Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, or keep it flowy with midi and maxi silhouettes. Mesh details add a little edge, while sleeveless minis and long-sleeve staples cover every season. Whether you’re layering up for a chill weekend or slipping into something light for a last-minute dinner date, these casual dresses are made to move with your mood—and 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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Elevated Cutout Mini Sweater Dress
This elevated mini sweater dress is a trendy staple for this fall season! It features a mock neckline, long fitted sleeves, waist cutouts that lead to the back, and a short, curve-hugging, bodycon silhouette. Style with strappy heels.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Waist cutouts that lead to the back
- Mini-length hem
- Fitted bodycon silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1469
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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All Business Sweater Mini Dress
All business with some pleasure! Take this sweater mini dress from office hours to happy hour. It features a sleeveless, v-neck, and a form-fitting silhouette. Complete the look with a chic clutch.
Shop More Styles: The Sweater Collection
Fit & Features
- Sleeveless, v-neck
- Form-fitting silhouette
- Mini-length hem
- Sweater rib-knit
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1529
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Struck By Sultry Halter Mini Dress
Get struck by this sultry halter mini dress sure to capture every eye in the room! The knit dress features a sleeveless halter neck with tie closure, a strappy cutout waist, and a form-hugging silhouette. Complete the look in sassy platform heels.
Fit & Features
- Sleeveless halter neck with tie closure
- Strappy cutout waist
- Form-hugging silhouette
- Mini-length hem
- Lined slinky knit fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4776
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Cool Slit Maxi Dress
Stroll outside looking casually cool and cute in this basic maxi dress design with a sleeveless scoop neck with bungee spaghetti straps, a form-hugging silhouette, and a high-cut side slit. Complete the look in a crop denim jacket and sneakers.
Fit & Features
- Sleeveless scoop neck
- Bungee spaghetti straps
- Form-hugging
- High-cut side slit
- Maxi-length hem
- Rib-knit fabric, lined, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4883
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Timeless Trend Collared Mini Dress
Totally timeless and trending, this collared mini dress will be such a staple in your year-round closet! It features long fitted bell sleeves with split cuffs, a V-neckline, a bodycon silhouette, and side and center front ruching that puts your curves on display! Complete the look in chic booties.
Fit & Features
- Long fitted bell sleeves with split cuffs
- Collared V-neckline
- Bodycon silhouette
- Center and side ruching
- Mini-length hem
- Stretchy smooth knit fabric
- Runs true to size
Style Number/Barcode: 05102-4899
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Off The Scale Snake Mini Dress
This snake mini dress will take your style to a new scale! It features a sleeveless square neck with sleek spaghetti straps and side ruched seams to accentuate your curves along the bodycon silhouette. Complete the look in a choker necklace.
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Snake print, knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4695
Category Name: Casual Dresses
Price: $9.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ruched Babe Mock Neck Bodycon Dress
Flaunt your babe status in this bodycon dress! It features long sleeves, a mock neckline, a ruched front, and a short-length hem. The dress is composed of a soft knit fabric with a moderate stretch
Fit & Features
- Long sleeves
- Mock neckline
- Ruched front
- Short-length hem, bodycon style
- Soft knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4290
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Highly Sophisticated Sweater Dress
This sleeveless sweater dress brings sultry-sophistication to every occasion! It features a halter neckline, side cutouts on the bodice, and a form-fitting silhouette on a mini-length hem. Complete the look in a classy blazer and heels.
Fit & Features
- Sleeveless, halter neckline
- Side cutouts
- Form-fitting silhouette
- Mini-length hem
- Soft sweater knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1377
Category Name: Casual Dresses
Price: $3.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Good For You Sweater Maxi Dress
Cause you like looking good for yourself! This sweater maxi dress is the perfect staple for your seasonal closet. It features long sleeves, a collared v-neckline, a form-hugging silhouette, and a flirty front cutout slit. Style with booties for an afternoon lunch.
Fit & Features
- Long sleeves
- Collared v-neckline
- Form-hugging silhouette
- Front cutout slit
- Maxi-length hem
- Ribbed knit fabric
- Fits true to size
Style Number/Barcode: 06005-1482
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On Top Of The Trends Cutout Mini Dress
Stay on top of the latest trends this fall with this casual yet chic mini dress! It features a sweetheart neckline with a center knot accent at the bust, dual asymmetric front cutouts at the waist, long fitted sleeves, and a short, form-hugging silhouette. The ribbed knit fabric has a moderate stretch for comfortable wear. Style with knee-high boots for a fall festival.
Fit & Features
- Sweetheart neckline, center knot detail at the bust
- Dual asymmetric front waist cutouts
- Long fitted sleeves
- Mini-length hem
- Fitted bodycon silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4320
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Marvelous Mod Mesh Short Dress
So marvelously mod, this marble print mesh dress has entered the chat. It features a sleeveless square neckline, spaghetti straps, and side ruched seams to accentuate your curves along the bodycon silhouette. Complete the look in chunky platform heels.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Marble print, mesh-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4819
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Rock Legend Graphic Choker Tunic
Showcase your rock babe status in this edgy graphic tunic top featuring short sleeves, a choker neck with a cutout accent and slash details, and a front script that reads, "Vintage Rock N Roll" along the form-fitting short hem. Complete the look in combat boots for a concert.
Fit & Features
- Short sleeves
- Choker neck with cutout accent
- Slash details
- Graphics front script "Vintage Rock N Roll"
- Form-fitting, short hem
- Jersey knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1414
Category Name: Casual Dresses
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Take A Look Sweater Midi Dress
Let everyone take a look at you in this sweet sweater midi dress perfect for the autumn season! This dress features a sleeveless halter neck with tie closure, a bodycon silhouette, and a cutout waist with a front slit along the hem. Complete the look in pointy-toe booties.
Fit & Features
- Sleeveless halter neck with tie closure
- Bodycon silhouette
- Cutout waist, front slit
- Midi-length hem
- Rib-knit sweater fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1416
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic Romance Floral Lace-Up Maxi Dress
Evoke chic romance on date night in this gorgeous floral maxi dress designed with an open lace-up strappy back and floor-length form-hugging silhouette. Style with a sleek handbag and stiletto heels.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Large floral print
- Sleeveless deep V-neckline
- Spaghetti straps
- Open cross-back lace-up strappy design
- Maxi-length hem, form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-000111
Category Name: Casual Dresses
Price: $7.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Swirl Of Splash Crew Mini Dress
A splash of this swirl print mini dress will instantly give your closet a fresh look! The dress features long fitted sleeves, a crew neckline, and a bodycon silhouette on smooth knit fabric with a moderate stretch. Complete the look in a crop denim jacket for a day out with friends!
Fit & Features
- Long fitted sleeves
- Crew neckline
- Bodycon silhouette
- Mini-length hem
- Swirl print
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4779
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Knit Your Average Sweater Dress
Level up in this curve-flaunting sweater dress featuring a sleeveless, scoop neckline, spaghetti straps, a bodycon silhouette, and a mini-length hem on ribbed knit fabric with plenty of stretch. Complete the look in a crop cardigan and booties.
Shop More Styles: The Sweater Collection
Fit & Features
- Sleeveless, scoop neckline
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Ribbed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1450
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
- Sleeveless, scoop neckline
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Edgy Stunner Graphic T-Shirt Dress
Show off an edgy style with this on-trend graphic t-shirt dress! It features a crew neckline with a notched design with safety pin detailing, short sleeves, a mini-length, fitted silhouette, and a motorcycle and eagle graphic with the script "American Motorcycles Road Lifestyle 1974." Complete your 'fit with combat boots.
Fit & Features
- Crew neckline, notched design, safety pin detailing
- Short sleeves
- Mini-length hem, form-hugging fit
- Motorcycle and eagle graphic
- Script that reads, "American Motorcycles Road Lifestyle 1974"
- Cotton-blend fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1445
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Coffee Date Ribbed Knit Midi Dress
This soft ribbed knit midi dress is perfect for fall coffee dates! It features a collared V-neckline, long fitted sleeves, a partial faux button-down front, a midi-length hem with a high front slit, and a form-hugging fit. Style with knee-high boots for a chic autumn look.
Fit & Features
- Collared V-neckline
- Long fitted sleeves
- Partial faux button-down front
- Midi-length hem, front slit
- Fitted silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4740
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Chic Ribbed Knit Midi Dress
Style up this casual chic ribbed knit midi dress for every day! It features a mock neckline, short sleeves, a midi-length hem, a form-hugging fit, and a high front slit. Complete the look with hoop earrings and ankle booties.
Fit & Features
- Mock neckline
- Short sleeves
- Midi-length hem
- Fitted bodycon silhouette
- Front slit
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4739
Category Name: Casual Dresses
Price: $19.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Animal Kingdom Zebra Satin Dress
You'll be the head of the animal kingdom in this fierce and femme zebra satin mini dress! It features a sleek and sleeveless cowl neck, spaghetti straps, and a curve-hugging silhouette. Complete the look in strappy heels for a wild night out!
Fit & Features
- Sleeveless cowl neck
- Spaghetti straps
- Curve-hugging silhouette
- Mini-length hem
- Zebra pattern
- Smooth satin with minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4532
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fall Ritual Poplin Shirt Dress
Your new fall favorite for wearing all season! This poplin shirt dress features long sleeves with buttoned cuffs, a collared neckline, front button-down closures, a fitted waist, a lower open-back design with lace-up, and a pleated, short skater silhouette. Complete the look in chic Panama hat and booties.
Fit & Features
- Long sleeves with buttoned cuffs
- Collared neckline
- Front button-down closures
- Fitted waist, lower open-back, lace-up
- Pleated, short skater silhouette
- Non-stretch poplin fabric
- Fits true to size
Style Number/Barcode: 05101-1771
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simple Life Crew Tank Midi Dress
All a girl needs is this basic crew tank midi dress perfect for dressing up or down! It features a sleeveless bodice, wide tank shoulder straps, a midi-length hem, and a bodycon silhouette on lined ribbed knit fabric with plenty of stretch. Style this mid-length dress with a jacket and suede booties.
Fit & Features
- Sleeveless crew neckline
- Wide tank shoulder straps
- Midi-length hem
- Bodycon silhouette
- Lined ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4772
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Everyday Ribbed Knit Midi Dress
Effortlessly chic for every day, this ribbed knit midi dress is a must-have for fall. It features a V-neckline, a combination of front spaghetti straps and long fitted sleeves, and a midi-length, curve-hugging silhouette. Style with ankle booties for coffee dates this season.
Fit & Features
- V-neckline
- Front spaghetti straps, long fitted sleeves
- Midi-length hem
- Fitted bodycon silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4975
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling Good Turtleneck Maxi Dress
Look and feel good in this rib knit maxi dress perfect for everyday styling! It features long sleeves, a turtleneck, a form-hugging silhouette, and a side-slit accent. Complete the look in mules for a dinner date.
Fit & Features
- Long fitted sleeves
- Turtleneck
- Form-hugging silhouette
- Side slit
- Maxi-length hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4861
Category Name: Casual Dresses
Price: $5.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale