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.

  • What A Look Ruched Mini Dress

    Create a head-turning look with a mini dress that stuns! The dress features a sleeveless square neckline, tank shoulder straps, a ruched body, and a mini-length silhouette. The dress is composed of smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with sunnies and a moto jacket. 

    Fit & Features

    • Sleeveless square neckline
    • Tank shoulder straps
    • Ruched body 
    • Mini length silhouette 
    • Smooth knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1121

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Mood Ribbed Knit Maxi Dress

    We're in the mood for basics! Slay in this dress that keeps it effortlessly chic. The dress features a trendy turtle neck, long sleeves, and a maxi length silhouette with a high center back slit. The dress is composed of a ribbed knit fabric that offers a form-hugging fit. Complete look with sneakers to nail those low-key vibes.

    Fit & Features

    • Turtle neck
    • Long sleeves
    • Maxi length silhouette
    • High center back slit
    • Ribbed knit fabric
    • Plenty of stretch
    • Form-hugging fit

    Style Number/Barcode: 05102-1117

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Preppy Vibes Collared Mini Dress

    Add some stylish preppy vibes to your look in this trendy mini dress! It features a collared neckline with a partial button-down front, short sleeves, and a mini-length, curve-hugging silhouette. The black sweater knit fabric showcases light brown striped detailing at the waist, a light brown collar and button-down front, and light brown hems at the sleeves. Complete your outfit with chunky sneakers and sleek hoop earrings.

    Fit & Features

    • Collared neckline
    • Partial button-down front
    • Short sleeves
    • Mini-length
    • Form-hugging fit
    • Sweater knit fabric with plenty of stretch
    • Striped detailing at the waist

    Style Number/Barcode: 06005-0938

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Back To Basics Ribbed Knit Midi Dress

    Bring your look back to basics with a knit midi dress that can be dressed up or dressed down for whatever mood you're in. The dress features a sleeveless V-neckline, tank-like shoulder straps, and a midi length silhouette. Complete look with clear mules. 

    Fit & Features

    • Sleeveless V-neckline
    • Tank-like shoulder straps
    • Midi length silhouette
    • Ribbed knit fabric
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0932

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Taking the Plunge Scoop Neck Midi Dress

    Take the plunge in this stylish midi sweater dress! The dress features a sleeveless scoop neckline, tank shoulder straps, and a bodycon silhouette on rib-knit fabric. Complete the look with mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless scoop neckline
    • Tank-shoulder straps
    • Bodycon silhouette
    • Midi-length hem
    • Rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1233

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Day Crochet Knit Midi Dress

    Keep it casual with a midi dress that will have you channeling your bohemian side. The dress features a sleeveless V-neckline, spaghetti straps, a tie waist belt, and a midi length silhouette, The dress is composed of a crochet knit fabric that offers a relaxed fit with a slight stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps 
    • Tie-waist belt
    • Midi length silhouette
    • Crochet knit fabric 
    • Relaxed fit, slight stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0921

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Level Up Ruched Knit Midi Dress

    Level up your basic look with this trendy ruched knit midi dress. It features a sleeveless bodice, bungee spaghetti straps, a square neckline, all-over ruched detailing, and a mid-length, curve-hugging silhouette. The soft brushed knit fabric includes a lining and offers plenty of stretch for comfortable wear. Complete your outfit with a layered necklace and sleek heels.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Strapless bra recommended
    • All-over ruched detailing
    • Mid-length, form-fitting style
    • Lined-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4437

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Ditsy Floral Smocked Mini Dress

    Level up the charm with this adorable ditsy floral printed mini dress! It features tie shoulder spaghetti straps, a square neckline with a ruffle trim, a tie-front at the bust, a high waist seam, and a smocked body with a mini-length, curve-hugging silhouette. Complete the look with hoop earrings and strappy sandals.

    Fit & Features

    • Tie shoulder spaghetti straps
    • Square neckline, ruffle trim
    • Tie-front at the bust
    • High waist seam
    • Smocked body
    • Short, form-hugging fit
    • Woven fabric, ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-1109

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Chic Plaid Mini Dress

    Oh-so-chic, this plaid mini dress is a staple you can take into the fall season! It features a trendy square neckline, spaghetti straps, and a short, curve-hugging silhouette. Style this knit dress with clear heels and a faux leather jacket.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Mini-length, form-hugging fit
    • Plaid print
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1105

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Cutie Cutout Ruched Mini Dress

    Keep it cute and casual with a mini dress that is perfect to dress up! The dress features a crew neckline, short sleeves, a twist knot accent at the center of the bodice, a cutout at the midriff, ruched side seams, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with sneakers.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Twist knot accent 
    • Cutout at midriff
    • Ruched side seams
    • Mini-length silhouette, form-hugging fit
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-1108

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Fab Ruffled And Smocked Mini Dress

    Keep it so fab in a smocked dress that keeps your look effortlessly cute! The dress features an off-the-shoulder neckline, a sweetheart bust with a tie-front, and short sleeves with a ruffled hem. The back features a stretchy smocked fabric to provide a relaxed fit. The dress is composed of a lined lightweight woven fabric that offers a form-hugging fit. Complete look with wedges.

    Fit & Features

    • Off-the-shoulder neckline
    • Short sleeves with a ruffled hem
    • Sweetheart bust with a tie-front
    • Smocked back 
    • Lightweight woven fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-1106

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Romance Ruched Mini Dress

    Start a floral romance with this pretty mini dress! The dress features an off-the-shoulder neckline, ruching at the bust, short sleeves, a cutout at the midriff, a ditsy floral print, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and earrings. 

    Fit & Features

    • Off the shoulder neckline
    • Ruching at bust
    • Short sleeves
    • Cutout at the midriff
    • Ditsy floral print
    • Smooth knit fabric, form-hugging fit, runs true to size
    • Mini length silhouette

    Style Number/Barcode: 05102-1103

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heart Of Glam Ruched Midi Dress

    Bring the romantic vibes in this casually-chic midi dress! It features a sleeveless bodice with a square neckline, bungee spaghetti straps, a square back, ruched detailing, and a mid-length, curve-hugging silhouette. Pair this dress with strappy heels and a sleek clutch to complete your look.

    Fit & Features

    • Bungee spaghetti straps
    • Square neckline
    • Square back
    • Ruched detailing
    • Mid-length, form-hugging fit
    • Lined knit fabric with plenty of stretch

     

    SHOP ALL HEART OF GLAM COLLECTION

    Style Number/Barcode: 05102-1104

    Category Name: Casual Dresses

    Price: $14.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Look In Plaid Knit Mini Dress

    Get a perfect look in this adorable plaid knit mini dress! It features a sleeveless bodice with spaghetti straps, a scoop neckline, and a short, curve-hugging fit. Pair this cute and casual dress with chunky sneakers and layer on a denim jacket.

    Fit & Features

    • Spaghetti straps
    • Scoop neckline
    • Short, form-hugging fit
    • Plaid print
    • Lightweight unlined knit fabric
    • Plenty of stretch

    Style Number/Barcode: 05102-1066

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sassy Chic Snake Print Ruched Mini Dress

    Keep it sassy with a snake print mini dress! The dress features a sleeveless square neckline, spaghetti straps, snake print, dual ruched drawstrings, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and hoops. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Snake print
    • Dual ruched drawstrings
    • Mini length silhouette
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 05102-1093

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Staple Open Back Ruched Mini Dress

    Make this mini dress a casual staple to rotate into your wardrobe. The dress features a crew neckline, short sleeves, a lower back keyhole, a ruched body, and a mini-length silhouette. Complete look with sneakers and hoops. 

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Lower back keyhole
    • Ruched body 
    • Mini length silhouette 
    • Cotton knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-1097

    Category Name: Casual Dresses

    Price: $18.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Retro Vibes Tie Dye Mini Dress

    Channel retro vibes with a mini dress that keeps it super cute! The dress features a sleeveless crew neckline, a tie-dye print, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a relaxed fit with a moderate stretch. Complete look with clear mules to let this print take center stage! 

    Fit & Features

    • Sleeveless
    • Crew neckline
    • Tie-dye print
    • Mini length silhouette
    • Brushed knit fabric
    • Relaxed fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1096

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Alluring And Chic Brushed Knit Mini Dress

    Create an alluring and chic everyday look with this must-have mini dress! It features a sleeveless bodice, a scoop neck and back, tie shoulder straps, and a mini-length, curve-hugging silhouette. Complete your outfit with heeled mules and a trendy shoulder bag.

    Fit & Features

    • Scoop neck and back
    • Tie shoulder straps
    • Short, form-hugging fit
    • Brushed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1088

    Category Name: Casual Dresses

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Getaway Linen Skater Dress

    Planning a weekend getaway? Don't forget to pack this adorable linen dress for an effortlessly chic look. The dress features a sleeveless V-neckline, halter spaghetti straps, a tie-back detail, a high waist, and a flirty and flowy skater silhouette. Style this dress with hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Halter spaghetti straps
    • Tie-back detail
    • High waist
    • Flowy skater skirt
    • Linen fabric
    • Runs true to size

    Style Number/Barcode: 05102-1085

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Forever Chic Satin Midi Dress

    Sleek and chic, this satin midi dress will be your new go-to! It features a sleeveless cowl neckline, dual spaghetti straps that lead to a cross-back design, and a mid-length fitted silhouette with a subtle flared hem. Style this dress with clear heels and a trendy shoulder bag.

    Fit & Features

    • Sleeveless cowl neckline
    • Dual spaghetti straps
    • Cross-back design
    • Mid-length fitted silhouette
    • Satin fabric
    • Runs true to size

    Style Number/Barcode: 05101-0942

    Category Name: Casual Dresses

    Price: $20.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutout Cutie Gauze Skater Dress

    Keep it cute with a skater dress that brings the style! The dress features a sleeveless V-neckline, waist cutouts with bar straps, a striped pattern, and a skater silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless V-neckline
    • Waist cutouts
    • Bar straps 
    • Striped pattern 
    • Skater silhouette 
    • Gauze knit 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-1084

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Glam Tie Dye Ruched Mini Dress

    Keep it so glam with a tie-dye dress that gives your look a retro feel! The dress features a sleeveless square neckline, bungee spaghetti straps, a tie-dye print, a ruched side seam, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look in new top-rated shoes. 

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Tie-dye print
    • Ruched side seam
    • Mini length silhouette 
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-1083

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Drawn To Tie Dye Ruched Mini Dress

    Get drawn to this cute dress that gives off those totally retro feels. The dress features a sleeveless crew neckline with a racer front, a tie-dye print, and ruched drawstrings that allow you to customize the length of the dress. The dress is composed of a mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with sleek hoops and mules. 

    Fit & Features

    • Sleeveless crew neckline
    • Racer bust
    • Tie-dye print
    • Ruched drawstrings 
    • Mini/midi length silhouette 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1080

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fabulously Retro Ruched Tie Dye Dress

    Keep it fab and retro with a mini dress that is perf for your next night out! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, dual ruched drawstrings, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and butterfly earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross straps
    • Dual ruched drawstrings 
    • Mini-length silhouette 
    • Smooth knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1079

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale