Casual Dresses

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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.

  • Weekend Vibes High Slit Striped Knit Maxi Dress

    This casual-chic striped knit maxi dress is perfect for your laid-back weekend vibes! Designed with stretchy ribbed knit with a thin striped pattern, it features a sleeveless scoop neckline with spaghetti straps, high-cut side slits on each side for added movement, and a form-hugging slim fit on the maxi-length silhouette. Style this long dress with strappy sandals.

    Fit & Features

    • Striped ribbed knit fabric, short knit lining, moderate stretch
    • Scoop neckline
    • Spaghetti straps
    • High side slits
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5778

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

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  • Lovely In Lace Ruffled Puff Sleeve Mini Dress

    You'll be looking oh-so-lovely in this adorable ruffled puff sleeve mini dress! The sheer floral lace fabric gives that dainty-chic vibe, while the partial knit lining provides coverage. The mini-length dress features a square neckline and sheer short puff sleeves with the cutest ruffle trim, a small bust cutout with a sleek ribbon tie-front design, and a flattering empire waist seam. The flowy A-line silhouette adds that effortless flair. Style this short dress with heeled mules for date night.

    Fit & Features

    • Sheer floral lace fabric with knit lining, minimal stretch
    • Square neckline, ruffle trim
    • Sheer short puff sleeves, ruffle trim
    • Bust cutout, tie-front design
    • Empire waist seam, hidden side zipper closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3338

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • City Of Love V-Neck Ruffle Babydoll Dress

    Grab your baguette, passport, and this babydoll dress cause the city of love is calling your name! The playful ruffled shoulder straps and convenient side pockets add a touch of whimsy to this flirty dress. The babydoll silhouette and ruffled tiered hem make it perfect to sweep through Paris looking adorable! Complete the look in strappy sandals and a purse.

    Fit & Features

    • Woven fabric
    • Ruffled shoulder straps
    • Side pockets
    • Babydoll silhouette
    • Ruffled tiered short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5423

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Coastal Dream Lace-Up Ruffled Maxi Dress

    A dreamy sleeveless maxi dress perfect for styling for beach city days or coastal vacations! The scoop neckline and bust tie accentuate your figure, while adjustable spaghetti straps provide the perfect fit. The lace-up back adds a touch of charm, while the flowy ruffled silhouette and maxi-length hem exude effortless chicness! Complete the look with strappy sandals and sunglasses.

    Fit & Features

    • Woven fabric, short knit stretchy lining
    • Scoop neckline with bust tie
    • Adjustable spaghetti straps
    • Lace-up back
    • Flowy tiered ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5565

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

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  • Whimsical Cutie Butterfly Polka Dot Satin Maxi Dress

    Soar toward any celebration in this whimsical and cute polka dot satin maxi dress! Featuring cap sleeves and a gorgeous butterfly lace trim sweetheart neckline, this dress adds a touch of elegance. The button-down back with a cutout accent completes the maxi silhouette, making you the center of attention! Complete the look in strappy block heels and a necklace.

    Fit & Features

    • Polka dot print, satin fabric, no stretch
    • Butterfly lace trim sweetheart neckline
    • Button-down back and zipper hook-eye closures
    • Cutout back accent
    • Maxi length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3555

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Dream Strapless Belted Skater Dress

    She’s giving flirty, fun, and just the right amount of edge. The strapless fit and belted waist make this denim skater dress the definition of standout style.

    Fit & Features

    • Denim fabric
    • Strapless fold-over neckline
    • Smocked back
    • Belted drop waist
    • Short pleated skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000232

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

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  • Effortlessly Chic Button Front Tunic

    Create an effortlessly chic everyday look with this classic tunic. It features a collared neckline, a complete button-down front, long sleeves, and a cinched waist effect for a figure-flattering silhouette. Style this tunic with sleek hoops and clear mules.

    Fit & Features

    • Collared neckline
    • Button-down front
    • Long sleeves, single-button details
    • Cinched waist effect
    • Pleating detail
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1497

    Category Name: Casual Dresses

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Adoring Cutie Sleeveless Lace-Up A-Line Mini Dress

    An attention-worthy A-line mini dress that'll have everyone adoring your cuteness! This square neck dress accentuates your curves while the lace-up back adds a touch of playfulness. The A-line silhouette and mini-length hem are perfect for any occasion. Complete the look in wedges and a clutch!

    Fit & Features

    • Smooth knit fabric lined with stretchy knit
    • Spagehtti straps
    • Square neckline
    • Lace-up
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5689

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Picture Perfect V-Neck Smocked A-Line Midi Dress

    You'll be the picture of perfection in this adorable A-line midi dress at showers or birthday brunch! With its flattering V-neckline and stretchy smocked bodice, this dress hugs your body in all the right places. The tie spaghetti straps add a touch of delicacy, while the V-cut waist seam and A-line silhouette create a flattering look along the midi-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Woven fabric lined with non-stretch woven
    • Tie spaghetti straps
    • V-neckline
    • Stretchy smocked bodice
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3560

    Category Name: Casual Dresses

    Price: $11.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Match Sleeveless Striped Ribbed Knit Mini Dress

    You and this striped knit mini dress are the perfect match for sunny days! With a playful scoop neckline and cutout back, this mini dress is a cute piece for any fun occasion. Its bodycon fit flatters your figure while the striped pattern adds a touch of quirkiness. The ribbed knit fabric offers a moderate stretch for comfortable wear. Complete the look with flat sandals.

    Fit & Features

    • Striped pattern
    • Ribbed knit fabric with moderate stretch
    • Scoop neckline
    • Tank shoulder straps
    • Cutout back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1940

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Details Basic Ruched Midi Dress

    The true style of this basic midi dress lies in the detail! Features a sleeveless square neckline, sleek bungee spaghetti straps, ruched seams down the sides to accentuate your curves, and a flattering bodycon silhouette. The dress is composed of a brushed soft knit fabric with a full-length lining. Complete the look with a chic handbag for a dinner date.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruched side seams
    • Bodycon silhouette
    • Midi-length hem
    • Brushed soft knit fabric, lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5146

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Artsy Play Abstract Mock Neck Mini Dress

    Play up your artsy side in this mesh mini dress totally giving those Y2K vibes! The mini dress features fitted long sleeves with split cuffs, a mock neckline, and a bodycon silhouette on mesh abstract printed fabric with a sheer mesh stretchy lining. Complete the look in chunky platform heels for a party!

    Fit & Features

    • Fitted long sleeves, split cuffs
    • Mock neckline
    • Bodycon silhouette
    • Mini-length hem
    • Abstract print on mesh fabric, sheer mesh stretchy lining
    • Runs true to size

    Style Number/Barcode: 05102-5398

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Off My Mind Cutout Long Sleeve Ribbed Knit Midi Dress

    Make an unforgettable appearance in this long-sleeved midi dress at brunch or casual parties! The midi dress is designed with an off-the-shoulder neckline, a twisted bust with a sultry cutout, and a bodycon fit on stretchy ribbed knit fabric. Complete the look in strappy heels.

    Fit & Features

    • Ribbed knit fabric with moderate stretch
    • Off-the-shoulder neckline
    • Fitted long sleeves
    • Twisted bust, cutout
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5280

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Smooth Silhouette Mock Neck Mini Dress

    Turn heads in this essential mini dress! Crafted with a double-lined smooth seamless knit fabric, the mini-length dress fits your body like a glove and features a mock neckline, fitted long sleeves, and a flattering bodycon silhouette. Make a statement and get compliments wherever you go styling this mini dress with combat boots and jacket.

    Fit & Features

    • Fitted long sleeves
    • Mock neckline
    • Bodycon silhouette
    • Mini-length hem
    • Double mesh lined smooth seamless knit fabric
    • Buttery soft and stretchy
    • Runs true to size

    Style Number/Barcode: 05102-5384

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sensational City Girl Strapless Cargo Mini Dress

    Hit the streets with a strapless mini dress that'll make you an instant sensational city girl! The strapless straight-across neckline and bodycon silhouette flatter any figure, while the front button closure and belt loop accents add a trendy touch. With a hidden front zipper, cargo flap pockets, and a mini-length hem, this woven dress is both fashionable and functional. Complete the look in lug boots for casual plans!

    Fit & Features

    • Cotton-blend woven fabric, minimal stretch
    • Strapless straight neckline with belt loop detailing
    • Front button closure
    • Hidden front zipper closure
    • Cargo flap pockets
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5503

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Make It Sexy Off-The-Shoulder Mini Dress

    Show off your curves in this sexy mini dress for weekend outings! The short dress features an off-the-shoulder neckline with a flirty bust keyhole tie, long sleeves with flared cuffs, side ruched seams to accentuate your figure, a bodycon silhouette, and a mini-length hem. Complete the look in lace-up stiletto heels and dare to be bold!

    Fit & Features

    • Off-the-shoulder neckline, bust keyhole tie
    • Long sleeves with flared cuffs
    • Side ruched seams, bodycon silhouette
    • Mini-length hem
    • Slinky knit fabric, sewn-in knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5212

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cute And Casual Everyday Ribbed Knit Midi Dress

    This ribbed knit midi dress is cute, casual, and perf for everyday styling! It features a sleeveless V-neckline, spaghetti straps, a midi-length hem with a side slit accent, and a form-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a cropped denim jacket and strappy mules.

    Fit & Features

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

    Style Number/Barcode: 05102-4934

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Showstoppin' Staple Long Sleeve Maxi Dress

    Put your curves on display in this basic maxi dress perfect for dressing up or down! The long dress features fitted long sleeves, a classic crew neck, and a flattering bodycon silhouette on hacci rib knit fabric. Complete the look with strappy heels and a purse!

    Fit & Features

    • Hacci rib knit fabric, plenty of stretch
    • Fitted long sleeves
    • Crew neckline
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5331

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Charm Ruffled Chiffon Tube Skater Dress

    Your go-to summer floral dress has arrived! With charming ruffles and skater silhouette, this short dress is perfect for shower celebrations, brunch, or day dates.

    Fit & Features

    • Floral print, chiffon fabric, stretchy knit lining
    • Strapless tube neckline
    • Stretchy, smocked fitted bodice
    • Skater silhouette
    • Ruffled short hem
    • Runs true to size

    Style Number/Barcode: 05101-4125

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Truly Chic High Slit Bodycon Midi Dress

    Create a truly chic look for dinner and drinks in this high slit bodycon midi dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, ruching down the side seams, an asymmetric midi-length hem creating a thigh-high side slit, and a bodycon fit to showcase your stunning silhouette. The lined smooth knit fabric offers plenty of stretch. Style with rhinestone fringe earrings to add a touch of glam!

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Ruched side seams
    • Asymmetric midi-length hem, thigh-high side slit
    • Bodycon silhouette
    • Smooth knit fabric, mini-length knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5521

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Fab Marble Print Mesh Mini Dress

    Oh so fab, you'll turn heads in this alluring marble print mesh mini dress. It features a sleeveless cowl neckline, adjustable spaghetti straps to customize the fit, a mini-length hem with a cute lettuce-edge trim, and a bodycon silhouette that will hug your natural curves. The airy sheer mesh fabric includes a full knit lining and features an all-over marble print pattern. Style with lace-up heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Mini-length hem, lettuce-edge trim
    • Bodycon silhouette
    • Marble print
    • Sheer mesh fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5509

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Right Impression V-Neck Floral Ruffle Skater Dress

    A cutie like you will always make the right impression in this floral skater dress on dates or at brunch!  Featuring sheer peasant long sleeves and a flattering V-neckline, this skater silhouette is completed with a ruffled short-length hem. The V-cut back with a spaghetti strap tie adds a touch of allure. Style this floral skater dress with block heels.

    Fit & Features

    • Floral print, chiffon fabric with woven lining, no stretch
    • V-neckline, V-cut back with spaghetti strap tie
    • Skater silhouette
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-2894

    Category Name: Casual Dresses

    Price: $6.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Look Ditsy Floral Chiffon Babydoll Dress

    Create the sweetest look for your summer plans with this adorable babydoll dress! The airy sheer chiffon fabric is detailed with a ditsy floral print and includes a full-length lining for coverage. The short dress features a sleeveless scoop neckline with ruching at the bust, adjustable spaghetti straps for a customized fit, a smocked back for added stretch, and a ruffled tiered A-line silhouette with an effortless flowy fit. Style with sneakers for a cute and casual summer outfit.

    Fit & Features

    • Ditsy floral print
    • Sheer chiffon fabric with stretchy knit lining
    • Ruched scoop neckline
    • Adjustable spaghetti straps
    • Smocked back
    • Ruffled tiered A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5451

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Strut And Snap Ribbed Knit Midi Dress

    Strut it out in a knit midi dress that is perf for every day! Designed with a ribbed knit fabric, this dress offers a form-hugging fit with a moderate stretch. It features a sleeveless square neckline, tank shoulder straps, a high side slit accented with glossy metal buttons, and a midi-length hem. Complete the look with mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Ribbed knit fabric with moderate stretch
    • Square neckline
    • Tank shoulder straps
    • Metal button accents
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-1167

    Category Name: Casual Dresses

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free