Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, or keep it flowy with midi and maxi silhouettes. Mesh details add a little edge, while sleeveless minis and long-sleeve staples cover every season. Whether you’re layering up for a chill weekend or slipping into something light for a last-minute dinner date, these casual dresses are made to move with your mood—and 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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All About Floral Sweetheart Crepe Skater Dress
Sweet and sassy, this floral skater dress is a must-have for your wardrobe! Featuring a trendy sweetheart neckline and adjustable spaghetti straps, this dress is perfect for any spring or summer occasion. Its skater silhouette and short-length hem will have you twirling all day, while the playful floral print will make you stand out in style! Complete the look with hoop earrings.
Fit & Features
- Floral print
- Stretchy crepe fabric, knit lining at the bust
- Sweetheart neckline
- Adjustable spaghetti straps
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3196
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Fling High Slit Ditsy Floral Knit Midi Dress
Embrace your flirtatious side in this adorable floral knit midi dress! The lightweight stretchy knit fabric is detailed with the cutest ditsy floral print pattern for the spring season. The mid-length dress features a crew neckline, short sleeves, a small back keyhole cutout, a large lower back cutout to add some allure, a high-cut front slit, and a bodycon silhouette to flaunt your curves. Style with hoop earrings and a charm necklace.
Fit & Features
- Stretchy knit fabric
- Ditsy floral print
- Crew neckline, short sleeves
- Back keyhole cutout, lower back cutout
- High front slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5653
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Make It Fierce Crew Neck Leopard Mesh Midi Dress
Make it fierce in this leopard mesh midi dress for cocktail hour or dinner out! This daring dress features a flattering crew neckline, short sleeves, and a bodycon silhouette for a bold look on mesh fabric with a wild leopard print! Complete the look in stiletto heels.
Fit & Features
- Leopard print
- Sheer mesh fabric, slip knit lining with stretch
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5601
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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Talking Sweet One-Shoulder Cutout Eyelet Lace Dress
Dress to impress in this sweet one-shoulder cutout eyelet lace dress guaranteed to turn heads as the lovely bride-to-be or graduate! Made from eyelet lace fabric, this bodycon dress will hug your curves in all the right places. This stunning mini-length dress features a trendy one-shoulder neckline, a flirty puff sleeve, and a sultry side drawstring cutout so you can customize the look. Style this dress with sandals and a tote bag.
Fit & Features
- Eyelet lace fabric lined with stretchy knit
- Drawstring side cut-out
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5715
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetest Allure Strapless Floral Eyelet Knit Midi Dress
Give off the sweetest allure this summer season in this floral eyelet knit midi dress! The stretchy sheer eyelet knit fabric is detailed with an adorable ditsy floral print and includes a full knit lining for coverage. The mid-length dress features a strapless straight-across elasticized neckline and a bodycon silhouette to highlight your gorgeous figure. Style with espadrille wedges for weekend brunch!
Fit & Features
- Stretchy sheer eyelet knit fabric, full knit lining
- Ditsy floral print
- Strapless straight elasticized neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5488
Category Name: Casual Dresses
Price: $5.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild West Glow Lace Up Mini Dress
Giving rodeo-ready meets it-girl chic. The faux suede finish and lace-up front serve sultry vibes that work from concerts to bachelorette trips to the country!
Fit & Features
- Micro faux suede fabric
- Halter V-neckline
- Front lace-up bust design
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000313
Category Name: Casual Dresses
Price: $22.97 $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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Charming Style Puff Sleeve Chiffon Skater Dress
Create the sweetest charming style for your spring and summer parties in this chiffon skater dress! The airy sheer chiffon fabric offers that breezy lightweight feel and includes a stretchy knit lining for coverage. The short dress features a ruched square neckline, adorable short puff sleeves, dual high waist seams, and a fit-and-flare skater silhouette for a flirty vibe with a ruffled hem. Pair with sneakers for a cute and casual look!
Fit & Features
- Sheer chiffon fabric with stretchy knit lining
- Ruched square neckline
- Short puff sleeves with elasticized hems
- High waist seams, back zipper with hook and eye closure
- Skater silhouette, ruffled hem
- Runs true to size
Style Number/Barcode: 05101-3056
Category Name: Casual Dresses
Price: $6.97 $38.90
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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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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Eye-Catching Vibes Cut Out Bodycon Mini Dress
Keep every eye on you in this bodycon mini dress for flawless vibes at parties! Made from a brushed soft knit double-lined fabric, this dress offers ultimate comfort and style. Featuring a square neckline, spaghetti straps, and a bodycon fit, this dress will enhance your curves and make you stand out. The side cut out and ruched seams add an edgy touch, while the mini-length hem flaunts your figure. Complete the look in sandals and earrings.
Fit & Features
- Brushed knit soft double-lined fabric, stretchy
- Spagehtti straps
- Side cut out, side ruched seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5640
Category Name: Casual Dresses
Price: $19.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Baby Got Open Back Poplin Woven Mini Dress
Get ready to turn heads in this open back poplin woven mini dress! This bodycon mini dress features a square neckline, spaghetti tie straps, and a spaghetti tie back strap for a playful twist along the sultry open back. Made with a lightweight poplin woven fabric, this dress is perfect for hot days and even hotter nights! Complete the look in heeled sandals and a purse.
Fit & Features
- Poplin woven fabric lined with stretchy knit
- Spagehtti tie straps and back strap
- Open back
- Hidden side zipper and hook-eye closure
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5760
Category Name: Casual Dresses
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lively Elegance Smocked Floral Babydoll Dress
Indulge in elegance in this elegant floral babydoll dress perfect for wedding showers or graduations! With its stretchy smocked bodice and adjustable straps, you'll get a perfect fit. The chiffon fabric and vibrant floral print add a touch of elegance to the playful babydoll silhouette and ruffled short-length hem. Complete the look in sandals.
Fit & Features
- Floral print, chiffon fabric lined with stretchy knit
- Adjustable spaghetti straps
- Stretchy smocked bodice
- Babydoll silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05102-5470
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Presence Strapless Slit Floral Maxi Dress
Your presence will always be charming in this ditsy floral maxi dress at wedding showers, brunch, or casual parties! Adorned in a stunning disty floral print, this strapless dress features a ruffle trim neckline and padded bra cups for flattering support. The curve-hugging silhouette, front slit, and maxi-length hem create a captivating look, while the brushed knit stretchy fabric ensures comfort. Pair with earrings and strappy sandals.
Fit & Features
- Ditsy floral print
- Brushed knit stretchy fabric
- Padded bra cups
- Front slit
- Curve-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-5541
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Day To Night Charm Lace-Up Ditsy Floral Mini Dress
Be effortlessly charming in this ditsy floral mini dress day to night! This dress features a flattering sweetheart neckline, sleek spaghetti straps, and a mini bow along the bust to accentuate your figure. The open lace-up back and bodycon silhouette add a touch of sexiness, while the ditsy floral print on stretchy ribbed knit fabric keeps you comfortable and looking cute! Complete the look in boots to edge up your allure.
Fit & Features
- Stretchy ribbed knit fabric, knit lining
- Ditsy floral print
- Sweetheart neckline, mini bow detail
- Spaghetti straps
- Open lace-up back
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5650
Category Name: Casual Dresses
Price: $6.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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High Intentions Sleeveless Knit Mini Dress
Take your wardrobe to the next level in this little black dress perfect for day or night plans! This mini dress boasts a sleeveless high square neckline and spaghetti straps for a chic and modern look. The bodycon silhouette hugs your curves, while the mini-length hem adds a touch of flirtatiousness. The lightweight knit fabric offers a moderate stretch. Complete the look in a trendy crop jacket, mules, and a purse!
Fit & Features
- Knit fabric with moderate stretch
- High square neckline
- Spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1881
Category Name: Casual Dresses
Price: $6.97 $38.90
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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Chic Side Of Town Strapless Mesh Midi Dress
Strut on looking chic in this strapless mesh midi dress on the town! Designed to flaunt your curves in a bodycon silhouette with side ruched seams, this midi dress is a total showstopper. Plus, the unique marble print on the lined mesh fabric is sure to receive many compliments! Style this dress with strappy heels to elevate your look.
Fit & Features
- Marble print, mesh fabric lined with knit
- Side ruched seams
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5474
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Delightful Cutie Corset Lace-Up Floral Midi Dress
If you aim to charm, this cute ditsy floral midi dress will sweep everyone off their feet at parties! Flaunt your femme figure in the sweetheart neckline, ruched underwire bust, and corset trim bodice. The A-line, midi-length silhouette, and front slit add a flattering look while the lace-up back allows for a customizable fit. Complete the look with a dainty necklace and mules.
Fit & Features
- Ditsy floral print
- Woven fabric lined with stretchy knit
- Underwire bust
- Lace-up, side zipper and hook-eye closure
- Front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-2995
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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
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Moonlit Bloom Abstract Floral Maxi Dress
Slip into something sleek—this mesh maxi dress flaunts an abstract floral print that gives the illusion of an hourglass figure for an effortless allure at every event you're seen at!
Fit & Features
- Abstract floral print, mesh-lined stretch fabric
- Scoop neckline
- Spaghetti straps
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000256
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Swing Into The Season Tie-Back Eyelet Skater Dress
Swing into the season in this charming eyelet skater dress perfect for birthday brunch to day dates! The cap sleeves and sweetheart neckline add a touch of romance, while the padded bra cups provide support. The tie-back design and fitted bodice add a playful twist to the skater silhouette and flirty ruffled short-length hem. Complete the look in strappy platform sandals and a purse!
Fit & Features
- Eyelet lace fabric with woven lining
- Padded bra cups
- Tie-back closure
- Skater silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05101-3121
Category Name: Casual Dresses
Price: $6.97 $49.90
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