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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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
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Casually Chic Smooth Knit Fitted Maxi Dress
This smooth knit fitted maxi dress is the casually chic style you need to elevate your 'fits. It features a strapless straight-across neckline, an all-over curve-hugging silhouette, a maxi-length hem, and a trendy back slit accent. The smooth knit fabric includes an airy sheer mesh lining and offers plenty of stretch for comfortable wear. Complete your looks with strappy mules and a mini handbag.
Fit & Features
- Strapless straight-across neckline
- Curve-hugging silhouette
- Maxi-length hem
- Back slit
- Smooth knit fabric, sheer mesh lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5175
Category Name: Casual Dresses
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Party Energy Cutout Bodycon Mini Dress
You'll bring the party energy in this sexy cutout bodycon mini dress! It features a sleeveless one-shoulder neckline, a sultry asymmetric bust cutout creating two front tank straps, a mini-length hem, and a curve-hugging silhouette that will flaunt your gorgeous figure. The smooth nylon fabric offers plenty of stretch. Style with clear heels.
Fit & Features
- Sleeveless one-shoulder neckline
- Asymmetric bust cutout
- Two front tank shoulder straps
- Mini-length hem
- Curve-hugging fit
- Nylon fabric, sewn-in lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5169
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Noteworthy Flirt Ruffled Lace-Up Mini Dress
Everyone will take note of your flirtiness in this mesh mini dress perfect for daytime parties! It features a sleeveless square neck, spaghetti straps that lace up along the open back, a bodycon silhouette, and all-over ruffled trim detail. Complete the look with statement earrings.
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Lace-up, open back
- Bodycon silhouette
- Mini-length hem
- All-over ruffled trim, mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5168
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Call You Sweetheart Ruffle A-Line Dress
Everyone will be calling you sweet in this short A-line dress as the bride-to-be or graduate! It features a sleeveless sweetheart neck, tank shoulder straps, a ruched bust seam, a flattering A-line silhouette, asymmetrical front ruffle trim, and a short-length hem. Complete the look with earrings and block heels.
Fit & Features
- Sleeveless sweetheart neck
- Tank shoulder straps
- Ruched bust seam
- A-line silhouette, asymmetrical ruffle trim
- Short-length hem
- Slinky knit stretchy fabric
- Runs true to size
Style Number/Barcode: 05101-2480
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Preppy Girl Plaid V-Neck Mini Dress
This plaid mini dress is for all the preppy girls! It features a sleeveless V-neckline, spaghetti straps, a bodycon fit, and a flirty front slit accent on stretchy knit fabric. Style with a cropped blazer and booties to complete the look!
Fit & Features
- Sleeveless V-neckline, spaghetti straps
- Bodycon fit
- Front slit accent
- Mini-length hem
- Plaid print
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5161
Category Name: Casual Dresses
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Match Plaid Lace-Up Mini Dress
Find your perfect match in this casual-chic plaid mini dress! Featuring a sleeveless square neckline, spaghetti straps, an open back with a cross-back lace-up strappy design, a mini-length hem, a form-hugging fit, and a classic plaid windowpane print, this dress is a stylish must-have. Pair with hoop earrings and clear mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open back, cross-back lace-up straps, tie closure
- Mini-length hem, form-hugging fit
- Plaid windowpane print
- Lined soft knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5159
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Looking Sensational Smooth Knit Maxi Dress
Rise to the occasion looking sensational in this basic smooth knit maxi dress perfect for dressing up or down! It features a sleeveless scoop neck, sleek spaghetti straps, a bodycon silhouette, and a flirty back-slit accent composed of double-lined smooth knit fabric. Complete the look in lucite mules for a bridal shower or casual party!
Fit & Features
- Sleeveless scoop neck, spaghetti straps
- Bodycon silhouette
- Back slit accent
- Maxi-length hem
- Double-lined smooth knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5158
Category Name: Casual Dresses
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Impressions Ruched Mini Dress
Make a bold impression out and about in this mesh mini dress perfect for parties or sexy brides! It features a sleeveless square neck, bungee spaghetti straps, side ruched seams that accentuate your curves, and a bodycon fit. Complete the look with heart-shaped earrings.
Fit & Features
- Sleeveless square neck
- Bungee spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Mesh fabric, nude stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5160
Category Name: Casual Dresses
Price: $5.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Double Take Strappy Back Mini Dress
This casual mini-dress will make everyone do a double-take! It features a sleeveless scoop neckline, spaghetti straps, an open back with a caged strap design, a bodycon silhouette, and a mini-length hem. The dress is composed of a stretchy rib knit fabric with a sewn-in knit lining. Complete the look in hoop earrings for a backyard bbq.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Open back, caged strap design
- Bodycon silhouette
- Mini-length hem
- Rib-knit fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5156
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale