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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Denim Dreams Lace-Up Mini Dress
Keep it dreamy with a denim mini dress that elevates your look! The dress features a sleeveless scoop neckline, spaghetti straps that lead to a lace-up back, vertical seams, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Lace-up back, lower back zipper and hook and eye closure
- Vertical seams
- Mini-length silhouette
- Denim fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4089
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic High-Slit Basic Maxi Dress
Basic yet oh-so-chic, this sleeveless maxi dress will be your new go-to. It features a crew neckline, tank shoulder straps, a sultry thigh-high side slit, and a floor-length fitted silhouette. Style this dress with sleek hoop earrings.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Thigh-high side slit
- Floor-length fitted silhouette
- Ribbed cotton fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4090
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Hooked In Denim Mini Dress
Get hooked in with this cute mini dress that is part glam, part casual! The dress features a strapless sweetheart neckline, hook and eye front closures, corset seams, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Strapless sweetheart neckline
- Hook and eye front closures
- Corset seams
- Mini-length silhouette
- Denim knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4081
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Color Me In Glam Tie Dye Mini Dress
Keep it colorfully glam with a mini dress that is everything! The dress features a sleeveless square neckline, spaghetti straps, a tie-dye hue, a ruched body throughout, and a mini-length silhouette. Complete look with mules and statement cuff.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Tie-dye hue
- Ruched body
- Mini length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4077
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Stunner Ribbed Knit Midi Dress
Stun on them with a stylish midi dress that makes a head-turning impression! The dress features a sleeveless V-neckline, spaghetti straps, an open back with an O-ring accent, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete outfit with clear mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Open back, O-ring accent
- Midi-length
- Ribbed knit fabric, knit lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4071
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stunning Style Cutout Maxi Dress
Showcase a stunning style this season in this trendy maxi dress. It features a sleeveless V-neckline, spaghetti straps, dual waist cutouts that lead to the back, and a floor-length, curve-hugging silhouette. Pair this sultry dress with hoop earrings and sleek heels.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Dual waist cutouts that lead to the back
- Floor-length, form-hugging fit
- Ribbed cotton fabric
- Runs true to size
Style Number/Barcode: 05102-4079
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mesmerizing Beauty Puff Sleeve Eyelet Skater Dress
Mesmerize with a skater dress that is perf for your next photoshoot! The dress features a square neckline, short puff sleeves, an eyelet pattern, and a skater silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Square neckline
- Short puff sleeves
- Eyelet pattern
- Skater silhouette
- Lightweight woven fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4073
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Totally Fab Tie Dye Ruched Mini Dress
Keep it totally fab with a ruched mini dress! The dress features a sleeveless square neckline, spaghetti straps, tie-dye print, a ruched body, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Tie-dye print
- Ruched body
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4078
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Darling Gingham Print Mini Dress
Stay on trend with a pretty mini dress that is perf for brunch with the squad! The dress features a sleeveless square neckline, spaghetti straps, gingham print, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Gingham print
- Mini length silhouette
- Knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4074
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tropical Sunsets Maxi Dress
Your dream vacation is calling! Pack this stunning tropical floral printed maxi dress for a gorgeous look. It features an off-the-shoulder square neckline, a fitted smocked bodice, short ruffled sleeves, a tie-front accent to highlight the waist, and a flowy, floor-length silhouette with a wrap-front design. Style this dress with sleek hoop earrings and strappy sandals.
Fit & Features
- Off-the-shoulder square neckline
- Fitted smocked bodice
- Short ruffled sleeves
- Tie-front detail
- Flowy, floor-length silhouette, wrap-front design
- Woven fabric, tropical floral print
- Runs true to size
Style Number/Barcode: 05102-4068
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Twist Long Sleeve Midi Dress
The twist back on this midi dress is pretty chic! It features long sleeves, a crew neckline, and a form-fitting silhouette. The dress is composed of a ribbed knit fabric with a moderate stretch. Perfect for styling with suede booties and a statement bracelet.
Fit & Features
- Long fitted sleeves
- Crew neckline
- Twisted open back detail
- Midi-length hem
- Form-fitting silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1075
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Carefree Bohemian Chic Cutout Maxi Dress
Channel a carefree vibe with a maxi dress that is so bohemian chic! The dress features a bohemian print, a sleeveless V-neckline, spaghetti straps, dual cutouts at the waist, and a maxi-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit. Complete look with sandals and tassel earrings.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Dual cutouts at the waist
- Knit fabric, bohemian print
- Maxi-length silhouette
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4063
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Nights Like This Cutout Mini Dress
Nights like this call for a stunning dress to celebrate with the squad! The dress features a sleeveless sweetheart neckline, waist cutouts, a double row of O-rings, a ruched body, and a mini-length silhouette. Complete look with rhinestone heels and statement earrings.
Fit & Features
- Sleeveless sweetheart neckline
- Waist cutouts
- O-Rings accents
- Ruched body
- Mini-length silhouette, form-hugging fit
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4060
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Florals Ribbed Knit Mini Dress
Bring the charm with a floral mini dress that is perf for your next brunch date! The dress features a sleeveless sweetheart neckline, tie-front, spaghetti straps, ditsy floral print, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit. Complete look with wedges.
Fit & Features
- Sleeveless sweetheart neckline
- Tie-front
- Spaghetti straps
- Ditsy floral print
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4062
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Carefree Style Tie-Dye Mini Dress
Showcase an effortless and carefree style this summer with this tie-dye mini dress! It features a sleeveless square neckline, spaghetti straps, side ruching with drawstrings at the hem, and a mini-length, curve-hugging silhouette. The soft brushed knit fabric offers a moderate stretch. Complete the look with casual sneakers.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Side ruching, drawstrings at the hem
- Short, form-hugging fit
- Brushed knit fabric, moderate stretch
- Tie-dye print
- Runs true to size
Style Number/Barcode: 05102-4057
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Making Waves Tie Dye Ruched Mini Dress
Make waves with a stylish mini dress that creates a commotion! The dress features a sleeveless V-neckline, a ruched center drawstring, a tie-dye print, spaghetti straps, and a mini-length silhouette. Complete look with clear mules.
Fit & Features
- Sleeveless V-neckline
- Ruched center drawstring
- Tie-dye print
- Spaghetti straps
- Mini length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4056
Category Name: Casual Dresses
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ditsy Floral Daze Ribbed Knit Mini Dress
Get caught in a floral daze with this cute mini dress! The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ditsy floral print
- Mini-length silhouette, ruching down the sides
- Ribbed knit fabric, knit lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-3119
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Flowy A-Line Mini Dress
Get an effortless look in this flowy boho-chic mini dress. It features a sleeveless subtle square neckline, adjustable spaghetti straps that lead to a cross-back design, a short A-line silhouette, and a drop hem with a cute ruffle detail. Style this dress with your fave pair of wedges.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Cross-back design
- Mini-length, A-line silhouette
- Drop hem, ruffle detail
- Double-lined gauze fabric
- Runs true to size
Style Number/Barcode: 05102-3099
Category Name: Casual Dresses
Price: $20.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Vibes Linen Mini Dress
Channel those flirty vibes with a mini dress that brings those girly details! The dress features an off-the-shoulder neckline, a tiered ruffle popover, a smocked waist, and an A-Line silhouette. The dress is composed of a linen knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges and hoops.
Fit & Features
- Off the shoulder neckline
- Tiered ruffle popover
- Smocked waist
- Mini length silhouette
- A-Line
- Linen knit fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-1058
Category Name: Casual Dresses
Price: $22.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Girly Vibes Gingham Babydoll Dress
Keep it super girly with a pretty babydoll dress that brings those good vibes this season! The dress features a sweetheart neckline, quarter-length balloon sleeves, a gingham print, and flared mini-length silhouette with a ruffled hem. The dress is composed of cotton knit fabric that offers a relaxed fit with a moderate stretch. Complete look with sandals.
Fit & Features
- Sweetheart neckline
- Quarter-length balloon sleeves
- Gingham print
- Ruffles
- Mini length silhouette
- Cotton knit fabric, additional knit lining
- Relaxed fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-3064
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Pick Ditsy Floral Mini Dress
This adorable ditsy floral mini dress is the perfect pick to add to your summer wardrobe! It features a sleeveless square neckline, thin ruffled shoulder straps, ruched detailing with a front drawstring, and a mini-length, curve-hugging silhouette. Style this dress with cute wedges for a weekend brunch.
Fit & Features
- Sleeveless square neckline
- Thin ruffled shoulder straps
- Ruched detailing, front drawstring
- Short, form-hugging fit
- Ribbed knit fabric, ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-2963
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortlessly Pretty Floral Mini Dress
Get an effortlessly pretty look in this adorable mini dress. It features short puff sleeves, a sweetheart neckline with a tie-front detail, a stylish waist cutout, and a mini-length, curve-hugging silhouette with a flirty ruffled hem. The dress is composed of a lightweight woven fabric with an all-over disty floral print and features a stretchy smocked body. Complete the look with a charm necklace.
Fit & Features
- Short puff sleeves, cinched hems
- Sweetheart neckline, tie-front detail
- Front waist cutout
- Short, form-hugging fit
- Tiered, ruffled hem
- Lightweight woven fabric, ditsy floral print
- Stretchy smocked body
- Runs true to size
Style Number/Barcode: 05102-3061
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Passion Sleeveless Mini Dress
Channel the romance with a floral mini dress that brings charm to your look. The dress features a sleeveless V-neckline, tie-front, spaghetti straps, ditsy floral print, and mini-length silhouette. Complete look with mules and a charm necklace.
Fit & Features
- Sleeveless V-neckline
- Tie-front
- Spaghetti straps
- Ditsy floral print
- Mini length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2692
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Let Style Bloom Ditsy Floral Tube Dress
Let your style bloom with a tube dress that is perf for those beach days! The dress features a strapless square neckline, a ditsy floral print, and a mini-length silhouette. Complete the look with mules and a crossbody.
Fit & Features
- Strapless square neckline
- Ditsy floral print
- Mini-length silhouette
- Lightweight ribbed knit fabric, knit lining
- Form-hugging fit, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-2876
Category Name: Casual Dresses
Price: $4.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance