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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Feline Good Leopard Print Mesh Mini Dress
Whether you are out on a date night, or out with the gals you'll be feelin' good in this feline inspired leopard print mesh mini dress! Dress up with heels and hoops, or dress down with booties and a leather jacket!
Fit & Features
- Spaghetti straps
- Square neck and back
- Ruched side detailing
- Short, curve hugging fit
- Sheer mesh leopard printed fabric
- Knit lining | Plenty of stretch
- Leopard print pattern
Style Number/Barcode: 05102-0402
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Smooth Like Satin Mini Dress
It's the perfect combo of sleek & sweet. Combat the chilly temps by throwing on a knit turtleneck underneath or a chunky sweater over.
Fits & Features
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Elastic Cord Straps
- Elastic Square Neckline With Vertical Darts At The Bust
- Mini Length Silhouette
- Fully Lined, Satin Fabric
- Curve Hugging Fit I Minimal Stretch
- Zipper Not Included
Style Number/Barcode: 05102-0405
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Elastic Cord Straps
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She's A Plaid Girl Mini Dress
It's true. Plaid girls have more fun.
Fits & Features
- Square Neckline
- Bungee Spaghetti Straps
- Mini Length Silhouette
- Textured Knit Composition I Velvet Plaid Print Throughout
- Curve Hugging Fit I Moderate Stretch
- Zipper Not Included
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0400
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beautifully Buttoned Ribbed Sweater Dress
Button up in this casually chic sweater dress to impress this season! It features a wrap V-neckline, long sleeves, a multi-button down accent on the left seam and a mini length silhouette. Dress is composed of an unlined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Zipper not included.Style Number/Barcode: 06005-0322
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Long Sleeve Ribbed Mini Dress
Keep it cozy with this pretty knit dress! It features a plunging V neckline, long puff sleeves and a mini length silhouette. Dress is composed of a ribbed knit fabric that offers a form hugging fit.
Burgundy: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Hunter: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0365
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cool Cat Leopard Off Shoulder Mini Dress
Leopard prints FTW. You'll be having a moment everywhere you go in the Cool Cat off shoulder mini dress!
Fits & Features
- Smocked Off Shoulder Neckline
- Roomy Cuffed Long Sleeves
- Elastic, Smocked Skirt
- Subtly Pleated, Mini-Length Hemline
- Form-Hugging Fit WIth Plenty Of Stretch
Style Number/Barcode: 05102-0397
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Leopard Print Wrap Front Midi Dress
You're quite the fierce fashionista, so this leopard print midi suits you! The dress features a sleeveless bodice, adjustable spaghetti straps, a wrap front V neckline, a V back with a hidden zipper closure, a high waist seam with a wrap front skirt with a faux tie detail, and a mid-length, flowy fit. Dress is comosed of a sheer textured woven fabric with a short woven lining.
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0396
Category Name: Casual Dresses
Price: $19.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Long Sleeve Knit Midi Dress
Keep it basic this season! The midi dress features a V neckline, fitted long sleeves vertical stripes and a midi length silhouette that rests slightly above the knee. Dress is composed of a lined knit fabric with a form hugging fit with a slight stretch. Zipper not included.
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0395
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Charming Ruffles Floral Mini Dress
Charm them all in ruffles and florals!
Fits & Features
- Sweetheart Neckline With Tie Front Accent I Square Back
- Adjustable, Ruffle Trim Spaghetti Straps
- Multi-Tiered, Ruffle Mini-Length Silhouette
- Lined Chiffon Fabric With Dainty Floral Print Against Solid Background
- Relaxed Fit With Slight Stretch
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 05101-0426
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Flair Smocked Mini Dress
Bring some flair to your fall look with this floral smocked mini! The dress features a slight sweetheart neckline, long sleeves with smocked cuffs, and a short hem with a drawstring at the front. Dress is composed of a smocked woven fabric that offers plenty of stretch and a curve hugging fit.
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0393
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Puff Sleeve Floral Mini Dress
Puff sleeves are so of the moment. Pair that with spring time florals and you've got yourself an adorably trendy fit! Pair this mini dress with some cute clear mules and wear either off the shoulder or on.
Fit & Features
- Short puff sleeves | Merrow edge trim
- Square neckline | Faux tie front detail
- High elastic banded waist
- Ruched side detailing
- Short, form hugging fit
- Small floral print
- Brushed knit fabric | Plenty of stretch
Model is 5'6.5" with 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05101-0420
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fab In Floral Brushed Knit Maxi Dress
Walk right in like you own the place! This maxi dress features romantic florals throughout and a flowy, trailing skirt. Wear some bold earrings and block heels for a perfect 'fit!
Fits & Features
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Spaghetti Straps
- Square Neckline | Elastic Back
- Maxi Length Silhouette | Dual Front Slit
- Brushed Knit Fabric
- Form Hugging Fit | Plenty Of Stretch
- Zipper Not Featured
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05101-0409
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spaghetti Straps
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Spring It On Floral Mini Dress
Bring on the sunny, spring weather! Look fresh in florals with the Spring It On mini dress! Wear your sleeves up or soak up some vitamin C by wearing it off the shoulder!
Fits & Features
- Short Sleeves With Elastic Shoulders & Cuffs I Can Be Worn Off Shoulder
- V Neckline I Square Back
- Keyhole Opening With Adjustable Ties
- Mini Length Silhouette
- Stretchy Woven Textured Mesh I Floral Prints
- Form Hugging Fit I Moderate Stretch
Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0392
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bring The Romance Off Shoulder Long Sleeve Skater Dress
Date night calls for a sweet and pretty look! Style with some soft curls, a cute crossbody, and sparkly finishing touches and you'll be ready for the night!
Fits & Features
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Elasticized, Off Shoulder Neckline I Tie At Center Front
- Off Shoulder Long Sleeves I Elastic Cuffs
- Crochet Waist Design
- Mini Length, Skater Style Skirt
- Brushed Knit Design I Floral Print
- Plenty Of Stretch
Style Number/Barcode: 05101-0401
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Elasticized, Off Shoulder Neckline I Tie At Center Front
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Long Sleeve Ribbed Midi Dress
We're totally loving knit this season girl! Create some seriously cute looks with a basic midi dress!
Fit & Features
- Off The Shoulder Neckline
- V-Neck Bust
- Fitted Long Sleeves
- Ribbed
- Knit
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0391
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flow With The Floral Skater Dress
Go with the flow of this pretty floral skater dress! Pair with some everyday sandals for an effortless, spring ready vibe.
Fit & Features
- Off the shoulder elastic banded neckline
- Three quarter length flowy sleeves
- High waist seam
- Skater skirt
- Sheer chiffon fabric | Knit lining
- Rose print
Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0410
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sassy Snaps Ribbed Midi Dress
Keep it sassy as you snap into this must have! The dress features a crew neck, fitted long sleeves, a curve hugging midi length silhouette and a multi row snap button detail on the left side seam. Dress is composed of an unlined ribbed knit fabric that offers a moderate stretch.
Model is 5'3" with a 32" bust, 22.5" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06005-0304
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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