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.

  • 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
  • Fashion Zilla Mock Neck Texture Mini Dress

    A fashionista like you will go crazy for this iconic mini dress! It features a mock neckline, cap sleeves, and a flattering bodycon silhouette on stylish textured mesh fabric with a stretchy knit lining. Complete the look in sleek sunglasses and booties for an edgy-fab vibe!

    Fit & Features

    • Mock neckline
    • Cap sleeves
    • Bodycon silhouette
    • Mini-length hem
    • Textured mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5278

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Colorful Sensation Abstract Print Maxi Dress

    Be the colorful sensation in whatever room you walk into wearing this abstract print midi dress! It features a sleeveless square neckline, spaghetti straps, a bodycon silhouette, and an adjustable ruched drawstring atop a sultry slit. Complete the look with a chic handbag for an art gallery opening or sunset cocktails!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Adjustable ruched drawstring, high slit
    • Maxi-length hem
    • Abstract print, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5279

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    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
  • Mesmerized By You Marble Print Mini Dress

    Make them mesmerized by your allure in this trendy marble print mini dress! It features a strapless angled neckline with flexible boning inserts to provide structure, a sultry corset-style bodice, a high waist seam, a mini-length hem, and a bodycon silhouette that will flaunt your figure. The lined crepe fabric features an all-over marble print pattern for an eye-catching look. Pair with lace-up heels for a night out.

    Fit & Features

    • Strapless angled neckline, flexible boning inserts
    • Corset-style bodice, back zipper, hook and eye closure
    • High waist seam
    • Mini-length hem, bodycon silhouette
    • Marble print
    • Crepe fabric, full-length knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5254

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Check Me Out Plaid Bodycon Mini Dress

    You'll be the object of everyone's gaze in this trendy plaid bodycon mini dress! It features a sleeveless square neckline, bungee spaghetti straps, a stylish lower back cutout, a mini-length hem, and a bodycon silhouette that will hug your natural curves. The stretchy brushed knit fabric features a chic windowpane plaid print. Complete your look with clear mules!

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Lower back cutout
    • Mini-length hem, bodycon silhouette
    • Plaid print
    • Brushed knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5230

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Style In Check Gingham Skater Dress

    Keep your style in check in this flirty gingham skater dress! It features a sleeveless square neck, spaghetti straps, a flattering skater silhouette, and a short-length hem. The dress is designed with an adorable gingham print on brushed knit fabric with a stretchy lining. Complete your look with a statement choker necklace and heels for a party!

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Skater silhouette
    • Short-length hem
    • Gingham print
    • Brushed knit fabric, stretchy lining
    • Runs true to size

      Style Number/Barcode: 05102-5349

      Category Name: Casual Dresses

      Price: $9.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Artsy Dreamer One Shoulder Abstract Maxi Dress

      Dreaming of an artsy wardorbe? Look no further than this abstract print maxi dress perfect for an art show or gallery opening! It features a sleeveless one-shoulder neckline, tank strap, a bodycon silhouette, and a side ruched seam atop a sultry high slit to show some skin. Complete the look with a rhinestone bracelet and heels.

      Fit & Features

      • Sleeveless one-shoulder neckline, tank strap
      • Bodycon silhouette
      • Side ruched seam, high side slit
      • Maxi-length hem
      • Abstract print, stretchy knit fabric
      • Runs true to size

      Style Number/Barcode: 05102-5258

      Category Name: Casual Dresses

      Price: $5.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Casual Flirt Sleeveless A-Line Short Dress

      Breeze in looking casual and flirty in this short dress at parties and date nights! It features a sleeveless square neck, spaghetti straps, and a flattering A-line silhouette on smooth knit fabric. Complete the look in a necklace and earrings set.

       Fit & Features

      • Sleeveless square neck
      • Spaghetti straps
      • A-line silhouette
      • Short-length hem
      • Smooth knit fabric, stretchy knit lining
      • Runs true to size

      Style Number/Barcode: 05102-5287

      Category Name: Casual Dresses

      Price: $19.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Trendy New Vibe One-Shoulder Skater Dress

      This adorable sleeveless skater dress will give off a trendy new vibe that will get all the compliments. It features an asymmetric one-shoulder neckline, dual adjustable spaghetti straps that continue to an asymmetric back strappy design, dual vertical seams down the front, a short-length hem, and a flared-out skater silhouette. The buttery-smooth knit fabric includes a full lining and has plenty of stretch. Style with clear mules!

      Fit & Features

      • Sleeveless asymmetric one-shoulder neckline
      • Dual adjustable spaghetti straps
      • Asymmetric back strappy design
      • Dual vertical seams down the front
      • Short-length hem, skater silhouette
      • Smooth knit fabric, full-length lining, plenty of stretch
      • Runs true to size

      Style Number/Barcode: 05102-5291

      Category Name: Casual Dresses

      Price: $9.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Shine All Way Metallic Woven Skater Dress

      Shine all way to and from the party in this breezy skater dress! It features a sleeveless V-neck, adjustable spaghetti straps, a stretchy smocked waist, and a flattering skater silhouette with a ruffled short-length hem. The dress is crafted from an airy woven fabric with shimmering metallic threads and has a stretchy knit lining. Complete the look in stiletto heels.

      Fit & Features

      • Sleeveless V-neck
      • Adjustable spaghetti straps
      • Stretchy smocked waist
      • Skater silhouette
      • Ruffled short-length hem
      • Metallic threads, airy woven fabric, stretchy knit lining
      • Runs true to size

      Style Number/Barcode: 05102-5405

      Category Name: Casual Dresses

      Price: $6.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Classic Allure Sleeveless A-Line Short Dress

      Showcase a classic allure in this chic sleeveless A-line short dress. It features a high mock neckline with tie-back straps, an open-back design, a fitted high waist seam, a short-length hem, and a flowy A-line silhouette. The buttery-smooth knit fabric includes a full lining and has plenty of stretch. Complete your look for happy hour with sleek pumps.

      Fit & Features

      • Sleeveless high mock neckline, tie-back straps
      • Open back
      • Fitted high waist seam
      • Short-length hem
      • A-line silhouette
      • Smooth knit fabric, full-length knit lining, plenty of stretch
      • Runs true to size

      Style Number/Barcode: 05102-5288

      Category Name: Casual Dresses

      Price: $5.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Fireside Flirt Off-The-Shoulder Midi Dress

      Minimal effort, maximum slay—this knit midi dress is the definition of chic. With its off-shoulder neckline, peekaboo cutout, and side slit, it’s your new go-to for dinner dates or rooftop wine bars.

      Fit & Features

      • Stretch rib knit fabric
      • Off-the-shoulder neckline
      • Fitted long sleeves
      • Cutout bodice
      • Front slit and button accents
      • Bodycon silhouette, midi-length hem
      • Runs true to size

      Style Number/Barcode: 06005-000118

      Category Name: Casual Dresses

      Price: $6.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Sweet Choice Floral Chiffon A-Line Mini Dress

      A sweet floral mini dress for all of your outdoor soirees! This dreamy dress features adorable short sleeves with ruffle trim, a pleated sweetheart neckline, a flirty open back with dual tie closures, a flattering A-line silhouette, and a ruffled hem. Complete the look with butterfly earrings for a whimsy charm.

      Fit & Features

      • Short sleeves, ruffle trim
      • Pleated sweetheart neckline
      • Open back, dual tie closures
      • A-Line silhouette, ruffled mini-length hem
      • Back zipper and hook-eye closure
      • Artsy floral print, chiffon fabric, woven lining
      • Runs true to size

      Style Number/Barcode: 05102-5388

      Category Name: Casual Dresses

      Price: $5.97 $52.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Ray Of Beauty Ruffled Short Skater Dress

      You'll be a bright ray of beauty in this adorable ruffled short skater dress! It features a V-neckline with a cute tie-front design, a front keyhole cutout, short puff sleeves with a ruffled trim, a high-rise stretchy smocked waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight sheer chiffon fabric includes a partial woven lining. Style with hoop earrings and clear mules for a day date!

      Fit & Features

      • V-neckline, tie-front design, front keyhole cutout 
      • Short puff sleeves, ruffled trim
      • High-rise stretchy smocked waist
      • Short skater skirt, tiered ruffled design
      • Fit and flare silhouette
      • Sheer chiffon fabric, partial woven lining, no stretch
      • Runs true to size

      Style Number/Barcode: 05102-5392

      Category Name: Casual Dresses

      Price: $9.97 $52.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Momemt To Marvel Chiffon A-Line Short Dress

      Everyone will take a moment to marvel at you in this breezy chiffon short dress perfect for an afternoon lunch date! Featuring a sleeveless cowl neckline adorned with self-tie spaghetti straps, a flirty low back design, a tie-waist belt, an A-line silhouette, and a short-length hem. The dress is designed with a dreamy marble print on airy chiffon fabric with a woven lining. Complete the look with a chic mini handbag and sandals.

      Fit & Features

      • Sleeveless cowl neckline
      • Self-tie spaghetti stra[s
      • Low-back design, hidden zipper and hook-eye closure
      • Tie-waist belt
      • A-line silhouette, short-length hem
      • Marble printed chiffon fabric, woven lining
      • Runs true to size

      Style Number/Barcode: 05102-5393

      Category Name: Casual Dresses

      Price: $6.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Kiss The Sky Floral Paisley A-Line Dress

      Look sky-high in this adorable floral paisley short dress! This stylish little number features a sleeveless, cowl neckline, crisscross open back, self-tie spaghetti straps that cross along the open back, a flattering A-line silhouette, and a ruffled hem. Complete the look with sassy stiletto heels for a dressy brunch or birthday!

      Fit & Features

      • Sleeveless cowl neckline
      • Self-tie spaghetti straps
      • Crisscross open back, hidden zipper and hook-eye closure
      • A-Line silhouette, short-length ruffle hem
      • Floral paisley print
      • Lined woven fabric, no stretch
      • Runs true to size

      Style Number/Barcode: 05102-5386

      Category Name: Casual Dresses

      Price: $5.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Season Of Fun Denim Collared A-Line Mini Dress

      It's the season of fun with this casual and cute denim mini dress perfect for everyday styling! It features long sleeves with dual button cuffs, a collared neckline, button-down front closures, two flap pockets, a belted waist with buckle closure, and a flattering A-line silhouette. Complete the look in sleek hoop earrings.

      Fit & Features

      • Long sleeves, dual button cuffs
      • Collared neckline
      • Button-down front closures, two flap pockets
      • Belted waist, buckle closure, belt loop accents
      • A-line silhouette, mini-length hem
      • Denim fabric, slight stretch
      • Runs true to size

      Style Number/Barcode: 05102-5402

      Category Name: Casual Dresses

      Price: $9.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Obsessed With Floral Chiffon Skater Dress

      Obsessed with floral? Let this chiffon skater dress into your blossoming collection! It features cap sleeves, a scoop neckline, a flirty front lace-up along the stretchy smocked bodice, and a flattering and flowy short-length hem. Complete the look with earrings and heels for a dressy occasion!

      Fit & Features

      • Cap sleeves
      • Scoop neckline
      • Front lace-up, stretchy smocked bodice
      • Skater silhouette, short-length hem
      • Back zipper and hook-eye closure
      • Floral print, airy chiffon fabric, woven lining, no stretch
      • Runs true to size

      Style Number/Barcode: 05102-5391

      Category Name: Casual Dresses

      Price: $5.97 $52.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Picking Daisies Chiffon Strappy Skater Dress

      The perfect dress you'll want to pluck from the garden! This dreamy skater dress features adorable puff short sleeves, a square neckline, and pleated bust, a cutout strappy front and back with ties, and a short-length hem on daisy printed chiffon fabric. Complete the look in cute sandals for a family party!

      Fit & Features

      • Puff short sleeves
      • Square neckline, pleated bust
      • Cutout strappy front and back, tie closure
      • Back hidden zipper and hook-eye closure
      • Skater-silhouette, short-length hem
      • Dainty printed chiffon fabric, woven lining, no stretch
      • Runs true to size

      Style Number/Barcode: 05102-5389

      Category Name: Casual Dresses

      Price: $9.97 $52.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Enchanting Romance Floral Chiffon Short Dress

      This airy floral chiffon short dress will make an enchanting entrance on your next date! It features a sleeveless sweetheart neckline with a built-in padded bust, a tie-front design with a small front keyhole cutout, tie-shoulder spaghetti straps, ruffled accents cascading down the dress, a short-length hem, and a flowy A-line silhouette. The blooming floral print chiffon fabric includes a full-length woven lining. Style with clear mules!

      Fit & Features

      • Sleeveless sweetheart neckline, padded bust
      • Tie-front design, small keyhole cutout
      • Tie-shoulder spaghetti straps, gold metal accents
      • High waist seam, hidden back zipper, hook and eye closure
      • Ruffled accents, short-length hem, A-line silhouette
      • Floral print, sheer chiffon fabric, woven lining, no stretch
      • Runs true to size

      Style Number/Barcode: 05102-5390

      Category Name: Casual Dresses

      Price: $9.97 $52.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Swirls Of Attraction Strappy Marble Print Midi Dress

      Attract all the attention when you step out in this marble print midi dress for dinner and drinks! It features a sleeveless scoop neckline, spaghetti straps, an open strappy back design, a bodycon silhouette, and a flattering side ruched seam and slit along the asymmetrical hem. Complete the look with a fab earrings set and heels.

      Fit & Features

      • Sleeveless scoop neckline, spaghetti straps
      • Open strappy back design
      • Bodycon silhouette
      • Side ruched seam and slit
      • Asymmetrical midi-length hem
      • Marble print, stretchy knit fabric
      • Runs true to size

      Style Number/Barcode: 05102-5259

      Category Name: Casual Dresses

      Price: $5.97 $37.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Flaunt Your 'Fit Ruched Bodycon Midi Dress

      You'll want to flaunt your sultry 'fit in this ruched bodycon midi dress that will showcase your gorgeous figure! It features a sleeveless sweetheart neckline with a padded bust, a twist-front design with a center keyhole cutout, spaghetti straps, ruching down the side seams, and a midi-length hem with a curve-hugging silhouette. The slinky knit fabric includes a full-length lining and has plenty of stretch. Style with lace-up heels!

      Fit & Features

      • Sleeveless sweetheart neckline, padded bust
      • Twist-front design, center cutout
      • Spaghetti straps
      • Ruched side seams
      • Midi-length hem, bodycon silhouette
      • Slinky knit fabric, full-length lining, plenty of stretch
      • Runs true to size

      Style Number/Barcode: 05101-2817

      Category Name: Casual Dresses

      Price: $5.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Frolic In Floral Tie Midi Dress

      Frolic all over town in this floral midi dress perfect for an afternoon tea with the girls! It features a sleeveless V-neck, spaghetti straps, a knot tie bust, a curve-hugging silhouette, and a flirty front slit. The dress is designed with a ditsy floral bud print on stretchy knit fabric. Complete the look in trendy wedge sandals.

      Fit & Features

      • Sleeveless V-neck
      • Spaghetti straps
      • Knot tie bust
      • Curve-hugging silhouette
      • Front slit, midi-length hem
      • Ditsy floral bud print, moderate stretch
      • Runs true to size

      Style Number/Barcode: 05102-4865

      Category Name: Casual Dresses

      Price: $19.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale