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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Charmed And Cute Polka Dot Chiffon Skater Dress
Envoke a charmed and cute style in this polka dot skater dress perfect for showers or graduates! Show off your curves with the sweetheart neckline and skater silhouette, while adding a touch of cuteness with the short puff sleeves. The tie-back adds a flirty detail and the short-length hem is perfect styling with trendy sneakers for a casual vibe.
Fit & Features
- Polka dot, chiffon fabric, woven lining, no stretch
- Sweetheart neckline
- Padded bra cups
- Back zipper hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3289
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Free Flowing Cutie V-Neck Ruffle Eyelet Maxi Dress
Flattering and breezy come together on this charming eyelet lace maxi dress perfect for spring days and summer cuteness! This dreamy dress features a flattering V-neckline, adjustable spaghetti straps, and charming button accents. The cutout waist and flowy silhouette accentuate your figure, while the tiered ruffled maxi hem adds a whimsy touch. Complete the look in wedge sandals and a floppy hat!
Fit & Features
- Eyelet lace fabric lined with woven fabric
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Cutout waist
- Ruffled maxi length hem
- Runs true to size
Style Number/Barcode: 05101-3286
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fun And Flirty Halter Neck Skater Dress
This adorable skater dress is perf for twirling and giving off those fun and flirty vibes at your next party! It features a sleeveless deep V-neckline with halter straps that lead to a tie-back design, an open back, dual high waist seams, and a short skater skirt with a fab fit and flare silhouette. The plisse woven fabric includes a full knit lining. Complete your look with a lariat necklace and platform heels.
Fit & Features
- Sleeveless deep V-neckline
- Halter straps, tie-back design
- Open back
- Dual high waist seams
- Short skater skirt, fit and flare silhouette
- Plisse woven fabric, full-length knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2908
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamy Escape Strapless Tropical Midi Dress
Serve chic looks on your dreamy escape in this tropical print midi dress. The stretchy lined knit fabric showcases a detailed tropical print pattern on the figure-flaunting silhouette. The bodice features a strapless elasticized straight-across neckline, leading to a bodycon fit with a mid-length hem. Style with combat booties to add some edge!
Fit & Features
- Stretchy knit fabric with knit lining
- Tropical print
- Strapless elasticized straight neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5539
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Vibes High Slit Tropical Knit Maxi Dress
Give off effortless vacay vibes in this high slit tropical knit maxi dress. The tropical palm leaf print on the lightweight knit fabric will have you looking like you're ready for a getaway, even if you're just grabbing drinks at a local happy hour! The dress is shaped with a sleeveless V-neckline and spaghetti straps, and features a high-cut side slit to showcase some leg on the form-hugging mid-length silhouette. Style with gold hoops and strappy wedges!
Fit & Features
- Stretchy knit fabric with a bust lining
- Tropical print
- Sleeveless V-neckline
- Spaghetti straps
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5537
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Polished Perfection Vest Pleated Short Dress
Capture polished perfection in this chic vest pleated short dress! Designed with a structured twill woven fabric, this dress features a fitted vest top with an A-line skirt. The top is shaped with a sleeveless V-neckline and tank shoulder straps, followed by a button-front design and an angled cropped hem for a snatched look. The chic waist cutout adds a touch of allure, leading to a fitted high waist and a flowy, pleated short-length hem. The dress includes a back zipper closure for effortless styling. Complete your look with gold hoops and strappy mules!
Fit & Features
- Non-stretch twill woven fabric
- Sleeveless V-neckline with tank shoulder straps
- Button-front design, angled cropped hem
- Back zipper with hook and eye closure
- Waist cutout, high-rise skirt with pleating
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5536
Category Name: Casual Dresses
Price: $5.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Modern Masterpiece Short Sleeve Marble Midi Dress
Your look will be a modern masterpiece in this marble print mesh midi dress - a stunning piece for art gallery openings or cocktail parties! The airy sheer mesh fabric is lined with a stretchy knit for comfortable wear. The short sleeves and crew neckline create a classic look, while the bodycon silhouette accentuates your curves down to the midi-length hem with a back slit for movement. Complete the look with a purse and strappy stiletto heels.
Fit & Features
- Marble print
- Sheer mesh fabric lined with stretchy knit
- Crew neckline
- Short sleeves
- Bodycon silhouette
- Back slit
- Runs true to size
Style Number/Barcode: 05102-5535
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cutest Look Ditsy Floral Ruched Knit Mini Dress
Create the cutest look for your weekend plans in this floral ruched knit mini dress! The adorable ditsy floral print on the soft and stretchy brushed knit fabric will give your casual look a flirtatious vibe! The short dress features a sleeveless square neckline with tie-shoulder spaghetti straps for a trendy detail and customized fit. The ruching down the side seams will show off your curves on the bodycon silhouette. Style this dress with hoop earrings and strappy mules for brunch with your girls!
Fit & Features
- Ditsy floral print
- Stretchy brushed knit fabric
- Sleeveless square neckline
- Tie-shoulder spaghetti straps
- Ruched side seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5533
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamy Floral Ruched Mesh Mini Dress
Walk into any party looking like a dream in this floral ruched mesh mini dress! The bold multi-colored floral print will capture all the attention, while the airy mesh fabric offers breezy comfortable wear. The mini-length dress features a sleeveless square neckline with adjustable spaghetti straps for a customized fit. The trendy ruched detailing down the side seams will accentuate your curves along the alluring bodycon silhouette. Style this short dress with hoop earrings and clear heels.
Fit & Features
- Floral print
- Sheer mesh, sewn-in knit lining
- Sleeveless square neckline
- Spaghetti straps
- Ruched side seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5534
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Compliment Me High Slit Knit Midi Dress
You'll spark up all the compliments in this simply chic high slit midi dress! Designed with a stretchy structured knit fabric, this dress is shaped with a sleeveless square neck and back with thin tank shoulder straps. The mid-length hem is accented with a high-cut side slit to show off some leg, and the bodycon silhouette will flaunt your stunning curves. Style with a faux leather jacket and heels to go bar-hopping!
Fit & Features
- Stretchy structured knit fabric
- Sleeveless square neck and back
- Tank shoulder straps
- High side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5526
Category Name: Casual Dresses
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gorgeous Aura Strapless Floral Tie-Dye Maxi Dress
Shine bright and serve a gorgeous aura in this strapless floral tie-dye maxi dress perfect for summertime soirees! The strapless neckline and lace-up back design exude effortless elegance, while the form-hugging fit accentuates your curves. The ruffled maxi-length hem adds a playful touch to this stunning dress. Complete the look with a ring set and sandals.
Fit & Features
- Floral tie-dye print, smooth knit fabric, moderate stretch
- Strapless neckline
- Lace-up back design
- Form-hugging fit
- Ruffled maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3277
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Truly Chic High Slit Bodycon Midi Dress
Create a truly chic look for dinner and drinks in this high slit bodycon midi dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, ruching down the side seams, an asymmetric midi-length hem creating a thigh-high side slit, and a bodycon fit to showcase your stunning silhouette. The lined smooth knit fabric offers plenty of stretch. Style with rhinestone fringe earrings to add a touch of glam!
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruched side seams
- Asymmetric midi-length hem, thigh-high side slit
- Bodycon silhouette
- Smooth knit fabric, mini-length knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5521
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Charmer Basic Rib Knit Maxi Dress
A basic maxi dress that brings everyday charm! This long rib knit dress features a square neckline, spaghetti straps, and a flattering bodycon silhouette, you'll love this maxi dress for any occasion. Complete the look in a cute crop jacket and your favorite sneakers!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Maxi-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5522
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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