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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Floral Romance Ruched Mini Dress
Start a floral romance with this pretty mini dress! The dress features an off-the-shoulder neckline, ruching at the bust, short sleeves, a cutout at the midriff, a ditsy floral print, 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 and earrings.
Fit & Features
- Off the shoulder neckline
- Ruching at bust
- Short sleeves
- Cutout at the midriff
- Ditsy floral print
- Smooth knit fabric, form-hugging fit, runs true to size
- Mini length silhouette
Style Number/Barcode: 05102-1103
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Heart Of Glam Ruched Midi Dress
Bring the romantic vibes in this casually-chic midi dress! It features a sleeveless bodice with a square neckline, bungee spaghetti straps, a square back, ruched detailing, and a mid-length, curve-hugging silhouette. Pair this dress with strappy heels and a sleek clutch to complete your look.
Fit & Features
- Bungee spaghetti straps
- Square neckline
- Square back
- Ruched detailing
- Mid-length, form-hugging fit
- Lined knit fabric with plenty of stretch
SHOP ALL HEART OF GLAM COLLECTION
Style Number/Barcode: 05102-1104
Category Name: Casual Dresses
Price: $14.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Look In Plaid Knit Mini Dress
Get a perfect look in this adorable plaid knit mini dress! It features a sleeveless bodice with spaghetti straps, a scoop neckline, and a short, curve-hugging fit. Pair this cute and casual dress with chunky sneakers and layer on a denim jacket.
Fit & Features
- Spaghetti straps
- Scoop neckline
- Short, form-hugging fit
- Plaid print
- Lightweight unlined knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-1066
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sassy Chic Snake Print Ruched Mini Dress
Keep it sassy with a snake print mini dress! The dress features a sleeveless square neckline, spaghetti straps, snake print, dual ruched drawstrings, 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 and hoops.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Snake print
- Dual ruched drawstrings
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1093
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Staple Open Back Ruched Mini Dress
Make this mini dress a casual staple to rotate into your wardrobe. The dress features a crew neckline, short sleeves, a lower back keyhole, a ruched body, and a mini-length silhouette. Complete look with sneakers and hoops.
Fit & Features
- Crew neckline
- Short sleeves
- Lower back keyhole
- Ruched body
- Mini length silhouette
- Cotton knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-1097
Category Name: Casual Dresses
Price: $18.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Retro Vibes Tie Dye Mini Dress
Channel retro vibes with a mini dress that keeps it super cute! The dress features a sleeveless crew neckline, a tie-dye print, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a relaxed fit with a moderate stretch. Complete look with clear mules to let this print take center stage!
Fit & Features
- Sleeveless
- Crew neckline
- Tie-dye print
- Mini length silhouette
- Brushed knit fabric
- Relaxed fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1096
Category Name: Casual Dresses
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Alluring And Chic Brushed Knit Mini Dress
Create an alluring and chic everyday look with this must-have mini dress! It features a sleeveless bodice, a scoop neck and back, tie shoulder straps, and a mini-length, curve-hugging silhouette. Complete your outfit with heeled mules and a trendy shoulder bag.
Fit & Features
- Scoop neck and back
- Tie shoulder straps
- Short, form-hugging fit
- Brushed knit fabric
- Runs true to size
Style Number/Barcode: 05102-1088
Category Name: Casual Dresses
Price: $12.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Getaway Linen Skater Dress
Planning a weekend getaway? Don't forget to pack this adorable linen dress for an effortlessly chic look. The dress features a sleeveless V-neckline, halter spaghetti straps, a tie-back detail, a high waist, and a flirty and flowy skater silhouette. Style this dress with hoop earrings and strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Halter spaghetti straps
- Tie-back detail
- High waist
- Flowy skater skirt
- Linen fabric
- Runs true to size
Style Number/Barcode: 05102-1085
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Forever Chic Satin Midi Dress
Sleek and chic, this satin midi dress will be your new go-to! It features a sleeveless cowl neckline, dual spaghetti straps that lead to a cross-back design, and a mid-length fitted silhouette with a subtle flared hem. Style this dress with clear heels and a trendy shoulder bag.
Fit & Features
- Sleeveless cowl neckline
- Dual spaghetti straps
- Cross-back design
- Mid-length fitted silhouette
- Satin fabric
- Runs true to size
Style Number/Barcode: 05101-0942
Category Name: Casual Dresses
Price: $20.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cutout Cutie Gauze Skater Dress
Keep it cute with a skater dress that brings the style! The dress features a sleeveless V-neckline, waist cutouts with bar straps, a striped pattern, and a skater silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Waist cutouts
- Bar straps
- Striped pattern
- Skater silhouette
- Gauze knit
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-1084
Category Name: Casual Dresses
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Glam Tie Dye Ruched Mini Dress
Keep it so glam with a tie-dye dress that gives your look a retro feel! The dress features a sleeveless square neckline, bungee spaghetti straps, a tie-dye print, a ruched side seam, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look in new top-rated shoes.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Tie-dye print
- Ruched side seam
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-1083
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Drawn To Tie Dye Ruched Mini Dress
Get drawn to this cute dress that gives off those totally retro feels. The dress features a sleeveless crew neckline with a racer front, a tie-dye print, and ruched drawstrings that allow you to customize the length of the dress. The dress is composed of a mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with sleek hoops and mules.
Fit & Features
- Sleeveless crew neckline
- Racer bust
- Tie-dye print
- Ruched drawstrings
- Mini/midi length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1080
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fabulously Retro Ruched Tie Dye Dress
Keep it fab and retro with a mini dress that is perf for your next night out! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, dual ruched drawstrings, 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 and butterfly earrings.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross straps
- Dual ruched drawstrings
- Mini-length silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1079
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Flirt Ditsy Floral Mini Dress
Capture hearts in this flirty ditsy floral printed mini dress that is perfect for spring! It features short puff sleeves, a sweetheart neckline with a tie-front detail, and a mini-length, curve-hugging silhouette. The dress is composed of a lightweight, stretchy knit fabric with no lining. Style this floral dress with cute wedges for brunch with the girls.
Fit & Features
- Short puff sleeves
- Sweetheart neckline
- Tie-front at the bust
- Short, form-hugging fit
- Ditsy floral print
- Stretchy unlined knit fabric
- Runs true to size
Style Number/Barcode: 05102-1078
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Stylish Snake Print Ruched Mini Dress
Keep it so stylish in a snake print mini dress that slays your night out outfits. The mini dress features a sleeveless crew neckline, a trendy snake print, ruched side seams, and a mini length silhouette. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Crew neckline
- Sleeveless
- Snake print
- Ruched side seams
- Brushed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-1077
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Rose Darling Floral and Lace Mini Dress
Let this flirty dress showcase your sweet and sultry side for date night! The dress features a sleeveless sweetheart neckline with lace trim, sleek spaghetti straps, a disty floral print, and a stunning matching lace trim at the hem. Complete your night out look with a moto jacket and mules.
Fit & Features
- Sleeveless sweetheart neckline with lace trim
- Sleek spaghetti straps
- Ditsy floral print
- Mini length silhouette
- Lace hem
- Smooth knit fabric with a knit lining
- Form-hugging fit, moderate stretch
Style Number/Barcode: 05101-0940
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Ribbed Knit Long Sleeve Mini Dress
Make a sleek statement with this long-sleeve mini dress, the epitome of chic simplicity. This figure-hugging silhouette, crafted from a soft ribbed knit fabric, offers both warmth and style. Featuring a high turtleneck for a touch of polished sophistication, this mini dress is perfect for transitioning from day to evening. Layer this ribbed knit mini-dress with an oversized faux leather blazer or stylish trench coat and knee-high boots for the perfected layered outfit.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Mini-length hem
- Curve-hugging fit
- Ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-0703
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Ruched Snake Print Mini Dress
You'll look so sultry and stylish in this trendy snake print mini dress. It features a V neckline, long fitted sleeves, front ruched detailing, and a short, curve-hugging fit. Pair this dress with sleek gold hoop earrings and a chic clutch for a night out.
Fit & Features
- V neckline
- Long fitted sleeves
- Front ruched detailing
- Mini length
- Form-hugging fit
- Snake print
- Knit fabric with plenty of stretch
Style Number/Barcode: 05102-1073
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Casual-Chic Moment Maxi Dress
Have a major casual-chic moment in this must-have maxi dress! It features short sleeves, a V neckline, and a flowy silhouette with a rounded hem and side slits. Tie the front hem in a knot to add a trendy detail. Pair this maxi dress with adorable new sandals for a laidback look.
Fit & Features
- Short sleeves
- V neckline
- Flowy silhouette
- Rounded hem and side slits
- Knit fabric with plenty of stretch
Style Number/Barcode: 05102-1072
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ready to Slay Ruched Mini Dress
Babe, you'll be ready to slay in this sleek mini dress! Perfect for date night or a GNI, style this chic must-have with lucite heels and a sleek satin clutch. The dress features a sleeveless crew neckline, a ruched drawstring at the side seam, and a mini-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch.
Fit & Features
- Crew neckline
- Sleeveless
- Ruched drawstring
- Mini-length silhouette
- Smooth knit fabric
- Form-hugging fit
- Moderate stretch
Style Number/Barcode: 05103-3744
Category Name: Casual Dresses
Price: $6.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Good Vibes Word Screen Ruched Dress
Showcase those good vibes in this trendy ruched dress! It features tank-like shoulder straps, a round neckline, side ties, and can be worn as a mini or midi dress. The knit fabric has an all-over word screen print for a cool look. Pair this dress with chunky sneakers to keep it casual or strappy heels for an elevated 'fit.
Fit & Features
- Tank-like shoulder straps
- Round neckline
- Ruched detailing
- Side ties at the hem
- Word screen print
- Knit fabric with plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-1071
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Vibes Tie Dye Mini Dress
Get major trendy vibes in this must-have tie dye mini dress. It features long fitted sleeves, a short, curve-hugging silhouette, and has flattering ruched detailing with side ties at the hem. The dress is composed of a lightweight knit fabric with plenty of stretch. Complete your look with chunky sneakers and gold hoop earrings.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Short, form-hugging fit
- Ruched detailing
- Side ties at hem
- Stretchy knit fabric
- Tie dye print
Style Number/Barcode: 05102-1070
Category Name: Casual Dresses
Price: $14.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry Style Snake Print Mini Dress
You'll definitely have that sultry style in this trendy snake print mini dress! It features spaghetti straps, a scoop neckline, and a short, curve-hugging silhouette. Pair this dress with a faux leather jacket for a girl's night out.
Fit & Features
- Spaghetti straps
- Scoop neckline
- Short, form-hugging fit
- All-over snake print
- Knit fabric with moderate stretch
Style Number/Barcode: 05102-1069
Category Name: Casual Dresses
Price: $19.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Play On Sleeveless Plaid Mini Dress
Keep it playful and poised in a dress that is totally on-trend, babe! The dress features a sleeveless scoop neckline, a plaid print, and a mini length silhouette. The dress is composed of a brushed knit fabric. Complete look with ankle booties.
Fit & Features
- Sleeveless scoop neckline
- Tank-straps
- Plaid print
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-1067
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free