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.

  • Sweetest Allure Strapless Floral Eyelet Knit Midi Dress

    Give off the sweetest allure this summer season in this floral eyelet knit midi dress! The stretchy sheer eyelet knit fabric is detailed with an adorable ditsy floral print and includes a full knit lining for coverage. The mid-length dress features a strapless straight-across elasticized neckline and a bodycon silhouette to highlight your gorgeous figure. Style with espadrille wedges for weekend brunch!

    Fit & Features

    • Stretchy sheer eyelet knit fabric, full knit lining
    • Ditsy floral print
    • Strapless straight elasticized neckline
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5488

    Category Name: Casual Dresses

    Price: $5.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Whimsical Beauty Strappy Back Textured Knit Skater Dress

    Radiate whimsical beauty in this gorgeous textured knit skater dress perfect for graduations or parties! The sheer textured knit fabric includes a full-length knit lining and offers plenty of stretch. The dress is shaped with a sleeveless square neckline and dual spaghetti straps leading to a bold open back with a cross-back strappy design. The high waist flows out to a short skater skirt with an adorable fit and flare silhouette. Style with hoop earrings and espadrille sandals.

    Fit & Features

    • Sheer textured knit fabric, full-length knit lining
    • Plenty of stretch
    • Square neckline, dual spaghetti straps
    • Open back, cross-back strappy design
    • High waist, short skater skirt
    • Fit and flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3142

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Floral Mindset Lace Up Mini Dress

    Discover your new mindset in this floral mini dress perfect for wedding showers or brunch! This bodycon dress features a square neckline, spaghetti straps, and a lace-up back for a flirtatious appeal. The side ruched seams accentuate your curves even more on the soft brushed knit fabric that offers a stretchy knit lining for coverage. Complete the look with a trendy purse.

    Fit & Features

    • Brushed knit soft fabric lined with stretchy knit
    • Ditsy floral print
    • Spaghetti straps, lace-up 
    • Side ruched seams
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5489

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Vibes Long Sleeve Chiffon Skater Dress

    This dreamy long sleeve chiffon skater dress has a flowy silhouette to give you that effortlessly ethereal look! The short dress is crafted with an airy sheer chiffon fabric for a lightweight feel, and includes a partial knit lining for coverage. The bodice is shaped with a V-neckline with a chic pleated surplice design, and the sheer long balloon sleeves have cinched hems. The back features a partially smocked design for added stretch. The high waist seam flows out to a short skater skirt with a fit and flare silhouette and a faux wrap-front design. Complete your outfit with block heels for a bridal shower or birthday party!

    Fit & Features

    • Sheer non-stretch chiffon fabric, partial knit lining
    • V-neckline with pleated surplice design
    • Long unlined balloon sleeves, elastic cinched hems
    • Smocked back, zipper with hook and eye closure
    • High waist seam
    • Short skater silhouette, faux wrap-front design
    • Runs true to size

    Style Number/Barcode: 05101-3139

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Favorite Fleur V-Neck Floral Chiffon Skater Dress

    Give them a twirl in this adorable floral chiffon skater dress at birthdays or graduation parties! Featuring puff short sleeves, a tie front bust, and a stretch smocked empire waist, this dress will hug your curves in all the right places. The skater silhouette and ruffled hem add a playful touch to this flowy chiffon dress. Complete the look with teardrop earrings.

    Fit & Features

    • Floral print, chiffon fabric lined with stretchy knit
    • V-Neckline, tie front
    • Skater silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05101-3135

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jet Set For Sun Strapless Tropical Midi Dress

    Jet set for fun under the sun in this tropical midi dress for endless compliments while on vacation! The midi-length dress features a strapless neckline, a form-hugging silhouette, a flirty side slit and asymmetrical hem, and an adjustable side drawstring so you customize the style. Complete the look in sandals for a sunset dinner!

    Fit & Features

    • Strapless neckline
    • Form-hugging silhouette
    • Adjustable side drawstring, side slit
    • Asymmetrical midi-length hem
    • Tropical print, mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5486

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Gorgeous Arrival Rose Floral Chiffon Maxi Dress

    Make a gorgeous arrival in this rose floral chiffon maxi dress for showers, birthdays, or family parties! The sweetheart neckline and adjustable spaghetti straps provide a flattering and comfortable fit, while the padded bra cups offer support and shape. The maxi-length hem and high front slit add a touch of sultry, making you feel so beautiful! Complete the look in chic wedge sandals and sunnies.

    Fit & Features

    • Rose floral print
    • Chiffon fabric lined with stretchy knit
    • Padded bra cups, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • High front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3128

    Category Name: Casual Dresses

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Swing Into The Season Tie-Back Eyelet Skater Dress

    Swing into the season in this charming eyelet skater dress perfect for birthday brunch to day dates! The cap sleeves and sweetheart neckline add a touch of romance, while the padded bra cups provide support. The tie-back design and fitted bodice add a playful twist to the skater silhouette and flirty ruffled short-length hem. Complete the look in strappy platform sandals and a purse!

    Fit & Features

    • Eyelet lace fabric with woven lining
    • Padded bra cups
    • Tie-back closure
    • Skater silhouette
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3121

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Flair Ruffled Wrap Chiffon Mini Dress

    This adorable floral chiffon mini dress will bring the flirty flair to your spring parties! Designed with a dainty floral print on lightweight lined chiffon fabric. This mini-length dress features a sleeveless sweetheart neckline with a built-in padded bust, spaghetti straps that lead to an open back with a cross-back strappy design, and a corset-style bodice with a fitted high waist. The A-line silhouette has a faux wrap-front creating the cutest asymmetric ruffled hem. Complete your look with strappy sandals.

    Fit & Features

    • Sheer chiffon fabric with knit lining, minimal stretch, dainty floral print
    • Sleeveless sweetheart neckline, padded bust
    • Spaghetti straps
    • Open back, cross-back straps with tie closure, lower zipper, hook and eye closure
    • Corset bodice, high waist seam
    • Faux wrap-front, asymmetric ruffled hem, A-line fit
    • Runs true to size

    Style Number/Barcode: 05101-3113

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Flair High Slit Ditsy Floral Knit Midi Dress

    Bring the sweet flair to date night in this high slit ditsy floral midi dress! The all-over ditsy floral print on the stretchy knit fabric is the perfect amount of sweetness with the sultry details of the mid-length dress. The sleeveless scoop neckline features a tie-front at the bust for a cute touch, spaghetti straps, an alluring thigh-high side slit to showcase some leg, and a slim-fit silhouette to showcase your figure. Style this midi dress with a faux leather jacket and heels!

    Fit & Features

    • Ditsy floral print, stretchy knit fabric
    • Sleeveless scoop neckline with bust tie
    • Spaghetti straps
    • Thigh-high side slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5485

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Smooth Silhouette Crew Neck Cutout Midi Dress

    Dress this smooth midi dress up or down for any occasion! With a sleek crew neckline and sultry front cutout with bar trim, this bodycon dress accentuates your curves for a flattering fit. Made with buttery soft fabric that has a stretchy knit lining, you'll feel both sexy and comfortable. Complete the look in a moto jacket and boots for weekend plans!

    Fit & Features

    • Sleeveless crew neckline
    • Front cutout with bar trim
    • Bodycon silhouette
    • Midi-length hem
    • Smooth buttery soft knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5482

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daydream Tie-Dye Bodycon Mini Dress

    You'll be lookin' like a daydream in this trendy tie-dye bodycon mini dress! Designed with an asymmetric tie-dye pattern on the airy mesh fabric, it features a sleeveless square neckline, bungee spaghetti straps, ruching down the side seams, a mini-length hem, and a bodycon silhouette to accentuate your curves. The sheer mesh fabric includes a full-length knit lining. Style this short dress with platform heels.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruched side seams
    • Mini-length hem, bodycon fit
    • Asymmetric tie-dye pattern
    • Sheer mesh fabric, full-length sewn-in knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5481

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Iconic Occasion Strapless Denim Mini Dress

    Impress with your OOTD in this strapless denim mini dress to channel iconic moments! The strapless neckline flaunts some skin, the flattering bodycon fit with flexible boning hugs your curves, and the mini-length hem adds a touch of playfulness. Complete the look in chic pointed-toe boots and a purse!

    Fit & Features

    • Denim fabric, stretchy knit lining
    • Strapless neckline
    • Back zipper and hook-eye closure
    • Flexible boning
    • Bodycon fit
    • Style runs large

    Style Number/Barcode: 05102-5484

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Blossom Sweetheart Floral Mesh Mini Dress

    Your amount of admirers will blossom when they see you in this sultry floral mesh mini dress! This flirty mini dress features a sweetheart neckline and padded bra cups for a flattering fit. Its adjustable spaghetti straps and ruched seams ensure the perfect bodycon silhouette. Complete the look in block heels.

    Fit & Features

    • Floral print, mesh fabric, sewn-in knit lining, moderate stretch
    • Sweetheart neckline
    • Adjustable spaghetti straps, padded bra cups
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5478

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Side Of Town Strapless Mesh Midi Dress

    Strut on looking chic in this strapless mesh midi dress on the town! Designed to flaunt your curves in a bodycon silhouette with side ruched seams, this midi dress is a total showstopper. Plus, the unique marble print on the lined mesh fabric is sure to receive many compliments! Style this dress with strappy heels to elevate your look.

    Fit & Features

    • Marble print, mesh fabric lined with knit
    • Side ruched seams
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5474

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Day Gal Strapless Ruffled Skater Dress

    Let your shoulders out in this strapless skater dress suited best for sunny days! This dress features a stretchy smocked bodice for a comfortable fit and a skater silhouette that will flatter your figure. The layered ruffled short-length hem adds a playful touch, and the cotton woven fabric ensures all-day comfort. Complete the look with a choker necklace.

    Fit & Features

    • Cotton woven fabric
    • Strapless straight neckline, no-slip strip
    • Stretchy smocked bodice
    • Layered ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5476

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tell Me About It Stud Strapless Denim Mini Dress

    Be the talk of the night in this strapless denim mini dress at parties or concerts! With a strapless neckline and non-slip grip lining, this bodycon dress ensures a perfect fit. The studded trim adds a touch of edgy charm, while the mini-length hem accentuates your legs. Complete the look in knee-high boots and a cowboy hat!

    Fit & Features

    • Denim fabric, slight stretch
    • Strapless neckline, non-slip grip lining
    • Back zipper and hook-eye closure
    • Studded trim along the front
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5473

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendsetting Effect Ruffled Denim Skater Dress

    You'll always make a trendsetting impression in this denim skater dress perfect for country concerts or the fair. Featuring a square neckline, wide shoulder straps, and faux button closures, this dress flatters your figure with its underbust seam and skater silhouette. The ruffled hem adds a fun touch to the stylish denim twill fabric. Complete the look in cute cowboy boots.

    Fit & Features

    • Denim twill fabric with minimal stretch
    • Square neckline
    • Wide shoulder straps
    • Back zipper and hook-eye closure
    • Ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5472

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Going Places Strapless A-Line Pleat Denim Mini Dress

    Look cute in this denim mini dress for all of the places you're going to! This dress features a strapless neckline with a non-slip grip lining for a secure fit. The fitted A-line silhouette flatters your figure, while the belted waist adds a trendy look to the pleated mini-length hem. Complete the look with hoop earrings and sandals!

    Fit & Features

    • Denim fabric with stretch
    • Non-slip grip lining, back zipper closure
    • Belted waist
    • Fitted A-line silhouette
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5471

    Category Name: Casual Dresses

    Price: $52.90

    Availability: Out of Stock

    Product Badge:
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  • Lively Elegance Smocked Floral Babydoll Dress

    Indulge in elegance in this elegant floral babydoll dress perfect for wedding showers or graduations! With its stretchy smocked bodice and adjustable straps, you'll get a perfect fit. The chiffon fabric and vibrant floral print add a touch of elegance to the playful babydoll silhouette and ruffled short-length hem. Complete the look in sandals.

    Fit & Features

    • Floral print, chiffon fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Stretchy smocked bodice
    • Babydoll silhouette
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5470

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • My Main Chic V-Neck Ruched Midi Dress

    Ultra-flattering and soft, this sleeveless midi dress will be your main chic style! The knee-length dress is designed with a classic V-neckline, spaghetti straps, side ruched seams, and a bodycon silhouette that shows off your curves on smooth-lined knit fabric. Complete the look with stiletto heels for a birthday brunch or bridal shower!

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Side ruched seams, bodycon silhouette
    • Midi-length hem
    • Lined smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5479

    Category Name: Casual Dresses

    Price: $6.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fabulous Icon Sleeveless Ribbed Knit Midi Dress

    An iconic knit midi dress that can go from day to night! Crafted from soft and stretchy ribbed knit fabric, this sleeveless dress offers a stylish square neckline, a flattering underbust seam, and a bodycon silhouette that will hug your curves in all the right places. Complete the look with a moto jacket and stiletto heels for a chic style.

    Fit & Features

    • Soft, stretchy ribbed knit fabric
    • Square neckline
    • Underbust seam
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-1853

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Impress Me Pinstripe Strapless Mini Dress

    This pinstripe mini dress is sure to impress! Featuring a strapless foldover neckline with non-slip grip lining, a stretchy smocked back, form-hugging silhouette, and a flirty front slit along the hem. Complete the look in a cropped blazer for a posh vibe!

    Fit & Features

    • Strapless foldover neckline
    • Non-slip grip lining
    • Stretchy smocked back
    • Form-hugging silhouette, front slit, mini-length hem
    • Back zipper and hook-eye closure
    • Pinstripe print, woven fabric, and lining
    • Runs true to size

    Style Number/Barcode: 05102-5469

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fawn Over You Marble Print Chiffon Skater Dress

    You'll be fawned over when in this marble print chiffon skater dress! From the adjustable spaghetti straps to the flattering square neckline, this dress has got you covered. The stretchy smocked bodice creates a comfortable and perfect fit, while the tie waist belt accentuates your curves. With a playful ruffled tiered short-length hem, this dress is perfect for twirling! Complete the look in wedges for a dressy occasion.

    Fit & Features

    • Marble print, chiffon lined fabric
    • Adjustable spaghetti straps
    • Square neckline
    • Tie waist belt, ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3081

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale