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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Art Of Style Abstract Print Midi Dress
Show everyone how it's done! This sleeveless midi dress features a square neck, spaghetti straps, a side ruched seam that accentuates your curves along the bodycon silhouette, and a high side asymmetrical slit. The dress is designed with an artsy abstract print on smooth knit fabric. Complete the look with earrings for an art gallery opening!
Fit & Features
- Sleeveless square neck, spaghetti straps
- Side ruched seam, bodycon silhouette
- High side asymmetrical slit
- Midi-length hem
- Abstract print, smooth knit fabric, moderate stretch
- Bust lining
- Runs true to size
Style Number/Barcode: 05102-5206
Category Name: Casual Dresses
Price: $5.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Charmed Mock Neck Bodycon Mini Dress
This bodycon mini dress would be charmed to make your acquaintance! A short dress that features fitted bell long sleeves and a mock neckline, and is composed of a rib knit fabric with a sewn-in knit lining. Style the mini dress with a chic crossbody bag for a day date!
Fit & Features
- Fitted bell long sleeves
- Mock neckline
- Bodycon silhouette
- Mini-length hem
- Rib knit fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5204
Category Name: Casual Dresses
Price: $5.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Totally Iconic Bubble Mesh Bodycon Mini Dress
Create a fabulous club look that is totally iconic with this bodycon mini dress! It features a sleeveless square neckline, bungee spaghetti straps, a mini-length hem, a bodycon silhouette that will flaunt your figure, and is composed of a textured bubble mesh fabric. The lined mesh fabric offers plenty of stretch. Style with platform heels.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Mini-length hem
- Bodycon fit
- Textured bubble mesh fabric, sewn-in knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5202
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flaunt Your Figure Bodycon Mini Dress
Flaunt your gorgeous figure in this curve-hugging mini dress! Featuring a sleeveless square neckline, bungee spaghetti straps, an alluring open back with a cross-back strap design, a mini-length hem, and a bodycon fit, you'll look amazing from any angle. The textured knit fabric offers plenty of stretch. Style with hoop earrings and clear heels.
Fit & Features
- Sleeveless square neckline, dart seam detailing
- Bungee spaghetti straps
- Open back, cross-back bungee strap design
- Mini-length hem
- Bodycon silhouette
- Textured knit fabric, smooth knit lining at the bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5205
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Style Icon Cutout Bodycon Midi Dress
This sultry-chic midi dress will level up your look and make you a casual style icon! It features a sleeveless asymmetric one-shoulder neckline with a tank strap, a bold asymmetric waist cutout for a hint of skin, a midi-length hem, and a bodycon silhouette that will hug your curves. The ribbed knit fabric offers plenty of stretch. Pair with clear mules.
Fit & Features
- Sleeveless asymmetric one-shoulder neckline
- Tank strap
- Asymmetric waist cutout
- Midi-length hem
- Bodycon silhouette
- Stretchy ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-5201
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Set The Curve Square Neck Maxi Dress
Set the tone for flaunting your curves in this essential maxi dress perfect for day or night styling! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, and a sexy center-back high slit on double-lined knit fabric with a buttery soft feel. Complete the look with a crop denim jacket and sandals for a sunset dinner date!
Fit & Features
- Sleeveless square neck, spaghetti straps
- Bodycon silhouette
- Center back high slit
- Maxi-length hem
- Double-lined knit fabric
- Buttery soft and stretchy
- Runs true to size
Style Number/Barcode: 05102-5200
Category Name: Casual Dresses
Price: $5.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic And Simple Smooth Knit Mini Dress
This chic and simple smooth knit mini dress is the elevated basic you need! It features a sleeveless mock neckline, tank shoulder straps, a mini-length hem, and a bodycon silhouette that will hug your natural curves. The buttery-soft and smooth double-lined knit fabric offers plenty of stretch. Style with hoop earrings and clear mules.
Fit & Features
- Sleeveless mock neckline
- Tank shoulder straps
- Mini-length hem
- Bodycon silhouette
- Soft and smooth double-lined knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5198
Category Name: Casual Dresses
Price: $5.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Real Showstopper Lace-Up Maxi Dress
A real showstopper of a maxi dress! Flaunt your best self in this sleeveless dress featuring a square neckline, spaghetti straps, an open lace-up back design, a ruched side seam, and a bodycon silhouette with a flattering high side asymmetrical slit on sleek knit fabric. Complete the look in block heels for a dinner date.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open lace-up back design
- Ruched side seam, bodycon silhouette
- High side asymmetrical slit, maxi-length fitted hem
- Sleek knit and stretchy fabric
- Runs true to size
Style Number/Barcode: 05102-5346
Category Name: Casual Dresses
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Plans Rib Knit Bodycon Maxi Dress
Casual plans? Look amazing in this sleeveless maxi dress for everything on your social calendar! It features a square neckline, spaghetti straps, a bodycon silhouette, and a fitted long hem on stretchy rib knit fabric. Complete the look in cute flower earrings and sandals.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Maxi, fitted long-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5195
Category Name: Casual Dresses
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Chaser Cowl Neck Mini Dress
The perfect mesh mini dress for a sunset dinner by the beach! It features a sleeveless cowl neckline, sleek bungee spaghetti straps, and side-ruched seams to accentuate your curves along the bodycon silhouette. Complete the look with a sleek choker and earrings.
Fit & Features
- Sleeveless cowl neckline
- Bungee spaghetti straps
- Side ruched seams, bodycon silhouette
- Mini-length hem
- Sunset beach graphic design
- Mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5197
Category Name: Casual Dresses
Price: $5.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Definite Yes High Slit Maxi Dress
This sleek high slit maxi dress is a definite yes for leveling up your casual looks! It features a sleeveless cowl neckline, spaghetti straps, a maxi-length hem with a thigh-high front slit to showcase some leg, and a slim-fit silhouette. The smooth knit fabric offers plenty of stretch. Style with strappy sandals for a lunch date!
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Maxi-length hem
- High front slit
- Slim-fit silhouette
- Smooth and stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5194
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Mood Cutout Bodycon Midi Dress
Keep your summer style sultry and on-trend with this curve-hugging bodycon midi dress. It features a sleeveless square neckline, thin tank shoulder straps, an asymmetric cutout that continues all around the waist with a sleek O-ring accent at the front, and a midi-length hem. The ribbed knit fabric offers plenty of stretch. Pair with strappy heels.
Fit & Features
- Sleeveless square neckline
- Thin tank shoulder straps
- Asymmetric cutout, all around the waist, metal O-ring accent
- Midi-length hem
- Bodycon fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5189
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Chill Crew Neck Knit Dress
You'll feel effortlessly chill in this basic midi dress perfect for looking cute on the go! It features short sleeves, a crew neck, a bodycon silhouette, a side slit accent, and a knee-length hem. The dress is composed of a soft hacci rib knit fabric with plenty of stretch. Style with trendy flat sandals for grabbing coffee!
Fit & Features
- Short sleeves
- Crew neck
- Bodycon silhouette
- Side slit accent
- Knee-length hem
- Hacci rib knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5190
Category Name: Casual Dresses
Price: $9.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute In The City V-Neck Knit Midi Dress
You'll be looking cute in the city in this casual midi dress perfect for a dinner date! It features bell long sleeves, a front and back V-neckline, and a flattering bodycon silhouette on rib knit fabric with a sewn-in knit lining. Complete the look with a chic crossbody bag.
Fit & Features
- Rib knit fabric, sewn-in knit lining
- Moderate stretch
- Bell long sleeves
- Front and back V-neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5192
Category Name: Casual Dresses
Price: $19.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Instant Fave Disty Floral Short Sleeve Midi Dress
This adorable disty floral midi dress will be an instant fave of yours for the summer season. It features a crew neckline, short fitted sleeves, a small top keyhole cutout at the back with a button closure, a larger lower back cutout, a high waist seam, a midi-length hem with a high front slit, and a form-hugging silhouette. The floral printed brushed knit fabric offers plenty of stretch. Style with espadrille sandals.
Fit & Features
- Crew neckline, short sleeves
- Small back keyhole cutout, button closure
- Larger lower back cutout, high waist seam
- Midi-length hem, front slit, form-hugging fit
- Ditsy floral print
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5184
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island Neutrals Halter Strappy Tropical Midi Dress
Unveil this chic tropical midi dress on the island! The cowl halter neckline and strappy open back add a touch of allure, while the bodycon silhouette and asymmetrical cut hem flatter your figure. Complete the look with cute block heel sandals and sunglasses!
Fit & Features
- Tropical print, smooth knit stretchy fabric
- Halter cowl neckline, spaghetti strap
- Strappy open back
- Bodycon fit
- Asymmetrical cut hem
- Runs true to size
Style Number/Barcode: 05102-5185
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Sultry Vibes Cutout Maxi Dress
Bring the casual sultry vibes to your weekend plans with this curve-hugging maxi dress. It features a sleeveless sweetheart neckline with a twist-front design, spaghetti straps, a bold waist cutout at the front, a maxi-length hem with a chic back slit accent, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch. Style with clear mules for drinks with the girls.
Fit & Features
- Sleeveless sweetheart neckline, twist-front design
- Spaghetti straps
- Waist cutout
- Maxi-length hem, back slit
- Bodycon fit
- Ribbed knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5186
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Stroll Rib Knit Midi Dress
Take a casual stroll looking cute in this rib knit midi dress essential for afternoon pick-me-ups with the girls! Featuring a sleeveless square neck, spaghetti straps, a form-hugging silhouette, and a sultry front slit along the hem. Complete the look with a layered choker necklace.
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Form-hugging silhouette
- Front slit
- Midi-length hem
- Rib knit fabric, bust lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5183
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Weekend Vibes One-Shoulder Midi Dress
This sultry curve-hugging midi dress gives off major summer weekend vibes! It features an asymmetric one-shoulder neckline with dual adjustable spaghetti straps, an alluring open back with an asymmetric strap design, a midi-length hem, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch. Style with platform wedges for dinner and drinks.
Fit & Features
- Sleeveless asymmetric one-shoulder neckline
- Dual adjustable spaghetti straps
- Open back, asymmetric strap design
- Midi-length hem
- Bodycon fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5173
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Loving Basics V-Neck Bodycon Tank Dress
Every girl loves her basics and this sleeveless tank dress is perfect for day or night styling! It features a sleeveless notch V-neckline, a bodycon silhouette, and a fitted mini-length hem on stretchy rib knit fabric. Complete the look in a layered choker necklace for a backyard dinner party or casual hang!
Fit & Features
- Sleeveless notch V-neckline
- Bodycon silhouette
- Fitted mini-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5176
Category Name: Casual Dresses
Price: $5.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Babe Tropical Print Maxi Dress
Create an iconic vacay babe look with this alluring tropical print maxi dress! It features a sleeveless square neckline, spaghetti straps, a flattering high waist seam, ruching down one side leading to a thigh-high slit, and a long-length hem with a curve-hugging silhouette. The lightweight knit fabric features an all-over tropical palm leaf print. Complete the 'fit with strappy sandals and sleek shades.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- High waist seam, ruched side seam, thigh-high slit
- Long-length hem, curve-hugging fit
- Tropical palm leaf print
- Knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5178
Category Name: Casual Dresses
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Time To Unwind Tropical Slit Midi Dress
Take time to relax and unwind on your next vacation...in this stylish tropical midi dress! It features a sleeveless square neck, spaghetti straps, a bodycon fit, and a front slit accent on slinky knit-lined stretchy fabric. Complete the look in cute platform wedges.
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Bodycon fit
- Front slit accent, midi-length hem
- Tropical palm leaf print
- Slinky knit fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5177
Category Name: Casual Dresses
Price: $5.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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La Quinta Ditsy Floral Rib Knit Mini Dress
Let your love for floral bloom in this rib knit mini dress perfect for a visit to the flower fields! It features a ruffle trim sweetheart neckline and puff short sleeves, a flirty bust lace-up, a bodycon silhouette, and a mini-length hem. Complete the look in cute flat sandals and earrings.
Fit & Features
- Ruffle trim sweetheart neckline
- Ruffle trim puff short sleeves
- Bust lace-up
- Bodycon silhouette
- Mini-length hem
- Ditsy floral print, stretchy rib-knit fabric
- Runs true to size
Style Number/Barcode: 05102-5171
Category Name: Casual Dresses
Price: $5.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dear Summer Eyelet Lace Open Back Dress
Make summer special looking so sweet in this eyelet lace mini dress for your upcoming daytime plans! It features adorable puff short sleeves, a square neckline, and an eye-catching open back with elasticized lattice straps and a bodycon silhouette. Complete the look in trendy platform wedges for brunch!
Fit & Features
- Puff short sleeves
- Square neckline
- Open back, elasticized lattice straps
- Bodycon silhouette
- Mini-length hem
- Eyelet lace fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5174
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free