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.

  • Playful Summer Sweetheart Ruffled Eyelet Midi Dress

    Looking for the perfect summer dress? Look no further than this playful sleeveless midi dress! With its flattering sweetheart neckline with a structured bust and adjustable spaghetti straps, this A-line silhouette dress will have you feeling confident and stylish. The ruffled midi-length hem and floral embroidered eyelet woven fabric add a touch of playfulness to this must-have dress! Complete the look with wedge sandals.

    Fit & Features

    • Floral embroidered eyelet woven fabric, stretchy knit lining
    • Sweetheart neckline, padded bust with underwire
    • Adjustable spaghetti straps, back zipper with hook and eye closure
    • High waist seam, A-line silhouette
    • Ruffled midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3015

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Darling Details Floral Eyelet Mini Dress

    This floral eyelet mini dress has darling details that make it perfect for spring and summer looks! Made from a beautiful floral printed woven eyelet fabric, this dress will make you feel like a blooming flower. With a flirtatious square neckline and bust keyhole tie, this dress is perfect for any occasion. The adjustable spaghetti straps ensure a perfect fit while the curve-hugging silhouette and mini-length hem show off your figure. Complete the look with a ring set.

    Fit & Features

    • Floral printed woven eyelet fabric with knit lining
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Square neckline, keyhole tie
    • Curve-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3013

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweeten Up Strappy Back Floral Chiffon Skater Dress

    Sweeten up any moment in this floral chiffon skater dress perfect for celebrations and showers! With a square neckline, spaghetti straps, and a playful strappy back design, this dress is perfect for any occasion. The skater silhouette and ruffled short-length hem add a flirty touch, while the ditsy floral print and chiffon fabric keep it light and whimsical. Complete the look in wedges.

    Fit & Features

    • Ditsy floral print, chiffon fabric lined with stretchy knit
    • Spagehtti straps, square neckline
    • Strappy back design
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5450

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daytime Cheer Fit And Flare Ruffle Floral Dress

    Spread daytime cheer in this fit and flare floral dress! Made from soft chiffon fabric, this dress is adorned with a ditsy floral print for a whimsical touch.  This playful dress features a sweetheart neckline with ruffle trim, adjustable spaghetti straps, and a charming keyhole bust tie. The stretchy smocked waist and tiered ruffled hem create a flattering fit and flare silhouette. Complete the look with a cute purse and sandals!

    Fit & Features

    • Ditsy floral print, chiffon fabric, stretchy knit lining
    • Ruffle trim sweetheart neckline
    • Adjustable spaghetti straps
    • Stretchy smocked waist
    • Fit and flare silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5447

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • More Than Sweet Tie Strap Fit-And-Flare Dress

    Who can imagine a look sweeter than this fit-and-flare dress? Showcase your darling side in this short eyelet dress at casual brunches or parties! This charming dress features a square neckline, tie shoulder straps, and a flattering fit-and-flare silhouette. With a tiered ruffled short-length hem and delicate eyelet lace fabric, this dress will have you looking and feeling your best. Complete the look in trendy sneakers for a cute style!

    Fit & Features

    • Sheer eyelet lace fabric with knit lining, moderate stretch
    • Square neckline
    • Tie shoulder straps
    • Fit-and-flare silhouette
    • Tiered ruffles
    • Runs true to size

    Style Number/Barcode: 05102-5532

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Endless Charm Crepe Floral Midi Dress

    Charm from day to night in this ditsy floral midi dress! Featuring a ruffle trim sweetheart neckline, spaghetti straps, and a flirty bust tie front. The form-hugging silhouette and front slit add a touch of allure, while the ditsy floral print on crepe fabric and midi-length hem keep it sweet and romantic. Complete the look in simple block heels for a dressy date or brunch!

    Fit & Features

    • Sleeveless ruffle trim sweetheart neckline
    • Spaghetti straps, bust tie front
    • Form-hugging silhouette
    • Front slit, midi-length hem
    • Ditsy floral print, crepe fabric, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5446

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Looking Long Sleeve Denim Mini Dress

    A denim mini dress features long sleeves, a classic collar neckline, flap pockets for style, and a flattering bodycon silhouette. Perfect for back-to-school and styling with sneakers or boots.

    Fit & Features

    • Denim fabric, minimal stretch
    • Long sleeves with button cuffs
    • Collar neckline
    • Front zipper closure
    • Flap pockets
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5448

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    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
  • Love's In The Air Floral Chiffon A-Line Dress

    Slip into romance! This dainty floral chiffon short dress features a sweetheart neckline and bust tie to accentuate your figure while the wide shoulder straps and underwire bust provide support. The corset-trim bodice and back lace-up design add a touch of romance along the flattering A-line silhouette and short-length hem. Complete the look with a ring set and sandals for a date or brunch!

    Fit & Features

    • Sleeveless sweetheart neckline
    • Wide shoulder straps
    • Underwire bust, tie front, side zipper and hook-eye closure
    • Corset-trim bodice, lace-up back design
    • A-line silhouette, short-length hem
    • Dainty floral print, chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-3007

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cascading Romance Ruffle Floral Skater Dress

    Get swept away into a world of romance in this floral skater dress perfect for a shower or date! The square neckline and tie-shoulder spaghetti straps add a touch of sweetness, while the stretchy smocked bodice ensures a comfortable fit. The skater silhouette and tiered ruffled hem make this dress perfect for twirling the night away. Complete the look with earrings.

    Fit & Features

    • Floral print, chiffon fabric with woven skirt lining
    • Square neckline
    • Tie-shoulder spaghetti straps
    • Stretchy smocked bodice
    • Skater silhouette with ruffles
    • Runs true to size

    Style Number/Barcode: 05101-2994

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Darling Delight Sleeveless Lace Trim Skater Dress

    When the occasion calls for flair, this sleeveless skater dress delivers with darling delight! Perfect for bridal showers, rehearsal dinners, and graduations. Made from a smooth chiffon fabric, the lace trim straps and hem add a delicate touch. Featuring a square neckline and ruched bust, the flattering skater silhouette will have you twirling all day! Complete the look in block heels.

    Fit & Features

    • Smooth chiffon fabric, stretchy knit lining
    • Square neckline, lace trim straps
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Lace trim short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3563

    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
  • Whimsical Appeal Puff Sleeve Chiffon Skater Dress

    Swiss dots add whimsical appeal to this charming chiffon skater dress perfect for birthdays, graduations, or showers! With sheer puff sleeves, a sweetheart neckline, and a tiered ruffled skater silhouette, this dress is both playful and flattering. Its short-length hem adds a touch of flirty charm. Complete the look in mules and a trendy purse!

    Fit & Features

    • Swiss dot chiffon fabric lined with stretchy knit
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-2999

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Delightful Cutie Corset Lace-Up Floral Midi Dress

    If you aim to charm, this cute ditsy floral midi dress will sweep everyone off their feet at parties! Flaunt your femme figure in the sweetheart neckline, ruched underwire bust, and corset trim bodice. The A-line, midi-length silhouette, and front slit add a flattering look while the lace-up back allows for a customizable fit. Complete the look with a dainty necklace and mules.

    Fit & Features

    • Ditsy floral print
    • Woven fabric lined with stretchy knit
    • Underwire bust
    • Lace-up, side zipper and hook-eye closure
    • Front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-2995

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamiest Summer Smocked Floral Chiffon Midi Dress

    Have the dreamiest summer romance in this floral chiffon midi dress perfect for dates and parties! This dress features a square neckline, adjustable spaghetti straps, and a stretchy smocked bodycon silhouette for a comfortable and flattering fit. The tiered ruffled midi-length hem adds a touch of femininity, while the floral print on chiffon fabric gives the prettiest look. Style this floral dress with earrings and block heels.

    Fit & Features

    • Floral print, chiffon fabric
    • Adjustable spaghetti straps
    • Square neckline
    • Stretchy smocked bodycon silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05101-2985

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Most Alluring Strapless Corset Abstract Mini Dress

    Feel your most alluring in this corset mini dress providing a cinched look you'll love flaunting out on the town! Featuring a flattering strapless neckline and flexible boning, this bodycon dress creates a sleek silhouette. The mini-length hem and abstract print add a touch of playfulness, while the mesh fabric keeps you on trend. Complete the look in platform heels.

    Fit & Features

    • Abstract print, mesh fabric lined with stretchy knit
    • Back zipper and hook-eye closure
    • Flexible boning
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5359

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    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
  • Bubbly Love Corset Skater Party Dress

    You'll always have people falling for you in this corset skater party dress at parties! The square neckline and adjustable spaghetti straps keep it trendy while the corset bodice and hidden front hook and eye fasteners provide a flattering silhouette. The stretchy smocked back and embroidered woven fabric add style to this playful bubble hem dress. Complete the look with earrings.

    Fit & Features

    • Embroidered woven fabric, sewn-in knit lining
    • Adjustable spaghetti straps
    • Square neckline
    • Hidden front hook and eye fasteners
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-2979

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Preppy Posh Strapless A-Line Pleated Mini Dress

    Look fabulously mod with this strapless mini dress! Made from smooth woven fabric, discover a next-level fashionista vibe in this dress featuring an A-line silhouette, belt loop accents along the waist, and a pleated mini-length hem for added flair. Complete the look in a blazer for weekend plans!

    Fit & Features

    • Strapless neckline
    • A-line silhouette
    • Belt loop accents along the waist
    • Pleated mini-length hem
    • Smooth woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5444

    Category Name: Casual Dresses

    Price: $6.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Button Up Babe Denim Strapless Mini Dress

    Look and feel like a total babe in this denim mini dress at concerts or parties! The short dress features a sweetheart neckline, bust seam detailing, a trendy asymmetrical button front design, a flattering bodycon silhouette, and a mini-length hem. Complete the look with a mini handbag.

    Fit & Features

    • Strapless sweetheart neckline
    • Bust seam detailing
    • Back zipper closure
    • Asymmetrical button front design
    • Bodycon silhouette, mini-length hem
    • Denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5443

    Category Name: Casual Dresses

    Price: $19.97 $62.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The 90s Are Calling Denim Strapless Mini Dress

    This denim mini dress celebrates the fashion of the 90s! The short dress creates a timeless classic look with its strapless neckline, button closure, belt loop accents, and skirt seam detailing to make a bold statement and flattering bodycon silhouette. Complete the look with on-trend chunky platform heels for a party!

    Fit & Features

    • Strapless neckline
    • Button closure, side zipper, belt loop accents
    • Skirt seam detailing
    • Bodycon silhouette
    • Mini-length hem
    • Denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5442

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Winter Chic Mock Neck Long Sleeve Skater Dress

    This chic short skater dress will elevate your casual winter looks! It features a mock neckline, long fitted sleeves, a high waist, a short-length hem, and an adorable fit and flare skater silhouette. The ribbed knit fabric offers plenty of stretch. Style this short dress with over-the-knee boots and hoop earrings for a coffee date!

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • High waist seam
    • Short-length hem
    • Skater silhouette
    • Lined ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5445

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirty Aura Puff Sleeve Floral Lace Skater Dress

    Captivate them with your flirty aura in the cutest floral lace skater dress! The dainty sheer floral lace fabric will give your look a soft feminine vibe and includes a partial woven lining for coverage. The bodice is shaped with a plunging V-neckline with a tie-front detail and sheer short puff sleeves with elasticized hems. The open back adds to the allure and features a tie-back design. The dual high waist seams lead to a fit-and-flare skater silhouette on a short-length hem that was made to twirl. Style this adorable dress with wedge heels for a spring or summer party!

    Fit & Features

    • Sheer floral lace fabric with partial woven lining, no stretch
    • Plunging V-neckline with tie-front
    • Short puff sleeves with elasticized hems
    • Open back, tie-back, lower back zipper with hook and eye closure
    • Dual high waist seams
    • Fit-and-flare skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-2967

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cadet Cutie Cargo Pocket Mini Dress

    Rise up in rank looking cute in this mini dress! The short dress features a sweetheart neckline, adjustable spaghetti straps, cargo-flap pockets along the bust, snap-button down closures, belt loop accents and side pockets, and a flattering bodycon silhouette. Complete the look in sleek hoop earrings for a day out with the girls!

    Fit & Features

    • Sleeveless sweetheart neckline, adjustable spaghetti straps
    • Cargo-flap pockets along the bust
    • Snap-button down closures
    • Belt loop accents, side pockets
    • Bodycon silhouette, mini-length hem
    • Texture woven fabric, minimal stretch
    • Runs small, recommend to size up

    Style Number/Barcode: 05102-5441

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale