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.

  • Perfect Style Plaid Mini Dress

    Showcase a chic and perfect style in this plaid mini dress that is a must-have for fall. It features a sleeveless square neckline, spaghetti straps, and a short, curve-hugging fit. Complete the outfit with a faux leather jacket to add an edgy vibe to the look.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Mini-length, form-fitting silhouette
    • Knit fabric, moderate stretch
    • Plaid print
    • Runs true to size

    Style Number/Barcode: 05102-1864

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Romance Asymmetrical Mini Dress

    Fall in love with this dreamy tropical printed mini dress that is a must-have for summer vacays. It features a sleeveless V-neckline, adjustable spaghetti straps, side ruched detailing, and a mini-length, curve-hugging silhouette with a trendy asymmetrical hem. Style this dress with cute mules.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Side ruched detailing
    • Short, form-hugging fit
    • Asymmetrical hem
    • Brushed knit fabric, plenty of stretch, tropical palm leaf print
    • Runs true to size

    Style Number/Barcode: 05102-1857

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • So Adored Cut Out Mini Dress

    Feel so beloved in this pretty mini dress! The dress features a scoop neckline, short sleeves, a midriff cutoff with tie waist accent, 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 look with platform heels. 

    Fit & Features

    • Scoop neckline
    • Short sleeves
    • Midriff cutout, tie waist accent 
    • Mini length silhouette
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1859

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Vibes Butterfly Printed Mini Dress

    Showcase those sweet and flirty vibes in this trendy knit mini dress. It features spaghetti straps, a square neckline, ruching down the sides, ties at the hem, and a short, form-hugging silhouette. The lightweight ribbed knit fabric has an adorable colorful butterfly print, making it a perf dress for the spring season. Complete your look with a denim jacket and strappy sandals.

    Fit & Features

    • Spaghetti straps
    • Square neckline
    • Ruched detailing and ties at the hem
    • Mini-length, curve-hugging fit
    • Unlined ribbed knit fabric
    • Plenty of stretch
    • Colorful butterfly print

    Style Number/Barcode: 05102-1705

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropics Babe High Slit Midi Dress

    Hit the tropics in this gorge midi dress! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, a tropical print, a ruched side seam, and a midi-length silhouette with a high side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a floppy hat and sandals. 

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross at the back 
    • Tropical print 
    • Ruched side seam 
    • Midi length silhouette, high side slit
    • Smooth knit fabric 
    • Form hugging fit, runs true to size

    Style Number/Barcode: 05102-1799

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfectly Plaid Knit Mini Dress

    You'll look perfectly stylish in this plaid mini dress that you can take from day to night! It features a sleeveless square neckline, spaghetti straps, and a short, form-fitting silhouette that will hug your curves. Style with sneakers for a casual daytime look, and layer on a faux leather jacket and style with ankle booties for night.

    Fit & Features

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

    Style Number/Barcode: 05102-1687

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Preppy And Trendy Plaid Ruched Mini Dress

    Keep it preppy in a plaid mini dress that is perf for your next brunch with the squad! The dress features a plaid print, a sleeveless square neckline, spaghetti straps, dual ruched drawstrings, and a mini-length silhouette. Complete look with mules and a jelly purse.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Plaid print
    • Dual ruched drawstrings
    • Mini length silhouette
    • Knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-1679

    Category Name: Casual Dresses

    Price: $19.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Totally Fab Tie Dye Midi Dress

    Keep it totally fab with a midi dress that channels those pretty vibes! The dress features a sleeveless V-neckline, spaghetti straps, a tie-dye print, and a midi silhouette with a high side slit. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules. 

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Tie-dye print
    • Midi silhouette
    • High side slit 
    • Lightweight woven fabric
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-1633

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Splash Of Style Tie Dye Midi Dress

    Add a splash of style with a pretty midi dress! The dress features a sleeveless cowl neckline, spaghetti straps, a strappy back design, a tie-dye print, and a midi-length silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with clear mules. 

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Strappy back design 
    • Tie-dye print
    • Midi length silhouette
    • Lightweight woven fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-1659

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Vibes Tie-Dye Knit Mini Dress

    Bring the casual vibes this season with this trendy tie-dye knit mini dress. It features a crew neckline, short sleeves, side ruching, and a mini-length, curve-hugging silhouette with side ties at the hem. Complete the look with cute sneakers for the perf everyday outfit.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Side ruching
    • Side ties at the hem
    • Short, form-hugging fit
    • Knit fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-1588

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy Glam Tie Dye Ruched Mini Dress

    Keep it dreamy in a tie-dye dress that channels a retro feel! The dress features a sleeveless square neckline, spaghetti straps, a ruched body, tie-dye print, and a mini-length silhouette. Complete look with wedges and a denim jacket for a cute date outfit. 

    Fit & Features

    • Sleeveless square neckline 
    • Spaghetti straps 
    • Ruched body
    • Tie-dye print 
    • Mini length silhouette
    • Brushed knit fabric 
    • Form hugging, moderate stretch, runs true to size

    Style Number/Barcode: 05102-1520

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Sweet Puff Sleeve Mini Dress

    Rock a look that's so sweet this season! The mini dress features an off-the-shoulder neckline with a sweetheart bust, short puff sleeveless, ruching at the bodice, and a mini-length silhouette. Complete your look with statement earrings and wedges. 

    Fit & Features

    • Off the shoulder neckline, sweetheart bust
    • Short puff sleeves
    • Ruching
    • Mini length silhouette
    • Knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

     

    Style Number/Barcode: 05102-1551

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Preppy And Trendy Plaid Mini Dress

    Keep it on a trend with a preppy plaid dress to channel those cool-girl vibes. The mini dress features a sleeveless square neckline, spaghetti straps, plaid print, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules. 

    Fit & Features

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

    Style Number/Barcode: 05102-1508

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Flirty Floral Mini Dress

    This flirty floral mini dress is a must-have for summer parties! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a back zipper closure, ruched detailing, and a short, form-hugging fit. Style this dress with a chic charm necklace and wedges.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Back zipper closure
    • Ruching
    • Mini-length, curve-hugging silhouette
    • Mesh fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05102-1497

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Instincts Basic Tube Dress

    Tap into your stylish instincts with a basic tube dress. The dress features a sleeveless square neckline and a midi-length silhouette. The dress is composed of a knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a jelly purse. 

    Fit & Features

    • Sleeveless square neckline
    • Midi length silhouette
    • Knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0975

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Drawn In With Glam Ruched Mini Dress

    Get drawn in with glam in a cute mini dress! The dress features a sleeveless V-neckline, spaghetti straps, a ruched drawstring at the center, and a mini-length silhouette. The dress is composed of a textured knit fabric that offers a form-hugging fit. Complete the look with hoops and mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Ruched drawstring at center
    • Mini length silhouette
    • Textured knit fabric 
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-1496

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Ruched Knit Mini Dress

    Create an effortless everyday outfit with this on-trend knit mini dress. It features a mock neckline, short sleeves, a front ruched detail with a drawstring, and a mini-length, curve-hugging silhouette. Complete the look with classic sneakers and a cute crossbody purse.

    Fit & Features

    • Mock neckline
    • Short sleeves
    • Front ruched detail with a drawstring
    • Short, form-hugging fit
    • Double-lined brushed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1478

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Vibes Sleeveless Mini Dress

    Showcase a gorgeous glow in this sunset-hued tie-dye mini dress! It features a sleeveless scoop neckline, tank shoulder straps, and a short, curve-hugging silhouette. The brushed knit fabric offers plenty of stretch. Style this dress with a denim jacket and sneakers for a casual look.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Mini-length, form-hugging fit
    • Brushed knit fabric, plenty of stretch
    • Tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-1483

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Staple Ribbed Knit Mini Dress

    This comfy ribbed knit mini dress will be a new casual staple in your closet. It features a sleeveless scoop neckline, adjustable spaghetti straps, and a short, curve-hugging silhouette with a rounded hem. Style this dress with a denim jacket and sneakers for the perf everyday look.

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps
    • Mini-length, form-hugging fit
    • Rounded hem
    • Ribbed sweater knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-0968

    Category Name: Casual Dresses

    Price: $4.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

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

    Elevate your everyday look with this casually chic mini dress. It features a sleeveless scoop neckline, tank shoulder straps, and a mini-length, curve-hugging silhouette. Style this ribbed knit dress with the matching jacket and sleek hoop earrings.

    Shop Matching Jacket: Casually Chic Ribbed Knit Cropped Jacket

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Short, form-hugging fit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1492

    Category Name: Casual Dresses

    Price: $19.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Into Florals Maxi Dress

    Spring into the season with a maxi dress that ushers in the romance. The dress features a sleeveless V-neckline, adjustable spaghetti straps that cross at the back, a floral print, and a flowy A-line silhouette. The dress is composed of a lined chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, cross back 
    • Floral print 
    • A-line silhouette, mini skirt length lining
    • Floral print
    • Lined chiffon fabric
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-0979

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Basic Chic Ribbed Knit Dress

    Style up your everyday outfit with this elevated basic dress. It features a crew neckline, short sleeves, side ruching that leads to a slit, and a curve-hugging silhouette. The ribbed knit fabric includes a lining and offers plenty of stretch. Complete your look with sneakers and cool shades for the day or a faux leather crossbody purse and mules for the night.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Side ruching
    • Side slit
    • Form-hugging fit
    • Lined ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-1466

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Must-Have Everyday Ribbed Knit Dress

    This must-have ribbed knit dress is perf for an everyday outfit! It features bungee spaghetti straps, a square neckline, ruching, and dual drawstrings at the hem. Style the dress as a mini and pair it with sneakers for a casual brunch with friends, or make the dress a midi length and style with clear heels for a date night.

    Fit & Features

    • Bungee spaghetti straps
    • Square neckline
    • High waist seam and side ruched detailing
    • Dual drawstrings
    • Style as a mini or midi dress
    • Ribbed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-1455

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale