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.

  • Chic Moves Long Sleeve Bodycon Mini Dress

    Showcase your silhouette in this chic bodycon mini dress! It features a V-neckline, long fitted sleeves, ruched detailing at the shoulders, a mini-length hem, and a curve-hugging fit. The smooth knit fabric offers plenty of stretch. Style with clear lucite heels.

    Fit & Features

    • V-neckline
    • Long fitted sleeves
    • Ruching at the shoulders
    • Mini-length hem
    • Fitted bodycon silhouette
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05103-4835

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Like A Dream Chiffon Skater Dress

    Look and feel like a dream in this chiffon skater dress perfect for baby showers or birthdays! It features an off-the-shoulder, ruffle trim sweetheart neckline, sheer peasant long sleeves with elastic cuffs, a lightly padded bust, and a flowy tiered ruffled short-length hem. Complete the look in cute mules.

    Fit & Features

    • Off-the-shoulder, smocked back
    • Ruffle trim sweetheart neck, lightly padded bust
    • Sheer peasant long sleeves, elastic cuffs
    • Fit and flare skater silhouette
    • Flowy tiered ruffled short-length hem
    • Chiffon fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2113

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vineyard Gal Floral Linen Skater Dress

    Perfect for vineyard weddings, wine tasting, and daytime soirees! This vintage-inspired floral linen dress features adorable puff short sleeves, a sweetheart neck with a bust tie, a lace-up back design, and a tiered fit and flare skater silhouette with a short hem. Complete the look in on-trend espadrille wedges.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neck, bust tie
    • Lace-up back design
    • Tiered fit and flare skater silhouette
    • Short-length hem
    • Vintage floral print, linen fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4919

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So In Love Floral A-Line Midi Dress

    You'll fall so in love with this floral midi dress to wear for day dates! It features a sleeveless square neckline, elastic ruched straps with lettuce-edge trim, an A-line silhouette, and a flirty front slit. The dress has a dainty rose floral print on stretchy knit-lined fabric. Complete the look in heeled sandals.

    Fit & Features

    • Sleeveless square neckline
    • Elastic ruched straps
    • Lettuce-edge trim
    • A-line silhouette
    • Front slit, midi-length hem
    • Dainty rose floral print, stretchy knit-lined fabric
    • Runs true to size

    Style Number/Barcode: 05102-4921

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine Girlie Crochet Chevron Sweater Dress

    Calling all the sunshine girlies! Slip on this playful crochet chevron sweater dress for backyard pool parties or vacations. It features a sleeveless halter V-neckline, tie-back spaghetti straps, an open back, a bodycon silhouette, and a mini-length hem with ribbed trim. Style with chunky platform heels for a complete look!

    Fit & Features

    • Sleeveless halter V-neckline
    • Tie-back spaghetti straps
    • Open back
    • Bodycon silhouette
    • Mini-length hem with ribbed trim
    • Chevron pattern, crochet sweater fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06005-1658

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Weekend Vibes Floral Mini Dress

    Give off those effortless weekend vibes in this adorable floral mini dress! It features a V-neckline with a twist-front design, a front keyhole cutout under the bust, adjustable spaghetti straps, a smocked design down the back and body of the dress, a mini-length hem with a form-hugging silhouette, and a ditsy floral print pattern. The woven fabric offers a moderate stretch. Style with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline, twist-front design
    • Keyhole cutout under the bust, adjustable spaghetti straps
    • Smocked design down the back and body of the dress
    • Mini-length hem, form-hugging fit
    • Ditsy floral print
    • Woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4920

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendsetting Style Chain Strap Mini Dress

    Show off your trendsetting style in this sleeveless bodycon mini dress! It features a scoop neckline, adjustable spaghetti straps with chunky chain-link accents, a mini-length hem, and a curve-hugging fit. The ribbed knit fabric offers plenty of stretch. Complete the look in this short dress with a mini handbag and clear mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps, chain-link accents
    • Mini-length hem
    • Form-hugging fit
    • Stretchy ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4917

    Category Name: Casual Dresses

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Brunch Eyelet Skater Dress

    This adorable skater dress is a perfect pick for weekend brunch! It features a sweetheart neckline, short puff sleeves with tie accents, a high waist seam, a short skater skirt with a ruffled hem, and a fit and flare silhouette. The lightweight knit fabric features a dainty eyelet pattern for the prettiest look. Style with espadrille wedges.

    Fit & Features

    • Sweetheart neckline, shirring at the bust
    • Short puff sleeves, cinched hems, tie accents
    • High waist seam
    • Short skater skirt, ruffled hem
    • Fit and flare silhouette
    • Eyelet knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4915

    Category Name: Casual Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • La Fleur Floral Mesh Midi Dress

    It's love at first sight in this floral midi dress perfect for day dates! It features a sleeveless square neck, spaghetti straps that lead to the lace-up, a bodycon silhouette, and an asymmetrical side slit cutout. The dress is composed of a floral print mesh fabric with a stretch knit lining. Complete the look in lace-up heels.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps, lace-up back
    • Bodycon silhouette
    • Asymmetrical side slit cutout
    • Midi-length hem
    • Floral print mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4913

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Timeless Love Rib Knit Maxi Dress

    You'll adore this rib knit maxi dress time and time again! Create your capsule wardrobe with this perfect dress featuring a sleeveless square neck, spaghetti straps, a curve-hugging silhouette, and a sultry side slit. Complete the look in a statement crop jacket, hoop earrings, and your go-to sneakers!

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Curve-hugging silhouette
    • Side slit
    • Maxi-length hem
    • Stretchy rib-knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4916

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casually Cute Floral Off-The-Shoulder Dress

    Step out looking casually cute in this floral mesh mini dress for lunch with the girls or a bridal shower! It features an off-the-shoulder neckline, sheer short-sleeve cuffs, a ruched bust, and side, and back ruched seams that accentuate your curves along the bodycon silhouette. Complete the look with a dainty ring set and heels.

    Fit & Features

    • Off-the-shoulder neckline
    • Sheer short-sleeve cuffs
    • Back zipper and hook-eye closure
    • Ruched bust, side and back seams
    • Bodycon silhouette, mini-length hem
    • Ditsy floral print, mesh fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4914

    Category Name: Casual Dresses

    Price: $5.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet And Spicy Scoop Neck Mini Dress

    Sweet and spicy, this mini dress is exactly what your next club night needs! It features a sleeveless scoop neckline, dual spaghetti straps, a strappy back design, and side ruched seams to accentuate your curves along the short bodycon silhouette. Complete the look in eye-catching stiletto heels.

    Fit & Features

    • Sleeveless scoop neckline
    • Dual spaghetti straps
    • Strappy back design
    • Side ruched seams, bodycon silhouette
    • Mini-length hem
    • Slinky knit fabric, bust lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-4804

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Factor Eyelet Lace Skater Dress

    Bring the cute factor by wearing this eyelet lace skater dress for picnics, brunch, or casual family parties! Featuring adorable puff short sleeves, a square neck with a ruched bust, a flirty tie-back closure, and a fit-and-flare silhouette and short hem. Complete the look with cute flower earrings.

    Fit & Features

    • Puff short sleeves
    • Square neck, ruched bust
    • Tie-back closure
    • Skater, fit and flare silhouette
    • Short-length hem
    • Eyelet lace fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4910

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet And Cute Floral Ruffle Short Dress

    Embrace your cuteness looking so sweet in this floral short dress - a perfect pick for family gatherings or parties! It features a sleeveless scoop neck, adjustable spaghetti straps, a trendy tie-back, a ruched bust, and a ruffle-layered short-length hem. Complete the look in bow heels.

    Fit & Features

    • Sleeveless scoop neck, adjustable spaghetti straps
    • Tie-back design
    • Ruched bust
    • Ruffle layered short-length hem
    • Ditsy floral print
    • Airy woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4911

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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

    Create an oh-so-sweet look in this darling puff sleeve mini dress! It features a square neckline, short puff sleeves, an open-back design with bar straps, a mini-length hem, and a form-hugging fit for a figure-flattering silhouette. The crepe fabric offers a moderate stretch. Style with clear heels for a dinner date.

    Fit & Features

    • Square neckline
    • Short puff sleeves, elastic cinched hems
    • Open-back design, dual elasticized bar straps
    • Mini-length hem
    • Form-hugging fit
    • Crepe fabric, knit lining at the bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2098

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Cute Eyelet Lace Mini Dress

    Achieve an effortless pretty and cute style in this eyelet lace mini dress for your casual dates or strolling downtown with the girls! The dress features adorable puff short sleeves, a ruffle trim sweetheart neckline with a front bust tie, a bodycon fit, and side ruching with an adjustable tie. Complete the look in trendy flat sandals.

    Fit & Features

    • Puff short sleeves
    • Ruffle trim sweetheart neckline
    • Front bust tie
    • Bodycon silhouette
    • Side ruching with adjustable tie
    • Mini-length hem
    • Eyelet lace fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4912

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Spring Vibes Floral Skater Dress

    This adorable floral skater dress will bring those sweet spring vibes to your look! It features a sweetheart neckline, short puff sleeves, a high waist, a short skater skirt with a ruffled hem, and a fit and flare silhouette. The lightweight chiffon fabric features a dainty floral print pattern. Style with strappy sandals.

    Fit & Features

    • Sweetheart neckline, short puff sleeves, elastic cinched hems
    • High waist seam, smocked back design
    • Short skater skirt, ruffled hem
    • Fit and flare silhouette
    • Small floral print
    • Chiffon fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2080

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Cool Girl High Slit Ribbed Knit Maxi Dress

    Showcase a casual cool girl style in this curve-hugging maxi dress. Designed with a stretchy ribbed knit fabric, it features a sleeveless crew neckline, tank shoulder straps, a trendy side cutout at the waist to showcase some skin, and an alluring thigh-high side slit on the maxi-length hem. Complete your look with clear mules.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Crew neckline
    • Tank shoulder straps
    • Side cutout at the waist
    • High side slit
    • Runs true to size

    Style Number/Barcode: 05102-4906

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Strolls Floral Tie-Back Skater Dress

    Your stroll through the garden party will be so sweet in this floral chiffon dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty tie-back design, and a fit-and-flare skater silhouette with a short hem. Complete the look in cute sandals.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Tie-back design
    • Fit and flare, skater silhouette
    • Short-length hem
    • Watercolor floral print
    • Airy chiffon, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4903

    Category Name: Casual Dresses

    Price: $9.97 $41.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In For Romance Short Skater Dress

    You'll be in for the romantic vibes of this short skater dress perfect for bridal showers or day dates! It features three-quarter-length puff sleeves, a sweetheart neck, a tie-front, and a fit and flare silhouette. The dress is composed of a swiss dot pattern cotton fabric with a smooth woven lining. Complete the look in simple block heels.

    Fit & Features

    • Three-quarter-length puff sleeves
    • Square neck, tie-front
    • Skater silhouette
    • Short-length hem
    • Swiss dot pattern, smooth woven lining
    • No stretch
    • Runs true to size

    Style Number/Barcode: 05102-4902

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cherish Me Eyelet Lace Skater Dress

    All eyes on you in this lovely eyelet lace skater dress as the bride-to-be or graduate! The dress features a sleeveless sweetheart neck with flirty ruffle trim, adjustable spaghetti straps, a front bust tie and button accents, and a tiered fit and flare silhouette with a ruffled short hem. Complete the look in platform sandals.

    Fit & Features

    • Sleeveless sweetheart neck with ruffle trim
    • Adjustable spaghetti straps
    • Front bust tie, button accents
    • Tiered, skater silhouette
    • Ruffled short-length hem
    • Eyelet lace cotton fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4907

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Daze Eyelet Tie Mini Dress

    If you've got sunshine on your mind, this eyelet mini dress is the one you want for those warmer days ahead. Featuring an off-the-shoulder ruffle neckline, short sleeve cuffs and spaghetti straps, a bust tie front design, and a bodycon silhouette. Complete the look in cute sandals for a family picnic!

    Fit & Features

    • Off-the-shoulder ruffle neckline
    • Short sleeve cuffs, spaghetti straps
    • Bust tie front design
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4908

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On The Verge Chiffon A-Line Midi Dress

    You'll be on the verge of a stylish breakthrough with the addition of this chiffon midi dress to your fashion closet! Effortless and breezy, this dress features a sleeveless v-neckline, halter spaghetti straps, a lace-up open back that lets you customize the fit, and an asymmetrical hem with a flirty slit. Complete the look with stiletto heels and a bracelet! 

    Fit & Features

    • Sleeveless v-neckline
    • Halter spaghetti straps
    • Lace-up open back
    • A-line silhouette
    • Asymmetrical midi-length hem, slit accent
    • Chiffon fabric, stretchy knit lining
    • Fits true to size

    Style Number/Barcode: 05102-4905

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Garden Of Roses Chiffon Midi Dress

    Frolic through the garden or your next soiree in this rose print chiffon midi dress! It features a sleeveless sweetheart neck, spaghetti straps, a ruched bust with a tie, and a slim A-line silhouette with a flirty front slit. Complete the look in strappy block heels.

    Fit & Features

    • Sleeveless sweetheart neck, spaghetti straps
    • Ruched bust with tie
    • Back zipper and hook-eye closure
    • Slim A-line silhouette
    • Front slit, midi-length hem
    • Rose print, airy chiffon fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2081

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale