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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Cutesy Flair Ruffled Denim Mini Dress
Show off a cutesy flair in this denim mini dress perf for festival season! You'll love the strapless ruffled neckline and matching ruffled A-line hem.
Fit & Features
- Denim fabric
- Strapless straight neckline, ruffled trim
- Vertical seams
- Drop waist
- Mini-length A-line silhouette, ruffled hem
- Runs true to size
Style Number/Barcode: 05102-000006
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
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Effortless Days A-Line Midi Tube Dress
Effortless days call for this woven midi tube dress designed with a smocked bodice with a geometric pattern and a flowy pleated A-line silhouette. Perfect for weekend plans, style with strappy sandals.
Fit & Features
- Poplin cotton woven fabric
- Strapless sweetheart neckline
- Smocked bodice, geometric pattern
- High-rise waist
- Side pockets
- Midi-length pleated A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000007
Category Name: Casual Dresses
Price: $11.97 $52.90
On Sale: Yes
Availability: Out of Stock
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Sunset Girl Abstract Halter Slit Maxi Dress
Need an unforgettable look? This abstract maxi dress will be the perfect companion for rooftop cocktails and parties, boasting a sultry halter neckline, cutout bodice, and high slit giving major sultry energy.
Fit & Features
- Abstract print, stretchy knit fabric, short knit stretch lining
- Halter neckline with tie straps, hoop insert
- Cutout bodice
- High side slit
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000003
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
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Into The Sun V-Neck Maxi Dress
Sun goddess maxi dress boasting a V-neckline with a unique metal accent and a body-skimming silhouette. Style with strappy sandals for a sunset dinner.
Fit & Features
- Textured knit fabric, soft knit stretchy lining
- V-neckline with metal accent
- Spaghetti straps
- Body-skimming silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000002
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
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Catch Flights Tropical Lace-Up Slit Maxi Dress
Booked the trip just for the outfit? Valid. This lace-up back maxi brings the heat with a tropical print and a leg-baring high slit that knows how to make an entrance.
Fit & Features
- Smooth knit stretchy fabric, tropical print, soft knit stretch lining
- Square neckline with spaghetti straps
- Bodycon silhouette
- Lace-up open back with tie closure
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000005
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
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Effortless Era Woven A-Line Midi Dress
Enter your effortless era in this woven A-line midi dress featuring a stretchy smocked bodice, hidden side pockets, and a pleated flowy silhouette with a side slit.
Fit & Features
- Poplin smooth cotton woven fabric with full-length woven lining
- Sleeveless square neckline, adjustable spaghetti straps
- Stretchy smocked bodice
- V-shaped waist
- Pleating, hidden side pockets
- Midi-length flowy A-line silhouette, high side slit
- Runs true to size
Style Number/Barcode: 05102-000001
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
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Bold Beauty Floral Maxi Dress
Just as bold as it is beautiful, this maxi dress is designed with a statement floral print on a body-skimming silhouette. It's perfect for your next vacation or weekend plans!
Fit & Features
- Floral print, mesh fabric, soft stretchy knit lining
- Strapless neckline
- Form-hugging bodice
- Relaxed maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6118
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
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Island Hottie Tropical Halter Slit Maxi Dress
Look hot to trot around the island on vacation in this tropical maxi dress! This stunning maxi features a crisscross halter neckline for a touch of elegance and a front slit to show off those curves.
Fit & Features
- Tropical palm print, stretchy knit fabric, bust knit lining
- Crisscross halter neckline, beaded
- Front slit
- Curve-hugging fit
- Flowy maxi length hem
- Runs true to size
Style Number/Barcode: 05102-6117
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
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Petals and Plans Floral Lace-Up Maxi Dress
For date nights, rooftop drinks, or weddings, this floral maxi dress is perfect for every event! The curve-hugging fit, flirty slit, and open lace-up back effortlessly flatters your figure and makes heads turn.
Fit & Features
- Floral print, mesh fabric, stretchy knit lining
- Square neckline
- Spaghetti straps
- Lace-up open back
- High front slit
- Curve-hugging fit, maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-4160
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
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Maui Nights Strapless Tropical Midi Dress
Booked a vacation? This tropical midi dress is here to make you look stylish for your getaway! Designed with a flattering bodycon silhouette and side slit for effortless sultriness.
Fit & Features
- Tropical print, mesh knit-lined fabric
- Strapless neckline
- Bodycon silhouette
- Side slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6120
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
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Summer-Coded Crochet Halter Mini Dress
Serve all the summer vibes in this crochet knit mini dress designed with a halter V-neck with a beaded trim on the straps. Style with espadrille wedges for sunset happy hour.
Fit & Features
- Sheer crochet knit fabric with knit lining, moderate stretch
- Sleeveless V-neckline
- Tie-back halter straps, beaded trim
- Partially open back
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6114
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Getaway Girlie Halter Bead Crochet Mini Dress
Your next getaway calls for this crochet mini dress! This dress has a stunning halter bead neckline that adds a touch of boho, a cutout accent, and a flattering bodycon silhouette.
Fit & Features
- Crochet lined fabric
- Halter beaded neckline, spaghetti strap ties
- Padded bra cups
- Back zipper hook-eye closure, lower ruched seam
- Cutout front accent
- Bodycon silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6116
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Destination Summer Tropical Linen Mini Dress
This cute mini dress was made for summer vacays featuring a contrast tropical print on lightweight linen fabric. The lace-up strappy back design offers a customized fit and a head-turning vibe.
Fit & Features
- Linen-blend woven fabric, woven lining
- Tropical print
- Sleeveless square neckline
- Spaghetti straps
- Open cross-back lace-up strappy design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6115
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hidden Treasure Lace-Up Shell Accent Midi Dress
Discover your new signature look with this irresistible midi dress featuring a unique shell accent neckline, lace-up back offers undeniable allure, and a sultry side slit creates movement.
Fit & Features
- Texture knit fabric, moderate stretch, stretchy knit lining
- V-neckline with shell accent trim
- Spaghetti straps
- Lace-up back
- Side slit
- Bodycon silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6119
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blissful Darling Halter Lace Skater Mini Dress
Twirl with bliss in this darling lace skater mini dress with a flirty halter neckline and open back. It's perfect for shower celebrations or a dressy date night!
Fit & Features
- Lace knit fabric, stretchy knit lining
- Halter V-neckline, tie closure
- Open back
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4157
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Carefree Energy Halter Bodycon Mini Dress
Be a cute sight in this halter mini dress boasting a flattering bodycon fit that perfectly flaunts your curves on vacay or a chic staycation!
Fit & Features
- Texture knit stretchy fabric
- Halter neckline, spaghetti strap ties
- Knotted bust accent
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-2302
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Falling For You Tropical Floral Slit Maxi Dress
Get the golden hour glow in this tropical floral maxi dress while on vacation! Featuring a chic square halter neckline and a form-hugging fit with a high side slit, this dress beautifully accentuates your silhouette.
Fit & Features
- Tropical floral print, mesh-lined fabric
- Square halter neckline, adjustable spaghetti straps
- Criss cross back
- Form-hugging silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6113
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On A Vacay Strapless Tropical Slit Maxi Dress
From sunny vacations to island getaways, this tropical maxi dress is destined to go with you on your next trip!
Fit & Features
- Tropical palm print, mesh fabric lined with stretchy knit
- Strapless neckline
- Form-hugging silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6110
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sun Kissed Strapless Floral Bodycon Mini Dress
Bare your sun kissed shoulders on vacay in this strapless mini dress with a statement floral print and flattering bodycon fit that flaunts your curves!
Fit & Features
- Mesh fabric, floral print, stretchy knit lining
- Strapless neckline
- Bodycon fit
- Mini-length hem
- Runs small
Style Number/Barcode: 05102-6112
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Picture Perfect Color Block Midi Dress
For a picture-perfect look you'll be reaching for this color block midi dress for any casual plans! The strapless fitted bodice accentuates your silhouette while the flowy midi-length hem creates an elegant movement as you walk. Plus, keep your hands warm in the convenient hidden side pockets!
Fit & Features
- Woven cotton-blend fabric, stretchy knit lining
- Strapless color block fitted bodice
- Hidden side pockets
- Back zipper and hook-eye closure
- Flowy midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6109
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kiss The Sun Tropical Lace-Up Slit Maxi Dress
Sipping a mai tai oceanside has never looked cuter in this tropical maxi dress! Made to turn heads, this maxi dress boasts a sexy lace-up back, form-hugging silhouette that shows off your curves, and a high front slit giving major allure.
Fit & Features
- Tropical print, mesh-lined fabric
- V-neckline
- Spaghetti straps
- Lace-up back
- Form-hugging silhouette, high front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6103
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Turn Heads Abstract Print Strapless High Slit Maxi Dress
Unveil a chic allure in this lined airy mesh maxi dress designed with an eye-catching abstract print to turn heads. It features a strapless straight-across neckline, a high-cut side slit to reveal some leg, and a fitted silhouette on the maxi-length hem.
Fit & Features
- Sheer mesh fabric with soft brushed knit lining, plenty of stretch
- Abstract print
- Strapless straight neckline
- High side slit
- Maxi-length fitted silhouette
- Runs true to size
Style Number/Barcode: 05102-6105
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Exceptional Cutie Striped Cutout Midi Dress
Strut like an exceptional cutie in this striped midi dress all season long! This strapless dress features a cutout bodice that adds a touch of playful sass, while the bodycon silhouette and midi-length hem hug your curves in all the right places.
Fit & Features
- Striped pattern, stretchy knit fabric
- Strapless neckline
- Cutout bodice
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2296
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Breezy Chic Belted A-Line Maxi Dress
Breezy chic, this A-line maxi dress is made with an airy gauze woven fabric accented with sheer lace insets. The belted waist leads to a long tiered flowy fit for that effortless vibe.
Fit & Features
- Gauze woven fabric with sheer lace insets
- Strapless sweetheart neckline with ruffled trim
- Bust cutout with tie-front detail, ruching, underbust seam
- Faux leather belted waist, gold metal buckle
- Maxi-length hem
- Tiered A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6106
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free