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.

  • Keeping Knit Chic Long Sleeve Midi Dress

    Keep it chic in this knit midi dress boasting an off-the-shoulder neckline and trendy button accents that lead to a flirty slit. Pair with boots.

    Fit & Features

    • Ribbed knit fabrication
    • Off-the-shoulder neckline, foldover accent
    • Long sleeves
    • Snap button accents at the hem
    • High side slit
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 06005-2137

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Forever Sweet Long Sleeve Drop Waist Skater Dress

    Stay forever sweet in this skater dress featuring a sleek square neckline and ruching that flatters your figure. Pair with heels.

    Fit & Features

    • Stretchy smooth knit fabric
    • Square neckline
    • Long fitted sleeves
    • Ruching
    • Drop waist
    • Mini-length tiered skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3745

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Silhouette Ribbed Knit Off-The-Shoulder Midi Dress

    Showcase a sleek silhouette in this ribbed knit midi dress featuring an off-the-shoulder neckline with a fold-over design and a mermaid silhouette to highlight your curves. Style with knee-high boots for a chic look.

    Fit & Features

    • Ribbed knit fabric, plenty of stretch
    • Off-the-shoulder neckline
    • Fold-over design, short sleeves
    • Midi-length mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5896

    Category Name: Casual Dresses

    Price: $14.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Casual Chic Icon Long Sleeve Knit Midi Dress

    Become an instant chic icon in this bodycon midi dress adorned with flare cuff long sleeves with flirty tie accents and a V-neckline. Pair with mules.

    Fit & Features

    • Lined brushed knit fabric, plenty of stretch
    • V-neckline
    • Long fitted sleeves with ruched slit flare accents, adjustable drawstrings
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5895

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

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  • Perfect Curves Ribbed Knit Off-The-Shoulder Midi Dress

    Showcase your perfect curves in this midi dress designed with soft ribbed knit fabric. It features an off-the-shoulder neckline with a chic fold-over design, long fitted sleeves, and a midi-length bodycon silhouette.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch
    • Off-the-shoulder neckline, fold-over design
    • Long fitted sleeves
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5894

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

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  • Cozy Knit Off-The-Shoulder A-Line Mini Dress

    Channel that cute and cozy vibe in this adorable soft ribbed knit mini dress featuring an off-the-shoulder straight neckline with a fold-over design, long fitted sleeves, and a short A-line silhouette. Style with knee-high boots for a fall date!

    Fit & Features

    • Soft ribbed knit fabric
    • Off-the-shoulder straight neckline, fold-over design
    • Long fitted sleeves
    • Mini-length A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5892

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

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  • Major Sweetheart Smocked Gingham Cotton Skater Dress

    This short skater dress features an adorable gingham print on lightweight lined cotton fabric. The smocked waist offers added stretch, while the fit-and-flare silhouette gives that flirty touch, perfect for a day date.

    Fit & Features

    • Gingham printed cotton fabric with woven lining, no stretch
    • Scoop neckline with keyhole cutout and tie-front
    • Adjustable spaghetti straps
    • Stretchy smocked waist
    • Short tiered skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5891

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Perfection Long Sleeve Knit Mini Dress

    This ribbed knit mini dress will create perfect casual 'fits! It features a square neckline, long fitted bell sleeves with cute flared-out hems, and a mini-length, form-hugging silhouette. The lined knit fabric offers plenty of stretch for comfortable wear. Style with knee-high boots.

    Fit & Features

    • Ribbed knit fabric, knit lining, plenty of stretch
    • Square neckline
    • Long fitted bell sleeves, flared hems
    • Form-hugging fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5889

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stripes In Style Off The Shoulder Mini Dress

    Stay stylish in this trendy off-the-shoulder mini dress showcasing a classic striped pattern and a form-hugging fit. Pair with knee-high boots.

    Fit & Features

    • Ribbed knit fabrication
    • Off-the-shoulder neckline
    • Long dolman sleeves
    • Stripes
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05102-5885

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Effortless Halter Bodycon Mini Dress

    From brunch to dinner date plans, this halter bodycon mini dress will always collect compliments! 

    Fit & Features

    • Mesh fabric, stretchy knit lining
    • Halter sweetheart neckline, tie closure, padded bra cups
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000189

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • Find Me In Plaid A-Line Mini Dress

    Tried and trendy, this plaid mini dress boasts a strapless folded neckline and a flattering A-line silhouette. Pair with boots.

    Fit & Features

    • Plaid pattern, soft knit fabric
    • Strapless folded neckline
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5884

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Stroll The Gardens Floral Corset Lace Skater Dress

    Stroll the gardens looking so pretty in this floral corset skater dress featuring delicate lace trim and a flattering flowy short-length hem that'll give you a dreamy feel. Pair with earrings and heels.

    Fit & Features

    • Floral pattern, woven fabric, woven lining with lace trim
    • Adjustable shoulder straps, sweetheart neckline
    • Corset bodice, underwire bust, flexible boning, lace trim
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Flowy short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3719

    Category Name: Casual Dresses

    Price: $9.97 $62.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Casual Affair Long Sleeve Ruched Midi Dress

    Make a casual-chic impression in this long sleeve ruched midi dress showcasing a folded off-the-shoulder neckline and a bodycon silhouette. Pair with heels.

    Fit & Features

    • Smooth knit-lined fabrication, moderate stretch 
    • Off-the-shoulder neckline, foldover accent
    • Fitted long sleeves
    • Ruching
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3723

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Flair Striped Knit Off-The-Shoulder Mini Dress

    Showcase a cozy flair in this mini dress made with striped ribbed knit fabric offering plenty of stretch for comfortable wear. It features an off-the-shoulder neckline with a fold-over design, long fitted sleeves, and a short A-line silhouette for an adorable vibe.

    Fit & Features

    • Striped ribbed knit fabric with plenty of stretch
    • Off-the-shoulder neckline, fold-over design
    • Long fitted sleeves
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5883

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Style Vibe Striped Knit Long Sleeve Mini Dress

    Lean into the cozy style vibes with this trendy striped ribbed knit mini dress featuring a mock neckline, long fitted sleeves, and a short bodycon silhouette to hug your curves. Pair with knee-high boots!

    Fit & Features

    • Striped ribbed knit fabric, plenty of stretch
    • Mock neckline, lettuce-edge trim
    • Long fitted sleeves, lettuce-edge trims
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5882

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Moment Off-The-Shoulder Bell Sleeve Mini Dress

    An off-the-shoulder mini dress that'll give you many chic moments! The crepe dress is designed with long fitted bell sleeves with flirty tie accents and a front slit for movement. Complete the look with a necklace.

    Fit & Features

    • Viscose crepe knit fabric with knit lining, moderate stretch
    • Off-the-shoulder sweetheart neckline, can be worn on the shoulder
    • Long fitted bell sleeves, tie accents
    • Front slit
    • Mini-length hem
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5881

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bohemian Chic Lace Off-The-Shoulder Skater Dress

    Channel that bohemian chic aesthetic in this airy sheer lace skater dress featuring an off-the-shoulder straight neckline with a fold-over design and sheer long fitted sleeves. The trendy V-shaped drop waist seam leads to a short uneven hem with a flowy skater silhouette.

    Fit & Features

    • Sheer lace fabric with partial knit lining, plenty of stretch
    • Off-the-shoulder straight neckline with fold-over design
    • Sheer long fitted sleeves
    • V-shaped drop waist seam
    • Short uneven hem
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3714

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Chic Choice Knit Off-The-Shoulder Maxi Dress

    This trendy ribbed knit maxi dress is a chic choice for the season offering plenty of stretch for comfortable wear. It features an off-the-shoulder fold-over neckline, long fitted sleeves, and a maxi-length bodycon silhouette accented with a back slit.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch
    • Off-the-shoulder neckline, fold-over design
    • Long fitted sleeves
    • Back slit
    • Maxi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2104

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Lace Off-The-Shoulder Drop Waist Romper

    Look like a daydream in this boho lace romper designed with a ruffled off-the-shoulder neckline and a flattering skater silhouette.

    Fit & Features

    • Sheer lace fabric with knit lining, moderate stretch
    • Off-the-shoulder straight neckline, ruffled overlay
    • V-shaped drop waist
    • Flowy shorts, skater silhouette
    • Romper in size small is 25" shoulder to hem with an 8.5" front rise and a 3" inseam
    • Runs true to size

    Style Number/Barcode: 06503-1228

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Chic Fall Vibe Ditsy Floral Corset Midi Dress

    Channel the chic fall vibe in this ditsy floral woven midi dress featuring a sleeveless sweetheart neckline with a ruched bust and tie-front detail, thin tank shoulder straps, and a corset-style bodice. The high waist leads to a flowy A-line silhouette accented with a high-cut front slit.

    Fit & Features

    • Ditsy floral-printed woven fabric
    • Sweetheart neckline, ruched bust, tie-front detail, underwire bust
    • Thin tank shoulder straps
    • Corset-style bodice with piping, high waist seam
    • Hidden side zipper and hook-eye closure
    • High front slit
    • Midi-length A-line fit
    • Runs true to size

    Style Number/Barcode: 05101-3706

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Silhouette Abstract Print Mesh Midi Dress

    Showcase a sultry silhouette in this sheer mesh midi dress designed with a multi-colored abstract print for a bold vibe. It features a mock neckline with long fitted sleeves, a bodycon silhouette to hug your curves, and a full-length knit lining with a scoop neckline and spaghetti straps.

    Fit & Features

    • Abstract printed sheer mesh fabric, plenty of stretch
    • Mock neckline
    • Long fitted sleeves
    • Midi-length bodycon fit
    • Full-length knit lining, scoop neckline, adjustable spaghetti straps
    • Runs true to size

    Style Number/Barcode: 05102-5879

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy Look Abstract Print Mesh Midi Dress

    Create a dreamy look to catch all the stares in this abstract print mesh midi dress designed with a high front slit on a curve-hugging bodycon silhouette.

    Fit & Features

    • Sheer mesh fabric with full-length brushed knit lining, high stretch
    • Abstract print
    • Sleeveless square neck and back
    • Spaghetti straps
    • Midi-length hem, high front slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5876

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Always Yours Strapless Bubble Hem Mini Dress

    A strapless mini dress boasts a flattering smocked bodice that hugs your curves and an adorable woven bubble hem skirt. Perfect for styling with heels for a party.

    Fit & Features

    • Strapless neckline
    • Stretchy knit smocked bodice
    • Woven bubble mini-length hem, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5877

    Category Name: Casual Dresses

    Price: $14.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sunny Days Floral Halter Skater Dress

    Sunny days call for this cute floral skater dress featuring tie-back straps and a breezy fit-and-flare silhouette!

    Fit & Features

    • Rayon woven fabric
    • Floral print
    • Sleeveless V-neckline
    • Tie-back halter straps
    • Open back, lower tie-back design
    • Short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5874

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free