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.
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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.
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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Gorgeous Muse Asymmetrical Midi Dress
Catch all the glances like the gorgeous muse you are in this printed midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a midi-length, asymmetrical hem, a curve-hugging silhouette, and an all-over geometric multi-print pattern. Complete the look with sleek hoop earrings.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Midi-length, asymmetrical hem, ruching down one side
- Form-fitting silhouette
- Geometric multi-print pattern
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5302
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Swirl Fun Chain Strap Midi Dress
Perfect for your next getaway, this swirl midi dress is a must to pack in your carry-on! It features a sleeveless square neck, half chain and adjustable spaghetti straps, a bodycon silhouette, and a flirty side slit. The dress is composed of a swirl print slinky-knit fabric with a sewn-in knit lining. Complete the look in heeled sandals.
Fit & Features
- Sleeveless square neck
- Half chain, adjustable spaghetti straps
- Bodycon silhouette
- Side slit, midi-length hem
- Swirl print
- Slinky knit fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5301
Category Name: Casual Dresses
Price: $6.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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
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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
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Feeling Amore Tie-Back A-Line Eyelet Mini Dress
Fall in love with this adorable eyelet mini dress perf for weekend plans. The flirty tie-back detail and ruffled A-line silhouette will get you all the compliments.
Fit & Features
- Eyelet knit fabric lined with stretchy knit
- Adjustable spaghetti straps
- Tie-back design
- Ruffled trim
- Short A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5434
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Vibes Eyelet Knit Layered Skater Dress
Show off pretty vibes in this adorable layered skater dress made with breezy eyelet knit fabric. Pair with sneakers for a cute casual look or wedges for a dressier style.
Fit & Features
- Stretchy sheer eyelet knit fabric, partial knit lining
- Square neckline
- Spaghetti straps
- Double-layered skater skirt
- Short fit-and-flare silhouette
- Runs true to size
Style Number/Barcode: 05102-5428
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Day Ruffled Ditsy Floral Skater Dress
You'll love every moment spent in this ditsy floral skater dress! The square neckline and spaghetti tie straps add a flirty touch, while the stretchy smocked bodice ensures a comfortable fit. With a playful ruffled skater silhouette and a mini-length hem, this dress is perfect for any occasion. Complete the look in wedges.
Fit & Features
- Ditsy floral print, woven fabric lined with knit
- Spaghetti tie strap
- Square neckline
- Ruffled skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5425
Category Name: Casual Dresses
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Appeal Puff Sleeve Eyelet Knit Skater Dress
The sweet eyelet design and adorable details give this puff sleeve skater dress a charming appeal! Made with an airy sheer eyelet knit fabric with a partial knit lining, this short dress is perfect for your spring and summer weekend outings. It features a square neckline with chic ruching at the bust, sheer short puff sleeves with a dainty ruffled trim, a sheer corset-style bodice to create a cinched look, and a fit-and-flare skater silhouette for a flirty vibe. Complete your outfit with hoop earrings!
Fit & Features
- Sheer eyelet knit fabric, partial knit lining, plenty of stretch
- Square neckline with ruched bust
- Sheer short puff sleeves, ruffled trim, elastic cinched hems
- Sheer corset-style bodice, stretchy high waist seam
- Fit and flare skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5427
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Catch A Cutie Short Sleeve Cutout Eyelet Skater Dress
Catch yourself a cutie wearing this eyelet skater dress to day parties this season! With playful puff sleeves and a flirty cutout. The sweetheart neckline and bust drawstring add a touch of romance, while the skater silhouette and tiered ruffled hem keep it fun and flirty. Complete the look in wedge sandals.
Fit & Features
- Eyelet fabric lined with stretchy knit
- Sweetheart neckline
- Adjustable bust drawstring, cutout
- Skater silhouette
- Tiered ruffles
- Runs true to size
Style Number/Barcode: 05102-5430
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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
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City Of Love V-Neck Ruffle Babydoll Dress
Grab your baguette, passport, and this babydoll dress cause the city of love is calling your name! The playful ruffled shoulder straps and convenient side pockets add a touch of whimsy to this flirty dress. The babydoll silhouette and ruffled tiered hem make it perfect to sweep through Paris looking adorable! Complete the look in strappy sandals and a purse.
Fit & Features
- Woven fabric
- Ruffled shoulder straps
- Side pockets
- Babydoll silhouette
- Ruffled tiered short-length hem
- Runs true to size
Style Number/Barcode: 05102-5423
Category Name: Casual Dresses
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale