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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Looking Sweet Eyelet Knit Tiered Skater Dress
You'll look extra sweet for your next weekend brunch in this adorable eyelet knit skater dress. The strapless neckline, ruched side seams, drop waist, and short tiered design are all flirty details you'll adore.
Fit & Features
- Sheer eyelet knit fabric with full-length knit lining, moderate stretch
- Strapless straight neckline
- Ruched side seams
- Drop waist
- Short tiered design, skater silhouette
- Runs true to size
Style Number/Barcode: 05102-6012
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Adorable Looks Tie Front Bodycon Midi Dress
All of your adorable looks this season will include this eyelet midi dress with a flirty tie front and bodycon silhouette. This dress is perfect for shower celebrations or graduations!
Fit & Features
- Eyelet fabric
- Tie front sweetheart neckline
- Spaghetti straps
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6008
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Life Is Sweet Eyelet Bodycon Ruffle Mini Dress
The sweetest eyelet mini dress for shower celebrations, graduations, or brunch! It boasts flirty tie shoulder straps, a flattering bodycon silhouette, and a ruffled hem for cute flair.
Fit & Features
- Eyelet fabric
- Square neckline, tie shoulder straps
- Bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6006
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Always Sweet Ruffled Eyelet Lace Mini Dress
Make your sweet impression in this eyelet lace mini dress detailed with ruffled straps and an adorable ruched neckline. The form-hugging fit will highlight your stunning curves.
Fit & Features
- Eyelet lace fabric lined with stretchy knit
- Sweetheart neckline, ruching
- Ruffled straps
- Mini-length form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-6002
Category Name: Casual Dresses
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Twist Off-The-Shoulder Soft Knit Mini Dress
The cashmere-like soft knit mini dress features an off-the-shoulder neckline, a popover accent with twist detail, long bell sleeves, faux wrap ties at the waist, and a fitted short-length hem. Complete a cozy stylish outfit with clear heels or ankle booties.
Fit & Features
- Soft cashmere-like knit fabrication
- Off-the-shoulder neckline
- Popover accent with twist detail
- Long bell sleeves
- Faux wrap ties at the waist
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-6003
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Flair Ditsy Floral Mini Dress
Show off a charming flair in this adorable ditsy floral mini dress designed with eyelet knit fabric. The sweet vibes of the print are the perfect pairing with the sassy short bodycon silhouette.
Fit & Features
- Sheer eyelet knit fabric with knit lining, high stretch
- Ditsy floral print
- Sleeveless square neckline, dainty rosette detail, eyelet trim
- Adjustable spaghetti straps
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5999
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simply Sunny Eyelet Knit Mini Skater Dress
This adorable mini skater dress is perfect for sunny weekend plans. Made with a breezy eyelet knit fabric, you'll love the flirty tie-back detail and fit-and-flare ruffled silhouette.
Fit & Features
- Eyelet knit fabric, sewn-in knit lining
- Scoop neckline
- Adjustable spaghetti straps
- Tie-back detail, lower open back
- Short skater silhouette, tiered ruffled hem
- Runs true to size
Style Number/Barcode: 05102-6000
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Look Eyelet Knit Skater Dress
Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette.
Fit & Features
- Eyelet knit fabric with knit lining
- Sleeveless square neckline, underbust seam
- Adjustable spaghetti straps
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6001
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tea Time Corset Lace-Up Floral Skater Dress
It's time to spill the tea at the garden party in this chic floral skater dress with a pretty corset bodice that snatches your waist and a lace-up back that turns heads!
Fit & Features
- Floral print, poplin woven lined lace trim fabric
- Square neckline, lace trim, underwire bust, wide shoulder straps
- Corset bodice, flexible boning, lace trim, lace-up back
- Drop waist seam
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3923
Category Name: Casual Dresses
Price: $9.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lovely In Eyelet A-Line Mini Dress
Make a lovely impression in this eyelet A-line mini dress at bridal showers or brunch with the girls!
Fit & Features
- Eyelet lace fabric, stretchy knit lining
- Strapless neckline
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5997
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spring Fling V-Neck Paisley Skater Dress
Swing into spring in this paisley skater dress for an adorable look all season! With a flirty halter V-neck and a flowy mini-length hem, this dress is ready for brunch or day dates.
Fit & Features
- Paisley print, chiffon fabric, woven lining
- Halter V-neck
- Spaghetti strap ties with tassels
- Stretchy smocked bodice
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5994
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Preppy Edit Pinstripe Mini Dress
The perfect dress for fall—this strapless pinstripe mini dress blends polished structure with playful pleats. Toss on a blazer or knee-high boots for seasonal chic.
Fit & Features
- Pinstripe pattern, woven fabric
- Strapless collared neckline
- Button front
- Fitted bodice
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5993
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Flirt Lace Trim Scoop Neck Knit Mini Dress
Fit & Features
- Soft rib knit fabric, moderate stretch
- Lace trim scoop neckline with bow tie
- Fitted long sleeves
- Bodycon silhouette
- Mini-length hem, dual slit accents
- Runs true to size
Style Number/Barcode: 06005-2199
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Destination Paradise V-Neck Floral Maxi Dress
The perfect floral maxi dress for your next getaway! Designed in a sleeveless silhouette, this dress features a flattering V-neckline, sleek spaghetti straps, and a form-hugging fit with a flowy floor-length hem. Complete the look with earrings.
Fit & Features
- Floral print, mesh lined fabric
- V-neckline
- Spaghetti straps
- Form-hugging fit
- Flowy floor-length hem
- Runs true to size
Style Number/Barcode: 05101-3915
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Buckled Beauty Off-The-Shoulder Knit Mini Dress
An off-the-shoulder mini dress perfect for everyday slays. It features long sleeves and a foldover neckline with trendy buckled accents and a bodycon silhouette. Complete the look with boots.
Fit & Features
- Stretchy rib knit fabric
- Off-the-shoulder neckline, folded with buckled accents
- Long sleeves
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5992
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Darling Vibe Ditsy Floral A-Line Midi Dress
Look oh-so-darling at weekend brunch in this ditsy floral A-line midi dress! The sleeveless sweetheart neckline is detailed with a dainty lace trim and tie-front design.
Fit & Features
- Woven fabric
- Ditsy floral print
- Sleeveless sweetheart neckline, dainty lace trim, lace trim spaghetti straps
- Tie-front detail, underbust seam
- Midi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5989
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Get Cutesy V-Neck Gingham Skater Dress
Get cutesy in this gingham skater dress for a dreamy look this spring to summer! With a lace trim neckline and flattering drop waist seam that accentuates your figure, this short dress looks like a dream.
Fit & Features
- Gingham print, poplin woven fabric, lined
- Laced trim V-neckline
- Spaghetti straps
- Button front details
- Drop waist seam
- Skater silhouette, short-length hem
- Runs true to size
Style Number/Barcode: 05102-5990
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunshine Dream Open Tie Back Floral Maxi Dress
A floral print adds to the dreamy charm of this flowy maxi dress boasting an open tie back design and ruffled silhouette perfect for beachside strolls or day parties.
Fit & Features
- Floral print, woven fabric, short woven lining
- Sweetheart neckline with bust tie
- Spaghetti straps
- Open tie back design
- Ruffled flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3912
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Blooms Floral Mesh Halter Maxi Dress
Showcase your beauty in this lined mesh maxi dress accented with a large floral print for a pretty vibe. It features a sleeveless cowl neckline, halter tie-back spaghetti straps with beaded detailing, an open back with lower tie-back straps, and a maxi-length hem with a form-hugging fit to highlight your curves.
Fit & Features
- Sheer mesh fabric with knit lining
- Large floral print pattern
- Cowl neckline
- Halter tie-back spaghetti straps, beaded details
- Open back, lower tie-back spaghetti straps, beaded details
- Maxi-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5988
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Plaid Mood Sleeveless A-Line Mini Dress
The plaid mesh mini dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, and an A-line silhouette. Complete the look with loafers for a preppy vibe.
Fit & Features
- Sheer mesh fabric with knit lining, plenty of stretch
- Plaid print
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5987
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Unforgettably Sweet Floral Bodycon Ruffle Mini Dress
Create an alluring look in this floral mini dress in a bodycon fit with a flirty ruffled hem. Perfect for shower celebrations and graduations!
Fit & Features
- Floral print, lace-lined fabric
- Strapless neckline
- Bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5985
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Many Admirers Open Back Bodycon Midi Dress
Crafted in a smooth knit fabric that hugs every curve, this cap sleeve midi dress will leave your admirers speechless! The dress boasts a showstopping open back while the bodycon silhouette flaunts your figure along the slit midi-length hem. Pair with stiletto heels.
Fit & Features
- Smooth knit stretchy fabric
- Cap sleeves
- Scoop neckline
- Open back
- Bodycon silhouette
- Midi-length hem, side slit
- Runs true to size
Style Number/Barcode: 05102-5984
Category Name: Casual Dresses
Price: $14.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Twist Of Chic High-Slit Knit Midi Dress
Bring a twist of chic to the every day with a midi dress that features an asymmetrical one-shoulder neckline with a trendy twist shoulder accent and a daringly high side slit. Complete look with slingback shoes to take you from the office to happy hour!
Fit & Features
- Stretchy knit fabrication
- Asymmetrical one-shoulder neckline
- Twist shoulder strap accent
- High side slit
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5983
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Showstopper Abstract Print Mesh Maxi Dress
Serve chic vibes in this airy-lined mesh maxi dress designed with a multi-colored abstract print for a bold allure. It features a strapless straight-across neckline, a high-cut side slit, and a long bodycon silhouette to showcase your stunning curves.
Fit & Features
- Abstract printed sheer mesh fabric with knit lining, plenty of stretch
- Strapless straight neckline
- High side slit
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5982
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale