Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, or keep it flowy with midi and maxi silhouettes. Mesh details add a little edge, while sleeveless minis and long-sleeve staples cover every season. Whether you’re layering up for a chill weekend or slipping into something light for a last-minute dinner date, these casual dresses are made to move with your mood—and 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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Trendy Girl Turtleneck Mini Dress
Hey trendy girl! Style up this adorable turtleneck mini dress for a cozy-chic look! It features long fitted sleeves, a short, curve-hugging silhouette, and viscose crepe fabric with plenty of stretch for comfortable wear. Pair this dress with chunky sneakers for an effortless everyday 'fit.
Fit & Features
- Turtleneck
- Long fitted sleeves
- Short, form-hugging fit
- Viscose crepe fabric with a lining
- Plenty of stretch
Style Number/Barcode: 05102-0956
Category Name: Casual Dresses
Price: $6.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Essential Ribbed Knit High Slit Midi Dress
Accessorize a ribbed knit midi dress for the perfect fall outfit. The dress features a plunging V-neckline, long fitted sleeves, and a bold high slit. Complete your outfit with thigh-high boots.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- V-neckline
- Long fitted sleeves
- High side slit
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-2079
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tie Dye Ruched Knit Mini Dress
Give your basic mini dress a trendy upgrade with this cute tie dye mini dress! It features short sleeves, a mini length silhouette, and drawstrings at each side with ruched detailing. Pair this dress with chunky sneakers for casual-cute vibe.
Fit & Features
- Crew neckline
- Short sleeves
- Mini length silhouette
- Drawstrings at each side
- Ruched detailing
- Tie dye print
- Knit fabric with plenty of stretch
Style Number/Barcode: 05102-1062
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Comfy-Chic Ribbed Knit Midi Dress
Look so comfy-chic in this adorable ribbed knit midi dress! It features a deep V neckline, adjustable spaghetti straps, and a mid-calf length curve-hugging fit. Pair this dress under a sleek faux leather moto jacket and accessorize with a layered necklace for a date night out.
Fit & Features
- V neckline
- Adjustable spaghetti straps
- Mid-length, form-hugging fit
- Ribbed knit fabric
Style Number/Barcode: 05102-1041
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stunning And Sultry Sweetheart Mini Dress
Create a stunning and sultry look in this gorgeous sweetheart mini dress! It features a sleeveless bodice with spaghetti straps, a mini length silhouette and a curve-hugging fit. Pair this dress with a faux leather jacket for a girl's night out.
Fit & Features
- Spaghetti straps
- Sweetheart neckline with seam detailing at the bust
- V back
- Short, form-hugging fit
- Ribbed knit fabric with plenty of stretch
Style Number/Barcode: 05102-1039
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sassy Snake Print Ruched Mini Dress
Keep it sassy in a snake print mini dress that hypnotizes them all. The dress features a sleeveless square neckline, a trendy snake print, ruched side seams, and a mini length silhouette. Pair your dress with chic hoops and a cute wristlet.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Snake print
- Ruched side seams
- Smooth knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0945
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Sleek Sleeveless Ruched Mini Dress
Create a sleek impression in this mini dress to stun on your next night out! The dress features a sleeveless square neckline, tank-like straps, ruched side seams, and a mini length silhouette. Complete look with a chunky statement necklace.
Fit & Features
- Sleeveless square neckline
- Tank straps
- Ruched side seams
- Smooth knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-1045
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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One Cute Day Floral Skater Mini Dress
If you're in the mood to look undeniably cute, this floral skater mini dress is just the ticket! Perfect for bridal showers, brunch, or a day date.
Fit & Features
- Floral print, eyelet woven fabric lined with stretchy knit
- Sweetheart neckline, built-in padded underwire bust
- Adjustable spaghetti straps
- Back stretchy smocked panel, zipper and hook-eye closure
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3994
Category Name: Casual Dresses
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keep It Stylish Ruched Mini Dress
Keep your 'fit stylish and on point in this curve-hugging ruched mini dress! It features long fitted sleeves, a short, form-hugging silhouette and front ruched detailing to create a flattering look. Pair this dress with heeled booties for the perf fall date night.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Short, form-hugging fit
- Front ruched detailing
- Drawstring at front hem
- Cotton fabric
Style Number/Barcode: 05102-1032
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Off The Shoulder Brushed Knit Mini Dress
Elevate your everyday style with this adorable brushed knit mini dress! It features an off the shoulder fold-over neckline with long fitted sleeves and a short, curve-hugging silhouette. Pair this dress with heeled booties for the perf winter date night with bae.
Fit & Features
- Off the shoulder fold-over neckline
- Long fitted sleeves
- Short, form-hugging fit
- Stretchy ribbed brushed knit fabric
- Stretchy knit lining
- Merrow edge hems
Style Number/Barcode: 05102-0917
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Chic Vibe Mini Sweater Dress
Get a major chic vibe in this adorable sweater mini dress! It features a trendy mock neckline, long fitted sleeves, and a short form-hugging fit with a side slit. Pair this dress with over the knee boots for the perf fall date night look.
Fit & Features
- Mock neckline
- Long fitted sleeves with ribbed hems
- Short, form-hugging fit
- Side slit
- Sweater knit fabric
- Moderate stretch
Style Number/Barcode: 06005-0734
Category Name: Casual Dresses
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stunning Snake Print Mesh Mini Dress
Stun in a trendy snake print dress that makes a stylish statement! Throw this dress on with your favorite black heels for your next GNO. The dress features a sleeveless square neckline, sleek bungee straps, and a snake print. The dress is composed of mesh fabric that offers a form hugging fit with a moderate stretch.
Fit & Features
- Sleeveless square neckline
- Bungee straps
- Snake print
- Mini length silhouette
- Mesh fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0936
Category Name: Casual Dresses
Price: $6.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Total Sweetheart Ribbed Mini Dress
Show off your sweet side in a dress that brings the charm. The dress features a plunging sweetheart neckline, long sleeves, 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 faux fur jacket.
Fit & Features
- Sweetheart neckline
- Long sleeves
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 06005-0707
Category Name: Casual Dresses
Price: $19.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Vibes Only Ribbed Knit Mini Dress
Rock a basic ribbed mini dress for your everyday looks! The dress features a sleeveless square neckline, bungee straps, and composed of a ribbed knit fabric. Complete look with chunky sneakers for that casual vibe.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 06002-0638
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feeling Knit Crew Neck Midi Dress
Fall for a knit dress to usher in those cozy vibes this season! The dress features a crew neckline, short sleeves, and is composed of a textured knit fabric with a moderate stretch. The dress offers a form-hugging fit. Complete the look with ankle booties.
Fit & Features
- Crew neckline
- Short sleeves
- Midi-length silhouette
- Textured knit fabric with knit lining
- Moderate stretch
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-0941
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Look Plaid Knit Mini Dress
Get the perfect look for date night in this adorable plaid knit mini dress! It features a square neckline and a mini length, curve-hugging silhouette. Pair this chic dress with heeled booties and sleek hoop earrings.
Fit & Features
- Spaghetti straps
- Square neck and back
- Short, form-hugging fit
- Allover plaid print
- Knit fabric
Style Number/Barcode: 05102-0801
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fall Back To Basics Ribbed Knit Ruched Mini Dress
Fall back on this basic dress to stun this season! The dress features V-neckline, long sleeves, and ruched side seams to adjust for a customized. Style your dress with ankle booties.
Fit & Features
- V-neckline
- Long sleeves
- Ruched side seams
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 05102-1019
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Setting The Trend Long Sleeve Cutout Mini Dress
This long sleeve mini dress sets the trend! It features a stylish crew neckline adorned with cutout and lattice accents that capture all the attention and a bodycon silhouette. Complete the look with chic boots.
Fit & Features
- Soft, stretchy rib knit fabric
- Fitted long sleeves
- Crew neckline
- Cutouts with lattice accents
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06005-2067
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Twist Front Ribbed Knit Mini Dress
Create a fab moment in a twist knot dress! The dress features a V-neckline with a twist knot accent, long sleeves, and a mini length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit. Complete your look with clear mules.
Fit & Features
- V-neckline with twist front accent
- Long sleeves
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 06005-0700
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Purrfect Match Leopard Print Tunic
This stylish leopard print tunic will be the purrfect match for you! It features a twist front detail with a tie back, long puff sleeves, and a short hem to elongate your legs. Pair this trendy tunic with some clear heels for an of the moment look.
Fit & Features
- Long puff sleeves
- V neckline
- Twist front detail
- Tie back
- Short hem
- Allover leopard print
- Woven fabric
Style Number/Barcode: 06003-1075
Category Name: Casual Dresses
Price: $16.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keepin' Knit Simple Ribbed Midi Dress
Keep it simple and stylish in this basic ribbed knit midi dress! It features long fitted sleeves and a mid-length, form-hugging silhouette to enhance your curves. Pair this dress with heeled booties for a casual date night look perf for the cooler months.
Fit & Features
- Long fitted sleeves
- V neckline
- Mid-length, form-fitting style
- Ribbed knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0890
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Off The Shoulder Ribbed Knit Cutout Mini Dress
Stun in a mini dress that brings sultry appeal with cutout details! The mini dress features an off the shoulder neckline, cutout detail at the bust with matching cutout detail at the midriff, and a mini length silhouette. Complete look with clear mules.
Fit & Features
- Off the shoulder neckline
- Cutout detail at the bust
- Cutout detail at the midriff
- Long sleeves
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0864
Category Name: Casual Dresses
Price: $19.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ribbed Knit O-Ring Mini Dress
Keep it chic in a ribbed knit dress that has a stylish twist! The mini dress features a trendy crew neckline, an O-ring accent with waist cutouts, and composed of a ribbed knit fabric that embraces curves. Complete look with clear mules for a head-turning look.
Fit & Features
- Crew neckline
- O-ring accent with waist cutouts
- Fitted long sleeves
- Mini length silhouette
- Ribbed knit fabric
- Form-hugging fit
Style Number/Barcode: 05102-0998
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Twist Knot Open Back Ribbed Mini Dress
Stun in a dress that makes them take a double-take with bold details! The dress features a crew neckline, fitted long sleeves, and a stunning open back with a twist knot bar strap accent. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules.
Fit & Features
- Crew neckline
- Fitted long sleeves
- Open back
- Twist knot bar strap
- Ribbed knit fabric
- Mini length silhouette
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0991
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance