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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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
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Paradise Babe Lace Up Tropical Floral Maxi Dress
Look like a babe in paradise in this tropical floral maxi dress perfect for your next getaway or beach day! Embrace the warm, tropical vibes in this maxi-length hem dress on an airy mesh fabric bursting with a tropical floral print. With its flowy silhouette and high slit, you'll feel like you're walking on clouds. The V-neckline and spaghetti straps add a trendy vibe while the lace-up detail adds a touch of playfulness. Complete the look in sandals and sunnies!
Fit & Features
- Tropical floral print
- Mesh fabric lined with knit, moderate stretch
- Lace-up
- Spaghetti straps
- High slit
- Maxi length hem
- Runs true to size
Style Number/Barcode: 05101-3241
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sheer Desire Square Neck Bodycon Mesh Midi Dress
Unveil a desirably chic look in this mesh midi dress at daytime parties and brunch! The adjustable spaghetti straps provide a customizable fit while the side ruching and bodycon silhouette accentuate your figure for a confident and alluring look. Elevate any occasion with this must-have dress by styling it with block heels and earrings!
Fit & Features
- Sheer mesh fabric lined with sewn-in knit
- Adjustable spaghetti straps
- Side ruching
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5506
Category Name: Casual Dresses
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling Flirtatious Floral Button Skater Dress
With a pretty floral pattern and button accents, this skater dress exudes flirtatious romance vibes! The mini-length dress boasts a flattering V-neckline, a lace-up back that turns heads, and a twirl-worthy skater silhouette. Pair with sneakers for a casual look.
Fit & Features
- Burnout floral pattern, woven fabric lined with stretchy knit
- V-neckline, adjustable spaghetti straps
- Lace-up back
- Faux button front accents
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3229
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sensational City Girl Strapless Cargo Mini Dress
Hit the streets with a strapless mini dress that'll make you an instant sensational city girl! The strapless straight-across neckline and bodycon silhouette flatter any figure, while the front button closure and belt loop accents add a trendy touch. With a hidden front zipper, cargo flap pockets, and a mini-length hem, this woven dress is both fashionable and functional. Complete the look in lug boots for casual plans!
Fit & Features
- Cotton-blend woven fabric, minimal stretch
- Strapless straight neckline with belt loop detailing
- Front button closure
- Hidden front zipper closure
- Cargo flap pockets
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5503
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trend Right Plaid Belted A-Line Mini Dress
Trend right in this plaid mini dress! It features a square neckline, spaghetti straps, a flattering A-line silhouette cinched with a belted waist, and a flirty pleated mini-length hem with an alluring plaid print. Complete the look with a crossbody bag.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Back zipper closure
- A-line silhouette, belted waist
- Pleated mini-length hem
- Plaid print, woven fabric, slight stretch
- Runs true to size
Style Number/Barcode: 05102-5505
Category Name: Casual Dresses
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Girl Power Leopard Print Strapless Midi Dress
Show off major girl power in this sexy leopard print midi dress that was made for all eyes on you. It features a strapless straight-across neckline, ruching down the side seams, a midi-length hem, and a bodycon silhouette to put your gorgeous figure on display. The lined sheer mesh fabric features an all-over leopard print pattern to amp up the look. Style this midi dress with strappy stilettos for a nightclub!
Fit & Features
- Strapless straight-across neckline, no-slip strip
- Ruched side seams, hidden side zipper, hook and eye closure
- Midi-length hem
- Bodycon silhouette
- Leopard print
- Sheer mesh fabric, mini-length knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05101-3211
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Blooms Floral Ruffle Chiffon Skater Dress
Let this tropical floral skater dress bloom into your summer lineup! With a sweetheart neckline featuring delicate ruffle trim, adjustable spaghetti straps and padded bra cups, this skater silhouette will flatter your figure. The mini-length hem adds a flirty touch to this tropical floral printed chiffon dress. Complete the look with a crossbody purse and sandals!
Fit & Features
- Tropical floral print
- Chiffon fabric with woven lining, no stretch
- Sweetheart ruffle trim neckline
- Padded bra cups
- Adjustable spaghetti straps
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3204
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Crush On You Sleeveless V-Neck Skater Dress
Everyone will end up with a crush on you in this sleeveless skater dress perfect for beach days or backyard parties! This playful dress features adjustable drawstring shoulder straps and a flattering V-neckline and back design. The fitted waist and skater silhouette create a feminine and flirty look along the short-length hem. Complete the look in heeled sandals.
Fit & Features
- Gauze woven fabric lined with stretchy knit
- Adjustable drawstring shoulder straps
- V-Neckline and back
- Fitted waist, skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5500
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Beauty Chiffon Burnout Floral Maxi Dress
Showcase your effortless beauty in this dreamy chiffon burnout floral maxi dress! Designed with a sheer chiffon fabric with a pretty burnout floral pattern, this airy maxi dress is perfect for romantic dates. The sleeveless bodice is shaped with a V-neckline and adjustable spaghetti straps that lead to a partially smocked back for added stretch. The button-down front leads to a high center slit for a chic detail on the flowy A-line silhouette. Style this long dress with a dainty charm necklace and stud earrings.
Fit & Features
- Sheer non-stretch chiffon fabric with burnout floral pattern, mini-length knit lining
- Sleeveless V-neckline
- Adjustable spaghetti straps, partially smocked back
- Button-down front, center slit
- Flowy A-line silhouette
- Strapless or sticky bra recommended
- Runs true to size
Style Number/Barcode: 05101-3200
Category Name: Casual Dresses
Price: $7.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale