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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Somewhere Tropical V-Neck Cutout Abstract Maxi Dress
This maxi dress plus you somewhere tropical equals the chicest vacation! The dress boasts a trendy cutout with a decor accent and a sultry side slit for effortless movement.
Fit & Features
- Abstract print, stretchy knit-lined fabric
- V-neckline with decor accent
- Spaghetti straps
- Cutout bodice, side slit
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6055
Category Name: Casual Dresses
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Admired Cutie Floral A-Line Midi Dress
Catch every eye when you breeze by in this floral midi dress with flirty details like a corset-inspired bodice and a flowy A-line silhouette!
Fit & Features
- Ditsy floral print, woven fabric lined with tulle and stretchy knit
- Sweetheart neckline with bust tie
- Lace trim wide shoulder straps
- Back zipper and hook-eye closure, stretchy smocked back
- A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-4053
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Ditsy floral print, woven fabric lined with tulle and stretchy knit
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Thriving Blooms Corset Floral Slit Midi Dress
Thrive with sweet energy in this floral midi dress perfect for brunches or dates! With a corset bodice that snatches your waist and a flirty front slit, this a-line dress will captive everyone. Pair with a necklace.
Fit & Features
- Ditsy floral print, woven fabric
- Wide shoulder straps, sweetheart neckline
- Corset bodice
- Side pockets
- A-line silhouette, front slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-4051
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay Bound Tropical Floral Ruched Knit Maxi Dress
Make sure to pack this tropical floral knit maxi dress for your next sunny vacay! The ruched bodycon silhouette will flaunt your stunning curves as you pose for those getaway pics.
Fit & Features
- Ribbed knit fabric, high stretch
- Tropical floral print
- Sleeveless cowl neckline
- Spaghetti straps
- Ruching
- Maxi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-6054
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Luxe Charm Cashmere Knit Hanky Hem Mini Dress
Channel a luxe aura in a ribbed cashmere-like knit dress that features a boat neckline, long fitted sleeves, a partially open back design, and a short hanky hem with an A-line silhouette. Complete the look with knee-high boots and leg warmers for a chic moment!
Fit & Features
- Ribbed cashmere-like knit fabrication, moderate stretch
- Boat neckline
- Long fitted sleeves
- Partial open back, tie-back spaghetti straps
- Mini-length hanky hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6053
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Effect Cap Sleeve Bodycon Floral Mini Dress
You'll have a flirty effect in this floral bodycon dress boasting pretty details like flattering cap sleeves, a tied bust, and a ruffled mini hem.
Fit & Features
- Floral print, eyelet knit fabric, stretchy knit lining
- Cap sleeves
- Sweetheart neckline, tied bust
- Bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6051
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Fave Floral Ruffled Skater Dress
This adorable ditsy floral skater dress will be your new flirty fave to style up all season! You'll love the tiered ruffled design and flowy fit-and-flare silhouette.
Fit & Features
- Woven fabric
- Ditsy floral print
- Strapless straight neckline
- Smocked bodice
- Tiered ruffled skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05102-6052
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Lovely Floral Eyelet Mini Dress
Oh-so-lovely, this floral eyelet knit mini dress is perfect for weekend brunch. You'll adore the short puff sleeves, sweet tie-front detail, and pretty A-line silhouette.
Fit & Features
- Sheer eyelet knit fabric with knit lining, plenty of stretch
- Dainty floral print
- Sweetheart neckline, ruched bust
- Keyhole cutout, tie-front detail
- Short puff sleeves, elastic cinched hems
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6050
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute And Cozy Mock Neck Knit Skater Dress
Fit & Features
- Stretchy rib knit fabric
- Mock neck
- Fitted long sleeves
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 06005-2241
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: S
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Cutest Twirl Long Sleeve Knit Skater Dress
Twirl into style in this long sleeve knit skater dress. Featuring a square neckline and skater silhouette, this ribbed knit is your go-to for effortless charm.
Fit & Features
- Stretchy rib knit fabric
- Fitted long sleeves
- Square neckline
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 06005-2243
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Enchanted Floral Slit A-Line Midi Dress
Turn heads in this enchanting floral midi dress boasting a flattering A-line silhouette and a front slit for effortless sashays all day!
Fit & Features
- Ditsy floral print, knit fabric lined with stretchy knit
- V-neckline, bust tie
- Spaghetti straps
- Front slit
- A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6048
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Vibe Floral Print Strapless Bodycon Mini Dress
Look gorgeous at your getaway and show off a bold vibe in this knit mini dress designed with a large floral print to turn heads. It features a strapless straight-across neckline and a short bodycon silhouette to hug your curves.
Fit & Features
- Smooth knit fabric with knit lining, plenty of stretch
- Large floral print
- Strapless straight neckline, no-slip strip
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-6047
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Falling For Charm Strappy Open Back Floral Mini Dress
Fall for the charm of this flirty floral mini dress with a head-turning strappy open back and A-line fit perfect for showing off at brunch or a spring date!
Fit & Features
- Floral print, stretchy knit fabric
- Halter V-neckline, spaghetti strap tie
- Open back, strappy spaghetti strap ties
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6042
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Just For Fun Strapless Floral A-Line Mini Dress
A floral mini dress made for fun and compliments! With a flattering strapless neckline and A-line silhouette, you'll look and feel your best.
Fit & Features
- Floral print, eyelet fabric lined with stretchy knit
- Strapless neckline
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6040
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Petit Blooms Floral Eyelet Midi Dress
Dainty floral makes this eyelet midi dress the cutest spring-to-summer style!
Fit & Features
- Dainty floral print, eyelet fabric, sewn-in knit lining
- Strapless neckline
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6043
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feeling Pretty Cute Floral Skater Short Dress
Nothing comes as close to cute as this floral skater dress! Perfect for shower celebrations or afternoon teas, this short dress boasts a pretty corset-inspired bodice and a voluminous hem.
Fit & Features
- Floral print, cotton woven fabric, tulle and woven linings
- Square neckline, bust tie
- Wide shoulder straps
- Back zipper and hook-eye closure
- Corset-inspired bodice, pleating
- Skater silhouette, short-length hem, pleated trim
- Runs true to size
Style Number/Barcode: 05101-4037
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blissful Cutie Floral Bodycon Midi Dress
Enter a state of blissful cuteness in this floral midi dress boasting a flattering bodycon fit perfect for layering with denim jacket.
Fit & Features
- Eyelet knit stretchy fabric, sewn-in knit lining
- Strapless neckline
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6044
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Charmer Ditsy Floral Strapless Mini Dress
Charm them with your adorable style in this lined eyelet knit mini dress with the cutest ditsy floral print. The form-hugging fit will highlight your curves.
Fit & Features
- Sheer eyelet knit fabric with knit lining, high stretch
- Ditsy floral print
- Strapless straight neckline
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-6046
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Electric Strapless Jean Denim Mini Dress
Unlock the power of style in this strapless denim jeans with a jean-like design and bodycon fit that stands out from the crowd!
Fit & Features
- Denim acid wash fabric with stretch
- Strapless neckline, button closure, belt loops
- Front zipper closure
- Jean-like design
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6045
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Bliss Tie-Back Slit Maxi Dress
Ideal for making a statement at any occasion, this artsy print maxi dress combines chic with effortless style. Featuring a flattering A-line silhouette and a stylish front slit, this dress offers a breezy look that turns heads with a tie-back design.
Fit & Features
- Artsy print, woven fabric, stretchy knit lining
- V-neckline
- Adjustable spaghetti straps
- Tie-back design
- A-line silhouette
- Front slit, flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6039
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute And Sunny Floral Skater Dress
Made for cute sunny day dressing, this floral mini dress flaunts adorable puff sleeves and a skater silhouette that flatters any figure!
Fit & Features
- Floral print, eyelet knit fabric, stretchy knit lining
- Puff short sleeves
- Square neckline, ruched bust
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6041
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flawless Beauty Eyelet A-Line Mini Dress
Make every heart flutter in this eyelet mini dress boasting a flirty bust tie and flattering A-line silhouette. Perfect for shower celebrations or brunch!
Fit & Features
- Eyelet knit stretchy fabric, stretchy knit lining
- V-neckline, spaghetti straps
- Bust tie
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6037
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fall In Love Floral Eyelet A-Line Mini Dress
A flirty floral mini dress to attend parties, brunch, and day dates! This sleeveless dress boasts a classy V-neckline and a flattering a-line silhouette on pretty eyelet woven fabric with a dainty floral print. Pair with mules.
Fit & Features
- Dainty floral print
- Eyelet woven fabric lined with stretchy knit
- V-neckline, adjustable spaghetti straps
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6038
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweetest Thing Strappy Back Halter Babydoll Dress
Experience the ultimate blend of sweet and sultry in this babydoll mini dress at shower celebrations or backyard parties! The delicate lace trim on the halter V-neckline adds a touch of femininity, while the strappy open back turns heads along the ruffled, flowy silhouette.
Fit & Features
- Woven fabric, woven lining
- Halter V-neckline, lace trim, bust tie
- Strappy open back, adjustable spaghetti straps
- Ruffled babydoll silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6036
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale