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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Swept Away Off-The-Shoulder Ruched Mini Dress
Get swept away with this glam mini dress that brings chic details! The dress features an off-the-shoulder neckline with short flutter sleeves, a sweetheart bust with a drawstring, a ruched body, 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. Complete look with wedges.
Fit & Features
- Off-the-shoulder neckline, short flutter sleeves
- Sweetheart bust with a drawstring
- Ruched body
- Mini-length silhouette
- Lined smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1167
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The One Ribbed Knit Midi Dress
This ribbed midi dress is the one you can't live without, bby! The dress features a sleeveless square neckline, supportive tank shoulder straps, a high side slit accented with metal snap buttons, 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 look with mules.
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- High side slit
- Snap buttons
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0955
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Basic Must-Have Midi Sweater Dress
This basic midi sweater dress is a must-have in your wardrobe. It features a sleeveless scoop neckline, tank shoulder straps, a mid-length, curve-hugging silhouette, and a ribbed sweater knit fabric that offers a moderate stretch. Style this dress with chic mules.
Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps
- Mid-length, form-hugging fit
- Ribbed sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0958
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Making Moves Sleeveless Mini Dress
Make stylish moves in this LBD that stuns! The dress features a halter neck with a halter neck strap, a partially open back, and a mini-length silhouette. Complete look with rhinestone heels and a rhinestone bracelet.
Fit & Features
- Halter neckline
- Halter neck strap
- Triangle-shaped bodice
- Partially open back
- Mini length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0962
Category Name: Casual Dresses
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Too Chic Ruffled Eyelet Mini Dress
You'll be looking too chic with a mini dress that brings all those cute deets! The dress features an elastic square neckline, short puff sleeves, a lace-up front, an eyelet design, and a mini-length silhouette with a ruffled hem. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Elastic square neckline, puff short sleeves
- Front lace-up
- Form-fitting, mini-length, ruffle hem
- Eyelet lace fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-1163
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling Sweet And Stylish Eyelet Mini Dress
Channel a sweet look with a floral dress that makes a flirty impression. The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print with eyelets, and a mini-length silhouette. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ditsy floral print
- Eyelets
- Mini length silhouette
- Lightweight woven fabric, relaxed fit, runs true to size
Style Number/Barcode: 05102-1130
Category Name: Casual Dresses
Price: $6.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All My Heart Ruched Mini Dress
Give all your love with this fluttery mini dress! The dress features an off the shoulder neckline with a sweetheart bust, a fab lace-up front, off the shoulder flutter sleeves, and a ruched body. The dress is composed of a double-lined cotton-blend fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Off the shoulder neckline
- Lace-up front
- Off the shoulder flutter sleeves
- Ruched body
- Mini length silhouette
- Double-lined cotton blend fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-1124
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fab And Retro Tie-Dye High Slit Maxi Dress
Keep it fab with a dress that channels a retro feel! The maxi dress features a sleeveless scoop neckline, spaghetti straps, a tie-dye print, a high side slit, and a maxi length silhouette. The dress is composed of a ribbed kit fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti strap
- Tie-dye print
- High side slit
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1122
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Drawn To You One-Shoulder Mini Dress
Everyone will be drawn to you in this chic one-shoulder mini dress! It features stylish ruched detailing, a drawstring at the hem, and a short, curve-hugging silhouette. Pair this dress with clear heels and a sleek clutch for your next night out.
Fit & Features
- Sleeveless one-shoulder neckline
- Ruched detailing
- Drawstring at the hem
- Mini-length, form-hugging fit
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-3784
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet And Chic Ruched Knit Mini Dress
Keep your style sweet and chic in this adorable ruched knit mini dress! It features a sweetheart neckline with a mini keyhole cutout and tie at the bust, short sleeves, ruching down the sides, and a short, curve-hugging silhouette. Complete your look with wedges and a cute handbag.
Fit & Features
- Sweetheart neckline
- Mini keyhole cutout and tie at the bust
- Short sleeves with cinched hems
- Ruching
- Mini-length, form-hugging fit
- Lined stretchy knit fabric
Style Number/Barcode: 05102-1123
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keep It Sleek Asymmetric Maxi Dress
Keep your look sleek and on-trend with this chic sweater maxi dress. It features a one-shoulder neckline with a tank shoulder strap and a curve-hugging maxi silhouette with a dramatic asymmetric hem creating a sultry side slit. Pair this sweater knit dress with clear heels and a new purse.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- One-shoulder neckline
- Tank shoulder strap
- Form-hugging maxi silhouette
- Asymmetric hem creating a side slit
- Sweater knit fabric
- Runs true to size
Style Number/Barcode: 06005-1295
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Boho-Chic Crochet Midi Dress
Bring the boho-chic vibes to your stylish summer look with this stunning midi dress! It features a sleeveless scoop neckline, spaghetti straps, a mid-length, curve-hugging silhouette, and a sheer crochet fabric with a trendy fringe hem. Wear this dress as a cover-up over your fave bikini for the perf poolside outfit.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Mid-length, form-hugging fit
- Sheer crochet fabric, fringe hem
- Runs true to size
Style Number/Barcode: 06005-0949
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Basics Sleeveless Midi Dress
Keep it stylish with a midi dress that can be dressed up! The dress features a sleeveless V-neckline, spaghetti straps, 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 look with clear mules and a metal cuff.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Midi-length silhouette
- Ribbed knit fabric
- Form-hugging fit
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0947
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Twist Ribbed Knit Midi Dress
Give your midi dress a stylish twist with chic details! The dress features a sleeveless crew neckline, a twist knot accent at the back with a lower back keyhole, 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 look with mules.
Fit & Features
- Sleeveless crew neckline
- Twist knot accent at back
- Lower back keyhole
- Midi length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0942
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Set It Off Ruched Mini Dress
Set off your look with a dress that showcases your luxe style! The dress features a sleeveless square neckline, tank straps, a ruched side seam, 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 clear mules.
Fit & Features
- Sleeveless square neckline
- Tank straps
- Ruched side seam
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1120
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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What A Look Ruched Mini Dress
Create a head-turning look with a mini dress that stuns! The dress features a sleeveless square neckline, tank shoulder straps, a ruched body, and a mini-length silhouette. The dress is composed of smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with sunnies and a moto jacket.
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Ruched body
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1121
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Mood Ribbed Knit Maxi Dress
We're in the mood for basics! Slay in this dress that keeps it effortlessly chic. The dress features a trendy turtle neck, long sleeves, and a maxi length silhouette with a high center back slit. The dress is composed of a ribbed knit fabric that offers a form-hugging fit. Complete look with sneakers to nail those low-key vibes.
Fit & Features
- Turtle neck
- Long sleeves
- Maxi length silhouette
- High center back slit
- Ribbed knit fabric
- Plenty of stretch
- Form-hugging fit
Style Number/Barcode: 05102-1117
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Preppy Vibes Collared Mini Dress
Add some stylish preppy vibes to your look in this trendy mini dress! It features a collared neckline with a partial button-down front, short sleeves, and a mini-length, curve-hugging silhouette. The black sweater knit fabric showcases light brown striped detailing at the waist, a light brown collar and button-down front, and light brown hems at the sleeves. Complete your outfit with chunky sneakers and sleek hoop earrings.
Fit & Features
- Collared neckline
- Partial button-down front
- Short sleeves
- Mini-length
- Form-hugging fit
- Sweater knit fabric with plenty of stretch
- Striped detailing at the waist
Style Number/Barcode: 06005-0938
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Back To Basics Ribbed Knit Midi Dress
Bring your look back to basics with a knit midi dress that can be dressed up or dressed down for whatever mood you're in. The dress features a sleeveless V-neckline, tank-like shoulder straps, and a midi length silhouette. Complete look with clear mules.
Fit & Features
- Sleeveless V-neckline
- Tank-like shoulder straps
- Midi length silhouette
- Ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0932
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Taking the Plunge Scoop Neck Midi Dress
Take the plunge in this stylish midi sweater dress! The dress features a sleeveless scoop neckline, tank shoulder straps, and a bodycon silhouette on rib-knit fabric. Complete the look with mules.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless scoop neckline
- Tank-shoulder straps
- Bodycon silhouette
- Midi-length hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1233
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Day Crochet Knit Midi Dress
Keep it casual with a midi dress that will have you channeling your bohemian side. The dress features a sleeveless V-neckline, spaghetti straps, a tie waist belt, and a midi length silhouette, The dress is composed of a crochet knit fabric that offers a relaxed fit with a slight stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Tie-waist belt
- Midi length silhouette
- Crochet knit fabric
- Relaxed fit, slight stretch
- Runs true to size
Style Number/Barcode: 06005-0921
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Level Up Ruched Knit Midi Dress
Level up your basic look with this trendy ruched knit midi dress. It features a sleeveless bodice, bungee spaghetti straps, a square neckline, all-over ruched detailing, and a mid-length, curve-hugging silhouette. The soft brushed knit fabric includes a lining and offers plenty of stretch for comfortable wear. Complete your outfit with a layered necklace and sleek heels.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Strapless bra recommended
- All-over ruched detailing
- Mid-length, form-fitting style
- Lined-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4437
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Ditsy Floral Smocked Mini Dress
Level up the charm with this adorable ditsy floral printed mini dress! It features tie shoulder spaghetti straps, a square neckline with a ruffle trim, a tie-front at the bust, a high waist seam, and a smocked body with a mini-length, curve-hugging silhouette. Complete the look with hoop earrings and strappy sandals.
Fit & Features
- Tie shoulder spaghetti straps
- Square neckline, ruffle trim
- Tie-front at the bust
- High waist seam
- Smocked body
- Short, form-hugging fit
- Woven fabric, ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-1109
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Chic Plaid Mini Dress
Oh-so-chic, this plaid mini dress is a staple you can take into the fall season! It features a trendy square neckline, spaghetti straps, and a short, curve-hugging silhouette. Style this knit dress with clear heels and a faux leather jacket.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Mini-length, form-hugging fit
- Plaid print
- Knit fabric
- Runs true to size
Style Number/Barcode: 05102-1105
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale