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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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
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Popular Poise Mock Neck Abstract Mini Dress
An abstract print mini dress features sheer fitted long sleeves, a mock neckline, and a flattering bodycon fit. Perfect for styling with stiletto heels.
Fit & Features
- Abstract print, mesh fabric, sewn-in knit lining
- Mock neckline
- Fitted sheer long sleeves
- Bodycon mini-length fit
- Runs true to size
Style Number/Barcode: 05102-5581
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chicly Femme Bodycon Abstract Mesh Midi Dress
A sleeveless midi dress features a square neckline and a bodycon silhouette that flaunts your curves. The abstract print mesh fabric offers an artsy look. Perfect for styling with stilettos.
Fit & Features
- Abstract print, mesh fabric
- Square neckline
- Spaghetti straps
- Bodycon midi-length fit
- Runs true to size
Style Number/Barcode: 05102-5580
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Set For Cuteness Twist Back Slit Rib Knit Maxi Dress
You and this maxi dress are set for cuteness all season long! Made with rib knit fabric, this dress is both comfortable and stylish, perfect for any occasion. Featuring a square neckline and shoulder straps, this dress offers a form-hugging fit that will accentuate your curves. The twist-back design adds a trendy touch while the high side slit and maxi-length hem provide an alluring appeal. Complete the look with sandals and sunnies!
Fit & Features
- Stretchy rib knit fabric
- Square neckline
- Shoulder straps
- Twist back design
- High side slit
- Form-hugging
- Runs true to size
Style Number/Barcode: 05102-5577
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Blissful Afternoons Corset A-Line Midi Dress
Enjoy an afternoon of bliss looking so sweet in this A-line midi dress at showers or semi-formal weddings! The sweetheart neckline and adjustable spaghetti straps accentuate your figure while the corset bodice with built-in padded underwire bust provides support. The flowy A-line silhouette and midi-length hem add elegance to your look. Complete the look in strappy heeled sandals.
Fit & Features
- Woven fabric lined with stretchy knit
- Adjustable spaghetti straps
- Sweetheart neckline
- Corset bodice, built-in padded underwire bust
- Back zipper and hook-eye closure
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3309
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always On Point Ruched Knit Mini Dress
This trendy ruched knit mini dress will have your everyday 'fits always on point! Made with a stretchy ribbed knit fabric for comfortable wear, this mini-length dress features a sleeveless scoop neckline with thin tank shoulder straps and ruched detailing to accentuate your curves on the bodycon silhouette. Style with a boyfriend blazer and heels for happy hour!
Fit & Features
- Stretchy ribbed knit fabric lined with knit
- Sleeveless scoop neckline
- Tank shoulder straps
- Ruching
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5569
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Laid Back Fave Crew Neck Tank Maxi Dress
Your new laid-back fave tank maxi dress for styling up or down for any occasion! Crafted from rib knit fabric, this crew neck dress offers a form-hugging fit and a maxi-length hem for a flattering silhouette. Complete the look in cute sandals and sunnies!
Fit & Features
- Rib-knit stretchy fabric
- Crew neck
- Form-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5573
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Admiring Style Strapless Ruffle High Low Denim Dress
Prepare for plenty of admiring stares when you're in this stylish denim strapless dress! This cute and casual dress features a sweetheart neckline and form-hugging fit, accentuating your curves in all the right places. The patchwork seam detailing adds a touch of unique style, while the high-low ruffled hem adds a playful and flirty element. Complete the look in platform shoes and sunnies!
Fit & Features
- Denim fabric, slight stretch
- Strapless sweetheart neckline
- Back zipper and hook-eye closure
- Form-hugging fit
- Ruffle high low hem
- Runs true to size
Style Number/Barcode: 05102-5574
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Made To Amaze Strapless Marble Bodycon Midi Dress
Everyone will admire your style in this strapless marble bodycon midi dress at the art show downtown! Made from a mesh fabric boasting a gorgeous marble print, you'll be sure to amaze. With a strapless neckline and side ruched seams, this dress hugs your curves in all the right places for a bodycon fit along the midi-length hem. Complete the look with stiletto heels.
Fit & Features
- Marble print, stretchy mesh fabric, sewn-in knit lining
- Strapless neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5576
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweeter Than Pie Scoop Neck Gingham Mini Dress
So on trend and sweeter than pie, this gingham mini dress is essential for spring-to-summer fun! This mini-length dress is made from woven fabric and features a charming gingham print that exudes effortless style. The scoop neckline and tank shoulder straps flatter your figure, while the form-hugging fit accentuates your curves. Complete the look in cute sandals and a mini purse!
Fit & Features
- Gingham print, woven fabric, slight stretch
- Back zipper closure
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5568
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Day Sleeveless Mermaid Denim Midi Dress
Look cute and casual wherever you go in this denim midi dress! Featuring spaghetti straps, a sweetheart neckline, a flattering mermaid silhouette, and a flared midi-length hem, this dress will have you looking and feeling amazing. Complete the look in strappy espadrille wedges.
Fit & Features
- Denim fabric, minimal stretch
- Spaghetti straps
- Sweetheart neckline
- Back zipper and hook-eye closure
- Mermaid silhouette
- Runs true to size
Style Number/Barcode: 05102-5567
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sway With Me Halter V-Neck Paisley Skater Dress
This breezy skater dress brings the romance with a halter neckline and swingy silhouette made to float with you. Perfect for golden hour snaps, weekend wandering, or spontaneous getaways!
Fit & Features
- Paisley print, woven fabric, bust lining
- Halter V-neckline with spaghetti strap ties
- Stretchy smocked bust
- Tie back design
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5575
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free