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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Square Neck Long Sleeve Midi Dress
The pairing possibilities are endless with this simple and chic piece!
Fits & Features
- Square Neckline
- Long Sleeves
- Midi Length Silhouette
- Smooth Knit Fabric
- Form Hugging Fit I Ample Stretch
- Zipper Not Included
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0379
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simply Stated Sleeveless Midi Dress
Simple and sleek is the statement you want to make! This dress features a sleeveless bodice, a scoop neckline, tank-like straps and a curve hugging midi length silhouette with side slit. Dress is composed of a knit fabric that offers a moderate stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0270
Category Name: Casual Dresses
Price: $9.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Zebra Front Slit Midi Dress
Make a bold first impression in this statement dress! Pair with your fave leather jacket and some heels for a cute OOTN!
Fits & Features
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Adjustable Spaghetti Straps
- V Neckline I Back Zip With Hook & Eye Closure
- Lined At The Bodice
- Midi Length Silhouette I Front Slit
- Woven Fabric I Zebra Print Throughout
- Relax Fit I No Stretch
Style Number/Barcode: 05102-0368
Category Name: Casual Dresses
Price: $12.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Adjustable Spaghetti Straps
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Tie Front Long Sleeve Mini Dress
Accessories and thigh-high boots are the way to go with this essential mini dress!
Fits & Features
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Square Neckline & Back
- Long Sleeves With Elastic Detailing At The Cuffs & Shoulders
- Mini Length Silhouette
- Tie Front Detail Along Skirt
- Brushed Knit Fabric
- Ample Stretch
Style Number/Barcode: 05102-0374
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Square Neckline & Back
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Rattle Me Snake Mini Dress
We're rattled by the FIERCE look you're serving!
Fits & Features
- Spaghetti Straps
- Sweetheart Neckline With Padded Cups
- Mini Length Silhouette
- Soft Knit Fabric With Snake Inspired Print Throughout
- Fully Lined
- Curve-Hugging Fit I Ample Stretch
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0377
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sultry And Fierce Satin Mini Dress
Sultry and oh so fierce, this satin mini is the one for you. It features a sleeveless bodice, bungee spaghetti straps, a square neck and back, and a short, curve huggng fit. The dress is composed of a smooth satin-like fabric with plenty of stretch.Style Number/Barcode: 05102-0376
Category Name: Casual Dresses
Price: $10.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Kiernan Glittering Mesh Party Dress
Get ready for a night that you will never forget, when you start the party in our glittering Kiernan skater dress that is fit for a princess!
Fit & Features
- V-neckline
- Adjustable spaghetti straps
- Square back | Zipper closure
- Fully lined with double layered glitter overlay
- Banded high waist line
- Pleated bodice
- Flowy mini hemline | Lightweight feel | Minimal stretch
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0305
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Smocked Off The Shoulder Mini Dress
Radiate in this sweet smocked piece! This linen dress features an off the shoulder design with ruffle trim, billowy sleeves with elastic cuffs, smocking at the midsection, and a pleated hem. It showcases a mini-length silhouette with a form hugging fit. Does not include zipper and has a moderate stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0375
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flirty In Florals Mini Dress
Charm them all in this flirty mini dress! Throw on an oversized denim jacket and some cute heels and you got yourself a lewk
Fits & Features
- Plunging V Neckline & Back
- Short Sleeves
- Mini Length Silhouette
- Knit Fabric With Floral Print
- Form Hugging
- Plenty Of Stretch
Style Number/Barcode: 05102-0373
Category Name: Casual Dresses
Price: $19.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On A Roll Long Sleeve Mini Dress
Look cozy and chic in the On A Roll mini dress! Pairs well with your fave boots and denim jacket.
Fits & Features- Turtleneck
- Long Sleeves
- Curve-Hugging Fit
- Mini Length, Scalloped Hemline
- Fully Lined
- Zipper Not Included
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0372
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Effortless Beauty Floral Skater Dress
You're all about that effortless beauty look. This floral skater dress has a flowy feel and a beyond gorg print that is totally your vibe.
Fit & Features
- Adjustable spaghetti straps
- Back zipper closure
- High square neck
- High waist seam
- Flowy skater skirt
- Floral print
- Chiffon fabric | Lining
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05101-0382
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Smooth Charmer Velvet Mini Dress
Look...but don't touch. You'll be looking extra vivacious in the Smooth Charmer mini dress!
Fits & Features
- Scoop Neckline
- Square Back
- Fixed Spaghetti Straps
- Mini Length Silhouette
- Form-Hugging Fit I Moderate Stretch
- Smooth Velvet Composition I Metallic Snake-Inspired Print Throughout
Style Number/Barcode: 05102-0370
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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V Neck Front Knot Midi Dress
Toss on some heels and you've got yourself a look! This dress features a V-neckline and decorative center front knot, short sleeves, and a midi-length silhouette with front slit. Composed of a stretchy and smooth textured knit, it offers a form hugging fit and ample stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0369
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hear Meow-Out Leopard Midi Dress
Fiercely command a room with this bold mini dress! They'll be listening to every fashion tip you got

Fits & Features
- Adjustable Spaghetti Straps Cross At Back
- Cowl Neckline I Back Zip
- Midi Length Silhouette I Side Slit
- Woven Fabric I Leopard-Inspired Print
- Relax Fit I Minimal Stretch
Style Number/Barcode: 05102-0371
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Hiss Me With That Mini Dress
Sssslither into this sassy number! It features a snake-inspired print, fixed shoulder straps, sweetheart neckline, and mini-length silhouette. Crafted from soft velvet and paired with a soft knit lining, this form-fitting piece extenuates all the right curves. Zipper not included.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0364
Category Name: Casual Dresses
Price: $11.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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A Casual Slay Long Sleeve Mini Dress
Oh you know, just a casual slay. This dress has all the features that we are obsessed with! A deep v neckline, an empire waist, matching buttons down the center, and long sleeves that are balloon style which adds a bohemian flare. Dress is composed of a linen material offers no stretch, and showcases a striking snake skin pattern. Lined at the skirt.
Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05103-0473
Category Name: Casual Dresses
Price: $20.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Poised In Plaid Sleeveless Mini Dress
Keep it poised with trendy plaid! The mini dress features a sleeveless bodice, a square neckline, tank-like straps and a mini length silhouette that hugs curves all over. The all over plaid season is perfect to stay on trend this season! Dress is composed of a knit fabric.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0363
Category Name: Casual Dresses
Price: $11.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stylish In Spots Tunic
Spotted! A stylish tunic perfect for transitioning to the fall season. It features a sleeveless bodice, spaghetti straps that tie at the neck and lead to a square back, a wrap front creating a V neckline, a hidden side zipper and hook and eye closure, a trendy twist front detail, and a short hem. The tunic is composed of a lightweight woven fabric with no stretch and includes a woven lining.Style Number/Barcode: 06003-0397
Category Name: Casual Dresses
Price: $4.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ribbed Knit Cut Out Midi Dress
Ward off the chill with this cozy for keeps midi-length dress.
Fits & Features
- Plunging V Neckline
- Long Sleeves
- Large Cut-Out Detail At Back
- Soft Knit Fabric I Fully Lined
- Ample Stretch
- Zipper Not Included
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0361
Category Name: Casual Dresses
Price: $13.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Dreaming Satin Midi Dress
We're dreaming of romance in this floral beauty! This midi dress perfectly pairs with stilettos and clutch for the perfect date night look!
Fit & Features
- V-Neckline
- Adjustable Spaghetti Straps | Cross-Back
- Floral Print
- Lined Satin Fabric
- Midi Length Silhouette
- Front Slit
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 05101-0367
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Satin Leopard Print Mini Dress
On the hunt for the perfect mini? Look no further than this sassy satin number. Featuring adjustable spaghetti straps and a square neckline, it also showcases a tonal leopard print and a daring slit at front. Fully lined, it offers minimal stretch and a zipper at the back.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0359
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stylishly Destructed Tunic
This tunic is destructed with all the style! It features a crew neckline, long fitted sleeves, a short hem, and distressed slit detailing on the top and toward the hem. Tunic is composed of a cotten blend fabric that offers moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06002-0276
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Viper Vixen Knot Mini Dress
Vamp it out girl with statement snake print in this trendy mini dress! It features a deep V neckline with a knot front detail, long fitted sleeves, and a curve-hugging, mini length silhouette with a wrap skirt detail. Pair this dress with strappy heels and a faux leather jacket.
Fit & Features
- Plunging V neckline
- Knot bodice
- Long fitted sleeves
- Snake print
- Mini length silhouette
- Form-hugging fit
- Smooth knit fabric with moderate stretch
Style Number/Barcode: 05102-0357
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Plus Crochet In Color Dress
This cute crochet dress is perfect for a day out! It features a V neckline, adjustable spaghetti straps that create an X back, a sheer crochet waist, and a short flared skirt with a full lining.
Style Number/Barcode: 15102-0018
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance