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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Ditsy Floral Doll Ruffle Mini Dress
OMG adorbs
Add a denim jacket and some white sneakers for a cute af 'fit! Fits & Features
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Ruffle Shoulder Straps
- Square Neckline & Back
- Mini Length Silhouette
- Smooth Knit Fabric I Ditsy Floral Print
- Curve Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0389
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruffle Shoulder Straps
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Adore Me Floral Mini Dress
Walk right into any room and everyone will be falling head over heels for this floral look!
Fits & Features
- Spaghetti Straps
- V Neckline
- Mini Length Silhouette
- Woven Fabric I Floral Print Throughout
- Curve Hugging Fit I Ample Stretch
- Zipper Not Featured
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0399
Category Name: Casual Dresses
Price: $9.97 $23.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spotted With Sass Cowl Neck Mini Dress
We are lovin' a cowl neck mini dress, no matter what the season! Pair with a leather jacket and boots on a chilly night, or simply pair with ur fave mules!
Fit & Features
- Cowl neckline | Spaghetti straps
- Form fitting silhouette
- Side slits | Mini hemline
- Spotted leopard print pattern
- Minimal stretch | Knit woven material
Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.Style Number/Barcode: 05102-0388
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mesmerizing In Mesh Lace Dress
Show off a little skin in this sexy dress! The sleek inner bodysuit provides perf coverage against the mesh skirt!
Fits & Features
- Adjustable Spaghetti Straps
- Unlined, Lace & Mesh Bodice I Underwire Bust
- Elastic Waistband
- Maxi Length Silhouette I Mesh Skirt
- Built-In Bodysuit With Dual Snap Button Closure I Cheeky Coverage
- Moderate Stretch
Style Number/Barcode: 05101-0397
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Satin Mini Dress
Keep it sleek in stunning satin to show off those curves girl!
Fit & Features
- Square Neckline
- Tank Straps
- Satin
- Rounded Hem
- Double Lined
- Form Hugging Fit | Moderate Stretch
- No Zipper
Burgundy: Model is 5'8" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Hunter: Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0386
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Snake It Away Metallic Mini Dress
Take on the night with this sassy mini dress!
Fits & Features
- Bungee Cord Spaghetti Straps
- Square Neckline & Back
- Metallic Knit With A Snake-Inspired Print
- Mini Length Silhouette
- Curve Hugging Fit
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0385
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Too Fab Knit Mini Dress
You'll be simply too fab in this hot little mini! The dress features a sleeveless bodice, bungee spaghetti straps, a square neck and back, and a short, curve-hugging fit. The double-lined knit fabric offers plenty of stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0548
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ribbed Long Sleeve Knit Dress
Fall back this season with a classic knit dress to pair with your fav layers!
Fit & Features
- Mockneck
- Fitted Long Sleeves
- Ribbed
- Lined Knit
- Bust Geometric Cut Out
- Form Fit
- Moderate Stretch
Style Number/Barcode: 05102-0384
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Satin Snake Print Mini Dress
Sleek with a chic snake print, this satin mini is a trendy find. The dress features a sleeveless bodice, bungee spaghetti straps, a square neck and back, and a short, curve hugging fit. The satin-like fabric has moderate stretch.Style Number/Barcode: 05102-0383
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Vivid Viper Mini Dress
Be prepared to pave the way to the dance floor in this seductive snake dress!
Fits & Features
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High Neckline
- Fitted Long Sleeves
- Deep V At The Back
- Ruching Along The Sides & Center Back
- Mid Thigh Length Silhouette
- Stretchy Knit I Snake Print Throughout
- Curve Hugging Fit I Ample Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0382
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Neckline
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Clad In Plaid Scoop Neck Mini Dress
Look pretty in plaid! Give your flannels a break and rock this cozy plaid mini dress.
Fits & Features
- Scoop Neckline
- Cap Sleeves
- Dart Detail At The Bust
- Plaid Print
- Mini Length Silhouette
- Form Hugging Fit
- Moderate Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0378
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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