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.

  • Butterfly Charm Ruched Mini Dress

    Bring the charm with a butterfly print dress that springs you into the season. The mini dress features a sleeveless square neckline, spaghetti straps, a butterfly print, a ruched body, 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 butterfly earrings and wedges. 

    Fit & Features

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

    Style Number/Barcode: 05102-1454

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Style Floral Mini Dress

    Showcase the sweetest style this summer season in this floral mini dress! It features a sleeveless bodice, spaghetti straps, a sweetheart neckline with a tie-front at the bust, and a mini-length, curve-hugging silhouette. The knit fabric has an all-over adorable ditsy floral print that will pair perfectly with a denim jacket and sandals.

    Fit & Features

    • Spaghetti straps
    • Sweetheart neckline
    • Tie-front at the bust
    • Short, form-hugging fit
    • Knit fabric, moderate stretch
    • Ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-1431

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirtatious Vibes Floral Mini Dress

    Bring the flirty vibes in this adorable floral mini dress perf for summer! It features an off-the-shoulder sweetheart neckline with a ruffle trim, a tie-front detail, short puff sleeves, an all-over ditsy floral print, and a mini-length, curve-hugging silhouette. Complete the look with cute wedges for a weekend brunch.

    Fit & Features

    • Off-the-shoulder sweetheart neckline, ruffle trim
    • Tie-front detail
    • Short puff sleeves
    • Ditsy floral print
    • Brushed knit fabric, moderate stretch
    • Short, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-1430

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tie Dye Ruched Mini Dress

    Keep it ruched and stylish with a dress that channels those retro vibes. The dress features a sleeveless square neckline, spaghetti straps, dual drawstrings, 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 wedges. 

    Fit & Features

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

     

    Style Number/Barcode: 05102-1438

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love At First Sight Mini Dress

    With you in this adorable ditsy floral dress, it will be love at first sight. The dress features thin ruffle shoulder straps, a V neckline with subtle ruching, and a short, curve-hugging silhouette. The lightweight knit fabric offers plenty of stretch. Complete your look with a classic denim jacket and sneakers.

    Fit & Features

    • Thin ruffle shoulder straps
    • V neckline with ruching
    • Mini-length, form-hugging fit
    • Knit fabric with plenty of stretch
    • Ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-1429

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Essential High Slit Ribbed Knit Maxi Dress

    Create a chic moment with a maxi dress that brings the chic details! The dress features a crew neckline, short sleeves, dual side cutouts, and a maxi silhouette accented with a high side slit. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with sneakers for a casual vibe.

    Fit & Features

    • Crew neckline
    • Short sleeves 
    • Dual side cutouts
    • Maxi length silhouette
    • High side slit
    • Ribbed knit fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-1420

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Flirt Floral Mini Dress

    Bring the flirtatious vibes in this adorable floral mini dress! It features a sleeveless square neckline, adjustable spaghetti straps, ruched detailing with drawstrings at the hem, and a mini-length, curve-hugging silhouette. Style this dress with sneakers for a cute and casual look.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Ruched detailing, drawstrings at the hem
    • Short, form-hugging fit
    • Ribbed knit fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05102-1404

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

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

    Keep it glam with a retro mini dress! The dress features a sleeveless square neckline, adjustable spaghetti straps, a tie-dye print, a ruched body, and a mini-length silhouette. Complete look with wedges. 

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Tie-dye print
    • Ruched body
    • Mini length silhouette
    • Form hugging fit 
    • Runs true to size

     

    Style Number/Barcode: 05102-1377

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Eyes On Me Eyelet Mini Dress

    Draw all eyes on you in this pretty mini dress! The dress features a sleeveless square neckline, spaghetti straps, a ruched mini length with drawstring, and an eyelet pattern throughout. The dress is composed of a lined lightweight woven fabric that offers a form hugging fit with minimal stretch. Complete look with block heels and a straw tote. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruched drawstring
    • Eyelet pattern
    • Mini length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 05102-1381

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beautiful Bloom Ruched Midi Dress

    Showcase your beauty in this stylish floral printed midi dress! It features spaghetti straps, a square neck and back, ruched detailing, and a mid-length, curve-hugging fit. Pair this dress with strappy heels and a rhinestone necklace for a romantic date night.

    Fit & Features

    • Spaghetti straps
    • Square neck and back
    • Ruched detailing
    • Mid-length
    • Form-hugging silhouette
    • Floral print
    • Knit fabric with plenty of stretch

    Style Number/Barcode: 05101-0949

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Go With The Flow Smocked Maxi Dress

    Go with the flow in a casual maxi dress that keeps your look effortlessly chic! The dress features a sleeveless square neckline, a smocked bodice, halter neck ties, a triple-row bar strap design, and a flowy maxi length silhouette. The dress is composed of a lined gauze fabric that offers a relaxed fit with slight stretch. Complete look with wedges and a floppy hat. 

    Fit & Features

    • Sleeveless square neckline
    • Smocked bodice
    • Halter neck ties
    • Triple-row bar strap
    • Maxi length silhouette
    • Lined gauze knit fabric
    • Relaxed fit, slight stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1362

    Category Name: Casual Dresses

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Fab Tie-Dye Mini Dress

    You'll be feelin' oh-so-fab in this trendy tie-dye mini dress. It features a sleeveless scoop neckline, spaghetti straps, ruched detailing with drawstrings at the hem, and a mini-length, curve-hugging silhouette. This dress would be perf for a casual date styled with a cute crossbody purse and clear heels.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Ruched detailing, drawstrings at the hem
    • Short, form-hugging fit
    • Ribbed knit fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-1334

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All Eyes On Me Eyelet Mini Dress

    Draw all eyes on you in this fab mini dress! The dress features a square neckline, short puff sleeves, ruching at the bodice, eyelet pattern, and a curve-hugging mini-length silhouette. The dress is composed of a lined woven fabric that offers minimal stretch. Complete look with clear mules. 

    Fit & Features

    • Square neckline
    • Short puff sleeves
    • Ruching 
    • Eyelet pattern 
    • Mini length silhouette 
    • Form hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-1291

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless And Chic Eyelet Mini Dress

    Effortless and chic, this eyelet mini dress is the perfect addition to your summer wardrobe. It features a sleeveless scoop neckline, tank shoulder straps, and a mini-length, curve-hugging silhouette. Style this dress with strappy sandals.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Short, form-hugging fit
    • Sheer eyelet fabric, full lining
    • Runs true to size

    Style Number/Barcode: 05102-1275

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dare Me Denim Mini Dress

    We dare you to strut your style in this dress! The dress features a sleeveless scoop neckline, corset seams at the bust, adjustable spaghetti straps, 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 mules and hoops. 

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps
    • Corset seams the bust
    • Mini length silhouette 
    • Denim fabric 
    • Form hugging fit, runs true to size

    Style Number/Barcode: 05102-1288

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Glam Ribbed Knit Maxi Dress

    Keep it casually glam with a maxi dress that is perf to dress up or down for brunch! The dress features a sleeveless V-neckline, a cute tie-front, adjustable spaghetti straps, a button-down front, and a maxi-length silhouette accented with a high center slit. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges and a floppy hat.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, tie-front 
    • Button-down front
    • Maxi-length silhouette, high center slit
    • Ribbed knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1347

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Fierce Leopard Print Mini Dress

    You'll be feelin' fierce and fashionable in this trendy leopard print mini dress! It features a strapless sweetheart neckline with a tie-front detail, a cutout under the bust, and a short, form-fitting style to hug your curves. Complete the look with chic mules.

    Fit & Features

    • Strapless sweetheart neckline
    • Tie-front
    • Cutout under the bust
    • Mini-length, form-hugging fit
    • Smocked woven fabric
    • Leopard print
    • Runs true to size

    Style Number/Barcode: 05102-1327

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Girl Summer Crochet Maxi Dress

    Keep it stylish with a crochet maxi dress that is perf for your summer adventures! The dress features a sleeveless V-neckline, a crochet waist, an open back with a crochet lace trim, and a maxi-length silhouette. The dress is composed of a woven fabric that offers a relaxed and flowy fit. Complete look with wedges and butterfly hoops.

    Fit & Features

    • Sleeveless V-neckline
    • Crochet waist
    • Open back, crochet lace trim, tie-back closure
    • Lower back hidden zipper and hook and eye closure
    • Maxi-length silhouette, relaxed fit
    • Lightweight woven fabric, short knit lining
    • Runs true to size

    Style Number/Barcode: 05102-1330

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • X Marks The Spot Denim Mini Dress

    Step up in a stylish denim dress that hits the style mark! The dress features a sleeveless scoop neckline, adjustable spaghetti straps that cross at the back, and a mini side slit. The dress is composed of a denim fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and hoops. 

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps, cross at back 
    • Mini length silhouette
    • Mini side slit
    • Denim fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 05102-1311

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Style Icon Gauze Cutout Maxi Dress

    Create a stylish moment with a maxi dress that is perf for the season! The dress features a plunging V-neckline, waist cutouts with bar straps, a high side slit, and a maxi 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 with bar straps
    • Maxi silhouette
    • Gauze knit fabric
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-1314

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Free-spirited Floral Beauty Sleeveless Maxi Dress

    Let your natural beauty glow in this pretty maxi dress! The dress features a floral print, V-neckline, spaghetti straps that cross at the back, a lace-up back, and a high side slit. The dress is composed of an airy chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with wedges and hoops. 

    Fit & Features

    • Floral print 
    • Sleeveless V-neckline
    • Spaghetti straps, cross at back 
    • Lace-up back 
    • High side slit
    • Maxi length silhouette
    • Chiffon fabric, relaxed fit, runs true to size

    Style Number/Barcode: 05101-0974

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish And Lovely Eyelet Mini Dress

    Keep it stylish and lovely with a mini dress that brings sweet details! The dress features a sleeveless square neckline with a mini tie front, adjustable spaghetti straps, an eyelet pattern, and a mini-length silhouette. Complete look with wedges. 

    Fit & Features

    • Sleeveless square neckline
    • Mini tie-front
    • Adjustable spaghetti straps
    • Eyelet pattern 
    • Mini length silhouette
    • Form hugging fit runs true to size

     

    Style Number/Barcode: 05102-1276

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy In Tie-Dye Satin Mini Dress

    Showcase your trendy style this summer season in this adorable satin mini dress. It features a sleeveless cowl neckline, adjustable spaghetti straps that lead to a cross-back design, ruched detailing with side ties, a short, curve-hugging silhouette, and a fab all-over tie-dye print. Complete the look with hoop earrings and clear heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Cross-back design
    • Ruching, side ties
    • Mini-length, form-hugging fit
    • Satin fabric, tie-dye print, mini skirt length knit lining
    • Runs true to size

    Style Number/Barcode: 05102-1322

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sprung On You Floral Lace-Up Mini Dress

    Get sprung on this cute floral mini dress! The dress features a sleeveless scoop neckline, spaghetti straps that lead to a cross-back lace-up back design, cute floral print, ruched side seams, and a mini-length silhouette. Complete the look with wedges and butterfly earrings for that brunch-ready look.

    Fit & Features

    • Sleeveless scoop neckline 
    • Spaghetti straps, cross at back 
    • Lace-up straps 
    • Floral print
    • Ruched side seams
    • Mini-length silhouette 
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-1243

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale