Casual Dresses

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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.

  • Nights Like This Cutout Mini Dress

    Nights like this call for a stunning dress to celebrate with the squad! The dress features a sleeveless sweetheart neckline, waist cutouts, a double row of O-rings, a ruched body, and a mini-length silhouette. Complete look with rhinestone heels and statement earrings.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Waist cutouts
    • O-Rings accents
    • Ruched body
    • Mini-length silhouette, form-hugging fit
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4060

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Second Take Denim Lace-Up Mini Dress

    Make them all take a second look at you in this stunning mini dress! The dress features a sleeveless square neckline, a backless design with a lace-up back, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Backless, lace-up straps
    • Mini length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

     

    Style Number/Barcode: 05102-0577

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Glam Tropical Maxi Dress

    Dazzle with an island-inspired look in this maxi dress that brings those vacay vibes! The dress features a sleeveless V-neckline, spaghetti straps, a tropical floral print, a high side slit, and a maxi length silhouette. Complete look with wedges and a floppy hat

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Tropical floral print
    • High side slit
    • Maxi length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05101-0318

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic And Captivating Mesh Maxi Dress

    Keep it chic and captivating with a mesh dress that wows! The dress features a sleeveless square neckline, adjustable spaghetti straps, a ruched drawstring at the hem, a high side slit, and a mini length lining with a sheer mesh maxi-length hem. Complete look with rhinestone heels

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps 
    • Ruched drawstring at the hem 
    • High side slit
    • Mini length lining, maxi-length hem
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0594

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunset Stunner Asymmetrical Midi Dress

    This dress will have you looking stunning as you watch the sunset on your next vacay! It features a sleeveless V-neckline, adjustable spaghetti straps, a beautiful tropical floral print, and a mid-length, curve-hugging silhouette with an asymmetrical hem. Style this dress with hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Back cross-back design
    • Ruched detailing
    • Mid-length, form-hugging fit, asymmetrical hem
    • Knit fabric, moderate stretch, tropical floral print
    • Runs true to size

    Style Number/Barcode: 05102-1860

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Fever Ribbed Knit Mini Dress

    Keep it stylish with a floral dress that is all the rage! The dress features a sleeveless sweetheart neckline, spaghetti straps, a tie-front at the bust, a ditsy floral print, 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 wedges.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Tie-front 
    • Ditsy floral print 
    • Mini-length silhouette 
    • Ribbed knit fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-2032

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic High-Slit Basic Maxi Dress

    Basic yet oh-so-chic, this sleeveless maxi dress will be your new go-to. It features a crew neckline, tank shoulder straps, a sultry thigh-high side slit, and a floor-length fitted silhouette. Style this dress with sleek hoop earrings.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Thigh-high side slit
    • Floor-length fitted silhouette
    • Ribbed cotton fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4090

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Vibes Sleeveless Maxi Dress

    Bring on the effortless vibes this season with this pretty maxi dress! It features a sleeveless square neckline, spaghetti straps, side pockets, and a flowy silhouette with an asymmetrical hem. Cinch the dress with a belt and style it with mules for an adorable look.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Side pockets
    • Flowy, relaxed fit
    • Asymmetrical hem
    • Smooth knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4171

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Jetsetter Tropical Print Maxi Dress

    Nail your vacay-bound look with a maxi dress that brings those tropical vibes! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, a high side slit, and a tropical palm leaf print. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges and sunglasses. 

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back 
    • High side slit
    • Tropical palm leaf print
    • Maxi length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

     

    Style Number/Barcode: 05102-0542

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho-Chic Crochet Midi Dress

    Bring the boho-chic vibes to your stylish summer look with this stunning midi dress! It features a sleeveless scoop neckline, spaghetti straps, a mid-length, curve-hugging silhouette, and a sheer crochet fabric with a trendy fringe hem. Wear this dress as a cover-up over your fave bikini for the perf poolside outfit.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Mid-length, form-hugging fit
    • Sheer crochet fabric, fringe hem
    • Runs true to size

    Style Number/Barcode: 06005-0949

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Stunner Ribbed Knit Midi Dress

    Stun on them with a stylish midi dress that makes a head-turning impression! The dress features a sleeveless V-neckline, spaghetti straps, an open back with an O-ring accent, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete outfit with clear mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Open back, O-ring accent
    • Midi-length
    • Ribbed knit fabric, knit lining
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4071

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Meant To Be Ruffled Mini Dress

    You and this dress are totally meant to be! The dress features a sleeveless V-neckline, spaghetti straps, lace-up back, a mini-length silhouette with a faux-wrap overlay, and ruffles. The dress is composed of a mesh fabric that offers a form-hugging fit with a moderate stretch. Complete the look with platform wedges and a butterfly necklace. 

    Fit & Features

    • Sleeveless V-neckline
    • Lace-up back 
    • Mini length silhouette
    • Faux-wrap overlay 
    • Ruffles 
    • Lined mesh fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-0758

    Category Name: Casual Dresses

    Price: $38.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All About Floral Lace Skater Dress

    Showcase your love for lace with a skater dress that says it all! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a sheer floral lace back, and a flirty and flowy skater silhouette. Complete the look with wedges.

    Fit & Features

    • Sleeveless V-neckline 
    • Adjustable spaghetti straps, sheer floral lace back
    • Hidden side zipper and hook and eye closure
    • Skater silhouette
    • Lined chiffon fabric 
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05101-0832

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cut It Out Babe Midi Dress

    Effortless, but make it extra. With a bold cutout bodice and sleek side slit, this midi dress hugs in all the right places for dates, brunch, or casual plans.

    Fit & Features

    • Stretchy rib knit fabric, contrast trim
    • Square neck, tank shoulder straps
    • Cutout bodice
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000045

    Category Name: Casual Dresses

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All My Love Ditsy Floral Mini Dress

    Keep it lovely and gorge with a mini dress that shows off your sweet side! The dress features a ditsy floral print, a sleeveless square neckline, spaghetti straps, a lower back keyhole with tie-back straps, and a skater silhouette with a ruffled hem. Complete look with chunky sneakers.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps 
    • Lower back keyhole
    • Tie-back straps
    • Skater silhouette, ruffled hem
    • Lightweight woven fabric, ditsy floral print
    • Relaxed fit, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4147

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Vibes Crochet Knit Maxi Dress

    Channel those vacay vibes with a maxi dress that brings those resort vibes! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a lower back keyhole with tie-back straps, and a maxi length silhouette. The dress is composed of a lined gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Lower back keyhole with tie-back straps
    • Maxi length silhouette
    • Lined gauze knit fabric
    • Form hugging fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0297

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mesmerizing Beauty Puff Sleeve Eyelet Skater Dress

    Mesmerize with a skater dress that is perf for your next photoshoot! The dress features a square neckline, short puff sleeves, an eyelet pattern, and a skater silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges

    Fit & Features

    • Square neckline
    • Short puff sleeves
    • Eyelet pattern 
    • Skater silhouette 
    • Lightweight woven fabric 
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4073

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Let Beauty Bloom Floral Midi Dress

    Let your beauty bloom with a midi dress that is perf for the season! The dress features a sleeveless cowl neckline, adjustable spaghetti straps that lead to a cross-back, a tropical floral print, ruching, and a midi-length silhouette with an asymmetrical hem. Complete look with wedges

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps 
    • Cross-back 
    • Tropical floral print 
    • Midi length silhouette 
    • Asymmetrical hem 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-0328

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Laid Back Glamour Crochet Knit Midi Dress

    Keep it effortlessly glam with a crochet-knit dress! The dress features a sleeveless V-neckline, a mini side slit, and a midi length silhouette. The dress is composed of a crochet knit fabric that offers a relaxed fit with a moderate stretch. Complete look with wedges

    Fit & Features

    • Sleeveless V-neckline
    • Mini side slit
    • Midi length silhouette
    • Crochet knit fabric 
    • Relaxed fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0674

    Category Name: Casual Dresses

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Total Knockout Knit Midi Dress

    Step up in this knockout midi dress that is all the rage! Perfect for stepping out for a casual lunch date or layer this dress for the perfect workwear outfit. The dress features a crew neckline, cap sleeves, and a midi-length silhouette accented with a high side slit. Elevate your look with square toe strappy mules and statement-making earrings!

    Fits & Features

    • Crew neckline
    • Cap sleeves
    • Midi length hem
    • High side slit
    • Ribbed knit fabric
    • Plenty of stretch, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-0897

    Category Name: Casual Dresses

    Price: $4.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Pick Ditsy Floral Mini Dress

    This adorable ditsy floral mini dress is the perfect pick to add to your summer wardrobe! It features a sleeveless square neckline, thin ruffled shoulder straps, ruched detailing with a front drawstring, and a mini-length, curve-hugging silhouette. Style this dress with cute wedges for a weekend brunch.

    Fit & Features

    • Sleeveless square neckline
    • Thin ruffled shoulder straps
    • Ruched detailing, front drawstring
    • Short, form-hugging fit
    • Ribbed knit fabric, ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-2963

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take Me Back Tropical Maxi Dress

    Get taken back to that dream vacay with a fab maxi dress! The dress features a sleeveless V-neckline, adjustable spaghetti straps that cross at the back, a tropical print, an open back, a smocked waist, and a flowy maxi length silhouette. Complete with wedges

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, cross at back 
    • Tropical print
    • Open back 
    • Smocked waist
    • Maxi length silhouette
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05101-0572

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty And Flowy Halter Skater Dress

    Showcase your flirty style in this adorable flowy skater dress! It features a sleeveless deep V-neckline, halter straps, dual tie-back accents, a high waist, and a flared-out skater skirt. Complete the look with rhinestone earrings and clear heels.

    Fit & Features

    • Sleeveless V-neckline
    • Halter straps, dual tie-back accents
    • High waist
    • Flowy skater skirt, fit and flare silhouette
    • Chambray fabric
    • Runs true to size

    Style Number/Barcode: 05102-0488

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Go With Florals Mini Dress

    Go with florals this season to channel gorge vibes! 

    Fit & Features 

    • Scoop Neckline | Spaghetti Straps
    • Lattice Back 
    • Floral Print
    • Lined Scuba Knit Fabric
    • Form Hugging Fit 
    • Moderate Stretch 


    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0325

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale