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.

  • Cutesy Flair Ruffled Denim Mini Dress

    Show off a cutesy flair in this denim mini dress perf for festival season! You'll love the strapless ruffled neckline and matching ruffled A-line hem.

    Fit & Features

    • Denim fabric
    • Strapless straight neckline, ruffled trim
    • Vertical seams
    • Drop waist
    • Mini-length A-line silhouette, ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-000006

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    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
  • Chic Vibes Only Strapless Drop Waist Romper

    Show off chic vibes only in this strapless drop waist romper designed with a tiered mini-length overlay with a short side slit. Perf for pairing with mules for happy hour!

    Fit & Features

    • Mesh fabric with knit lining, high stretch
    • Strapless straight neckline
    • Drop waist design
    • Ruching
    • Tiered mini-length overlay, small bow detail, short side slit
    • Fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000023

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

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  • Cute And Cozy Mock Neck Knit Skater Dress

    Fit & Features

    • Stretchy rib knit fabric
    • Mock neck
    • Fitted long sleeves
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2241

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, L

  • Floral Passion Sleeveless Lace-Up Maxi Dress

    The maxi dress features a sleeveless square neckline supported with additional built-in flexible boning, an abstract floral pattern, a lace-up back design, and a bold high-side slit. Complete the look with stiletto heels for the perfect date night outfit. 

    Fit & Features

    • Mesh fabric, sewn-in knit lining
    • Sleeveless square neckline
    • Built-in-boning
    • Floral pattern
    • Lace-up back design
    • High side slit
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3773

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Seashell Cove Strappy Back Crochet Mini Dress

    Channel beachy vibes with this crochet mini dress. The strappy back and bodycon silhouette enhance your curves while the wrap mini-length hem features a whimsical seashell trim. 

    Fit & Features

    • Crochet fabric, sewn-in knit lining
    • Strapless neckline, non-slip grip lining
    • Strappy back with tassel strings
    • Bodycon silhouette
    • Wrap mini-length hem with seashell trim
    • Runs true to size

    Style Number/Barcode: 05102-000012

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Tropical Mood Strapless Midi Dress

    This tropical midi dress will have you looking like a warm weather cutie on vacation or a weekend escape!

    Fit & Features

    • Tropical print, knit fabric with stretchy knit lining
    • Strapless neckline
    • Form-hugging bodice
    • Flared midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000014

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Beauty So Divine Floral Satin A-Line Mini Dress

    Boast a beautiful allure in this floral satin mini dress featuring a delicate lace trim and flattering A-line silhouette. Pair with heels.

    Fit & Features

    • Floral print, silky satin fabric
    • Spaghetti straps
    • Lace trim sweetheart neckline
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3778

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirtatious Scene Halter Lace Skater Dress

    Make it a flirty scene in this lace skater dress boasting a sultry halter V-neckline with metal accents and a flattering tiered ruffled mini-length hem. Complete the look with boots.

    Fit & Features

    • Lace-lined fabric
    • Halter V-neckline with metal accents
    • Skater silhouette
    • Tiered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4095

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Sunny Eyelet Knit Mini Skater Dress

    This adorable mini skater dress is perfect for sunny weekend plans. Made with a breezy eyelet knit fabric, you'll love the flirty tie-back detail and fit-and-flare ruffled silhouette.

    Fit & Features

    • Eyelet knit fabric, sewn-in knit lining
    • Scoop neckline
    • Adjustable spaghetti straps
    • Tie-back detail, lower open back
    • Short skater silhouette, tiered ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-6000

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • No You Hang Up Tube Mini Dress

    Get ready to wow in this tube mini dress for your next date! This dress is designed with an alluring twist bust with a keyhole cutout that shows some skin, while the form-hugging A-line silhouette accentuates your curves.

    Fit & Features

    • Texture knit stretchy fabric
    • Strapless tube sweetheart neckline
    • Twist bust, keyhole cutout
    • Form-hugging, A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000018

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Alluring 'Fit Plunging Halter Mini Dress

    Create an alluring 'fit for sunset drinks in this textured knit mini dress featuring a plunging V-neck with a bust tie accent, halter straps, and a bold open back with a tie-back design. The short, bodycon silhouette will flaunt your gorgeous curves.

    Fit & Features

    • Sheer textured knit fabric with knit lining, high stretch
    • Sleeveless plunging V-neckline, bust tie accent
    • Tie-back halter spaghetti straps
    • Open back, tie-back spaghetti straps
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000020

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Effortless Days Strapless Bodycon Midi Dress

    A trendy babe like you needs this effortless strapless bodycon midi dress for easy styling! 

    Fit & Features

    • Double-lined rib knit stretchy fabric
    • Strapless neckline
    • Bodycon fit
    • Flowy midi-length hem
    • Extra glitter for maximum sparkle - may have some natural fallout
    • Runs true to size

    Style Number/Barcode: 05102-000021

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Coastal Cute Striped Bodycon Mini Dress

    An effortless striped mini dress for days spent by the coast or in the city! With a flattering strapless neckline and bodycon silhouette, this dress is perfect for layering.

    Fit & Features

    • Striped print, stretchy knit fabric
    • Strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000017

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cutest Twirl Long Sleeve Knit Skater Dress

    Twirl into style in this long sleeve knit skater dress. Featuring a square neckline and skater silhouette, this ribbed knit is your go-to for effortless charm.

    Fit & Features

    • Stretchy rib knit fabric
    • Fitted long sleeves
    • Square neckline
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2243

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Chic Update Convertible Ruched Long Dress

    The perfect sleeveless long dress to update your chic wardrobe! The dress features a convertible neckline allowing for versatile styling like a halter or an off-the-shoulder look atop the form-hugging slim silhouette. Pair with earrings.

    Fit & Features

    • Smooth knit fabric
    • Convertible neckline
    • Halter or off-the-shoulder
    • Form-hugging slim silhouette
    • Long length hem
    • Runs true to size

    Style Number/Barcode: 05102-000023

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Chic Twist Tie-Back Striped Midi Dress

    A chic twist on a classic sundress. This head-turning midi dress is designed with an open tie-back with button accents and hidden side pockets that keep your hands warm!

    Fit & Features

    • Striped print, woven fabric, woven lining
    • V-neckline
    • Spaghetti straps
    • Open tie-back design, lower button accents
    • Hidden side pockets
    • A-line silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000022

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Breezy As Can Be Strapless Ruffled Midi Dress

    This midi dress will be your go-to choice from shower celebrations to sunset dinners. Cascading ruffles create a feminine silhouette that flows with your movements, while the midi hem lets you show off your shoes.

    Fit & Features

    • Gauze woven fabric, woven lining
    • Strapless smocked stretchy bodice
    • Ruffled cascading silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000027

    Category Name: Casual Dresses

    Price: $15.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cutie Style Striped Knit Bodycon Mini Dress

    Show off your cutie style in this adorable mini dress made with striped ribbed knit fabric with high stretch. The strapless sweetheart neckline features a knot detail at the bust and a small keyhole cutout for a trendy detail.

    Fit & Features

    • Striped ribbed knit fabric, knit bust lining, high stretch
    • Strapless sweetheart neckline, no-slip strip
    • Knot detail at the bust, small keyhole cutout
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000016

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Savor The Moment Halter Cutout Maxi Dress

    Step into the spotlight in this halter maxi dress on vacation or for some summer fun! Featuring a striking halter neckline adorned with elegant hardware and a shimmering stone insert, this bodycon dress offers a bold cutout design that highlights your figure.

    Fit & Features

    • Smooth knit stretchy fabric
    • Halter neckline with tie closure
    • Hardware and stone insert
    • Cutout accents
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000030

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Vacay Scandal Tropical Cutout Maxi Dress

    Booked the trip? Now bring the drama in this tropical maxi dress! With metal hardware and skin-baring cutouts, this maxi is not for blending in—it's bold, body-hugging, and built for after-hours.

    Fit & Features

    • Tropical print, mesh fabric, smooth stretchy knit lining
    • Halter neckline with hardware accents, spaghetti strap tie
    • Bandeau-style cutout bodice with center metal U-ring
    • Ruched high waist with hardware accent
    • High front slit on a body-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000032

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • 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:
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  • Such A Flirt Lace Trim Scoop Neck Knit Mini Dress

    Fit & Features

    • Soft rib knit fabric, moderate stretch
    • Lace trim scoop neckline with bow tie
    • Fitted long sleeves
    • Bodycon silhouette
    • Mini-length hem, dual slit accents
    • Runs true to size

    Style Number/Barcode: 06005-2199

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cup Of Tea Striped Halter Midi Dress With Pockets

    Look cute spilling the tea in this striped midi dress boasting a flattering A-line fit adorned with hidden side pockets perfect for keeping your hands warm!

    Fit & Features

    • Striped print, cotton-blend woven fabric, woven lining
    • Halter plunge neck with ties
    • Back zipper closure
    • Hidden side pockets
    • A-line fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000033

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free