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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Bold Allure Abstract Print Mesh Midi Dress
Show up and stun in this airy mesh midi dress accented with a trendy abstract print for a bold allure. The dress features a crew neckline, short cap sleeves, and a form-hugging silhouette to highlight your curves.
Fit & Features
- Abstract printed sheer mesh fabric with partial knit lining, plenty of stretch
- Lettuce edge hems
- Crew neckline
- Short cap sleeves
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5628
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Note To Self Ribbed Knit A-Line Mini Dress
Note to self, this sleeveless mini dress is a must-have for every day! Perfect for any occasion, this stretchy ribbed knit dress will surely become a staple in your wardrobe. It features a crew neckline with tank straps and a flattering A-line silhouette with a flirty front slit on the mini-length hem. Complete the look with an oversized blazer and a sleek necklace.
Fit & Features
- Soft and stretchy ribbed knit fabric
- Crew neckline
- Tank shoulder straps
- Front slit
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5632
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always Eye-Catching Halter Ruffle Chiffon Mini Dress
You'll look positively eye-catching in this floral mini dress at weddings or garden parties! The halter crew neckline and open back ooze elegance, while the ruffled bodycon silhouette flatters your curves. With a mini-length hem, this dress is perfect for any occasion. Complete the look with earrings.
Fit & Features
- Floral print, mesh fabric, stretchy knit lining
- Halter crew neckline, spaghetti strap tie
- Open back
- Ruffled bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5627
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Delightful View Collared Scenic Waist Skater Dress
You'll be such a delightful view in this collared skater dress strolling the streets of Silicy or downtown! Featuring long sleeves with buttoned cuffs and a collared V-neckline, hidden front hook and eye fasteners provide a seamless look, and a scenic printed waist and short skater silhouette add a touch of charm. Complete the look in heels and a crossbody purse.
Fit & Features
- Gauze woven fabric with lining, no stretch
- Collared V-neckline
- Hidden front hook and eye fasteners
- Scenic printed waist
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5638
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charmed Sweetness Lace-Up Floral Skater Dress
Charm everyone with your sweetness in this floral skater dress with a flirty lace-up back and a ruffled short hem perfect for any weekend plans.
Fit & Features
- Floral print, woven fabric, bust lining
- V-neckline, wide shoulder straps, padded bra cups
- Lace-up back
- Ruffled skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05102-5622
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Miami Nights Sleeveless Tropical Slit Maxi Dress
Turn up the heat in Miami in this tropical maxi dress on vacay! The square neckline and spaghetti straps accentuate your curves in a form-hugging fit while the high side slit adds a touch of sassy sophistication. Let the tropical print and maxi-length hem transport you to a paradise getaway! Complete the look in sandals.
Fit & Features
- Tropical print, knit fabric, stretchy short lining
- Spaghetti straps
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5624
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Social Butterfly Square Neck Floral Mini Dress
A dreamy butterfly floral mini dress perfect for social girlies! The mini-length dress features a square neckline that showcases a ribbon trim for romance, adjustable spaghetti straps to get a perfect fit, front metal closures, and a form-hugging silhouette that will flatter your figure. Complete the look in lace-up stiletto heels and a purse for a date!
Fit & Features
- Woven fabric lined with stretchy knit
- Butterfly floral print
- Adjustable spaghetti straps
- Ribbon trim, front metal closures
- Back zipper and hook-eye closure
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-5623
Category Name: Casual Dresses
Price: $5.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Arrived In Style Strapless Knit Mini Dress
Arrive in this stylish strapless mini dress for brunch or parties! The contrasting folded neckline adds a touch of boldness while the slim-fit silhouette shows off your curves perfectly on the smooth knit fabric. The mini-length hem features a subtle A-line fit. Complete the look in platform heels.
Fit & Features
- Smooth knit fabric lined with stretchy knit
- Strapless folded contrast neckline
- Slim-fit silhouette
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Mini-length A-line hem
- Runs true to size
Style Number/Barcode: 05102-5621
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Flawless Crew Neck Textured Midi Dress
Getting ready is a breeze with this casual crew neck midi dress for an effortlessly flawless vibe! Featuring classic cap sleeves and a flattering crew neck, this bodycon dress will hug your curves in all the right places down to the alluring midi-length hem on textured mesh fabric. Complete the look in platform sneakers.
Fit & Features
- Textured sheer mesh fabric
- Stretchy slip lining with adjustable spaghetti straps
- Crew neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5625
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adorably Chic Bow-Detailed Ruffled Mesh Mini Dress
This bow-detailed ruffled mesh mini dress is so adorably chic and perfect for date nights or parties! Made with an airy sheer mesh fabric with a full-length knit lining, this dress gives those effortless breezy vibes. The sleeveless square neckline shapes the bodice, and the adjustable spaghetti straps offer a customized fit. The dress features a ruffled tiered silhouette for the cutest look, detailed with dainty bow accents. The tiers have elastic seams for stretch. The flowy A-line fit on the mini-length hem will give your 'fit a feminine touch. Style with lace-up heels.
Fit & Features
- Non-stretch sheer mesh fabric, stretchy knit lining
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruffled tiered silhouette with bow accents
- Elastic seams for stretch
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5618
Category Name: Casual Dresses
Price: $6.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Leave An Impression Twist Cutout Knit Midi Dress
Leaving an impression will be easy with this sleeveless knit midi dress! Perfect for vacation or a weekend spent at the beach, this dress features a flattering scoop neckline, spaghetti straps, a head-turning twist cutout back design, a bodycon fit, and a sultry side slit along the midi-length hem. Complete the look in strappy espadrille wedges.
Fit & Features
- Knit fabric, moderate stretch
- Scoop neckline
- Spaghetti straps
- Twist back cutout
- Side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1950
Category Name: Casual Dresses
Price: $17.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On The Prowl V-Neck Leopard A-Line Mini Dress
This leopard mini dress calls for a night on the prowl for the best cocktail! Boast a fierce-sultry vibe in this sleeveless dress featuring a flattering V-neckline, adjustable spaghetti straps for the perfect fit, and an A-line silhouette that gracefully shows off your curves along the mini-length hem. Complete the look in an edgy faux leather jacket.
Fit & Features
- Leopard print, mesh fabric line with stretchy knit
- Adjustable spaghetti straps
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5615
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Blooming Bouquet Sleeveless Floral Mesh Mini Dress
Get ready to bloom in this floral mesh mini dress at a girl's brunch or evening soiree! The sleeveless crew neckline and bodycon silhouette highlight your curves, while the bold floral print and mesh fabric add a touch of feminine charm. Complete the look in simple stiletto heels.
Fit & Features
- Blooming floral print
- Sheer mesh fabric with knit lining, plenty of stretch
- Crew neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5612
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweeten Me Up Square Neck Cutout A-Line Midi Dress
Sweeten your style in this breezy A-line midi dress perfect for bridal showers, day dates, or brunch! With a sleeveless square neckline and adjustable spaghetti straps, this cotton midi dress offers a flattering fit while the stretchy smocked bust with lace-up detail adds a touch of sweetness. The cutout back with elasticized straps adds a hint of daring to the fitted bodice and A-line silhouette. Complete the look in strappy sandals for a chic allure.
Fit & Features
- Lightweight cotton woven fabric with lining
- Adjustable spaghetti straps
- Smocked lace-up bust
- Cutout back
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05102-5611
Category Name: Casual Dresses
Price: $6.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Destined For Love Lace-Up Short Skater Dress
You'll be destined for love in this short skater dress perfect for dressy parties! This flirty dress features a square neckline, adjustable spaghetti straps, and a lace-up back for a perfect fit. The skater silhouette and short-length hem add a playful touch, while the burnout pattern on the mesh fabric adds a touch of intrigue. Complete the look in block heels.
Fit & Features
- Burnout pattern, mesh fabric, tulle and stretchy knit lining
- Square neckline
- Adjustable spaghetti straps
- Lace-up, back zipper and hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3319
Category Name: Casual Dresses
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Afternoons Collar Open Back Skater Dress
Enjoy a sunny afternoon looking like a cutie in this skater dress perfect for a girl's day! With a sleek halter collar neckline and flattering button-down front, this dress will accentuate your figure with its fitted high waist seam. The playful open back with tie closure adds a touch of allure, while the skater silhouette and short-length hem create a fun and flirty look. Complete the look in strappy sandals and earrings.
Fit & Features
- Lightweight woven fabric with lining
- Open back with tie closure
- Button down front
- Back zipper and hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5616
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Striped Delight Surplice Collared Mini Dress
You're sure to have a day full of sweetness in this delightful striped mini dress perfect for upcoming weekend plans! This dress is designed with chic long sleeves with button cuffs, along with a flattering collar V-neckline and wrap tie waist belt for that cinched look. The surplice mini-length hem adds a touch of sass while the pleated form-hugging fit accentuates your curves. Complete the look in clear sandals and earrings.
Fit & Features
- Striped non-stretch woven lightweight fabric
- Collared V-neckline
- Long sleeves with buttoned cuffs
- Wrap tie waist belt with pleating
- Surplice mini-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5610
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreaming Of Paradise Cowl Neck Tropical Midi Dress
Let your vacation or getaway be filled with sand and compliments when you're in this tropical midi dress! Featuring a cowl neckline and adjustable spaghetti straps for a perfect fit, this bodycon dress also boasts a side slit and midi-length hem. Complete the look with sunglasses and sandals!
Fit & Features
- Tropical print, stretchy knit fabric
- Adjustable spaghetti straps
- Cowl neckline
- Bodycon fit
- Side slit
- Runs true to size
Style Number/Barcode: 05102-5613
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute Feels Off-The-Shoulder Sweater Mini Dress
Feel cute in this off-the-shoulder sweater mini dress all year round! The folded off-the-shoulder neckline adds a flirty touch, while the bodycon fit accentuates your curves perfect for a day or night on the town. Complete the look in block heels.
Fit & Features
- Sweater knit fabric, moderate stretch
- Off-the-shoulder neckline
- Bodycon fit
- Mini-length
- Runs true to size
Style Number/Barcode: 06005-1947
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Getaway Tropical Print Flowy Maxi Dress
This tropical print flowy maxi dress is giving major weekend getaway energy! The breezy lightweight woven fabric is detailed with a tropical leaf-outlined print, perf for your next vacay. The maxi-length dress features a sleeveless square neckline and adjustable spaghetti straps for a customized fit. The high waist leads to a cute tie-back design, followed by a lower back cutout for a hint of skin. The dress flows out in an A-line silhouette with a stylish tiered design. Complete your look with gold hoops and strappy sandals.
Fit & Features
- Tropical printed woven fabric
- Sleeveless square neckline
- Adjustable spaghetti straps
- High waist with tie-back design, lower back cutout
- Flowy A-line fit with a tiered design
- Runs true to size
Style Number/Barcode: 05102-5609
Category Name: Casual Dresses
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Back To Basics Ribbed Knit Midi Dress
Every girl needs this basic ribbed knit midi dress in her line up! The dress features a classic crew neckline and short sleeves perfect for layering with a sweater or jacket and a form-hugging fit.
Fit & Features
- Ribbed knit fabric with brushed knit lining, plenty of stretch
- Crew neckline
- Short sleeves
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5603
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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Inspired Charm Strapless Watercolor Print Mini Dress
Envoke an inspired charm in this watercolor print mini dress and capture attention at parties or casual dinners! With its strapless straight-across neckline and bodycon silhouette, this mini dress will accentuate your curves and flatter your figure. Made from airy lined mesh fabric with an eye-catching watercolor print, this dress is a must-have for any fashion-forward girlie! Complete the look in stiletto heels and a purse!
Fit & Features
- Watercolor print
- Mesh fabric lined with stretchy knit
- Strapless straight neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5605
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Good Times Bodycon Abstract Print Mini Dress
A mini dress that calls for good times only at casual parties or weekend plans! Designed with an alluring abstract print on mesh fabric, this dress is both chic and versatile. The sleeveless crew neckline and bodycon silhouette highlight your curves, while the side ruched seams flatter your figure. Complete the look with a mini shoulder bag and heels.
Fit & Features
- Abstract print
- Mesh fabric, sewn-in knit lining, stretchy
- Side ruched seams
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5606
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale