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.

  • Stylish Jeanius Strapless Denim Mini Dress

    You're kind of a genius for showing off this strapless denim mini dress everywhere you go! Set the trend in this short dress with a classic jean style with belt loop accents and a flattering bodycon fit.

    Fit & Features

    • Denim fabric
    • Strapless neckline with belt loop accents
    • Jean-style design
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5936

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sun Coast Dream Paisley Bodycon Slit Maxi Dress

    Enjoy a vacay or day out by the sunshine coast in this paisley maxi dress with a flattering bodycon fit and side slit for effortless movement!

    Fit & Features

    • Paisley boho print, mesh fabric, sewn-in brushed knit lining
    • Square neckline
    • Spaghetti straps, criss cross back
    • Bodycon silhouette
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5928

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • Flirty Silhouette Lace Trim Plaid Mini Dress

    Flirty and adorable, this plaid woven mini dress features a sleeveless sweetheart neckline with a dainty eyelet lace and ribbon trim and front bow detail, spaghetti straps, and a short form-hugging silhouette to highlight your curves. Style with hoop earrings and sleek mules.

    Fit & Features

    • Plaid woven-blend fabric with moderate stretch, knit lining at the bust
    • Sweetheart neckline with lace and ribbon trim, front bow detail
    • Ruched bust, underbust seam
    • Spaghetti straps
    • Mini-length form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5934

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

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  • Chic Night Out Abstract Print Mesh Midi Dress

    Create a chic vibe to grab drinks with the girls in this airy mesh midi dress designed with a bold abstract print pattern. The dress features a sleeveless mock neckline, tank shoulder straps, ruching at the waist, and a bodycon silhouette to flaunt your curves.

    Fit & Features

    • Sheer mesh fabric with brushed knit lining, plenty of stretch
    • Abstract print
    • Mock neckline
    • Tank shoulder straps
    • Ruched waist
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5929

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Basic Cutie Long Sleeve Knit Midi Dress

    The perfect cute and basic midi dress for all of your styling needs! The dress is designed with a flattering square neckline that shapes the form-hugging fit and flattering midi-length hem. Pair with a dainty necklace.

    Fit & Features

    • Stretchy rib knit fabric
    • Fitted long sleeves
    • Square neckline
    • Form-hugging fit
    • Relaxed midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5933

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

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  • Artsy Babe Paisley Bodycon Slit Midi Dress

    Strut like an artsy babe in this paisley mesh midi dress showcasing a flattering bodycon silhouette with a flirty front slit. Complete the look with a handbag.

    Fit & Features

    • Paisley print, mesh fabric, stretchy knit lining
    • Square neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5932

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

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  • Pretty In Plaid Sleeveless Knit Mini Dress

    Look and feel pretty in this plaid mini dress, which boasts a flirty V-neckline and bodycon silhouette that shows your curves! Pair with a leather jacket and flats.

    Fit & Features

    • Woven knit fabrication
    • Sleeveless v-neckline
    • Spaghetti straps
    • Plaid print 
    • Side slit
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05102-5930

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

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  • Gorgeous Silhouette Sleeveless Bodycon Midi Dress

    Flaunt your gorgeous figure in this midi dress designed with smooth nylon fabric offering plenty of stretch. It features a sleeveless scoop neck and back design, tank straps, and a midi-length bodycon silhouette to showcase your curves.

    Fit & Features

    • Smooth nylon fabric with plenty of stretch
    • Scoop neck and back
    • Tank shoulder straps
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5931

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • Adorable Look Plaid Print Strapless Skater Dress

    Adorably chic will be your vibe in this woven skater dress designed with a classic plaid print. It features a strapless subtle sweetheart neckline, a drop waist, and a short pleated skater silhouette for that cute flair.

    Fit & Features

    • Plaid printed woven fabric
    • Strapless sweetheart neckline
    • Back zipper closure
    • Drop waist
    • Mini-length pleated skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5925

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Toasty Sweetheart V-Neck Bodycon Knit Midi Dress

    This sleeveless ribbed knit midi dress features a striking V-neckline and bodycon fit with a front slit detail for movement. Perfect for layering with a jacket and heels.

    Fit & Features

    • Stretchy ribbed knit fabric
    • V-neckline
    • Spaghetti straps
    • Front slit
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-2221

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

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  • Elevated Leopard Print Woven A-Line Midi Dress

    Trendy and elevated, this leopard-printed woven midi dress features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, and a partially smocked back for added stretch. The high front slit adds a bold vibe to the mid-length A-line silhouette.

    Fit & Features

    • Leopard-printed woven fabric, no stretch
    • Square neckline, underbust seam
    • Adjustable spaghetti straps
    • Partially smocked back design
    • High front slit
    • Midi-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5923

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Carefree Chic Long Sleeve Ribbed Knit Midi Dress

    An off-the-shoulder midi dress perfect for those carefree days! It features fitted long sleeves and a bodycon fit that shows off your curves. Pair with sneakers.

    Fit & Features

    • Ribbed knit fabrication, stretchy knit lining
    • Off-the-shoulder neckline
    • Fitted long sleeves
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5924

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

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  • Spring Has Sprung Floral Bubble Hem Skater Dress

    Let your beauty bloom in this adorable floral skater dress with the sweetest allure. The corset bodice will highlight your waist while the short skater skirt offers the cutest fit-and-flare silhouette.

    Fit & Features

    • Floral-printed woven fabric with knit lining, minimal stretch
    • Sleeveless sweetheart neckline, padded bust with underwire
    • Thin tank shoulder straps
    • Corset bodice, tie-front detail, high waist seam
    • Smocked back design, zipper with hook and eye closure
    • Short skater skirt with bubble hem, fit and flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3826

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • All About You High Neck Floral Mini Dress

    Slip into this floral mini dress and command attention wherever you go. This bodycon silhouette hugs your curves in all the right places, while the chic high neck adds a touch of sophistication.

    Fit & Features

    • Floral print, mesh-lined fabric
    • High neck
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5921

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Chic Style Ribbed Knit Off-Shoulder Midi Dress

    Minimal effort, major effect. This off-shoulder ribbed knit midi dress is your go-to for sleek confidence with a side of chic style. Pairs perfectly with a red lip and your best “don’t need to try” attitude.

    Fit & Features

    • Ribbed knit fabric, plenty of stretch
    • Asymmetric off-shoulder neckline, fold-over design
    • Long fitted sleeves
    • High-cut side slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5919

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Casual Chic Style Long Sleeve Ribbed Knit Midi Dress

    The perfect blend of casual and chic, this ribbed knit midi dress features a V-neckline, long fitted sleeves, and a form-hugging silhouette. Style with hoop earrings and sneakers for a cute everyday look.

    Fit & Features

    • Hacci ribbed knit fabric, plenty of stretch
    • V-neckline
    • Long fitted sleeves
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5920

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Flawless Style Knit Off-The-Shoulder Long Sleeve Mini Dress

    Show off your stunning curves in this form-hugging mini dress made with pointelle knit fabric with plenty of stretch. It features a chic off-the-shoulder neckline with a fold-over design, long fitted sleeves, and ruched side seams along the short bodycon silhouette.

    Fit & Features

    • Pointelle knit fabric with knit lining, plenty of stretch
    • Off-the-shoulder neckline with fold-over design
    • Unlined long fitted sleeves
    • Ruched side and back seams
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5917

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Twirling Beauty Halter Floral Skater Dress

    Twirl through the day in this floral skater dress boasting a lace trim halter neckline for added romance and a flirty mini-length hem to show off your shoes.

    Fit & Features

    • Floral print, woven fabric lined with tulle and woven linings
    • Lace trim halter neckline, tie straps, tie bust
    • Pleated detailed bodice, back zipper and hook-eye closure
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3817

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Lovely Nights Strapless Lace Ruffle Skater Dress

    Have a lovely night in this strapless lace dress boasting a flattering skater silhouette adorned with flirty ruffles perfect for dancing! Pair with a necklace.

    Fit & Features

    • Lace fabric, stretch knit lining
    • Strapless neckline
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000939

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: L

  • Sweet Spice Corset Lace-Up Floral Midi Dress

    Sweet and spice combine on this floral midi dress designed with a stylish lace-up back, corset bodice, and a flirty front slit for movement. Complete the look with mules.

    Fit & Features

    • Ditsy floral print, smooth woven fabric, woven lining
    • Sleeveless sweetheart neckline with tie
    • Shoulder straps, side zipper and hook-eye closure
    • Lace-up back design
    • Underwire bust, corset bodice
    • Front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3819

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Preppy-Chic Belted And Pleated Skater Dress

     This preppy-chic twill skater dress features a collared neckline with a partial button-down front, short cap sleeves, and a subtle drop waist with a belted design. The mini-length pleated skater fit adds that flirty touch to the short silhouette.

    Fit & Features

    • Twill woven fabric, slight stretch
    • Collared neckline, button-down front
    • Cap sleeves
    • Belted drop waist
    • Mini-length pleated skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5915

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Idea Of Bliss Corset Lace-Up Floral Skater Dress

    Bold and pretty blooms dance across this dreamy floral skater dress perfect for sunshine dressing! The dress boasts an adorable corset bodice with lace trim and a back lace-up that turns heads while the voluminous skater silhouette has a romantic lace trim lining.

    Fit & Features

    • Floral print, woven fabric, multiple linings with lace trim
    • Strapless neckline with bow, flexible boning
    • Side zipper and hook-eye closure
    • Corset bodice, lace trim, lace-up back
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3793

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Here To Flirt Drop Waist Ruffled Skater Dress

    This adorable skater dress features a ribbed knit top with a sleeveless crew neckline and tank shoulder straps, a trendy V-shaped drop waist, and a tiered ruffled chiffon A-line silhouette for a flirty accent. Style with mules for a date night or sneakers to keep it casual!

    Fit & Features

    • Ribbed knit and chiffon fabrics, moderate stretch
    • Crew neckline, tank shoulder straps
    • V-shaped drop waist
    • Tiered ruffled design
    • Short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5910

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Style In Stride V-Neck Collar Denim Mini Dress

    Your best bet is this collar denim mini dress for a unique look at concerts or festivals! Set the trend in this sleeveless bodycon dress perf for styling with western boots.

    Fit & Features

    • Vintage-inspired denim fabric, minimal stretch
    • Collar V-neckline
    • Zip-up front closure
    • Faux front pockets
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5914

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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