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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Romance For One Rose Tie-Front Dress
Romance yourself! Look sweet in this rose print casual dress on a day date or brunch. It features a sleeveless sweetheart neck, spaghetti straps, bust tie-front, and keyhole, side ruched seams to accentuate your figure along the mini, bodycon silhouette. Style with a denim jacket to complete the look!
Fit & Features
- Sleeveless sweetheart neck, spaghetti straps
- Bust tie-front and keyhole
- Side ruched seams
- Bodycon silhouette, mini-length hem
- Ditsy rose print
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4929
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flourish In Floral Print Mini Dress
Flourish for spring in this dainty floral mini dress you'll love styling for casual plans! It features a sleeveless scoop neck with a tie-front bust, spaghetti straps, and a bodycon fit on stretchy rib knit fabric. Complete the look with new trendy sandals.
Fit & Features
- Sleeveless scoop neck, spaghetti straps
- Tie-front bust
- Bodycon fit
- Mini-length hem
- Dainty floral print, stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-4930
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Silhouette One-Shoulder Midi Dress
Showcase a sultry silhouette in this chic sleeveless midi dress that will hug your curves! The midi dress features an asymmetric one-shoulder neckline with a thin tank strap and a trendy O-ring accent, a bold cutout at the bust for an alluring vibe, an asymmetric midi-length hem creating a thigh-high side slit, and a bodycon fit. Style with lace-up heels for a date night.
Fit & Features
- Sleeveless asymmetric one-shoulder neckline
- Thin tank shoulder strap, O-ring accent
- Bust cutout, high waist seam, side ruching
- Asymmetric midi-length hem, high side slit
- Bodycon fit
- Ribbed knit fabric. moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4927
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tie Dye Over Bodycon Mini Dress
You'll tie-dye over this casual mini dress to add some color to your closet for warmer seasons ahead! It features a square neck, bungee spaghetti straps, and side ruched seams that accentuate your curves along the bodycon silhouette. The dress is composed of stretchy mesh fabric with a sewn-in knit lining. Complete the look in a cropped denim jacket and sneakers.
Fit & Features
- Sleeveless, square neck
- Bungee spaghetti straps
- Side ruched seams, bodycon silhouette
- Mini-length hem
- Tie-dye pattern, mesh fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4931
Category Name: Casual Dresses
Price: $19.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Strike Again Marble Print Mini Dress
Strike a stunning look every time you're in this knit mini dress at parties or nights out! It features a sleeveless one-shoulder neckline, dual spaghetti straps with a sultry cutout, a bodycon silhouette, and a trendy marble print on stretchy knit fabric. Complete the look in sandals.
Fit & Features
- Sleeveless one-shoulder neckline
- Dual spaghetti straps
- Cutout bust
- Bodycon silhouette
- Mini-length hem
- Marble print, knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4932
Category Name: Casual Dresses
Price: $5.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sway With Me Eyelet Lace Skater Dress
You'll look sweet as can be in this eyelet lace skater dress perfect for swaying with the music at day parties! Designed with a sheer eyelet lace fabric and knit lining, it features a sleeveless V-neckline, adjustable spaghetti straps for a customized fit, a flirty tie-back design, and a flattering fit and flare silhouette with a short hem. Complete the look in lace-up heels.
Fit & Features
- Sheer eyelet lace fabric, knit lining, minimal stretch
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Tie-back design
- High waist seam
- Fit and flare skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5466
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet As Me Eyelet Lace Skater Dress
This eyelet lace dress is sure to be the sweetest style in your closet! It features puff short sleeves, a sweetheart neck with a bust tie, ruched bust, and a fit and flare skater silhouette. Complete the look with a ring set and heels.
Fit & Features
- Puff short sleeves
- Sweetheart neck, bust tie
- Ruched bust
- Fit and flare skater silhouette
- Short-length hem
- Eyelet lace, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4924
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Here To Twirl Ruffled Skater Dress
With this skater dress on, you're just here to twirl at the graduation party or birthday! It features a sleeveless square neck, adjustable spaghetti straps, a flirty tie-back design, and a flattering fit and flare short-length silhouette with a layered ruffled hem. Complete the look in rhinestone fringe earrings.
Fit & Features
- Sleeveless square neck, adjustable spaghetti straps
- Tie-back design
- Fit and flare, skater silhouette
- Layered ruffled short-length hem
- Woven fabric, sewn-in knit lining
- Runs true to size
Style Number/Barcode: 05101-2119
Category Name: Casual Dresses
Price: $5.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic To Be Lace Crepe Mini Dress
They can also pronounce you chic to be with this gorgeous crepe mini dress on! Perfect for bridal showers, rehearsal dinners, and other celebrations. Featuring a sleeveless sweetheart neck, wide straps, a lovely lace-lined bust with underwire and a bow, a pleated side seam, and a crepe bodycon skirt. Complete the look in rhinestone mules.
Fit & Features
- Sleeveless sweetheart neck
- Wide straps, back zipper and hook-eye closures
- Lace-lined bust, underwire, bow
- Pleated side seam
- Crepe bodycon skirt
- Lined, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2122
Category Name: Casual Dresses
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Moves Long Sleeve Bodycon Mini Dress
Showcase your silhouette in this chic bodycon mini dress! It features a V-neckline, long fitted sleeves, ruched detailing at the shoulders, a mini-length hem, and a curve-hugging fit. The smooth knit fabric offers plenty of stretch. Style with clear lucite heels.
Fit & Features
- V-neckline
- Long fitted sleeves
- Ruching at the shoulders
- Mini-length hem
- Fitted bodycon silhouette
- Knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05103-4835
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feelin' Like A Dream Chiffon Skater Dress
Look and feel like a dream in this chiffon skater dress perfect for baby showers or birthdays! It features an off-the-shoulder, ruffle trim sweetheart neckline, sheer peasant long sleeves with elastic cuffs, a lightly padded bust, and a flowy tiered ruffled short-length hem. Complete the look in cute mules.
Fit & Features
- Off-the-shoulder, smocked back
- Ruffle trim sweetheart neck, lightly padded bust
- Sheer peasant long sleeves, elastic cuffs
- Fit and flare skater silhouette
- Flowy tiered ruffled short-length hem
- Chiffon fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2113
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vineyard Gal Floral Linen Skater Dress
Perfect for vineyard weddings, wine tasting, and daytime soirees! This vintage-inspired floral linen dress features adorable puff short sleeves, a sweetheart neck with a bust tie, a lace-up back design, and a tiered fit and flare skater silhouette with a short hem. Complete the look in on-trend espadrille wedges.
Fit & Features
- Puff short sleeves
- Sweetheart neck, bust tie
- Lace-up back design
- Tiered fit and flare skater silhouette
- Short-length hem
- Vintage floral print, linen fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4919
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So In Love Floral A-Line Midi Dress
You'll fall so in love with this floral midi dress to wear for day dates! It features a sleeveless square neckline, elastic ruched straps with lettuce-edge trim, an A-line silhouette, and a flirty front slit. The dress has a dainty rose floral print on stretchy knit-lined fabric. Complete the look in heeled sandals.
Fit & Features
- Sleeveless square neckline
- Elastic ruched straps
- Lettuce-edge trim
- A-line silhouette
- Front slit, midi-length hem
- Dainty rose floral print, stretchy knit-lined fabric
- Runs true to size
Style Number/Barcode: 05102-4921
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunshine Girlie Crochet Chevron Sweater Dress
Calling all the sunshine girlies! Slip on this playful crochet chevron sweater dress for backyard pool parties or vacations. It features a sleeveless halter V-neckline, tie-back spaghetti straps, an open back, a bodycon silhouette, and a mini-length hem with ribbed trim. Style with chunky platform heels for a complete look!
Fit & Features
- Sleeveless halter V-neckline
- Tie-back spaghetti straps
- Open back
- Bodycon silhouette
- Mini-length hem with ribbed trim
- Chevron pattern, crochet sweater fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06005-1658
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Weekend Vibes Floral Mini Dress
Give off those effortless weekend vibes in this adorable floral mini dress! It features a V-neckline with a twist-front design, a front keyhole cutout under the bust, adjustable spaghetti straps, a smocked design down the back and body of the dress, a mini-length hem with a form-hugging silhouette, and a ditsy floral print pattern. The woven fabric offers a moderate stretch. Style with espadrille sandals.
Fit & Features
- Sleeveless V-neckline, twist-front design
- Keyhole cutout under the bust, adjustable spaghetti straps
- Smocked design down the back and body of the dress
- Mini-length hem, form-hugging fit
- Ditsy floral print
- Woven fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4920
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendsetting Style Chain Strap Mini Dress
Show off your trendsetting style in this sleeveless bodycon mini dress! It features a scoop neckline, adjustable spaghetti straps with chunky chain-link accents, a mini-length hem, and a curve-hugging fit. The ribbed knit fabric offers plenty of stretch. Complete the look in this short dress with a mini handbag and clear mules.
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps, chain-link accents
- Mini-length hem
- Form-hugging fit
- Stretchy ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-4917
Category Name: Casual Dresses
Price: $5.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Brunch Eyelet Skater Dress
This adorable skater dress is a perfect pick for weekend brunch! It features a sweetheart neckline, short puff sleeves with tie accents, a high waist seam, a short skater skirt with a ruffled hem, and a fit and flare silhouette. The lightweight knit fabric features a dainty eyelet pattern for the prettiest look. Style with espadrille wedges.
Fit & Features
- Sweetheart neckline, shirring at the bust
- Short puff sleeves, cinched hems, tie accents
- High waist seam
- Short skater skirt, ruffled hem
- Fit and flare silhouette
- Eyelet knit fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4915
Category Name: Casual Dresses
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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La Fleur Floral Mesh Midi Dress
It's love at first sight in this floral midi dress perfect for day dates! It features a sleeveless square neck, spaghetti straps that lead to the lace-up, a bodycon silhouette, and an asymmetrical side slit cutout. The dress is composed of a floral print mesh fabric with a stretch knit lining. Complete the look in lace-up heels.
Fit & Features
- Sleeveless square neck
- Spaghetti straps, lace-up back
- Bodycon silhouette
- Asymmetrical side slit cutout
- Midi-length hem
- Floral print mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4913
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Timeless Love Rib Knit Maxi Dress
You'll adore this rib knit maxi dress time and time again! Create your capsule wardrobe with this perfect dress featuring a sleeveless square neck, spaghetti straps, a curve-hugging silhouette, and a sultry side slit. Complete the look in a statement crop jacket, hoop earrings, and your go-to sneakers!
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Curve-hugging silhouette
- Side slit
- Maxi-length hem
- Stretchy rib-knit fabric
- Runs true to size
Style Number/Barcode: 05102-4916
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Cute Floral Off-The-Shoulder Dress
Step out looking casually cute in this floral mesh mini dress for lunch with the girls or a bridal shower! It features an off-the-shoulder neckline, sheer short-sleeve cuffs, a ruched bust, and side, and back ruched seams that accentuate your curves along the bodycon silhouette. Complete the look with a dainty ring set and heels.
Fit & Features
- Off-the-shoulder neckline
- Sheer short-sleeve cuffs
- Back zipper and hook-eye closure
- Ruched bust, side and back seams
- Bodycon silhouette, mini-length hem
- Ditsy floral print, mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4914
Category Name: Casual Dresses
Price: $5.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet And Spicy Scoop Neck Mini Dress
Sweet and spicy, this mini dress is exactly what your next club night needs! It features a sleeveless scoop neckline, dual spaghetti straps, a strappy back design, and side ruched seams to accentuate your curves along the short bodycon silhouette. Complete the look in eye-catching stiletto heels.
Fit & Features
- Sleeveless scoop neckline
- Dual spaghetti straps
- Strappy back design
- Side ruched seams, bodycon silhouette
- Mini-length hem
- Slinky knit fabric, bust lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4804
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute Factor Eyelet Lace Skater Dress
Bring the cute factor by wearing this eyelet lace skater dress for picnics, brunch, or casual family parties! Featuring adorable puff short sleeves, a square neck with a ruched bust, a flirty tie-back closure, and a fit-and-flare silhouette and short hem. Complete the look with cute flower earrings.
Fit & Features
- Puff short sleeves
- Square neck, ruched bust
- Tie-back closure
- Skater, fit and flare silhouette
- Short-length hem
- Eyelet lace fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4910
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet And Cute Floral Ruffle Short Dress
Embrace your cuteness looking so sweet in this floral short dress - a perfect pick for family gatherings or parties! It features a sleeveless scoop neck, adjustable spaghetti straps, a trendy tie-back, a ruched bust, and a ruffle-layered short-length hem. Complete the look in bow heels.
Fit & Features
- Sleeveless scoop neck, adjustable spaghetti straps
- Tie-back design
- Ruched bust
- Ruffle layered short-length hem
- Ditsy floral print
- Airy woven fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4911
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Oh-So-Sweet Puff Sleeve Mini Dress
Create an oh-so-sweet look in this darling puff sleeve mini dress! It features a square neckline, short puff sleeves, an open-back design with bar straps, a mini-length hem, and a form-hugging fit for a figure-flattering silhouette. The crepe fabric offers a moderate stretch. Style with clear heels for a dinner date.
Fit & Features
- Square neckline
- Short puff sleeves, elastic cinched hems
- Open-back design, dual elasticized bar straps
- Mini-length hem
- Form-hugging fit
- Crepe fabric, knit lining at the bust, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2098
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale