Casual Dresses

Loading...

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.

  • All This Allure Strappy Halter A-Line Skater Dress

    You'll be irresistible in this A-line skater dress on a night out! This stunning dress features a plunging halter neckline and a strappy back, adding a touch of allure to any occasion, while the mini-length hem offers a flirty touch.

    Fit & Features

    • Smooth knit fabric, stretchy knit lining
    • Plunge halter neckline, bar accent, tie straps
    • Strappy back with spaghetti strap tie
    • A-Line skater silhouette
    • Seam detailing, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000102

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M

  • Definition Of Cute Off-The-Shoulder Mini Dress

    Prance around like the cutie you are in this off-the-shoulder mini dress! The playful ruffles add movement and feminine charm while the flattering form-hugging silhouette showcases your curves.

    Fit & Features

    • Woven smocked stretchy fabric
    • Ruffle off-the-shoulder neckline
    • Form-hugging silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000096

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Always Eye-Catching Halter Ruffle Chiffon Mini Dress

    You'll look positively eye-catching in this floral mini dress at weddings or garden parties! The halter crew neckline and open back ooze elegance, while the ruffled bodycon silhouette flatters your curves. With a mini-length hem, this dress is perfect for any occasion. Complete the look with earrings.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Halter crew neckline, spaghetti strap tie
    • Open back
    • Ruffled bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5627

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Arrived In Style Strapless Knit Mini Dress

    Arrive in this stylish strapless mini dress for brunch or parties! The contrasting folded neckline adds a touch of boldness while the slim-fit silhouette shows off your curves perfectly on the smooth knit fabric. The mini-length hem features a subtle A-line fit. Complete the look in platform heels.

    Fit & Features

    • Smooth knit fabric lined with stretchy knit
    • Strapless folded contrast neckline
    • Slim-fit silhouette
    • Mini-length A-line hem
    • Runs true to size

    Style Number/Barcode: 05102-5621

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bohemian-Chic Geometric Striped Halter Maxi Dress

    Channel a bohemian chic vibe with this breezy halter maxi dress perfect for summer. The lightweight woven fabric showcases a geometric striped print in stylish neutral hues. The long dress features a sleeveless plunging V-neckline, halter spaghetti straps that can be crossed in the front for a trendy look, and a tie-back design at the neck. The alluring open back leads to lower tie-back straps and a lower cutout accent. You'll love the hidden side pockets and high side slit on the effortless, flowy silhouette. Complete the look with strappy sandals.

    Fit & Features

    • Geometric striped print
    • Woven fabric, no stretch
    • Plunge V-neckline, halter spaghetti straps, tie-back design
    • Open back, lower tie-back straps, lower cutout
    • Side pockets
    • Side slit, flowy fit
    • Runs true to size

    Style Number/Barcode: 05102-5842

    Category Name: Casual Dresses

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • Spring Has Sprung Floral Woven Skater Dress

    Let your beauty bloom in this adorable floral woven skater dress! The lightweight lined woven fabric is accented with a dainty floral print for the sweetest allure. The short dress features a sleeveless sweetheart neckline with a padded bust and structured underwire for support. The corset-style bodice will snatch your waist and highlight your bust with a tie-front detail. The thin smocked shoulder straps lead to a smocked back design for added stretch with a zipper closure. The high waist flows out to a short skater skirt with a trendy bubble hem and a fit and flare silhouette. Pair with platform heels for the cutest party look!

    Fit & Features

    • Floral woven fabric with knit lining, minimal stretch
    • Sleeveless sweetheart neckline, padded bust with underwire
    • Thin tank shoulder straps
    • Smocked back design, zipper and hook and eye closure
    • Corset bodice, tie-front detail, high waist seam
    • Short skater skirt with bubble hem, fit and flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3187

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Sunshine Puff Sleeve Floral Babydoll Dress

    Sipping mocktails in the sunshine is always cuter in this floral babydoll dress perfect for showers and graduations! The artsy floral print adds a touch of whimsy, while the organza sheer fabric keeps you comfortable and breezy. Boasting sheer puff sleeves, a square neckline, and a short-length babydoll silhouette that is so flattering! Complete the look in dainty earrings and heels.

    Fit & Features

    • Artsy floral print
    • Sheer organza woven fabric, stretchy knit lining
    • Square neckline
    • Short puff sleeves with ruffled hems
    • Back zipper with hook and eye closure
    • Babydoll silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3005

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tuscan Charm Strapless Slit Eyelet Maxi Dress

    You'll be so charming in Tuscan wearing this eyelet maxi dress as the stunning new bride or chic traveler! The eyelet fabric adds a touch of delicacy, making it the perfect dress for any occasion. With a form-hugging fit and a high-side slit, this dress exudes confidence and elegance! Complete the look with earrings.

    Fit & Features

    • Eyelet fabric, sewn-knit lining, minimal stretch
    • Strapless neckline
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5637

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    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
  • Vineyard Gal Floral Woven Skater Dress

    This vintage-inspired floral woven dress is perfect for vineyard weddings, wine tastings, and daytime soirees! The skater dress features adorable short puff sleeves, a sweetheart neckline with a bust tie, a lace-up back design, and a tiered fit-and-flare skater silhouette with a short hem. The lined woven fabric showcases a vintage floral print pattern. Style this short dress with on-trend strappy mules.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline, bust tie
    • Lace-up back design, tie closure
    • Tiered fit-and-flare skater silhouette
    • Short-length hem
    • Vintage floral print, lined woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2966

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Admired Scoop Neck A-Line Mini Dress

    You'll always admire having this sleeveless mini dress for dressing up or down! Made from lined stretchy rib knit fabric, this dress hugs your curves in a flattering A-line silhouette. The scoop neckline and thin spaghetti straps add a flattering look. Style with a cute jacket and your favorite sneakers!

    Fit & Features

    • Stretchy rib knit fabric, full knit lining
    • Spaghetti straps
    • Curve-hugging, A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5652

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always On Point Ruched Knit Mini Dress

    This trendy ruched knit mini dress will have your everyday 'fits always on point! Made with a stretchy ribbed knit fabric for comfortable wear, this mini-length dress features a sleeveless scoop neckline with thin tank shoulder straps and ruched detailing to accentuate your curves on the bodycon silhouette. Style with a boyfriend blazer and heels for happy hour!

    Fit & Features

    • Stretchy ribbed knit fabric lined with knit
    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Ruching
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5569

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Forever Chic Sleeveless Wrap Mini Dress

    You'll look forever chic in this sleeveless wrap mini dress perf for everyday styling! Designed with a stretchy brushed knit fabric, it features a double-lined design at the top for added coverage. The mini-length dress is shaped with a square neckline, thin tank shoulder straps, a faux wrap-front with the cutest tie detail at the waist, and a form-hugging fit to showcase your curves. Pair with slip-on sandals.

    Fit & Features

    • Stretchy brushed knit fabric, double-lined top
    • Square neckline
    • Tank straps
    • Faux wrap-front with tie detail
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5761

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Oh-So-Cute Puff Sleeve Lace-Up Gingham Mini Dress

    Oh-so-cute and sweet! This gingham mini dress is sure to charm at brunch and picnics. You'll have comfort and style, made from a gauze woven fabric boasting a cheery gingham print line with a stretchy knit. With puff sleeves and a V-neckline, this bodycon dress flatters your figure and adds a fun touch with its lace-up back. The mini-length hem and playful gingham print make it perfect for any spring-to-summer event. Complete the look in sandals and sunnies!

    Fit & Features

    • Gingham print, gauze woven fabric lined with stretchy knit
    • V-neckline
    • Lace-up, back zipper and hook-eye closure
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5438

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bon Voyage Sweetheart Floral Chiffon Skater Dress

    Say bon voyage looking darling in this floral chiffon skater dress whether you're heading out on your honeymoon or a trip abroad! Made from an airy chiffon fabric showcasing an adorable ditsy floral print that will make you stand out in the crowd. The sweetheart neckline and bust tie add a touch of romance while the skater silhouette and ruffled hem give it a playful twist. Complete the look with luxe earrings.

    Fit & Features

    • Ditsy floral print, chiffon fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • Sweetheart neckline
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5714

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt Alert Strapless Ruffle Mini Dress

    Bring the playful drama—this strapless mini dress hugs in all the right places with ruched detail and finishes with a flirty ruffle hem. Perfect for nights when you want your dress to do all the talking.

    Fit & Features

    • Smooth knit stretch fabric
    • Tube strapless neckline
    • Bodycon fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000274

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Forever Sweet Off-The-Shoulder Mesh Mini Dress

    Be the center of attention in this sweet mesh mini dress for birthday brunches or tea parties! The off-the-shoulder sweetheart neckline and sheer puff sleeves add a touch of romance, while the padded bust and ruched seams enhance your figure. Made with swiss dot mesh fabric, this bodycon dress also features adjustable drawstrings for a customizable fit. Complete the look in flat sandals and a purse for a cute style!

    Fit & Features

    • Swiss dot mesh stretchy fabric lined with knit
    • Padded bra cups
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3254

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Into Action Floral Skater Dress

    Spring into your seasonal closet by adding this floral skater dress! It features a sleeveless V-neck, adjustable spaghetti straps, a ruched bust with tie-front detail, and a fit-and-flare silhouette with a short ruffled hem. The dress is composed of chiffon fabric with a stretchy knit lining. Complete the look in trendy wedge sandals and a bracelet.

    Fit & Features

    • Sleeveless V-neck, adjustable spaghetti straps
    • Ruched bust, tie-front detail
    • Back zipper and hook-eye closure
    • Fit and flare skater silhouette
    • Short ruffled hem
    • Floral print, chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4889

    Category Name: Casual Dresses

    Price: $5.97 $43.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • RSVP To Cute Ditsy Wildflower Tie A-Line Midi Dress

    RSVP yes to shower or birthday invites when you have this cute ditsy wildflower tie A-line midi dress in your closet! Embellished with a ditsy wildflower print, this midi-length dress is sure to turn heads. With short puff sleeves and a square neckline, this dress is perfect for casual-dressy occasions. The tie front bust adds a touch of whimsy while the a-line silhouette and front slit provide movement and a flattering look. Complete the look with luxe earrings and tennis shoes.

    Fit & Features

    • Ditsy wildflower print
    • Woven fabric lined with stretchy knit
    • Tie front bust, back zipper and hook-eye closure
    • Front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3008

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Oopsie Daisy Sleeveless A-Line Mini Dress

    Oopsie daisy this sleeveless mini dress must've caught you by a sweet surprise! Crafted from a soft brushed knit fabric with an adorable floral print, this dress is a must-have for spring and summer. Features a flattering V-neckline with an adjustable drawstring tie and an A-line silhouette. Complete the look with a denim jacket and sandals for a casual occasion!

    Fit & Features

    • Floral print, brushed knit fabric lined with knit
    • Adjustable drawstring neckline
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5686

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy Escape Strapless Tropical Midi Dress

    Serve chic looks on your dreamy escape in this tropical print midi dress. The stretchy lined knit fabric showcases a detailed tropical print pattern on the figure-flaunting silhouette. The bodice features a strapless elasticized straight-across neckline, leading to a bodycon fit with a mid-length hem. Style with combat booties to add some edge!

    Fit & Features

    • Stretchy knit fabric with knit lining
    • Tropical print
    • Strapless elasticized straight neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5539

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Always Sweet Ruffled Bodycon Eyelet Lace Mini Dress

    Make your sweet impression in this eyelet lace mini dress at bridal showers, graduations, or birthdays! Crafted from an eyelet lace fabric that adds a touch of chic to this mini-length dress boasting a square neckline, ruffled straps, and a flattering bodycon fit. Complete the look with a sleek choker.

    Fit & Features

    • Eyelet lace fabric lined with stretchy knit
    • Ruffled straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5429

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale