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.

  • 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

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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

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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

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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

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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

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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

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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: 05101-3813

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • 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

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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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  • Cosmic Chic Tie-Dye Knit Midi Dress

    The ribbed knit dress features a scoop neckline, fitted long sleeves, a tie-dye pattern, and a midi-length hem accented with a center slit at the hem. Complete the look with ankle booties for a casually chic vibe. 

    Fit & Features

    • Ribbed knit fabrication
    • Scoop neckline
    • Long sleeves
    • Tie-dye pattern
    • Center slit at back of hem
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 06005-2132

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Adorable Stunner Strapless A-Line Mini Dress

    You'll be an adorable stunner in this mini dress designed with crepe fabric with a contrast color block outline for a chic look. It features a strapless straight-across neckline, a high waist seam, and a short A-line silhouette to add that flirty flair.

    Fit & Features

    • Crepe fabric, stretchy knit lining
    • Contrast color block outline
    • Strapless straight neckline
    • High waist seam
    • Back zipper closure
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3801

    Category Name: Casual Dresses

    Price: $14.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Contrast Tube Mini Dress

    Sophisticated yet flirty, this strapless mini dress turns heads with its fitted bodice and pleated skirt. Add heels and jewelry for lunch in the city or a chic wine bar with the girls!

    Fit & Features

    • Woven fabric, contrast design
    • Tube strapless neckline
    • Fitted bodice
    • Pleated flare mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5913

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Dream Of Me Corset Lace-Up Floral Midi Dress

    Dreamy days call for this floral midi dress that makes your cottagecore romance a reality! With a gorgeous corset bodice, lace-up back, and voluminous A-silhouette, this dress is stunning for bridal showers or garden parties.

    Fit & Features

    • Delicate floral print, woven fabric, tulle and woven linings
    • V-neckline, adjustable spaghetti straps
    • Hidden side zipper and hook-eye closure
    • Corset bodice, flexible boning, lace-up back
    • Voluminous A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3795

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Attention-Worthy Camo Print Bodycon Mini Dress

    Create an attention-worthy 'fit in this camo-printed woven mini dress featuring a strapless straight-across neckline accented with dual flap pockets, a secure back zipper closure, cargo-style pockets on each side, and a bodycon silhouette to showcase your curves. Complete the look with a bomber jacket and combat boots!

    Fit & Features

    • Camouflage printed twill woven fabric
    • Strapless straight neckline, dual flap pocket accents
    • Back zipper hook-eye closure
    • Dual cargo flap pockets
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5909

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cute Ease Cap Sleeve Cutout Midi Dress

    This cap sleeve midi dress is ready to elevate any casual day look to a cute level! Designed in a flattering bodycon silhouette, this dress boasts a flirty cutout back and a back slit for effortless movement. 

    Fit & Features

    • Stretchy rib knit fabric
    • Cap sleeves
    • Scoop neck
    • Cutout back
    • Center back slit
    • bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5908

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Blooming Beauty Floral Print Mesh Maxi Dress

    Let your beauty bloom with a mesh maxi dress that features a sleeveless sweetheart neckline with lace trim, a bodycon-fit silhouette, and a pretty floral print throughout! Complete your date night look with stiletto heels! 

    Fit & Features

    • Sheer mesh fabric with knit lining, plenty of stretch
    • Floral print
    • Sleeveless sweetheart neckline, lace trim
    • Spaghetti straps
    • Bodycon-like fit
    • Long maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001591

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • 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
  • Fab Trendsetter Leopard Print Drop Waist Mini Dress

    Fab trendsetter will be your vibe in this leopard print mini dress featuring an off-the-shoulder neckline with short sleeves, a drop waist seam, and an asymmetric tiered mini-length hem with an A-line fit. Style with knee-high boots!

    Fit & Features

    • Leopard-printed brushed knit fabric, plenty of stretch
    • Off-the-shoulder neckline, short sleeves
    • Drop waist seam
    • Asymmetric tiered mini-length hem
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5904

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale