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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Sweeten Me Up Square Neck Cutout A-Line Midi Dress
Sweeten your style in this breezy A-line midi dress perfect for bridal showers, day dates, or brunch! With a sleeveless square neckline and adjustable spaghetti straps, this cotton midi dress offers a flattering fit while the stretchy smocked bust with lace-up detail adds a touch of sweetness. The cutout back with elasticized straps adds a hint of daring to the fitted bodice and A-line silhouette. Complete the look in strappy sandals for a chic allure.
Fit & Features
- Lightweight cotton woven fabric with lining
- Adjustable spaghetti straps
- Smocked lace-up bust
- Cutout back
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05102-5611
Category Name: Casual Dresses
Price: $6.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Destined For Love Lace-Up Short Skater Dress
You'll be destined for love in this short skater dress perfect for dressy parties! This flirty dress features a square neckline, adjustable spaghetti straps, and a lace-up back for a perfect fit. The skater silhouette and short-length hem add a playful touch, while the burnout pattern on the mesh fabric adds a touch of intrigue. Complete the look in block heels.
Fit & Features
- Burnout pattern, mesh fabric, tulle and stretchy knit lining
- Square neckline
- Adjustable spaghetti straps
- Lace-up, back zipper and hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3319
Category Name: Casual Dresses
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Afternoons Collar Open Back Skater Dress
Enjoy a sunny afternoon looking like a cutie in this skater dress perfect for a girl's day! With a sleek halter collar neckline and flattering button-down front, this dress will accentuate your figure with its fitted high waist seam. The playful open back with tie closure adds a touch of allure, while the skater silhouette and short-length hem create a fun and flirty look. Complete the look in strappy sandals and earrings.
Fit & Features
- Lightweight woven fabric with lining
- Open back with tie closure
- Button down front
- Back zipper and hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5616
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Striped Delight Surplice Collared Mini Dress
You're sure to have a day full of sweetness in this delightful striped mini dress perfect for upcoming weekend plans! This dress is designed with chic long sleeves with button cuffs, along with a flattering collar V-neckline and wrap tie waist belt for that cinched look. The surplice mini-length hem adds a touch of sass while the pleated form-hugging fit accentuates your curves. Complete the look in clear sandals and earrings.
Fit & Features
- Striped non-stretch woven lightweight fabric
- Collared V-neckline
- Long sleeves with buttoned cuffs
- Wrap tie waist belt with pleating
- Surplice mini-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5610
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreaming Of Paradise Cowl Neck Tropical Midi Dress
Let your vacation or getaway be filled with sand and compliments when you're in this tropical midi dress! Featuring a cowl neckline and adjustable spaghetti straps for a perfect fit, this bodycon dress also boasts a side slit and midi-length hem. Complete the look with sunglasses and sandals!
Fit & Features
- Tropical print, stretchy knit fabric
- Adjustable spaghetti straps
- Cowl neckline
- Bodycon fit
- Side slit
- Runs true to size
Style Number/Barcode: 05102-5613
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute Feels Off-The-Shoulder Sweater Mini Dress
Feel cute in this off-the-shoulder sweater mini dress all year round! The folded off-the-shoulder neckline adds a flirty touch, while the bodycon fit accentuates your curves perfect for a day or night on the town. Complete the look in block heels.
Fit & Features
- Sweater knit fabric, moderate stretch
- Off-the-shoulder neckline
- Bodycon fit
- Mini-length
- Runs true to size
Style Number/Barcode: 06005-1947
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Getaway Tropical Print Flowy Maxi Dress
This tropical print flowy maxi dress is giving major weekend getaway energy! The breezy lightweight woven fabric is detailed with a tropical leaf-outlined print, perf for your next vacay. The maxi-length dress features a sleeveless square neckline and adjustable spaghetti straps for a customized fit. The high waist leads to a cute tie-back design, followed by a lower back cutout for a hint of skin. The dress flows out in an A-line silhouette with a stylish tiered design. Complete your look with gold hoops and strappy sandals.
Fit & Features
- Tropical printed woven fabric
- Sleeveless square neckline
- Adjustable spaghetti straps
- High waist with tie-back design, lower back cutout
- Flowy A-line fit with a tiered design
- Runs true to size
Style Number/Barcode: 05102-5609
Category Name: Casual Dresses
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Back To Basics Ribbed Knit Midi Dress
Every girl needs this basic ribbed knit midi dress in her line up! The dress features a classic crew neckline and short sleeves perfect for layering with a sweater or jacket and a form-hugging fit.
Fit & Features
- Ribbed knit fabric with brushed knit lining, plenty of stretch
- Crew neckline
- Short sleeves
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5603
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Make It Fierce Crew Neck Leopard Mesh Midi Dress
Make it fierce in this leopard mesh midi dress for cocktail hour or dinner out! This daring dress features a flattering crew neckline, short sleeves, and a bodycon silhouette for a bold look on mesh fabric with a wild leopard print! Complete the look in stiletto heels.
Fit & Features
- Leopard print
- Sheer mesh fabric, slip knit lining with stretch
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5601
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Inspired Charm Strapless Watercolor Print Mini Dress
Envoke an inspired charm in this watercolor print mini dress and capture attention at parties or casual dinners! With its strapless straight-across neckline and bodycon silhouette, this mini dress will accentuate your curves and flatter your figure. Made from airy lined mesh fabric with an eye-catching watercolor print, this dress is a must-have for any fashion-forward girlie! Complete the look in stiletto heels and a purse!
Fit & Features
- Watercolor print
- Mesh fabric lined with stretchy knit
- Strapless straight neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5605
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Good Times Bodycon Abstract Print Mini Dress
A mini dress that calls for good times only at casual parties or weekend plans! Designed with an alluring abstract print on mesh fabric, this dress is both chic and versatile. The sleeveless crew neckline and bodycon silhouette highlight your curves, while the side ruched seams flatter your figure. Complete the look with a mini shoulder bag and heels.
Fit & Features
- Abstract print
- Mesh fabric, sewn-in knit lining, stretchy
- Side ruched seams
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5606
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Yet Classy One-Shoulder Ribbed Knit Midi Dress
Keep casual yet classy in this must-have sleeveless midi dress perfect for your next weekend plans! This sleek and stylish dress features a trendy one-shoulder neckline and a chic cutout accent. The bodycon silhouette and side slit not only add a flirty touch but also flatter your figure on the stretchy ribbed knit fabric. Complete the look with a chic clutch and heels.
Fit & Features
- Stretchy ribbed knit fabric with short knit lining
- One-shoulder neckline, tank strap
- Cutout accent
- Bodycon silhouette
- Side slit
- Runs true to size
Style Number/Barcode: 05102-5591
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Trend Crew Neck Bodycon Midi Dress
A sleeveless midi dress that'll keep you majorly trendy! Perfect for casual plans or vacations, this midi dress is designed with a flattering crew neckline, bodycon silhouette, and front ruched seam, this dress will accentuate your figure. The front slit adds a touch of drama, while the rib knit fabric offers a sewn-in knit lining for extra coverage. Complete the look with chic sandals and sunnies!
Fit & Features
- Rib-knit stretchy fabric, sewn-in knit lining
- Bodycon silhouette
- Front ruched seam and slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5596
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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If You Pleats Sleeveless Pleated A-Line Mini Dress
Prep up your style with this pleated mini dress for casual plans! With a flattering square neckline and delicate spaghetti straps, this a-line dress boasts an adjustable waist belt and pleated mini hem for added charm. Complete the look with a crop denim jacket.
Fit & Features
- Woven fabric, slight stretch
- Spaghetti straps
- Back zipper closure
- A-line silhouette
- Pleated
- Runs true to size
Style Number/Barcode: 05102-5590
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Design Cutout Bodycon Knit Midi Dress
This bodycon midi dress features a sultry lower back cutout and back slit accent for a chic allure. The curve-hugging dress is made with a lined, soft, brushed knit fabric offering plenty of stretch for comfortable wear.
Fit & Features
- Lined brushed knit fabric, plenty of stretch
- Square neckline
- Tank shoulder straps
- Lower back cutout
- Back slit
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5595
Category Name: Casual Dresses
Price: $14.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Natural Sweetheart Halter Marble Print Midi Dress
Look naturally cute for any occasion in this marble print midi dress! The cowl halter neckline and flowy silhouette add a relaxed style, while the side slit and midi-length hem add flirty touches. Complete the look in strappy sandals and a clutch!
Fit & Features
- Marble print, mesh fabric lined with stretchy knit
- Cowl halter neckline with tie closure
- Flowy silhouette
- Side slit
- Runs true to size
Style Number/Barcode: 05102-5593
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Smooth Silhouette Square Neck Tank Midi Dress
Effortlessly chic and oh-so-flattering, this sleeveless midi dress will become your new favorite go-to. This bodycon dress has a sleeveless square neckline and tank straps and hugs your curves in all the right places. The midi-length hem adds a touch of sophistication, while the rib knit fabric lining ensures comfort all day long. Complete the look in a layered necklace for any occasion!
Fit & Features
- Rib knit fabric, sewn-in knit lining, stretchy
- Bodycon fit
- Midi-length
- Runs true to size
Style Number/Barcode: 05102-5587
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Effortless Ribbed Knit Bodycon Midi Dress
This bodycon midi dress is the perfect blend of effortless and chic! Designed with a stretchy ribbed knit fabric for that comfortable fit, this mid-length dress features a trendy sleeveless square neck and back design with thin tank shoulder straps. The ribbed design on the body-hugging silhouette will flaunt your gorgeous figure. Layer on a faux leather jacket and pair with ankle booties for a night out!
Fit & Features
- Stretchy ribbed knit fabric
- Sleeveless square neck and back
- Tank straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5585
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beauty On Vacay Cutout Abstract Maxi Dress
From seaside dinners to dancing under the moonlight, this abstract print maxi dress will have you looking like a beauty on the island! It features delicate spaghetti straps, a sweetheart neckline with an O-ring bust insert, a cutout bodice to reveal some skin, and a flattering bodycon silhouette and maxi-length hem. Complete the look with strappy wedges.
Fit & Features
- Abstract print, knit fabric, short knit lining
- Spaghetti straps
- Sweetheart neckline
- O-ring bust insert, cutout
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5584
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The Best Yet Sleeveless Crew Neck Slit Maxi Dress
The best has come with this stylish basic maxi dress perfect for dressing up or down for any occasion! Crafted from a soft knit fabric, you'll adore this sleeveless dress for its comfort and versatility. The crew neckline gives off a classic vibe while the bodycon silhouette flaunts your curves down to the maxi-length hem with a flirty side slit for movement. Complete the look with a jacket, heels, and a crossbody bag!
Fit & Features
- Soft knit fabric, short lining, plenty of stretch
- Sleeveless crew neckline
- Tank straps
- Side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5588
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Darling Flirtation Tie Strap V-Neck Floral Mini Dress
Imagine how darling and flirty you'll be in this floral mini dress at brunch and parties! The delicate floral print on brushed knit soft fabric adds a playful and romantic touch, perfect for any occasion. Features a plunging neckline and charming tie straps to accentuate your curves while the bodycon fit and mini-length hem add a touch of allure. Complete the look in cute sandals.
Fit & Features
- Floral print, brushed knit fabric lined with stretchy knit
- Tie straps, V-neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5589
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Country Girl Cow Print Ruched Knit Mini Dress
Create a cute country girl 'fit for festival season with this adorable cow print mini dress! The lightweight brushed knit fabric offers plenty of stretch to dance all day. The sleeveless bodice has a classic square neck and back design with spaghetti straps. Ruching down the side seams will accentuate your curves on the form-hugging mini-length silhouette. Style this bodycon dress with a cropped denim jacket and rhinestone cowboy boots!
Fit & Features
- Stretchy brushed knit fabric
- Cow print
- Sleeveless square neck and back
- Spaghetti straps
- Ruched side seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5582
Category Name: Casual Dresses
Price: $6.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stay Sweet Flutter Sleeve Ditsy Floral Mini Dress
Stay sweet in the cutest ditsy floral mini dress, perfect your for weekend plans! The stretchy brushed knit fabric features an adorable ditsy floral print for the prettiest vibe. The mini-length dress is shaped with a sweetheart neckline with flirty ruching and short flutter sleeves for an effortless look. The bodycon silhouette will flaunt your gorgeous figure. Style with hoop earrings and strappy sandals!
Fit & Features
- Ditsy floral print
- Stretchy brushed knit fabric
- Sweetheart neckline with ruching
- Short flutter sleeves
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5586
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Striking Impression Sleeveless Slit Mesh Maxi Dress
Impress with your striking style in this sleeveless mesh maxi dress perfect for dressy occasions! This dress will show off your curves with a square neckline, adjustable spaghetti straps, and a form-hugging fit. The sheer slit maxi-length hem adds a touch of elegance and allure. Complete the look with strappy stiletto heels.
Fit & Features
- Sheer mesh fabric, partial knit lining
- Square neckline
- Adjustable spaghetti straps
- Form-hugging fit
- Sheer slit mesh maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-5583
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free