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.

  • Sunny Chic Floral Strapless Skater Dress

    Live out your cottagecore dreams in this chic floral strapless skater dress, perfect for sunny days. You'll love the tie-back bow design and adorable fit-and-flare silhouette.

    Fit & Features

    • Swiss dot woven fabric
    • Small floral pattern
    • Strapless straight neckline
    • Ruched high waist, tie-back bow design
    • Short pleated skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3852

    Category Name: Casual Dresses

    Price: $11.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

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  • Contemporary Sleek Bodycon Midi Dress

    Made in a soft rib knit fabric that snatches your figure, this sleeveless midi dress offers a contemporary and sleek style with a sleeveless square neckline and a bodycon silhouette. Pair with hoop earrings and a blazer.

    Fit & Features

    • Soft rib knit fabric, moderate stretch
    • Square neckline
    • Wide angled shoulder straps
    • Bodycon silhouette
    • Center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5951

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • Edgy In Plaid Scoop Neck Mesh Mini Dress

    Show your edge in this plaid mesh mini dress featuring a flattering scoop neckline and form-hugging fit with a hanky-style hem. Complete the look with a cardigan.

    Fit & Features

    • Plaid print, mesh fabric, stretchy knit lining
    • Spaghetti straps
    • Scoop neckline
    • Form-hugging fit
    • Hanky-style mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5952

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

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  • Trendy Fave Open Back Long Sleeve Knit Mini Dress

    This trendy ribbed knit mini dress features a crew neckline, long fitted sleeves, and a bold lower open back with a tie-back strap design. The short bodycon silhouette will highlight your curves and is perf for pairing with knee-high boots.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch
    • Crew neckline
    • Long fitted sleeves
    • Open lower back with tie-back straps
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5948

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sharp Lines Asymmetrical Long Sleeve Midi Dress

    Strike a fierce impression in a ribbed knit dress with an asymmetrical off-the-shoulder neckline, a pleated popover accent, fitted long sleeves, and a midi-length hem. Complete the look with strappy heels for the perfect work-to-happy hour look! 

    Fit & Features

    • Ribbed knit fabrication
    • Asymmetrical off-the-shoulder neckline
    • Pleated popover accent at the neckline
    • Long sleeves
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5947

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Inspired Art Abstract Bodycon Mini Dress

    Bring a little extra artsy glamour to any plans in this abstract bodycon mini dress sure to inspire many compliments! 

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Adjustable spaghetti straps
    • Square neckline, padded bra cups
    • Front ruched drawstring
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-5952

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • Elevated Button-Down Drop Waist Mini Dress

    So elevated, this adorable mini dress is designed with a textured knit fabric and a sleek button-down front. It features a sleeveless square neckline with tank straps, a drop waist, and a short pleated A-line silhouette for that cute flair.

    Fit & Features

    • Textured knit fabric, sewn-in knit lining
    • Square neckline
    • Tank shoulder straps
    • Button-down front
    • Drop waist
    • Mini-length pleated A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3842

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

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  • So Adored Sleeveless Bow Trim Crepe Mini Dress

    Embrace romance in this crepe mini dress that features a sleeveless square neckline with tank-like straps, a charming bow accented trim under the bust, and a flared mini-length hem with an A-line silhouette. Complete your look with sleek flats!

    Fit & Features

    • Crepe fabric with knit lining, moderate stretch
    • Sleeveless square neckline, dart seams
    • Tank-like shoulder straps
    • Bow accented trim under bust
    • Back zipper closure
    • Flared mini-length hem, A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3840

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • Trend Moment Denim Belted Pleat Mini Dress

    Hit the streets in this of-the-moment denim mini dress with a trendy belted design and flirty pleated hem!

    Fit & Features

    • Denim fabric, moderate stretch
    • Strapless neckline
    • Back zipper and hook-eye closure
    • Belted design
    • Bodycon fit
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5944

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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  • Always A Good Time Long Sleeve Midi Dress

    A basic midi dress every fashionista needs to create bold looks. The dress features side ruched seams and a bodycon silhouette to accentuate your curves while the midi-length hem makes it perfect for styling with boots or heels. 

    Fit & Features

    • Rib knit fabric, stretchy knit lining
    • Fitted long sleeves
    • Square neckline
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5940

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sleek Vibes Off The Shoulder Knit Midi Dress

    Keep it sleek and stylish in a ribbed knit dress that features a v-neckline that can be worn off-the-shoulder, fitted long sleeves, and a midi-length hem. Complete the look with sneakers to add a casual touch! 

    Fit & Features

    • Lined ribbed knit fabrication
    • V-neckline and off-the-shoulder 
    • Long sleeves
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5942

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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  • Mesmerizing Glam Abstract Ruched Midi Dress

    Step out and mesmerize in a midi dress that features a sleeveless square neckline, ruching throughout to enhance curves, and an abstract marble print. Complete look with strappy heels for a look that's ready for date night!

    Fit & Features

    • Lined mesh fabrication
    • Sleeveless square neckline
    • Ruching
    • Abstract marble print
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5937

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

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  • Cute Flirt Drop Waist Ruffled Hem Mini Dress

    Show off your stunning figure in this smooth knit mini dress featuring a boat neckline, long fitted sleeves, a cute scoop back, a drop waist design, and a short tiered ruffled hem with an A-line fit for that flirty flair. Style with strappy mules!

    Fit & Features

    • Smooth nylon knit fabric, plenty of stretch
    • Boat neckline
    • Long fitted sleeves
    • Scoop back
    • Drop waist
    • Tiered ruffled mini-length hem, A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5938

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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  • 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

    Product Badge:
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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

    Product Badge:
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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

    Product Badge:
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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

    Product Badge:
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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

    Product Badge:
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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

    Product Badge:
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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

    Product Badge:
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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

    Product Badge:
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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