Casual Dresses
Casual fall dresses that keep up with your plans—coffee runs, brunch dates, weekend hangs, and everything in between. Slip into long-sleeve silhouettes, cozy sweater knits, and soft ribbed jersey styles that make getting dressed feel easy. Go fitted in a bodycon mini, keep it polished with a midi, or lean into a long, flowy shape for an effortless finish. Layer your favorites with the season’s latest jackets for a look that feels warm, styled, and ready for whatever lands on your calendar.
Now Trending
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.
-
Getaway Bound Tropical Cowl Neck Maxi Dress
You'll be ready for your getaway with this tropical maxi dress in your carry-on! It features a sleeveless cowl neckline, spaghetti straps that crisscross in the back, a curve-hugging slim silhouette, and a flirty front slit. Complete the look in espadrille wedges and sunnies!
Fit & Features
- Sleeveless cowl neckline, bust lining
- Spaghetti straps, crisscross back
- Curve-hugging, slim silhouette
- Front slit
- Maxi-length hem
- Tropical print, smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4999
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
She Knows Style Eyelet Lace Skater Dress
Breeze into every occasion in this stylish eyelet lace skater dress! It features a sleeveless square neck, spaghetti straps, a ruched bust, and a flattering fit and flare short-length hem. The sheer eyelet lace fabric includes a full knit lining and offers plenty of stretch. Complete the look with statement block heels for a wedding shower or birthday lunch!
Fit & Features
- Sleeveless square neck, spaghetti straps
- Ruched bust
- Fit and flare, skater silhouette
- Short-length hem
- Sheer eyelet lace fabric, full knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4998
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Lovely In Floral Lace Trim Midi Dress
You'll be a sight for sore eyes in this lovely floral midi dress - a flirty option for garden weddings, dressy birthdays, and day dates! The sleeveless dress features a sweetheart neckline with a romantic eyelash lace trim, adjustable spaghetti straps, a curve-hugging bodice, and a slit accent along the flowy hem. Complete the look with earrings and heels.
Fit & Features
- Sleeveless sweetheart neckline, padded wired bust, eyelash lace trim
- Adjustable spaghetti straps, back zipper, hook and eye closure
- Curve-hugging bodice
- Slit accent, midi-length hem, A-line silhouette
- Delicate floral print
- Sheer woven fabric, full lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2228
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Picnic Time Gingham Mini Dress
You'll be the cutest girl in this gingham casual dress at the picnic! It features ruffle trim puff short sleeves, a sweetheart neck with a lace-up bust, a bodycon silhouette, and a mini-length hem on stretchy rib knit fabric. Complete the look in sandals.
Fit & Features
- Ruffle trim puff short sleeves
- Sweetheart neck, lace-up bust
- Bodycon silhouette
- Mini-length hem
- Gingham print
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-4995
Category Name: Casual Dresses
Price: $27.90
Availability: Out of Stock
Product Badge:- Sale
-
Flirtatious Charm Cutout Midi Dress
Say hello to this adorable cutout midi dress that will bring those cute and fun vibes! This midi dress features an off-the-shoulder sweetheart neckline and short fitted sleeves. The center knot detail at the bust with a tie-front adds a charming touch, while the dual waist cutouts add a hint of playfulness. The midi-length hem with a high side slit showcases your legs for a sassy look. With its form-hugging silhouette and ribbed knit fabric offering plenty of stretch, this dress ensures both comfort and style. Complete your outfit with a pair of sandals to bring that flirtatious charm!
Fit & Features
- Off-the-shoulder sweetheart neckline
- Center knot detail at the bust, tie-front design
- Dual waist cutouts
- Midi-length hem, high side slit
- Form-hugging fit
- Ribbed knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4992
Category Name: Casual Dresses
Price: $6.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Freshly Picked Floral Skater Dress
Freshly picked from the garden. This floral skater dress is ready for your springtime festivities! It features short puff sleeves, a sweetheart neck with a tie-front closure, an open lace-up back design, and a tiered ruffled short-length hem. Complete the look in trendy new mules.
Fit & Features
- Short puff sleeves
- Sweetheart neck, tie-front closure
- Open lace-up back design
- Skater silhouette
- Tiered ruffle short-length hem
- Watercolor floral print, non-stretch fabric, woven lining
- Runs true to size
Style Number/Barcode: 05102-4993
Category Name: Casual Dresses
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Color Me Cute Linen V-Neck Skater Dress
Color you cute in this linen skater dress perfect for layering over your swimsuit on a beach day or pool party! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty ruffled underbust trim, and a tiered color block ruffled short-length silhouette. Style with trendy espadrille wedges.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Ruffled underbust trim
- Tiered ruffle layered skater silhouette
- Short-length hem
- Color block pattern
- Airy woven linen fabric, partial lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4994
Category Name: Casual Dresses
Price: $5.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
A Flare To Remember Skater Dress
You'll be unforgettable in this short skater dress perfect for twirling into baby showers, brunches, and family parties! Featuring a sleeveless plunge v-neckline, spaghetti straps that cross and tie along the open back, and a fit-and-flare silhouette. The dress is composed of airy printed chiffon fabric with a smooth woven lining. Style with strappy mules and a clutch!
Fit & Features
- Sleeveless plunge v-neckline
- Spaghetti straps
- Open back, cross strap design, tie closure
- Fit and flare skater silhouette
- Short-length hem
- Airy printed chiffon fabric, smooth woven lining
- Runs true to size
Style Number/Barcode: 05102-4988
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sweet Like Honey Linen Skater Dress
You'll be sweet like honey in this breezy linen skater dress for afternoon tea or a weekend brunch! The dress features adorable puff short sleeves, a ruffle trim sweetheart neck, a ruched bust, and a fit and flare silhouette with a ruffled hem. Style with heeled sandals to complete the look.
Fit & Features
- Puff short sleeves
- Ruffle trim sweetheart neck, ruched bust
- Back zipper and hook-eye closure
- Fit and flare skater silhouette
- Ruffle short-length hem
- Linen fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4991
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Sunset Marvel Lace-Up Mini Dress
Everyone will marvel at you in this marble print mini dress featuring a sleeveless square neck, spaghetti straps that lace up along the back, and a bodycon silhouette. The mini-length dress is composed of a marble-printed mesh fabric with a stretch knit lining. Complete the look in platform wedges for dinner by the beach!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Lace-up back
- Bodycon silhouette
- Mini-length hem
- Marble print, mesh fabric, stretch knit lining
- Runs true to size
Style Number/Barcode: 05102-4990
Category Name: Casual Dresses
Price: $5.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Modern Marvel One-Shoulder Mini Dress
Strut looking like a modern work of art in this marble-printed mini dress all over town! It features a sleeveless one-shoulder neck, an adjustable spaghetti strap, a side adjustable ruched string, and a bodycon silhouette. Complete the look with hoop earrings.
Fit & Features
- Sleeveless one-shoulder neck
- Adjustable spaghetti straps
- Side ruched string
- Bodycon silhouette
- Mini-length hem
- Marble-printed mesh fabric, stretch knit lining
- Runs true to size
Style Number/Barcode: 05102-4989
Category Name: Casual Dresses
Price: $5.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
In Paradise Tropical Print Midi Dress
You'll be ready for your paradise getaway with this tropical print midi dress! It features a sleeveless V-neck, spaghetti straps, a sultry cutout back, a bodycon silhouette, and an asymmetrical side slit cutout. Complete the look in wedges.
Fit & Features
- Sleeveless V-neck, spaghetti straps
- Cutout back
- Bodycon silhouette
- Asymmetrical side slit cutout
- Midi-length hem
- Tropical print, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-4987
Category Name: Casual Dresses
Price: $19.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Art Show Marble Print Midi Dress
Look like a work of art in this marble print midi dress all over town! It features a sleeveless cowl neckline, spaghetti straps, a form-hugging fit with ruching down one side, and an asymmetrical side slit cutout on a smooth and stretchy knit fabric. Complete the look with hoop earrings.
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Form-hugging fit, ruching down one side
- Asymmetrical side slit cutout
- Midi-length hem
- Marble print, smooth knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4986
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Text Me Later Strappy Back Mini Dress
Their text can wait. You'll be too busy catching all the attention in this casual mini dress featuring a sleeveless square neck, bungee spaghetti straps, a strappy open-back, and a bodycon silhouette. The dress is composed of a texture knit fabric with a stretchy lining. Complete the look in a crop denim jacket.
Fit & Features
- Sleeveless square neck
- Bungee spaghetti straps
- Strappy open back
- Bodycon silhouette
- Mini-length hem
- Texture knit fabric, stretchy lining
- Runs true to size
Style Number/Barcode: 05102-4981
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Swing My Way Eyelet Lace Midi Dress
This eyelet lace midi dress is sure to get your crush's attention! It features a sleeveless V-neckline, adjustable spaghetti straps, button front accents, a flattering A-line silhouette, and a front slit along the hem. Complete the look in clear block heels for a daytime soiree!
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Button front accents
- A-line silhouette
- Front slit, midi-length hem
- Eyelet lace fabric, partial woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4982
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Casual Perfection Ribbed Knit Mini Dress
This ribbed knit mini dress will create perfect casual 'fits! It features a square neckline, long fitted bell sleeves with cute flared-out hems, and a mini-length, form-hugging silhouette. The lined knit fabric offers plenty of stretch for comfortable wear. Style with knee-high boots.
Fit & Features
- Square neckline
- Long fitted bell sleeves, flared hems
- Mini-length hem, form-hugging fit
- Ribbed knit fabric, knit lining, plenty of stretch
- Style runs small
Style Number/Barcode: 05102-5217
Category Name: Casual Dresses
Price: $5.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Dreamy In Floral Satin Midi Dress
Create a dreamy look in this floral satin midi dress for brunch or bridal showers! It features a sleeveless cowl neckline, adjustable spaghetti straps, a curve-hugging slim silhouette, and a flirty side slit accent. Complete the look in heeled mules.
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Curve-hugging, slim silhouette
- Side slit accent
- Midi-length hem
- Floral print, silky satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4985
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
True Romance Floral Chiffon Lace Dress
Fall for this floral chiffon dress to add romance this season! The dress features a sleeveless V-neckline, adjustable spaghetti straps, an lovely lace back with a lower cutout, and a flattering skater short-length silhouette. Complete the look with a dainty ring set.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Lace back, lower cutout
- Skater silhouette
- Tiered short-length hem
- Floral watercolor print
- Airy chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2220
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Trip To The Tropics Printed Midi Dress
You'll look like you're ready to whisk away on a tropical vacay in this printed midi dress! It features a sleeveless V-neckline, spaghetti straps, a midi-length hem, a hip-hugging fit and an A-line silhouette, a thigh-high front slit, and an eye-catching tropical palm leaf print. Style with trendy wedges.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Midi-length hem, hip-hugging fit, A-line silhouette
- High front slit
- Tropical palm leaf print
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4979
Category Name: Casual Dresses
Price: $19.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Garden Chic Floral Chiffon Midi Dress
Enchanting and chic, this floral chiffon midi dress is perfect for a garden wedding. It features a sleeveless sweetheart neckline with a bust outline, adjustable spaghetti straps, a high waist seam, a smocked back panel with a zipper closure, a midi-length hem with a high front slit, and a flowy A-line silhouette. The airy chiffon fabric features a romantic blooming floral print alongside a dainty flower pattern. Style with clear block heels.
Fit & Features
- Sleeveless sweetheart neckline, padded bust and outline
- Adjustable spaghetti straps
- High waist seam, stretchy smocked back, zipper and hook-eye closure
- Midi-length hem
- Front slit, A-line silhouette
- Floral print, chiffon fabric, smooth stretchy knit lining
- Style runs small
Style Number/Barcode: 05101-2212
Category Name: Casual Dresses
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Lovely Seeing You Floral Chiffon Midi Dress
They'll be pleased to make your lovely acquaintance looking so romantic in this floral chiffon midi dress as the perfect wedding guest! The sleeveless dress features a sweetheart neckline, adjustable spaghetti straps, a stretchy smocked back, a built-in padded bust, and a flattering front slit along the flowy hem. Complete the look with clear lucite block heels and a clutch.
Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Stretchy smocked back, zipper and hook-eye closure
- Built-in padded bust
- Front slit, midi-length hem
- Garden rose print, airy chiffon, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2214
Category Name: Casual Dresses
Price: $5.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Extra Flair Floral Skater Dress
You'll be a darling delight in this short skater dress perfect for parties and ceremonies! It features three-quarter-length puff sleeves, a square neck, a smocked back, and a fit and flare silhouette. The dress is composed of a floral burnout woven fabric with a chiffon lining and no stretch. Style with earrings and a choker to complete the look!
Fit & Features
- Three-quarter-length puff sleeves
- Square neck
- Smocked back
- Fit and flare skater silhouette
- Short-length hem
- Floral burnout woven fabric, chiffon lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2211
Category Name: Casual Dresses
Price: $5.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Everlasting Pretty Floral Chiffon Skater Dress
Freshen up your closet in this pretty floral chiffon dress for a blissful day date to jaunt through a garden party! It features sheer peasant long sleeves, a smocked and stretchy V-neck bodice, a fit and flare silhouette, and a flowy short-length hem. The dress is designed with a gorgeous floral pattern on airy chiffon with a stretchy knit lining. Complete the look with strappy platform heels.
Fit & Features
- Sheer peasant long sleeves
- Smocked and stretchy V-neck bodice
- Back zipper closure
- Skater silhouette
- Flowy short-length hem
- Floral pattern, chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4977
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Vacay Queen Tropical Floral Midi Dress
Slay in all of your vacation pics like the stylish queen you are in this tropical floral midi dress! It features a sleeveless square neckline, spaghetti straps, a midi-length hem, a bodycon silhouette that will hug your curves, and a bold tropical floral print pattern. The sheer mesh fabric includes a stretch knit lining. Complete the look with clear mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Midi-length hem
- Bodycon silhouette
- Tropical floral print
- Sheer mesh fabric, stretch knit lining
- Runs true to size
Style Number/Barcode: 05102-4980
Category Name: Casual Dresses
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale