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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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
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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
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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
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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
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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
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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
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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
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Exquisite Charm A-Line Floral Mini Dress
The perfect floral mini dress pick for your weekend plans! Showcasing a flattering sweetheart ruffle neckline and a-line silhouette, this dress will capture your heart. Pair with heels.
Fit & Features
- Ditsy floral print, cotton knit fabric lined
- Strapless sweetheart ruffle neckline
- Padded bra cups
- Back zipper and hook-eye closure
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6033
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Arrival Tie-Front Slit Midi Dress
Arrive in this charming bodycon midi dress showcasing a flirty bust tie-front and a front slit to give you effortless movement.
Fit & Features
- Eyelet lace fabric lined with stretchy knit
- Sweetheart neckline, tie-front bust
- Spaghetti straps
- Bodycon silhouette
- Front slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6032
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always Sunny Strapless Ruffle Eyelet Mini Dress
This eyelet mini dress is perfect for any sunny day and will be a favorite for shower celebrations, brunch, or graduations! The dress boasts a stretchy smocked bodice that hugs your figure while the ruffled mini-length hem adds a flirty allure.
Fit & Features
- Eyelet woven-lined fabric
- Strapless neckline
- Stretchy smocked bodice
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4019
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreamy Vibes V-Neck Floral Mesh Maxi Dress
An effortless and dreamy floral mesh maxi dress to slip into for date night or dinners on vacay! The sleeveless dress is designed with a flattering V-neckline, delicate adjustable spaghetti straps, and a form-hugging fit that leads to the flowy floor-length hem. Pair with a hair accessory.
Fit & Features
- Floral print, mesh fabric, stretchy knit lining
- V-neckline, adjustable spaghetti straps
- Form-hugging fit
- Flowy floor-length hem
- Runs true to size
Style Number/Barcode: 05101-4012
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Caught Your Eye Strapless Lace-Up Skater Dress
Catch every eye in this eyelet skater dress with a flirty lace-up bust and a flowy mini-length hem perfect for twirling at parties!
Fit & Features
- Eyelet cotton fabric with woven cotton lining
- Strapless neckline, lace-up bust, padded bra cups
- Skater silhouette
- Flowy mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4009
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Talker Strappy Back Halter Skater Mini Dress
Sweeten any room with your vibe in this halter skater dress, which flaunts a strappy open back that turns heads with every wear!
Fit & Features
- Woven fabric, stretchy knit lining
- Halter V-neckline with spaghetti strap tie
- Open back with tie-back detail
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6029
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ace The Test Open Tie Back Skater Dress
This skater dress understood the assignment. Featuring a flattering halter V-neckline and a chic open tie-back design, this mini-length dress will have you feeling confident and cute for any casual occasion!
Fit & Features
- Woven fabric
- Halter V-neckline, spaghetti strap ties
- Open tie-back design
- Flowy skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6030
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Effortless Tie-Front Ruffled Skater Dress
Make your weekend outfits so effortless with this adorable tie-front skater dress. The lightweight gauze fabric paired with the ruffled skater silhouette creates that breezy, flowy fit you'll love.
Fit & Features
- Gauze woven fabric with smooth woven fabric, no stretch
- Sleeveless V-neckline, padded bust, bust tie accent, keyhole cutout
- Adjustable spaghetti straps
- Partially smocked back
- High waist seam
- Short skater silhouette, tiered ruffled design
- Runs true to size
Style Number/Barcode: 05102-6027
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Easily Stunning Strapless Cutout Striped Mini Dress
Take a stroll looking stunning in this striped mini dress with a sexy cutout and bodycon silhouette to flaunt your figure!
Fit & Features
- Striped print, stretchy knit fabric
- Strapless sweetheart neckline
- Button accents, cutout bodice
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-2233
Category Name: Casual Dresses
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free