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.

  • 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
  • Alluring Trendsetter Halter Midi Dress

    Show off your alluring trendy style in this sleek curve-hugging midi dress! It features a cross-front halter neckline with tie-back straps, a cold-shoulder design with long fitted sleeves, and a midi-length asymmetric hem creating a chic high side slit. The smooth knit fabric includes a full lining. Complete the look with your fave mules.

    Fit & Features

    • Cross-front halter neckline, tie-back straps
    • Cold-shoulder design
    • Long fitted sleeves
    • Midi-length asymmetric hem, high side slit
    • Form-hugging silhouette
    • Knit fabric, full lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4904

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Fresh Ditsy Floral Mini Dress

    Feel fresh and flirty in this floral mini-dress for your next daytime outing! It features puff short sleeves, a square neck with a bust tie, a bodycon silhouette, and a ditsy floral print on stretchy knit fabric. Style with block heels to complete the look!

    Fit & Features

    • Puff short sleeves
    • Square neck, bust tie
    • Bodycon silhouette
    • Mini-length hem
    • Ditsy floral print
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4900

    Category Name: Casual Dresses

    Price: $36.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Timeless Trend Collared Mini Dress

    Totally timeless and trending, this collared mini dress will be such a staple in your year-round closet! It features long fitted bell sleeves with split cuffs, a V-neckline, a bodycon silhouette, and side and center front ruching that puts your curves on display! Complete the look in chic booties.

    Fit & Features

    • Long fitted bell sleeves with split cuffs
    • Collared V-neckline
    • Bodycon silhouette
    • Center and side ruching
    • Mini-length hem
    • Stretchy smooth knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4899

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfectly Stylish Sleeveless Ribbed Knit Midi Dress

    Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules.

    Fit & Features

    • Stretchy ribbed knit fabric
    • V-neckline
    • Spaghetti straps
    • High front slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-1645

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In Plain Sight Smooth Knit Maxi Dress

    This casual maxi dress will have you looking sultry on your off-duty days! This maxi dress is perfect for layering under your favorite sweaters or jackets for coffee runs and hangouts. It features a sleeveless square neckline, spaghetti straps, and a bodycon silhouette on stretchy, soft, and smooth modal knit fabric with a partial mesh lining. Complete the look in this long dress with an oversized jacket and sneakers.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Maxi-length hem
    • Smooth knit modal fabric, partial mesh lining
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4897

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cargo Without Plaid Short Dress

    You can't go without this plaid short dress perfect for autumn days and layering for winter nights! The dress features a sleeveless square neck, spaghetti straps, side flap pockets, and a bodycon silhouette. Complete the look in a basic long sleeve top and lug booties.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Side flap pockets
    • Bodycon silhouette
    • Short-length hem
    • Plaid pattern, knit fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05102-4898

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hit The Tropics V-Neck Midi Dress

    Ready for vacay babe? Hit the tropics in this perfect midi dress featuring a sleeveless V-neck, adjustable spaghetti straps, a side ruched seam, bodycon fit, and an asymmetrical side slit cutout. Complete the look in cute platform wedges.

    Fit & Features

    • Sleeveless V-neck
    • Adjustable spaghetti straps
    • Side ruched seam, bodycon fit
    • Asymmetrical midi hem, side slit cutout
    • Tropical print
    • Smooth knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4896

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Getaway Midi Sweater Dress

    This adorable retro print sweater dress is giving major weekend getaway vibes! It features a sleeveless scoop neckline, a front O-ring accent with a small keyhole cutout, tank shoulder straps, a scoop-back design, a midi-length hem, and a form-hugging silhouette. The sweater knit fabric features a trendy retro-inspired multi-print pattern. Style with espadrille sandals.

    Fit & Features

    • Sleeveless scoop neckline
    • Front O-ring accent, small keyhole cutout
    • Tank shoulder straps, scoop-back design
    • Midi-length hem, form-hugging fit
    • Retro-inspired multi-print pattern
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1642

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Can't Resist Chiffon Floral Skater Dress

    No one can resist you in this chiffon floral dress - a staple for all of the upcoming soirees! It features a sleeveless V-neckline, adjustable spaghetti straps, a tie-back closure, and a flattering skater short silhouette. Complete the look in faux leather mules.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Tie-back closure
    • Skater silhouette
    • Short-length hem
    • Floral print, chiffon fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2057

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Oasis Tropical Cutout Skater Dress

    Enter a sweet oasis looking cute in this tropical woven skater dress ready for some serious island time! Featuring adorable puff short sleeves, a V-neckline, a back cutout with trim detail, a stretchy smocked back, and a tiered fit-and-flare short-length silhouette. The airy sheer woven fabric features a tropical floral print pattern and includes a knit lining. Complete the look in strappy wedges.

    Fit & Features

    • Tropical floral print
    • Sheer woven fabric, knit lining, minimal stretch
    • Puff short sleeves, elastic cinched hems, tie-back straps
    • V-neckline, cutout back with trim detail
    • Stretchy smocked back
    • Tiered fit-and-flare skater silhouette, short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-4890

    Category Name: Casual Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dream Look Floral Ruched Mini Dress

    Create your dream look for a spring date in this adorable floral mini dress! It features a sleeveless sweetheart neckline with ruching at the bust, spaghetti straps, an open back with a lace-up strappy design, ruching down the side seams, a mini-length hem, and a curve-hugging silhouette. The lined mesh fabric features a dainty rose print pattern for the prettiest look. Style with clear heels.

    Fit & Features

    • Sleeveless sweetheart neckline, ruching at the bust, spaghetti straps
    • Open back, lace-up strappy design, tie closure
    • Ruching down the side seams
    • Mini-length hem, form-hugging fit
    • Dainty rose print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4888

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Into Action Floral Skater Dress

    Spring into your seasonal closet by adding this floral skater dress! It features a sleeveless V-neck, adjustable spaghetti straps, a ruched bust with tie-front detail, and a fit-and-flare silhouette with a short ruffled hem. The dress is composed of chiffon fabric with a stretchy knit lining. Complete the look in trendy wedge sandals and a bracelet.

    Fit & Features

    • Sleeveless V-neck, adjustable spaghetti straps
    • Ruched bust, tie-front detail
    • Back zipper and hook-eye closure
    • Fit and flare skater silhouette
    • Short ruffled hem
    • Floral print, chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4889

    Category Name: Casual Dresses

    Price: $5.97 $43.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Oh My Darling Floral Halter Mini Dress

    Let your crush know you've entered the room in this retro-cute mini dress perfect for getting their attention at parties! It features a sleeveless sweetheart neckline with a flirty ruffle trim, halter straps with tie-back closure, an underwire bust, a bodycon silhouette, and a curved ruffle trim hem. The dress is designed with an adorable ditsy floral print on mesh-lined fabric. Complete the look in strappy mules.

    Fit & Features

    • Sleeveless sweetheart neckline, ruffle trim
    • Halter straps, tie-back closure
    • Underwire bust
    • Bodycon silhouette
    • Ruffle trim, curved mini-length hem
    • Ditsy floral print, mesh-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4892

    Category Name: Casual Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Deets Crepe Lace-Up Midi Dress

    This crepe midi dress has the pretty deets you're looking for! The dress features a sleeveless square neck, spaghetti straps, an open lace-up back with tie closure, a ruched bust, and a bodycon silhouette. Complete the look in chic flat sandals.

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Open lace-up back, tie closure
    • Ruched bust
    • Bodycon silhouette
    • Midi-length hem
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4891

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Easy Breezy In Floral Chiffon Dress

    Easy, breezy, and beautiful! You'll adore this floral chiffon dress perfect for bridal showers or dressy spring parties. It features an off-the-shoulder, sweetheart neck, ruffled short-sleeve cuffs, a padded bust, a smocked back, and a flowy skater silhouette with a ruffled short hem. The dress is composed of an airy chiffon with a rose floral bouquet print and a stretchy knit lining. Complete the look in strappy sandals.

    Fit & Features

    • Off-the-shoulder, sweetheart neck, padded bust
    • Ruffled short sleeve cuffs
    • Smocked back, zipper nad hook-eye closure
    • Flowy skater silhouette, ruffled short hem
    • Rose floral bouquet print
    • Airy chiffon, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2052

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale