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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Cozy Love Mock Neck Midi Dress
This midi dress is what dreams are made of! It features a cozy brushed rib-knit fabric designed with a mock neck, fitted long sleeves, and a bodycon silhouette. The knit fabric offers a moderate stretch. Style with a crop denim jacket to complete the look!
Fit & Features
- Mock neck
- Fitted long sleeves
- Bodycon silhouette
- Midi-length hem
- Super soft brushed rib-knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5035
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Favorite Pick Ruched Slit Midi Dress
Your new favorite midi dress for looking stylish and cute! It features a sleeveless square neck, sleek bungee spaghetti straps, a bodycon silhouette, and a side slit with a ruched drawstring that lets you customize the fit. The midi dress is composed of a rib-knit fabric with lining and plenty of stretch. Complete the look in trendy flat sandals for a bridal shower or brunch!
Fit & Features
- Sleeveless square neck
- Bungee spaghetti straps
- Bodycon silhouette
- Side slit, ruched adjustable drawstring
- Midi-length hem
- Rib knit-lined fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5034
Category Name: Casual Dresses
Price: $5.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Romance V-Neck Midi Dress
Effortless and romantic, this sleeveless midi dress is a staple to have for every occasion! It features a V-neckline with a twisted bust, spaghetti straps, a form-hugging silhouette, and a sultry front slit. The mid-length dress is stretchy and double-lined. Complete the look in rhinestone mules.
Fit & Features
- Sleeveless V-neckline, spaghetti straps
- Twisted bust
- Form-hugging silhouette
- Front slit
- Midi-length hem
- Double-lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5033
Category Name: Casual Dresses
Price: $5.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Strolling The Garden Floral Chiffon Midi Dress
Stroll the garden looking effortlessly enchanting in this floral chiffon midi dress! It features a sleeveless sweetheart neckline with a flirty bust tie, adjustable spaghetti straps, a stretchy smocked back, and a hem slit. Complete the look in strappy sandals for an outdoor wedding.
Fit & Features
- Sleeveless sweetheart neckline
- Bust tie, adjustable spaghetti straps
- Stretchy smocked back
- Slit accent, midi-length hem
- Ditsy floral print, airy chiffon, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2312
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dinner With A View Tropical Slit Maxi Dress
You may be on vacay with incredible views but you'll be the main attraction in this tropical maxi dress perfect for dining on the island! It features a sleeveless square neck, adjustable spaghetti straps, a front adjustable ruched drawstring that lets you customize the style, a sultry front slit, and a flattering slim curve-hugging silhouette. The maxi dress is composed of a slinky knit fabric with a tropical print and a short stretchy knit lining. Complete the look in strappy heels.
Fit & Features
- Sleeveless square neck, adjustable spaghetti straps
- Front adjustable ruched drawstring
- Slim curve-hugging silhouette
- Front high slit
- Maxi-length hem
- Tropical print, slinky knit fabric, short stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5031
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always Charming Floral Eyelet Lace Dress
Always charming and cute, this floral eyelet lace dress boasts adorable allure! It features puff short sleeves, a square neck, a tie-back design, and a flattering skater silhouette and short-length hem. Complete the look in strappy sandals for a baby shower or family party.
Fit & Features
- Puff short sleeves
- Square neck
- Tie-back design
- Skater silhouette
- Short-length hem
- Ditsy floral print, eyelet lace, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5030
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simple And Stunning Ruched Mini Dress
Simple and stunning, this classic mini dress is a closet staple. It features a sleeveless cowl neckline with a draped design, tank shoulder straps, a scoop back design, ruching down the side seams, a mini-length hem, and a bodycon silhouette that will hug your curves. Style with strappy mules for a dinner date or party.
Fit & Features
- Sleeveless cowl neckline
- Tank shoulder straps
- Scoop back design
- Ruched side seams
- Mini-length hem, bodycon silhouette
- Double-lined smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5028
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pop On Over Bubble Hem Skater Dress
Pop on over to every party you're invited to in this poplin skater dress featuring adorable puff short sleeves, a wired V-neckline, a high waist seam, and a flattering fit and flare silhouette with a short bubble hem design. The poplin woven fabric includes a sewn-in knit lining. Style this skater dress with rhinestone strappy heels to complete the look!
Fit & Features
- Puff short sleeves, cinched hems
- Wired V-neckline, back zipper, hook and eye closure
- High waist seam
- Fit and flare skater silhouette
- Short bubble hem design
- Poplin woven fabric, sewn-in knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2299
Category Name: Casual Dresses
Price: $6.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Linked Together Chain Cutout Mini Dress
You and this mini dress are the perfect links! Flaunt your curves in this sleeveless dress featuring a square neck, adjustable spaghetti straps, a side cutout with a chainlink detail, and a bodycon silhouette. The double-lined knit fabric offers a moderate stretch. Complete the look with hoop earrings for a party!
Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Side cutout, chainlink detail
- Bodycon silhouette
- Mini-length hem
- Double-lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5024
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunshine On My Mind Linen Midi Dress
This flowy linen midi dress was made for sunny days! It features a sleeveless V-neckline with a ruffled trim, adjustable spaghetti straps, a fitted bodice with dual high waist seams, and a midi-length hem with a relaxed A-line silhouette and a tiered, ruffled design. The airy linen fabric includes a full knit lining. Style with wedges for a dreamy look.
Fit & Features
- Sleeveless V-neckline, ruffled trim
- Adjustable spaghetti straps, hidden back zipper, hook and eye closure
- Fitted bodice, dual high waist seams
- Midi-length hem, flowy A-line silhouette
- Tiered, ruffled design
- Semi-sheer linen fabric, full knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5023
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Legend Lace-Up Graphic Short Dress
Everyone will make way for you, a major legend walking through! This graphic short dress flaunts your edgy-cool girl style featuring a sleeveless scoop neckline, spaghetti straps, dual side lace-up plackets that reveal some skin, a short bodycon fit, and a front script that reads, "Legend" with graphic detailing. Complete the look with a chain choker necklace and earrings.
Fit & Features
- Sleeveless scoop neckline, spaghetti straps
- Dual side lace-up plackets, cutouts
- Short bodycon fit
- Front script reads, "Legend", graphic details
- Mini-length hem
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1525
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trip To Paradise Tropical Print Maxi Dress
This bold and alluring tropical print maxi dress calls for a trip to paradise! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, a floor-length hem with a thigh-high front slit, and a flowy silhouette. The smooth knit fabric showcases a tropical palm leaf print. Style with strappy sandals for sunset drinks.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross-back design
- High waist seam
- Floor-length hem, high front slit, flowy silhouette
- Tropical palm leaf print
- Knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5025
Category Name: Casual Dresses
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute View Ditsy Floral Chiffon Skater Dress
You'll be a cute view in this ditsy floral chiffon dress at casual family parties or weekend getaways! It features puff short sleeves, a sweetheart neck, a front bust ruched drawstring, a stretchy smocked back, and a skater silhouette with a short-length hem. The dress is composed of a chiffon fabric with a ditsy floral print and a stretchy knit lining. Complete the look in trendy sandals.
Fit & Features
- Puff short sleeves, elastic ruffled hems
- Sweetheart neckline
- Front bust ruched drawstring
- Stretchy smocked back
- Skater silhouette, short-length hem
- Ditsy floral print, chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5022
Category Name: Casual Dresses
Price: $5.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always Picked First Floral Lace-Up Dress
You'll always be picked first in this floral mini dress perfect for afternoon soirees! It features a sleeveless square neck, spaghetti straps that shape the lace-up open back, a bodycon silhouette, and a mini-length hem. The dress is designed with a watercolor floral print on knit fabric with a stretch lining. Complete the look in adorable wedge sandals.
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Lace-up, open-back
- Bodycon silhouette
- Mini-length hem
- Watercolor floral print, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5020
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Paint Me In Floral V-Neck Maxi Dress
This floral maxi dress will fit like a dream and give off major artsy vibes! It features a sleeveless V-neckline, spaghetti straps, a hip-hugging fit, and a sultry front slit along the flowy hem. Complete the look in dainty earrings for a daytime soiree!
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Hip-hugging fit
- Front slit, flowy maxi-length hem
- Floral watercolor print
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5018
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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One More Moment Sweater Dress
Make a lasting impression leaving the pool party in this chic cover-up sweater dress! It features a sleeveless square neck, spaghetti straps that lead to an open back with lace-up closure, a form-fitting silhouette, and a high side slit atop the midi-length hem. Complete the look with sandals and sunglasses.
Fit & Features
- Sleeveless square neck, spaghetti straps
- Open back, lace-up closure
- Form-fitting silhouette
- Side slit, midi-length hem
- Sweater knit fabric, slightly sheer, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1688
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Time To Escape Tropical Print Maxi Dress
Get ready to escape on a gorgeous getaway in this sultry tropical print maxi dress! It features a sleeveless asymmetric one-shoulder neckline with a spaghetti strap, a bold and alluring asymmetric waist cutout with a trendy O-ring accent, a hip-hugging fit that will hug your natural curves, and a floor-length hem with a thigh-high side slit to showcase some leg. The all-over palm leaf print on the stretchy knit fabric captures those tropical oasis vibes. Style with strappy sandals.
Fit & Features
- Sleeveless asymmetric one-shoulder neckline
- Single adjustable spaghetti strap
- Asymmetric waist cutout, O-ring accent
- Hip-hugging fit, floor-length hem, high side slit
- Tropical palm leaf print
- Knit fabric, mini-length lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5016
Category Name: Casual Dresses
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sunset Happy Hour Ruffled Skater Dress
This skater dress was made for sunset happy hours this season! It features a sleeveless V-neckline, halter tie-back straps, an open back, a stretchy smocked high waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight twill fabric includes a woven lining. Style this short dress with espadrille sandals and a mini handbag.
Fit & Features
- Sleeveless V-neckline
- Halter tie-back straps, open back
- Stretchy smocked high waist
- Short skater skirt, tiered ruffled design
- Fit and flare silhouette
- Twill fabric, woven lining
- Runs true to size
Style Number/Barcode: 05102-5531
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Notice Me Lace Ruffle Mini Dress
Make 'em' stop and stare at you in this lace mini dress as the chic bride-to-be or gorgeous graduate! The dress features a sleeveless V-neckline, adjustable spaghetti straps that crisscross along the back, a form-hugging fit, and a flirty asymmetrical ruffle trim hem. Complete the look in block heel sandals.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Crisscross back
- Form-hugging fit
- Ruffle trim mini-length hem
- Lace fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2637
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Perfection Mock Neck Sweater Dress
Showcase chic perfection in this classic ribbed knit sweater dress. It features a mock neckline, long fitted sleeves with puff accents at the shoulders, and a short, curve-hugging silhouette. The knit fabric offers plenty of stretch. Style with knee-high boots.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Puff shoulders
- Mini-length hem
- Form-hugging silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1681
Category Name: Casual Dresses
Price: $15.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Give Me Butterflies Square Neck Skater Dress
Show up to the party in this short skater dress and give everyone a fluttery heart for you! It features three-quarter-length puff sleeves, a square neck, a smocked back, and a fit and flare silhouette. The dress is designed with delicate butterfly embroidery on twill woven fabric with a woven lining. Complete the look with lace-up sandals.
Fit & Features
- Three-quarter-length puff sleeves
- Square neck
- Smocked back
- Fit and flare, skater silhouette
- Short-length hem
- Butterfly embroidery, twill woven fabric and lining
- Runs true to size
Style Number/Barcode: 05102-5009
Category Name: Casual Dresses
Price: $5.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Show Face Abstract Print Mini Dress
Show your artsy-chic side in this mesh mini dress perfect for a movie date or casual plans with friends! It features a sleeveless square neck, sleek bungee spaghetti straps, side ruched seams to accentuate your curves, and a bodycon silhouette. The dress is designed with an abstract face print on mesh fabric with a stretchy knit lining. Complete the look in a trendy crop jacket and sandals.
Fit & Features
- Sleeveless square neck
- Bungee spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Abstract face print, mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5014
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cue The Charm Linen Off-The-Shoulder Dress
This linen skater dress cues the charm you'll be bringing to wine tasting with the ladies or a birthday brunch! It features a cute off-the-shoulder ruffle trim neckline with elasticized short-sleeve cuffs, a tie-waist belt, and a flattering short-length tiered ruffle hem. Complete the look with a dainty tennis bracelet and sandals.
Fit & Features
- Off-the-shoulder ruffle trim neckline
- Elasticized short-sleeve cuffs
- Back zipper and hook-eye closure
- Tie-waist belt
- Skater silhouette, short-length tiered ruffle hem
- Linen fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2341
Category Name: Casual Dresses
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Endless Sunshine Linen Tie-Back Midi Dress
For the sun-soaked days ahead, this linen midi dress will make a cute companion! It features a sleeveless square neck, adjustable spaghetti straps, a flirty tie-back closure, and a flowy ruffled hem. Style with trendy sandals and sunglasses.
Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Tie-back closure
- Flowy ruffled midi hem
- Airy linen fabric, slight stretch
- Runs true to size
Style Number/Barcode: 05102-5012
Category Name: Casual Dresses
Price: $5.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance