket and sneakers for the perf cute and casual outfit.

      Fit & Features

      • Collared V-neckline
      • Short sleeves
      • Mini-length, form-hugging fit
      • Plaid print
      • Knit fabric, moderate stretch
      • Runs true to size

      Style Number/Barcode: 05102-4244

      Category Name: Casual Dresses

      Price: $9.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Sweet Beauty A-Line Midi Dress

      Bring a sweet style to your everyday look with this adorable flowy midi dress. It features a square neckline, half-length puff sleeves, a partially smocked back, a high waist, and a mid-length, A-line silhouette with a tiered hem. Complete the outfit with sleek hoop earrings and cute mules.

      Fit & Features

      • Square neckline
      • Half-length puff sleeves, elastic cinched hems
      • Partially smocked back
      • High waist
      • Mid-length, A-line flowy silhouette, tiered hem
      • Cotton fabric, no stretch
      • Runs true to size

      Style Number/Barcode: 05102-4243

      Category Name: Casual Dresses

      Price: $9.97 $54.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Basic And Trendy Collared Mini Dress

      Basic and trendy, this knit mini dress is a summer must-have. It features a sleeveless collared V-neckline, a button-down front, ruched detailing, and a short, curve-hugging silhouette. Style this dress with casual sneakers for the perf everyday look.

      Fit & Features

      • Sleeveless collared V-neckline
      • Button-down front
      • Ruching
      • Mini-length, form-hugging fit
      • Knit fabric
      • Runs true to size

      Style Number/Barcode: 05102-4238

      Category Name: Casual Dresses

      Price: $19.97 $39.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • One Of A Kind A-Line Mini Dress

      Stun in this one-of-a-kind dress that is pef for any occasion! The dress features a square neckline, short puff sleeves, and an A-line silhouette. The dress is composed of a lined textured woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges. 

      Fit & Features

      • Square neckline
      • Short puff sleeves
      • A-line silhouette
      • Mini length 
      • Textured lined woven fabric
      • Relaxed fit, runs true to size

      Style Number/Barcode: 05102-4239

      Category Name: Casual Dresses

      Price: $9.97 $48.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Chic Crew Ribbed Knit Mini Dress

      Show em' all that you roll with the chic crew in this fab mini dress! The dress features a crew neckline with a racer bust, a ruched body, and a mini side slit. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a denim jacket. 

      Fit & Features

      • Sleeveless crew neckline
      • Racer bust
      • Ruching
      • Mini side slit
      • Ribbed knit fabric
      • Form hugging fit, moderate stretch 
      • Runs true to size 

      Style Number/Barcode: 05102-4240

      Category Name: Casual Dresses

      Price: $6.97 $28.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Set It Off Ruffled Bodycon Dress

      Set off your night with a head-turning bodycon that raises the heat! The dress features a sleeveless wrap V-neckline, spaghetti straps, a ruched body, and a mini-length silhouette with a ruffled hem. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with rhinestone heels and a clutch. 

      Fit & Features

      • Sleeveless wrap V-neckline
      • Spaghetti straps
      • Ruched body
      • Mini length silhouette, ruffled hem 
      • Smooth knit fabric
      • Form-hugging fit, moderate stretch
      • Runs true to size

      Style Number/Barcode: 05102-4464

      Category Name: Casual Dresses

      Price: $9.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Collared And Chic Button Down Dress

      Keep it chic with a dress that is part trendy, part casual. The dress features a collared neckline, a button-down front, ruching, long sleeves, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules and gold earrings.

      Fit & Features

      • Collared neckline
      • Button-down front
      • Ruching 
      • Long sleeves
      • Mini length silhouette
      • Ribbed knit fabric
      • Form hugging fit, moderate stretch, runs true to size

      Style Number/Barcode: 05102-4235

      Category Name: Casual Dresses

      Price: $9.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Casually Fab Tie-Dye Mini Dress

      Get a casually fab look in this on-trend tie-dye mini dress. It features a crew neckline, short sleeves, ruched detailing down the sides with ties at the hem, and a short, curve-hugging silhouette. Style this dress with a denim jacket and sneakers.

      Fit & Features

      • Crew neckline
      • Short sleeves
      • Ruching down the sides
      • Ties at the hem
      • Mini-length, form-hugging fit
      • Ribbed knit fabric, plenty of stretch, tie-dye print
      • Runs true to size

      Style Number/Barcode: 05102-4233

      Category Name: Casual Dresses

      Price: $9.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale