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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Limelight Lace-Up Bandage Dress
Look back at it. Flaunt your hourglass in this lace-up bandage dress featuring a sleeveless, boat neckline, spaghetti straps, a mini bodycon silhouette, and an open-back with an alluring lace-up design with tie-closure. Composed of a seamless bandage-knit fabric with minimal stretch. Finish the look in stiletto heels for a night out.
Fit & Features
- Sleeveless, boat neckline
- Spaghetti straps
- Open-back, lace-up design with tie-closure
- Mini bodycon silhouette
- Seamless bandage-knit fabric
- Fits true to size, minimal stretch
Style Number/Barcode: 06005-1302
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Only The Best Cutout Sweater Dress
Treat yourself to the best sweater midi dress to have this season! It features fitted long sleeves, an asymmetrical neckline with contrast trim, a form-hugging silhouette, and a flirty side waist cutout with contrast trim. Style with block heels to complete the look!
Fit & Features
- Fitted long sleeves
- Asymmetrical neckline, contrast trim
- Form-hugging silhouette
- Side waist cutout, contrast trim
- Midi-length hem
- Rib-knit sweater fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1639
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Contemporary Girl Sweater Midi Dress
Breeze in looking like a chic contemporary girl in this sweater midi dress! It features an on-trend cold shoulder with adjustable halter spaghetti straps, fitted long sleeves, a bodycon silhouette, and a front-side slit accent. Complete the look with lace-up heels for a dinner date!
Fit & Features
- Cold shoulder
- Adjustable halter spaghetti straps
- Fitted long sleeves
- Bodycon silhouette
- Front side slit, midi-length hem
- Sweater rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1613
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rendezvous In Satin Slip Midi Dress
Have a chic rendezvous in this satin slip midi dress featuring a sleeveless V-neck, bungee spaghetti straps, a fitted a-line silhouette, and a sultry front slit along the hem. The dress is composed of smooth, non-stretch satin fabric. Complete the look in lace-up stiletto heels.
Fit & Features
- Sleeveless V-neck
- Bungee spaghetti straps
- Fitted a-line silhouette
- Front slit
- Midi-length hem
- Non-stretch woven satin fabric
- Runs true to size
Style Number/Barcode: 05101-2383
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wonderful Winter Sweater Midi Dress
Slay all season no matter the weather in this sweater midi dress perfect for casual or dressy events! It features fitted long sleeves, a mock neck, a bust cutout, and a form-hugging silhouette with a flirty front slit. The dress is composed of a stretchy rib-knit fabric. Pair with booties to complete the look.
Fit & Features
- Fitted long sleeves, mock neck
- Bust cutout
- Form-hugging silhouette
- Front slit accent
- Midi-length hem
- Rib-knit sweater fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1579
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Time To Slay Bodycon Midi Dress
It's your time to slay in this simple yet chic bodycon midi dress! It features an asymmetrical boat neckline with a partial off-the-shoulder design, long fitted sleeves with thumb hole accents, a midi-length hem, and a curve-hugging silhouette. The smooth knit fabric offers plenty of stretch. Style with strappy heels.
Fit & Features
- Asymmetrical boat neckline, partial off-the-shoulder design
- Long fitted sleeves, thumb hole accents
- Midi-length hem
- Curve-hugging fit
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5006
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Swirls Of Style Satin Midi Dress
Stylish marble swirls capture all the attention on this satin midi dress featuring a sleeveless v-neck, adjustable spaghetti straps, flexible boning inserts along the bodice, and a curve-hugging silhouette with a front slit accent. Complete the look in a casual crop jacket.
Fit & Features
- Sleeveless v-neck, adjustable spaghetti straps
- Flexible boning inserts
- Back zipper and hook-eye closure
- Front slit, curve-hugging, midi-length hem
- Marble print
- Satin fabric, knit lining, no stretch
- Fits true to size
Style Number/Barcode: 05102-4867
Category Name: Casual Dresses
Price: $5.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Made For You Marble Mesh Mini Dress
This eye-catching marble mesh mini dress was made for you to style up and create a chic 'fit! It features a crew neckline, sheer long fitted sleeves, a mini-length hem, a bodycon silhouette that will hug your curves, and an all-over alluring marble print pattern. The partially lined mesh fabric offers plenty of stretch. Complete your look with strappy stilettos.
Fit & Features
- Crew neckline
- Sheer long fitted sleeves
- Mini-length hem
- Bodycon silhouette
- Marble print
- Sheer mesh fabric, partial knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4847
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Winter Chic Style Midi Sweater Dress
You'll adore the winter chic style of this midi sweater dress! Featuring a mock neckline, long fitted sleeves, a midi-length hem, and a form-hugging silhouette, this sweater dress is a perfect choice for casual holiday parties. The cozy brushed ribbed knit fabric offers plenty of stretch for comfortable wear. Style with ankle booties.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Midi-length hem
- Form-hugging fit
- Brushed ribbed knit fabric, knit lining down the body
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5039
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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
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Sweet And Off-The-Shoulder Sweater Skater Dress
Look sweet on chilly days in this darling sweater mini dress featuring a cute folded, off-the-shoulder neckline and forever flattering skater silhouette.
Fit & Features
- Rib knit stretchy fabric
- Folded off-the-shoulder neckline
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000013
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Back Of My Mind Crepe Slip Dress
You'll be unforgettable once they see you in this crepe slip dress perfect for casual parties and celebrations! It features a sleeveless V-neck, spaghetti straps, a form-hugging silhouette, and a sultry front slit along the midi-length hem. Style with simple hoop earrings to complete the look!
Fit & Features
- Sleeveless V-neck, spaghetti straps
- Form-hugging silhouette
- Front slit accent
- Midi-length hem
- Crepe fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4826
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wrap It Up Cable Knit Sweater Dress
Wrap yourself up in style this season! Cue compliments whenever you're in this cable knit sweater midi dress featuring long balloon sleeves, a v-neckline, and a surplice bodice with a tie-front waist belt and a bodycon silhouette. Style with pointed-toe booties to complete the look!
Fit & Features
- Long balloon sleeves
- V-neckline
- Surplice bodice
- Tie-front waist belt
- Bodycon silhouette
- Midi-length hem
- Cable knit fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 05102-4818
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Seasonal Surprise Color Block Dress
Mix it up this season! Step out in this trendy color block mini dress featuring fitted long sleeves, a scoop neck, and a bodycon silhouette on stretchy rib-knit fabric. Style with over-the-knee boots to complete the look!
Fit & Features
- Fitted long sleeves
- Scoop neck
- Bodycon silhouette
- Mini-length hem
- Color block pattern
- Rib-knit fabric, double-lined, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4952
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flirty In Fall Cable Knit Dress
Stay flirty and cozy this fall in this cable knit midi dress! It features long sleeves, a mock neck, a bodycon silhouette, and a sultry open-back design. Perfect for styling with faux suede booties for your weekend plans!
Fit & Features
- Long sleeves
- Mock neck
- Bodycon silhouette
- Open-back design
- Midi-length hem
- Soft cable knit sweater fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1614
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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First Pick Henley Knit Maxi Dress
Cute and stylish, this maxi dress will be your first pick for looking good always! It features fitted long sleeves, a v-neckline with button front closures, a bodycon silhouette, and is composed of stretchy rib-knit fabric. Style with booties to complete the look!
Fit & Features
- Fitted long sleeves
- V-neckline
- Button-front closures
- Bodycon silhouette
- Maxi-length hem
- Rib-knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5036
Category Name: Casual Dresses
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always Cozy Turtleneck Mini Dress
You'll forever be cozy in this soft and stretchy brushed knit mini dress! It features a turtleneck, long fitted sleeves, and a short, curve-hugging, bodycon silhouette. Style with a plaid blanket scarf and knee-high boots.
Fit & Features
- Turtleneck
- Long fitted sleeves
- Mini-length hem
- Fitted bodycon silhouette
- Double-lined brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4811
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Play The Game Checker Mini Dress
Play the game of style with this checkered mini dress and you'll definitely get a checkmate! The sleeveless dress features a square neck, tank-style straps, flexible boning inserts, a bodycon silhouette, and a mini-length hem. Complete the look in a crop denim jacket for a casual daytime outing.
Fit & Features
- Sleeveless, square neck, tank-style straps
- Flexible boning inserts
- Back zipper and hook-eye closure
- Bodycon fit, short-length hem
- Checkered pattern
- Rib-knit fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4877
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Style Warm Up Sweater Knit Dress
Cozy up this season in style! This sweater mini dress is the best of both worlds featuring cozy dolman sleeves, a surplice v-neckline, belted tie-front waist, and a bodycon silhouette. The dress is composed of soft cable and rib-knit fabric that offers plenty of stretch. Style with knee-high boots to complete the look!
Fit & Features
- Dolman sleeves
- Surplice v-neckline
- Belted tie-front waist, belt loop accents
- Bodycon silhouette, mini-length
- Cable and rib-knit sweater fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1572
Category Name: Casual Dresses
Price: $20.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In The Knit Cable Sweater Dress
A fashionista like you needs to set the trends! Step it up this season in this staple cable knit sweater dress featuring a ribbed mock neck and long sleeves, a bodycon silhouette, and a short-length hem. Style with knee-high boots and a jacket to complete the look!
Fit & Features
- Ribbed mock neck and long sleeves
- Bodycon silhouette
- Short-length hem
- Cable knit design
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1564
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Winter Chic Off-The-Shoulder Sweater Dress
This adorable ribbed knit sweater dress will give you a chic look for the winter season! It features an off-the-shoulder neckline with a fold-over design, long fitted sleeves, a midi-length, curve-hugging silhouette, and a high front slit. The knit fabric offers a moderate stretch for comfortable wear. Style with knee-high boots.
Fit & Features
- Off-the-shoulder neckline, fold-over design
- Long fitted sleeves
- Midi-length hem, fitted bodycon silhouette
- High front slit
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1578
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Classic Chic Mock Neck Sweater Dress
This classic chic sweater dress is perfect for styling up or down this winter season. It features an on-trend mock neckline, long fitted sleeves, a short, curve-hugging silhouette, and a front slit accent. The knit fabric offers plenty of stretch. Pair with knee-high boots and sleek hoops.
Fit & Features
- Ribbed mock neckline
- Long fitted sleeves
- Mini-length hem, front slit
- Curve-hugging silhouette
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1616
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cargo Without Plaid Short Dress
You can't go without this plaid short dress perfect for autumn days and layering for winter nights! The dress features a sleeveless square neck, spaghetti straps, side flap pockets, and a bodycon silhouette. Complete the look in a basic long sleeve top and lug booties.
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Side flap pockets
- Bodycon silhouette
- Short-length hem
- Plaid pattern, knit fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 05102-4898
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale