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.

  • Get Cutesy V-Neck Gingham Skater Dress

    Get cutesy in this gingham skater dress for a dreamy look this spring to summer! With a lace trim neckline and flattering drop waist seam that accentuates your figure, this short dress looks like a dream.

    Fit & Features

    • Gingham print, poplin woven fabric, lined
    • Laced trim V-neckline
    • Spaghetti straps
    • Button front details
    • Drop waist seam
    • Skater silhouette, short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5990

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sunshine Dream Open Tie Back Floral Maxi Dress

    A floral print adds to the dreamy charm of this flowy maxi dress boasting an open tie back design and ruffled silhouette perfect for beachside strolls or day parties.

    Fit & Features

    • Floral print, woven fabric, short woven lining
    • Sweetheart neckline with bust tie
    •  Spaghetti straps
    • Open tie back design
    • Ruffled flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3912

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

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  • Pretty Blooms Floral Mesh Halter Maxi Dress

    Showcase your beauty in this lined mesh maxi dress accented with a large floral print for a pretty vibe. It features a sleeveless cowl neckline, halter tie-back spaghetti straps with beaded detailing, an open back with lower tie-back straps, and a maxi-length hem with a form-hugging fit to highlight your curves.

    Fit & Features

    • Sheer mesh fabric with knit lining
    • Large floral print pattern
    • Cowl neckline
    • Halter tie-back spaghetti straps, beaded details
    • Open back, lower tie-back spaghetti straps, beaded details
    • Maxi-length hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5988

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

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  • Plaid Mood Sleeveless A-Line Mini Dress

    The plaid mesh mini dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, and an A-line silhouette. Complete the look with loafers for a preppy vibe.

    Fit & Features

    • Sheer mesh fabric with knit lining, plenty of stretch
    • Plaid print
    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Mini-length hem
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5987

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

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  • Unforgettably Sweet Floral Bodycon Ruffle Mini Dress

    Create an alluring look in this floral mini dress in a bodycon fit with a flirty ruffled hem. Perfect for shower celebrations and graduations!

    Fit & Features

    • Floral print, lace-lined fabric
    • Strapless neckline
    • Bodycon silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5985

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

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  • Many Admirers Open Back Bodycon Midi Dress

    Crafted in a smooth knit fabric that hugs every curve, this cap sleeve midi dress will leave your admirers speechless! The dress boasts a showstopping open back while the bodycon silhouette flaunts your figure along the slit midi-length hem. Pair with stiletto heels.

    Fit & Features

    • Smooth knit stretchy fabric
    • Cap sleeves
    • Scoop neckline
    • Open back
    • Bodycon silhouette
    • Midi-length hem, side slit
    • Runs true to size

    Style Number/Barcode: 05102-5984

    Category Name: Casual Dresses

    Price: $14.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

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  • Twist Of Chic High-Slit Knit Midi Dress

    Bring a twist of chic to the every day with a midi dress that features an asymmetrical one-shoulder neckline with a trendy twist shoulder accent and a daringly high side slit. Complete look with slingback shoes to take you from the office to happy hour! 

    Fit & Features

    • Stretchy knit fabrication
    • Asymmetrical one-shoulder neckline
    • Twist shoulder strap accent
    • High side slit
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5983

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Chic Showstopper Abstract Print Mesh Maxi Dress

    Serve chic vibes in this airy-lined mesh maxi dress designed with a multi-colored abstract print for a bold allure. It features a strapless straight-across neckline, a high-cut side slit, and a long bodycon silhouette to showcase your stunning curves.

    Fit & Features

    • Abstract printed sheer mesh fabric with knit lining, plenty of stretch
    • Strapless straight neckline
    • High side slit
    • Maxi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5982

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Classic And Sleek Knit Off-Shoulder Long Sleeve Midi Dress

    Classic and sleek, this stretchy knit midi dress features an asymmetric off-shoulder neckline with long fitted sleeves, ruching at the waist to accentuate your curves, and a bodycon silhouette. Style with stiletto heels for a chic outing!

    Fit & Features

    • Jersey knit fabric with plenty of stretch
    • Asymmetric off-shoulder neckline
    • Long fitted sleeves
    • Ruched waist
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5977

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Stylish Twist Ribbed Knit Mini Dress

    Add a stylish twist to your look with a mini dress that features a plunging sweetheart neckline with a twisted accent at the center and fitted long sleeves. Complete look with knee-high boots. 

    Fit & Features

    • Ribbed knit fabrication
    • Sweetheart neckline
    • Twist accent at the center of a bust
    • Fitted long sleeves
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 06005-2182

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cute In Plaid Strapless Plaid A-Line Mini Dress

    Look and feel cute in this plaid strapless dress with a flattering A-line silhouette and a mini-length hem. Complete the look with a choker necklace.

    Fit & Features

    • Plaid print, woven fabric, woven lining
    • Strapless neckline
    • Back zipper closure
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5980

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Modern Babe Sleeveless Belted Mini Dress

    Take the city streets by storm in this sleeveless mini dress with a chic belted waist that cinches your look together from office hours to cocktail hour!

    Fit & Features

    • Woven fabric with stretch
    • Crew neckline
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Dual faux leather belted waist
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5979

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off To A Chic Start One-Shoulder Mini Dress

    Your night will be looking oh-so-chic in this one-shoulder mini dress featured in a flattering bodycon fit that accentuates your curves! 

    Fit & Features

    • Smooth knit-lined fabric, moderate stretch
    • One-shoulder neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5976

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Serving Sleek Square Neck Bodycon Midi Dress

    Serve a gorgeous sleek silhouette in this brushed knit midi dress featuring a sleeveless square neckline, thin tank straps, and a midi-length bodycon fit to hug your curves. Style with hoop earrings and stiletto heels.

    Fit & Features

    • Brushed knit fabric with knit lining, plenty of stretch
    • Square neckline
    • Thin tank shoulder straps
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5975

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet As Honey Strapless Floral Skater Dress

    Look and feel oh-so-sweet in this strapless floral skater dress with a flirty ruffled hem perfect for day dates or parties!

    Fit & Features

    • Floral print, woven fabric, stretchy knit lining
    • Strapless neckline
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3881

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Trendy Era Drop Waist A-Line Mini Dress

    Enter your trendy era with this woven mini dress featuring a sleeveless square neckline and a halter strap accented with a buckle trim detail. The drop waist design leads to a short pleated A-line silhouette.

    Fit & Features

    • Woven fabric
    • Square neckline
    • Halter strap with buckle trim detail
    • Partially open back, zipper closure
    • Drop waist design
    • Mini-length pleated A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5974

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Muse Square Neck Bodycon Mini Dress

    Show off your sleek chic style in this bodycon mini dress featuring a sleeveless square neckline, tank-like shoulder straps, and a short form-hugging silhouette. Style with stiletto heels for a rooftop bar!

    Fit & Features

    • Lined rayon knit fabric, plenty of stretch
    • Square neckline
    • Tank-like shoulder straps
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5970

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Polished Demure Belted Pleated Skater Dress

    A pretty and polished sleeveless skater dress designed with a tiered pleated mini skirt and a sleek faux leather belt that cinches the look together. 

    Fit & Features

    • Woven fabric
    • Sleeveless crew neckline
    • Back zipper and hook-eye closure
    • Faux leather belt
    • Skater silhouette
    • Tiered pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5971

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cozy Prep Collared Long Sleeve Knit Skater Dress

    This preppy skater dress is designed with ribbed sweater knit fabric for all the cozy vibes. It features a henley collared V-neckline with button detailing, long fitted sleeves, and a short pleated skater silhouette for that cute flair.

    Fit & Features

    • Ribbed sweater knit fabric
    • Henley collared V-neckline, button detailing 
    • Long fitted sleeves
    • Mini-length pleated skater silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2173

    Category Name: Casual Dresses

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love's A Picnic Strapless Gingham A-Line Midi Dress

    Be loved and admired by everyone who sees you in this gingham midi dress showcasing a flattering A-line silhouette with convenient side pockets to keep your hands warm!

    Fit & Features

    • Gingham print, woven fabric, tulle and woven linings
    • Strapless neckline
    • Back zipper closure, stretch smocked panel
    • Side pockets
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3870

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sassy Sweet Floral Chiffon Ruffled Skater Dress

    Sassy and sweet, this floral chiffon skater dress will be your new brunch go-to! The strapless smocked bodice and ruffled skater silhouette are feminine details you'll adore.

    Fit & Features

    • Chiffon fabric, stretchy knit lining
    • Small floral print
    • Strapless straight neckline
    • Smocked bodice
    • High waist seam
    • Tiered ruffled design, short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5967

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Compelling Romantic Off-The-Shoulder Pleated Maxi Dress

    Make a toast to looking lovely in this off-the-shoulder pleated maxi dress as the bride-to-be or party guest! With a flowy silhouette and flattering drop waist seam, you'll look and feel so dreamy.

    Fit & Features

    • Smooth knit stretch fabric
    • Folded off-the-shoulder neckline
    • Drop waist seam
    • Pleated flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3867

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Keeping Knit Cute One-Shoulder Long Sleeve Mini Dress

    Keep it cute for any plans in this bodycon mini dress featuring a sassy one-shoulder neckline, long fitted sleeves for comfort, and crafted on soft hacci brushed knit fabric. Complete the look with sleek heels.

    Fit & Features

    • Soft hacci knit fabric, high stretch
    • One-shoulder neckline
    • Long fitted sleeves
    • Ruched side seams
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5965

    Category Name: Casual Dresses

    Price: $18.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute As A Button Mock Neck Knit Midi Dress

    A cute midi dress that elevates your everyday style! The rib knit dress is designed with a chic mock neck and fitted long sleeves adorned with front button accents and a flattering bodycon silhouette. Pair with a handbag and heels.

    Fit & Features

    • Rib knit fabric, moderate stretch
    • Mock neck
    • Fitted long sleeves
    • Front button accents
    • Center back slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2172

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free