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.

  • Daydreamer Tie-Dye Ruffled Chiffon Mini Dress

    Your daydreams will come true in this stunning tie-dye chiffon mini dress. It features a sleeveless V-neckline with a ruffled overlay, adjustable spaghetti straps, an elasticized high waist seam with a cute tie-front belt to highlight your waist, a ruffled and tiered short silhouette, and a flowy A-line fit. The sheer airy chiffon fabric features a pretty watercolor-like tie-dye pattern and includes a woven lining. Pair with clear heels for weekend brunches or day dates!

    Fit & Features

    • Sleeveless V-neckline, ruffled overlay
    • Adjustable spaghetti straps
    • Elasticized high waist seam, tie-front belt
    • Ruffled and tiered short silhouette, A-line fit
    • Watercolor-like tie-dye pattern
    • Sheer chiffon fabric, full woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5329

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • I'm So Rare Marble Long Sleeve Mini Dress

    Look one-of-a-kind in this marble print mini dress! The short dress features sheer fitted long sleeves, a crew neck, a flattering bodycon silhouette, and a mini-length hem on marble-printed mesh fabric. Dare to be rare and style the mini dress with a ring set for day or night plans!

    Fit & Features

    • Sheer fitted long sleeves
    • Crew neck
    • Bodycon silhouette
    • Mini-length hem
    • Marble print
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5327

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Casual Chills Long Sleeve Slit Mini Dress

    Look cute in this mini dress for casual chills with friends or daytime outings! The mini dress features a classic crew neckline, bell long sleeves, a flattering bodycon silhouette, and a flirty front slit along the hem on rib knit fabric. Complete the look with booties and a handbag!

    Fit & Features

    • Bell long sleeves
    • Crew neckline
    • Bodycon silhouette
    • Front slit, mini-length hem
    • Rib knit fabric
    • Minimal stretch
    • Style runs small

    Style Number/Barcode: 05102-5326

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Summer Breeze Ruffled Cotton Skater Dress

    Capture an iconic summer look perfect for day parties in this breezy ruffled cotton skater dress! It features a crew neckline, adorable short puff sleeves, a small back keyhole cutout, a stretchy smocked high waist, a short ruffled and tiered skater skirt with pleated detailing, and a flattering fit and flare silhouette. The lightweight cotton fabric includes a woven skirt lining. Style with strappy sandals.

    Fit & Features

    • Crew neckline, short puff sleeves, elastic cinched hems
    • Small back keyhole cutout, button closure
    • Stretchy smocked high waist
    • Short ruffled and tiered skater skirt, pleating
    • Fit and flare silhouette
    • Cotton fabric, woven skirt lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5323

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine Beauty Floral Ruffled Short Dress

    This adorable floral ruffled short dress was made for sunny summer days! It features a sleeveless square neckline, adjustable spaghetti straps that lead to a cross-back design, a flowy relaxed A-line silhouette, and a drop waist seam with a ruffled short-length hem. The dress showcases a dainty floral embroidered pattern on the lightweight cotton fabric. Style with espadrille sandals for a day party!

    Fit & Features

    • Sleeveless square neckline, elasticized back hem
    • Adjustable spaghetti straps, cross-back design
    • Flowy A-line silhouette
    • Drop waist seam, ruffled short-length hem
    • Dainty floral embroidered pattern
    • Cotton fabric, full woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5322

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Be Mine Ditsy Floral A-Line Midi Dress

    Make this ditsy floral midi dress be yours for the summer and beyond! It features a sleeveless V-neckline, adjustable spaghetti straps, a trendy tie-back cutout design, and a flattering A-line silhouette, front slit with a frayed trim, and midi-length hem. Complete the look in block heels for a dressy soiree!

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Tie-back cutout design
    • Hidden side zipper closure
    • A-line silhouette, front slit, frayed trim
    • Midi-length hem
    • Ditsy floral print, airy woven fabric, short chiffon lining
    • Runs true to size

    Style Number/Barcode: 05102-5320

    Category Name: Casual Dresses

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Stylish Sway Ruffled Tiered Short Dress

    Keep your daytime look sweet in this lightweight woven short dress perfect for stylishly swaying to your summer playlist! It features a V-neck and back, a wrap-front design with a dainty crochet trim, tie-back spaghetti straps, short sleeves with ruffled trims, a sheer crochet trim waist, a short-length hem with an adorable ruffled and tiered silhouette, and a flowy A-line fit. The gauze fabric includes a partial woven lining. Pair with strappy sandals.

    Fit & Features

    • V-neck and back, wrap-front design, tie-back straps, metal beaded accents
    • Short sleeves, ruffled trims
    • Sheer crochet waist and trim
    • Hidden back zipper, hook and eye closure
    • Short-length hem, ruffled and tiered silhouette, A-line fit
    • Gauze fabric, partial woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5321

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Amazing Long Bell Sleeve Mini Dress

    A simply amazing little black dress you'll adore wearing on dressy occasions! It features a square neckline, long bell sleeves with trendy ruched adjustable ties and slit accents, a flattering bodycon silhouette, and a mini-length hem. The dress is composed of a double-lined soft brushed knit fabric. Complete the look with a chic mini purse and heels.

    Fit & Features

    • Double-lined soft brushed knit fabric
    • Moderate stretch
    • Square neckline
    • Long bell sleeves, ruched adjustable ties, slit accents
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5318

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Isn't She A Beauty Woven Lace Skater Dress

    Let everyone admire your beauty in this woven skater dress! The sassy sweet dress features a sleeveless sweetheart neckline and shoulder straps with delicate sheer lace trim, a front bust tie, and a corset-seam bodice leading to the flowy short-length hem. The airy woven fabric includes a stretchy knit lining. Complete the look with heeled sandals.

    Fit & Features

    • Sleeveless bodice, sheer lace trim
    • Sweetheart neckline, shoulder straps
    • Corset seam bodice, bust tie
    • High waist seam, skater silhouette
    • Flowy short-length hem
    • Airy woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5439

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Summer Days Ruffled Cotton Skater Dress

    Capture the perfect casual-chic summer vibe with this lightweight ruffled cotton skater dress. It features a pleated V-neckline with a ruffled collar and a tie-front design, short puff sleeves with ruffled hems, sheer crochet inserts down the bodice and along the skirt, a stretchy smocked high waist, a short ruffled and tiered skater skirt with a layered design, and a flattering fit and flare silhouette. The cotton fabric includes a woven skirt lining. Style with strappy mules.

    Fit & Features

    • Pleated V-neckline, ruffled collar, tie-front design, tassel accents
    • Short puff sleeves, elastic cinched ruffled hems
    • Sheer crochet inserts down the bodice and along the skirt
    • Stretchy smocked high waist
    • Short ruffled and tiered skater skirt, layered design, fit and flare silhouette
    • Cotton fabric, woven skirt lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5324

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Chic Paisley Mesh Ruched Midi Dress

    Dreamy boho and chic come together on this paisley print mesh midi dress you'll love for wine nights with bae! It features a cowl neckline  adorned with a shoulder strap and bungee spaghetti strap, a flattering bodycon silhouette, and a side ruched seam atop a slit and asymmetrical hem. Complete the look with strappy heels and earrings.

    Fit & Features

    • Sleeveless cowl neckline
    • Shoulder strap, bungee spaghetti strap
    • Bodycon silhouette, side ruched seam
    • Side slit, asymmetrical midi-length hem
    • Paisley print, mesh fabric, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2924

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Saint Tropez Chic Floral Mesh Maxi Dress

    Perfect for a trip to Saint Tropez or embracing a Parisian vibe, this chic floral mesh maxi dress is exactly what you need! The long dress features a sleeveless square neck, bungee spaghetti straps, side ruched seams to accentuate your curves, a flattering bodycon silhouette, and a maxi-length hem. The maxi dress is designed with a dreamy floral print on airy mesh fabric with a stretchy knit lining. Complete the look with a dainty bracelet and sandals.

    Fit & Features

    • Sleeveless square neck
    • Bungee spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Maxi-length hem
    • Floral print, mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5315

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blissfully Beautiful Ditsy Floral Mini Dress

    Embrace the summer season looking blissfully beautiful in this adorable ditsy floral mini dress! It features a sleeveless round neckline with an adjustable tie-front design, a ruched bust with a small front cutout, spaghetti straps, a mini-length hem with a short front slit, and a slim-fit A-line silhouette. The ditsy floral printed knit fabric has a lightweight feel and offers plenty of stretch. Style with espadrille sandals for a weekend outing.

    Fit & Features

    • Sleeveless round neckline, adjustable tie-front design
    • Ruched bust, small front cutout, spaghetti straps
    • Mini-length hem, short front slit
    • Slim-fit A-line silhouette
    • Ditsy floral print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5313

    Category Name: Casual Dresses

    Price: $5.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's All That Strapless Midi Dress

    Feel confident in this stylish midi tube dress! The knee-length dress features a soft and comfortable textured knit fabric, combined with its strapless neckline and bodycon silhouette, making this the perfect look for any occasion. Style the midi dress with sleek heels for a birthday brunch.

    Fit & Features

    • Strapless neckline
    • Bodycon silhouette
    • Midi-length hem
    • Textured knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5311

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Change Of Season Long Sleeve Ribbed Knit Midi Dress

    Step out this season in this casual-chic long sleeve midi dress! It features a V-neckline with a button design at the bust, long fitted sleeves, a midi-length hem with dual high-cut side slits, and a form-hugging fit. The lightweight ribbed knit fabric offers plenty of stretch for comfortable wear. Style this midi dress with a moto jacket and ankle booties for an edgy elevated look.

    Fit & Features

    • Stretchy ribbed knit fabric
    • V-neckline, two-button design
    • Long fitted sleeves
    • Dual side slits
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5310

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Another Day Long Sleeve Sweater Midi Dress

    Another day, another slay in this sweater midi dress - perfect for pumpkin patches, grabbing a PSL, or meeting up with friends! The knee-length dress features fitted long sleeves, a crew neckline, a bodycon silhouette, and a flirty front slit on soft and stretchy rib knit fabric. Complete the look in booties and a chic crossbody bag.

    Fit & Features

    • Fitted long sleeves
    • Crew neckline
    • Bodycon silhouette
    • Front slit accent
    • Midi-length hem
    • Soft, stretchy sweater rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5305

    Category Name: Casual Dresses

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Demeanor Mock Neck Ribbed Knit Midi Dress

    Stay sweet and comfy in this ribbed knit midi dress perfect for any occasion! Designed with cap sleeves, a mock neckline, and a flattering bodycon silhouette, this mid-length dress is trend-worthy with a flirty front slit along the hem. Complete the look with a cute crop jacket and booties!

    Fit & Features

    • Stretchy ribbed knit fabric
    • Mock neckline
    • Cap sleeves
    • Bodycon fit
    • Front slit, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5304

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Out For A Ride Denim Moto Belted Mini Dress

    This moto denim mini dress brings edgy perfection for your next ride downtown! It features a sleeveless lapel collar neckline, a front exposed zipper closure, a flattering bodycon silhouette, and a belted waist with belt loop accents and buckle closure. Complete the look in sleek hoop earrings.

    Fit & Features

    • Sleeveless lapel collar neckline
    • Front exposed zipper closure
    • Bodycon silhouette
    • Belted waist, belt loop accents, buckle closure
    • Mini-length hem
    • Denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5307

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Caught On-Trend Basic V-Neck Midi Dress

    Get caught on trend always in this basic midi dress for casual slays! It features cap sleeves, a V-neckline, a flattering bodycon silhouette, and a midi-length hem on soft modal knit fabric with a stretchy mesh lining. Complete the look with a ring set and heels.

    Fit & Features

    • Cap sleeves
    • V-neckline
    • Bodycon silhouette
    • Midi-length hem
    • Soft modal knit fabric, stretchy mesh lining
    • Runs true to size

    Style Number/Barcode: 05102-5306

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • See Through Me X-Ray Graphic Maxi Dress

    See through the ordinary and showcase your unique style! This graphic maxi dress features a scoop neckline, adjustable spaghetti straps, an X-ray graphic bust and front design, a flattering bodycon silhouette, and a back slit on smooth knit fabric. Complete the look in a sassy crop denim jacket for day or night plans!

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps,
    • Back zipper and hook-eye closure
    • X-ray graphic bust and front design
    • Bodycon silhouette, maxi-length hem, back slit
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5297

    Category Name: Casual Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artistic Muse Abstract Strapless Midi Dress

    You'll be the artsy muse in this abstract print mesh midi dress for gallery openings or an evening downtown! It features a strapless cowl neckline, flattering side ruched seams that accentuate your curves, a bodycon silhouette, and a side slit accent. Complete the look in clear strap heels for a seamless style!

    Fit & Features

    • Strapless cowl neckline
    • Back zipper and hook-eye closure
    • Side ruched seams, side slit
    • Bodycon silhouette, midi-length hem
    • Abstract print
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5295

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Extra Flare V-Neck Skater Dress

    Give your look extra flare in this sweet sleeveless skater dress! It features a V-neckline, tank shoulder straps, and a flattering fit and flare short-length silhouette. The dress is composed of a smooth knit fabric with plenty of stretch. Complete the look in rhinestone stiletto heels for a birthday or a dressy date night!

    Fit & Features

    • Sleeveless V-neckline
    • Tank shoulder straps
    • Skater silhouette
    • Short-length hem
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5292

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Abstract Moment Mesh Mock Neck Midi Dress

    Step out in this stylish mesh midi dress and not miss a single moment to have all eyes on you! The knee-length dress features a feminine mock neck with back button closures, fitted sheer long sleeves, and bodycon silhouette with abstract print on mesh fabric. Complete the look with gold hoop earrings for an art gallery opening and dinner downtown!

    Fit & Features

    • Mock neck, back button closures
    • Fitted sheer long sleeves
    • Bodycon silhouette
    • Midi-length hem
    • Abstract print
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5294

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Make It Cute Sleeveless Ruched Slit Midi Dress

    For casual plans and outings, make your look cute in this sleeveless midi dress perfect for inspiring your inner fashionista! It features a square neck, spaghetti straps, a form-hugging fit, a side ruched seam that accentuates your curves, a side slit, and a midi-length hem. Complete the look with a crop jacket and heels!

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Form-hugging fit
    • Side ruched seam, slit
    • Midi-length hem
    • Stretchy brushed knit soft fabric
    • Runs true to size

    Style Number/Barcode: 05102-5290

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale