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.

  • 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:
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  • 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:
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  • 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:
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  • 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:
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  • 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:
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  • 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:
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  • 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:
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  • 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:
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  • 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
  • Look So Sweet Floral Applique Skater Party Dress

    Effortlessly steal the show in this skater party dress at graduations or showers! Made with organza sheer fabric and adorned with delicate floral applique, this dress is sure to turn heads and make you feel like the belle of the ball. Designed with a flattering square neckline and adjustable spaghetti straps, the skater silhouette and short-length hem exude flirty charm so everyone will fall for you! Complete the look in strappy platform heels.

    Fit & Features

    • Floral appliques
    • Sheer organza fabric with woven lining
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3084

    Category Name: Casual Dresses

    Price: $56.90

    Availability: Out of Stock

    Product Badge:
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  • Compliment Collector Corset Eyelet Skater Dress

    You'll be collecting all the compliments in this heart eyelet skater dress perfect for brides-to-be, birthday girlies, and graduates! This playful dress features puff short sleeves, a sweetheart neckline, and a corset bodice with flexible boning for a flattering fit. The skater silhouette and short-length hem make it perfect for any occasion. Complete the look in wedge sandals.

    Fit & Features

    • Eyelet heart pattern fabric, woven lining
    • Sweetheart neckline
    • Flexible boning
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3080

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Covetable Charm Strapless Mini Skater Dress

    From casual outings to chic occasions, this strapless skater dress is one you'll covet for charming looks every time! The non-slip grip lining along the strapless neckline ensures a secure fit while the ruched bodycon bodice flatters your figure. The skater silhouette and pleated short-length hem add a playful touch to this poplin dress! Complete the look in sandals and sunnies.

    Fit & Features

    • Poplin stretchy fabric, sewn-in knit lining
    • Back zipper and hook-eye closure
    • Strapless square neckline
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3079

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ray Of Beauty Lace-Up Corset Skater Dress

    You'll be a ray of beauty in this chic lace-up corset skater dress! Designed with a lightweight woven fabric with a stretchy knit lining, this adorable short dress captures the summer season. It features an alluring sleeveless corset-style bodice with a ruched sweetheart neckline and a tie-front detail at the bust. The thin adjustable tank straps lead to a lace-up strappy back design to find your perfect fit. The angled high waist seam flows out to a fit-and-flare skater silhouette with pleating for a flirtatious vibe. Complete the look with platform heels!

    Fit & Features

    • Cotton woven fabric, stretchy knit lining
    • Corset-style bodice, ruched sweetheart neckline, tie-front bust
    • Thin adjustable tank straps
    • Lace-up strappy back, tie closure
    • Side zipper with hook and eye closure
    • Fit-and-flare skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3641

    Category Name: Casual Dresses

    Price: $11.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picturesque Cutie Corset Lace-Up A-Line Midi Dress

    Create a cute picturesque 'fit in this corset A-line midi dress! The corset bodice and lace-up back add a touch of allure to the sweet silhouette.

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Sweetheart neckline, tie-front detail
    • Thin adjustable straps
    • Corset bodice, lace-up back
    • High waist seam
    • Midi-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3069

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunny Days Off Scoop Neck Smocked Skater Dress

    Grab your favorite sunnies cause it's time to take a sunny stroll in this skater dress down by the beach or to the coffee shop! With adjustable straps and a stretchy smocked bust, this dress provides the perfect fit every time. The playful ruffled skater silhouette and short-length hem make it a must-have for any sunny day. Complete the look with strappy sandals.

    Fit & Features

    • Airy woven fabric with woven lining
    • Adjustable spaghetti straps
    • Scoop neckline
    • Stretchy smocked bust
    • Ruffled skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5462

    Category Name: Casual Dresses

    Price: $39.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Patchwork It Belted Denim Mini Dress

    Elevate your style with this patchwork denim mini dress! Featuring a flattering square neckline, spaghetti straps, and a bodycon silhouette, this dress will hug your curves in all the right places. The exposed front zipper closure and flap pockets add a modern touch, while the adjustable waist belt cinches your waist for a perfect fit. Complete the look with platform heels for a daytime party!

    Fit & Features

    • Patchwork design
    • Non-stretch denim fabric
    • Exposed front zipper closure
    • Adjustable waist belt
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5459

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tea Time Ruffled Short Skater Dress

    It's time for afternoon tea and this skater dress will make an adorable entrance! Get ready to sashay in this dress featuring a ruffle trim square neckline and tiered ruffled short-length hem to add a playful touch to the skater silhouette. And with adjustable spaghetti straps and a stretchy smocked bodice, you'll be comfortable all day. Complete the look in chic wedges and a flouncy hat.

    Fit & Features

    • Woven fabric lined with woven fabric
    • Ruffle trim neckline
    • Adjustable spaghetti straps
    • Stretchy smocked bodice
    • Tiered ruffled short-length hem
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3059

    Category Name: Casual Dresses

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Darling Appeal Sleeveless Ruffled Midi Dress

    You'll always give off a darling appeal in this sleeveless midi dress for casual occasions! With a classic square neckline and dual spaghetti straps, this dress is perfect for any occasion. The stretchy smocked bodice ensures a comfortable fit while the A-line silhouette and ruffled midi-length hem add a flattering touch. Complete the look in sandals and a crossbody bag.

    Fit & Features

    • Woven fabric, no stretch
    • Square neckline
    • Dual spaghetti straps
    • Stretchy smocked bodice
    • A-Line ruffled silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5457

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charming Style Puff Sleeve Chiffon Skater Dress

    Create the sweetest charming style for your spring and summer parties in this chiffon skater dress! The airy sheer chiffon fabric offers that breezy lightweight feel and includes a stretchy knit lining for coverage. The short dress features a ruched square neckline, adorable short puff sleeves, dual high waist seams, and a fit-and-flare skater silhouette for a flirty vibe with a ruffled hem. Pair with sneakers for a cute and casual look!

    Fit & Features

    • Sheer chiffon fabric with stretchy knit lining
    • Ruched square neckline
    • Short puff sleeves with elasticized hems
    • High waist seams, back zipper with hook and eye closure
    • Skater silhouette, ruffled hem
    • Runs true to size

    Style Number/Barcode: 05101-3056

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Delightfully Chic Ruffled Floral Chiffon Midi Dress

    Create a delightfully chic outfit for weekend parties in this airy floral chiffon midi dress! Designed with a lightweight sheer chiffon fabric with a lining for coverage, this mid-length dress is accented with a blooming rose print in subtle hues for a simply gorgeous look. It features a square neckline, adjustable spaghetti straps with dainty ruffled accents, a fitted high waist, and a flowy A-line silhouette detailed with a high front slit and feminine ruffled hem. Complete the look with hoop earrings.

    Fit & Features

    • Rose-printed chiffon fabric, stretchy knit lining
    • Square neckline
    • Adjustable spaghetti straps with ruffled accents
    • High waist, back zipper with hook-eye closure
    • A-line fit
    • Front slit, ruffled hem
    • Runs true to size

    Style Number/Barcode: 05101-3046

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale