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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Trendy Girl Next Door Strapless Denim Mini Dress
Create a trendy girl next door vibe in this denim cargo mini dress! Made with a stretchy cotton-blend denim fabric, this dress features a strapless straight-across neckline, a secure back zipper closure, faux chest pockets, and large cargo-style flap pockets at the waist. The form-hugging silhouette will flaunt your gorgeous figure. Style this mini-length dress with cowboy boots for a country concert!
Fit & Features
- Cotton-blend denim fabric, moderate stretch
- Strapless straight neckline, front no-slip strip
- Back zipper with hook and eye closure
- Faux chest pockets
- Cargo flap pockets
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5524
Category Name: Casual Dresses
Price: $11.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty In Floral Sweetheart Bodycon Mini Dress
Step out in this flirty floral mini dress for Valentine's Day, dates, and parties! Showcasing a ditsy floral print on soft brushed knit fabric, this dress features a bust tie keyhole, side ruching, and a bodycon fit, to accentuate your figure. Complete the look with a mini purse and heels.
Fit & Features
- Ditsy floral print, brushed knit fabric with stretch
- Spaghetti straps
- Bust tie keyhole
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5523
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Abstract Beauty Printed High Slit Midi Dress
You'll fall in love with the abstract beauty of this chic printed midi dress! Crafted from a sheer woven fabric with a full-length knit lining, this mid-length dress features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, a partially open back with a cross-back strap design and lower back straps, a high-cut side slit to showcase some leg, a flowy A-line silhouette, and an all-over multi-colored abstract print pattern to catch everyone's eye. Style with a layered necklace and clear heels for a gallery opening!
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Partially open back, cross-back strap design, lower back straps
- Mid-length hem, high-cut side slit, flowy A-line silhouette
- Multi-colored abstract print
- Sheer woven fabric, full-length knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5525
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Style On Point Bodycon Mini Dress
Keep your style on point with this simply chic bodycon mini dress. It features a sleeveless mock neckline, tank shoulder straps, ruching down the side seams to accentuate your curves, a mini-length hem, and a bodycon silhouette. The double-lined smooth knit fabric offers plenty of stretch for comfortable wear. Pair this short dress with strappy heels to grab drinks!
Fit & Features
- Sleeveless mock neckline
- Tank shoulder straps
- Ruched side seams
- Mini-length hem
- Bodycon silhouette
- Double-lined smooth knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5520
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Creative Side Abstract Print Mesh Mini Dress
A mesh mini dress that showcases your creative side in a stunning abstract print that'll have all eyes on you at parties! With a flattering mock neckline, fitted long sleeves with flared slit cuffs, and a bodycon silhouette, this mini dress elevates your every day with stylish detail. Complete the look in sleek mules and earrings.
Fit & Features
- Abstract print, mesh fabric lined with mesh
- Long sleeves with flared slit cuffs
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5516
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Smooth Silhouette Long Sleeve Ruched Mini Dress
Embrace your curves in this must-have mini dress! The short dress features fitted long sleeves and a scoop neckline for a flattering look, while the side ruched seams and bodycon silhouette accentuate your curves. Crafted from a double-lined buttery soft fabric that fits like a glove with plenty of stretch. Layer with a jacket and a trendy shoulder bag to complete the look!
Fit & Features
- Fitted long sleeves
- Scoop neckline
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Double-lined buttery soft knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5519
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Profound Bloom Off-The-Shoulder Floral Skater Dress
You'll be blossoming from all the compliments you'll get wearing this off-the-shoulder floral dress! This skater dress features a playful sweetheart neckline, a bust tie, and a ruffled short-length hem bringing plenty of sass and sweetness to your style. Complete the look with earrings and strappy sandals for any occasion!
Fit & Features
- Floral print, woven fabric, bust lining
- Off-the-shoulder, sweetheart neckline
- Padded bra cups, back zipper and hook-eye closure
- Skater silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05101-3459
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Mood High Slit Floral Knit Maxi Dress
This adorable high slit floral knit maxi dress is a sweet addition to your spring wardrobe! The dainty floral print on the stretchy knit fabric will create an effortlessly chic look for your casual weekend plans. The dress is shaped with a sleeveless V-neckline and spaghetti straps, while the flowy A-line fit on the maxi-length hem will give you that breezy silhouette you love. Style with hoop earrings and strappy mules.
Fit & Features
- Knit fabric with moderate stretch
- Dainty floral print
- Sleeveless V-neckline
- Spaghetti straps
- High front slit
- Flowy A-line fit
- Runs true to size
Style Number/Barcode: 05102-5518
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweeter Than Ever Floral Eyelet Knit Mini Dress
Create the sweetest springtime vibe in this adorable eyelet knit mini dress! The airy sheer knit fabric is detailed with dainty floral eyelet embroidery and includes a knit lining for coverage. The dress features a sleeveless scoop neckline with a ruched bust and cute tie-front detail, spaghetti straps, and a bodycon silhouette to highlight your figure along the mini-length hem. Style this short dress with sleek hoops and heeled sandals.
Fit & Features
- Sheer knit fabric with floral eyelet embroidery, knit lining
- Moderate stretch
- Sleeveless scoop neckline
- Ruched bust with tie-front detail
- Spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5517
Category Name: Casual Dresses
Price: $6.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pretty Bloom Floral Ruffled Mesh Mini Dress
This blooming floral ruffled mesh mini dress will give off the prettiest vibes at spring parties! The stretchy lined mesh fabric showcases a bold floral print to capture all the compliments. The sleeveless sweetheart neckline and adjustable spaghetti straps shape the bodice, while the ruching at the bust and down the seams accentuate your curves on the bodycon silhouette. The mini-length dress features a ruffled sash accent at the side that cascades down for that effortless flair. Style with nude heels.
Fit & Features
- Floral printed stretchy sheer mesh fabric, knit lining
- Sleeveless sweetheart neckline, padded bust
- Adjustable spaghetti straps
- Ruching
- Ruffled sash
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3272
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fall For You Swiss Dot Chiffon Babydoll Dress
Make them fall head over heels for you in this adorable babydoll dress! The airy sheer chiffon fabric features a dainty swiss dot pattern to exude charm, and includes a woven lining for coverage. The sleeveless bodice is shaped with a V-neckline with a flirty tie-front design at the bust and a small keyhole cutout. The adjustable spaghetti straps will let you find your perfect fit, leading to a partial smocked back for added stretch. The empire seam flows out to a short-length A-line hem with the cutest babydoll silhouette. Style with platform heels for a party!
Fit & Features
- Sheer chiffon fabric with swiss dot pattern, woven lining
- V-neckline, tie-front bust design, keyhole cutout
- Adjustable spaghetti straps, smocked back
- Empire waist
- A-line fit
- Strapless or sticky bra recommended
- Runs true to size
Style Number/Barcode: 05101-3265
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gorgeous Entrance Lace Trim Printed Midi Dress
Admiring attention will come your way in this mesh midi dress making a gorgeous entrance into parties or dressy wine bars! Showcasing a unique vintage-inspired print, this midi dress brings the charm with a lace trim sweetheart neckline, adjustable spaghetti straps, and a built-in padded underwire bust eliminating the need for a bra. The side ruched seams and bodycon silhouette effortlessly hug your curves for a stunning look. Style the midi dress with a chic mini purse and strappy mules.
Fit & Features
- Vintage-inspired print
- Mesh fabric lined with stretch knit
- Lace trim
- Adjustable spaghetti straps
- Built-in padded underwire bust
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-3267
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Paisley Babe Cowl Neck Slit Maxi Dress
Get ready to turn heads in this paisley maxi dress! This sleeveless dress features a flirty cowl neckline, delicate spaghetti straps, and a flowy silhouette that's perfect for a day out or a backyard dinner party. With a high front slit and stunning paisley print, this maxi dress is sure to become a staple in your wardrobe. Complete the look in flat sandals.
Fit & Features
- Paisley print, stretchy knit fabric
- Spaghetti straps
- High front slit
- Flowy silhouette
- Runs true to size
Style Number/Barcode: 05102-5513
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Downtown Chic Abstract Print Midi Dress
This alluring abstract print midi dress is a stylish pick for a dinner date downtown! It features a mock neckline, long fitted sleeves, a midi-length hem, a form-hugging silhouette, and an all-over abstract multi-print pattern. The sheer and stretchy mesh fabric includes a sleeveless full-length knit lining with adjustable spaghetti straps. Pair this trendy midi dress with gold hoops and clear heels.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Midi-length hem, form-hugging fit
- Abstract multi-print pattern
- Sheer mesh fabric, sleeveless full-length knit lining, adjustable spaghetti straps
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5491
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All About You Lace-Up Floral Mesh Mini Dress
Everyone will take notice of you in this floral mesh mini dress at parties and dressy dinners! This floral print dress is designed with a delicate cowl neckline and spaghetti straps to create a flattering silhouette, while the lace-up back adds a flirtiness. The side ruched seams hug your curves for a bodycon fit, while the mini-length hem is perfect for showing off your legs. Complete the look in strappy sandals and a clutch!
Fit & Features
- Floral print, stretchy mesh fabric with sewn-in knit lining
- Spaghetti straps
- Lace-up
- Side ruched seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3262
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Forever Sweet Off-The-Shoulder Mesh Mini Dress
Be the center of attention in this sweet mesh mini dress for birthday brunches or tea parties! The off-the-shoulder sweetheart neckline and sheer puff sleeves add a touch of romance, while the padded bust and ruched seams enhance your figure. Made with swiss dot mesh fabric, this bodycon dress also features adjustable drawstrings for a customizable fit. Complete the look in flat sandals and a purse for a cute style!
Fit & Features
- Swiss dot mesh stretchy fabric lined with knit
- Padded bra cups
- Back zipper and hook-eye closure
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-3254
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Artsy Mood Asymmetric Abstract Knit Midi Dress
Play up your going-out look adding an artsy vibe with this abstract midi dress! The stretchy knit fabric showcases a trendy abstract print for that cool-girl aesthetic. The mid-length dress features a sleeveless square neckline and spaghetti straps, ruched detailing down the side seam to accentuate your curves on the bodycon silhouette, and a high-cut asymmetric hem creating a sultry slit. Style with clear heels for a rooftop bar.
Fit & Features
- Abstract printed stretchy knit fabric, knit bust lining
- Sleeveless square neckline
- Spaghetti straps
- Ruched side seam
- Asymmetric hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5511
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Abstract printed stretchy knit fabric, knit bust lining
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Fashionable Chic Sweater Maxi Dress
Perfect for any occasion, this fashion-forward sweater maxi dress delivers the perfect blend of comfort and style. Featuring a flattering bodycon silhouette, tank straps, and a sweetheart neckline for added appeal, this luxuriously soft sweater knit maxi dress will take your look to the next level. Layer on a faux leather jacket for an effortless and cool style!
Fit & Features
- Sleeveless sweetheart neckline
- Spaghetti straps
- Bodycon silhouette
- Maxi-length hem
- Sweater ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1898
Category Name: Casual Dresses
Price: $3.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bold New Look Corset Lace-Up Linen Skater Dress
Make a bold impression in this corset linen skater dress all season long! The sweetheart neckline with a bust tie and adjustable straps provides a flattering fit while the flexible boning supports your shape. The strappy lace-up back adds a touch of playfulness to the skater silhouette and short-length hem. Complete the look in wedge sandals and a handbag.
Fit & Features
- Linen blend fabric lined with stretchy knit
- Sweetheart neckline with bust tie
- Adjustable straps, side zipper and hook-eye closure
- Strappy lace-up back
- Flexible boning
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3256
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Garden Of Romance Tie Back Rose Floral A-Line Dress
Let your love bloom for this rose floral chiffon midi dress perfect for garden parties and weddings! Featuring a square neckline, adjustable spaghetti straps, and a tie-back for the perfect fit, this flowy A-line silhouette dress will have you feeling flirty and feminine. With a front slit and midi-length hem, it's perfect for styling with chic stiletto heels.
Fit & Features
- Rose floral print, chiffon fabric lined with stretchy knit
- Square neckline
- Adjustable spaghetti straps
- A-Line silhouette
- Front slit
- Runs true to size
Style Number/Barcode: 05101-3257
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Abstract Babe Ruched Mesh Midi Dress
Let your look do the talking in this mesh midi dress! With an eye-catching abstract print and adjustable spaghetti straps, this midi dress will show off your style while the bodycon fit and side-ruched seams enhance your curves. Complete the look in trendy mules for an art show downtown!
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Side ruched seams
- Bodycon silhouette, midi-length hem
- Abstract print, mesh fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5508
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Classic In Plaid Pleated Mini Dress
Stay classic and chic in this plaid mini dress! Featuring a flattering square neckline and spaghetti straps, this bodycon dress also has a chic side pleated seam and a faux wrap mini-length hem. Complete the look in a sleek moto jacket and boots.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps, back zipper and hook-eye closure
- Pleated side seam
- Bodycon silhouette
- Wrap mini-length hem
- Plaid print, woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5507
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirt And Twirl Puff Sleeve Tie-Back Skater Dress
Flirt and twirl in this cute skater dress at parties and day dates! The puff short sleeves and square neckline add a touch of charm, while the tie-back design and skater silhouette create a flattering fit. Complete the look with hoop earrings.
Fit & Features
- Crepe woven fabric, stretchy knit lining
- Square neckline
- Tie-back detail
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3243
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Allure Tie-Front Ruffled Skater Dress
Captivate with your charming allure in this pretty tie-front ruffled skater dress! Designed with a breezy gauze woven fabric, this short dress is the perfect lightweight style for weekend dates. It features a sleeveless V-neckline with the cutest tie-front bow design, a built-in padded bust, adjustable spaghetti straps so you can find your perfect fit, and a smocked back for added stretch. The high waist flows out to a tiered ruffled skater skirt with an adorable fit-and-flare silhouette. Complete your look with hoop earrings and heeled sandals.
Fit & Features
- Gauze woven fabric with woven lining, no stretch
- V-neckline with tie-front, padded bust
- Adjustable spaghetti straps
- High waist, smocked back
- Tiered ruffled design
- Fit-and-flare skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5720
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale