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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Good To Grow Floral Satin Mini Dress
Flaunt the florals cause you look good to go! Go for a sultry look by wearing it off the shoulder or wear the short sleeves up. Slip into your favorite heels and you're all set!
Fits & Features
- Short Sleeves I Can Be Worn Off Shoulder
- Lace Trim Scoop Neckline I Self Tie At Center Front I Keyhole Opening
- Empire Waist
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette
- Satin-Like Fabric I Floral Print
- Form Hugging Fit I Minimal Stretch
Style Number/Barcode: 05101-0459
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Summer Sweetheart Striped Mini Dress
Bring the sweet vibes to your summer look with this adorable mini dress. It features a sleeveless square neckline, spaghetti straps, a tie-back detail, and a short, curve-hugging silhouette. The ribbed knit fabric has a cute all-over striped print. Style this dress with casual sneakers.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Tie-back detail
- Mini-length, form-hugging fit
- Ribbed knit fabric, striped print
- Runs true to size
Style Number/Barcode: 05102-0443
Category Name: Casual Dresses
Price: $7.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Support Smocked Skater Dress
Grow through what you go through. Look and feel uplifted in this cute AF floral dress! Throw on a crop denim jacket and some sneakers for an OOTD!
Fits & Features
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Self Tie Spaghetti Straps
- Square Neckline
- Smocked Bodice
- Mini Length I Skater Silhouette
- Woven Fabric I Smooth Knit Lining
- Ample Stretch
Style Number/Barcode: 05102-0444
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Self Tie Spaghetti Straps
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Button Up In Denim Frayed Dress
Button up in this denim dress to make a fun statement bby!
Fit & Features
- Collared Neckline
- Small Chest Pockets | Button Down Front
- Short Sleeves
- Zipper Front Closure | Side Pockets
- Frayed Hem
- Medium Wash Denim
- Relaxed Fit | Slight Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0436
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All That Skater Dress
There's no denying, carry all that confidence girl in this flirty skater dress!
Fit & Features
- V-Neckline
- Cross-Back Spaghetti Straps
- Ponte-Knit Fabric
- A-Line Skater Silhouette
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05101-0475
Category Name: Casual Dresses
Price: $19.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Persuasion Smocked Mini Dress
Get on this sweet trend this season! Brighten up your closet with pretty florals to make a charming impression! Pair mini dress with your fav wedges to complete the look!
Fit & Features
- Square Neckline | Tie Front Accent
- Adjustable Spaghetti Straps
- Smocked Waist and Back
- Floral Print
- Lined Lightweight Woven Fabric
- Mini Length Silhouette
- Relaxed Fit | Minimal Stretch
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0445
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Denim Dreamer Tie Front Dress
Look oh so dreamy in denim in this adorable tie front dress! Perf for a spring day out with your gal pals.
Fit & Features
- Collared | Half snap button down front
- Long sleeves | Single buttons to cuff
- Two buttoned chest pockets
- Tie front detail | Front waist cut out
- Two slanted pockets at the waist | Two back pockets
- Front button | Hidden zipper closure
- Short, form hugging fit
Style Number/Barcode: 05102-0435
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ribbed Knit Ditsy Floral Mini Dress
Keep it sweet in a ditsy floral dress. Perfect for brunch, this mini dress features a sleeveless bodice with a sweetheart neckline and supportive tank-like straps. The back features an open back with two ribbed bar back straps. The relaxed fit waist leads to a curve-hugging mini-length silhouette. Keep accessories minimal to let the ditsy floral print command attention.
Fit & Features
- Sleeveless bodice
- Sweetheart neckline
- Open back with bar straps
- Ditsy floral print
- Mini length silhouette
Style Number/Barcode: 05102-0439
Category Name: Casual Dresses
Price: $13.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Denim Diva Sleeveless Mini Dress
Dare to impress in denim! This denim mini dress can easily dressed up with the perfect pair of pumps and animal print!
Fit & Features
- Sweetheart Neckline | Padded Cups
- Adjustable Spaghetti Straps
- Lace Up Front | Metal Grommets
- Contrast Stitching
- Denim Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0437
Category Name: Casual Dresses
Price: $14.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Playful Petals Floral Chiffon Off Shoulder Mini Dress
Let your feminity show and flow in this darling mini dress!
Fits & Features
- Off Shoulder, Foldover Neckline
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette I Detachable Waist Tie I Wrap Skirt
- Chiffon Lined Fabric
- Moderate Stretch
Style Number/Barcode: 05101-0464
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Long Sleeve Ribbed Mini Dress
It may be cold, but you're heating up in this ribbed mini dress!
Fits & Features
- Surplice V Neckline I V Back
- Fitted Long Sleeves
- Mini Length Silhouette
- Midweight Ribbed Knit Fabric
- Curve Hugging Fit I Moderate Stretch
Black: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Ivory: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 06005-0361
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Mesh Well Ruched Mini Dress
A stunning little ruched dress is just what you need to show off those never-ending curves!
Fits & Features
- Elastic Cord Straps
- Square Neckline With Elastic Interior Band
- Mini Length Silhouette With Ruching Down The Sides
- Fully Lined, Mesh Fabric
- Curve Hugging Fit | Ample Stretch
- Zipper Not Included
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0432
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruched Hour Mini Dress
This fiery number is calling your name. You'll be stopping traffic in this one!
Fits & Features
- Dual Shoulder Straps
- Square Neckline
- Ruched Drawstring
- Form Hugging Fit
- Moderate Stretch
- Fully Lined
Style Number/Barcode: 05102-0433
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Forever Floral Mesh Burnout Velvet Mini Dress
Look forever stunning in gorg florals with this adorable little mini dress!
Fit & Features
- Spaghetti straps
- Cowl neckline
- Short fit
- Sheer mesh fabric with burnout velvet floral appliques
- Stretchy knit lining
Style Number/Barcode: 05102-0429
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Nothin' But A Sweet Thing Floral Mini Dress
Honey you ain't nothin' but a sweet thannng when you step out in this floral mini ruched dress. We are already dreaming of that spring wardrobe!
Fit & Features
- Modest v-neckline
- Lace up bust detailing
- Tank straps | Off- shoulder straps
- Form fitting silhouette | Mini hemline
- Brushed knit material
- Ruched down the center
- Floral pattern | Slight stretch
Style Number/Barcode: 05102-0431
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Carine Metallic Glitter Ruched Mini Dress
Special Occasion
Almost instantly, Carine's glitter metallic shine will draw eyes your way. You'll be loving her figure-flattering fit that'll have you look and feel amazing. Don't forget to include some stiletto heels and earrings to really finish the look!
Fits & Features
- Adjustable Spaghetti Straps
- V Neckline I Padded Bust
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette
- Ruched Down Center Front, Back & Sides
- Smooth Woven Glitter Knit I Fully Lined
- Form Hugging Fit I Minimal Stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0326
Category Name: Casual Dresses
Price: $36.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Basic Buttoned Sweater Dress
Keep it gorge with buttons this season! The sweater dress features a mock neck, short sleeves, a multi row button detail and a midi length silhouette with a mini side slit. Dress is composed of knit fabric that offers a relaxed fit with a moderate stretch.Style Number/Barcode: 06005-0357
Category Name: Casual Dresses
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tropics Vibe Plunging Mini Dress
Transport to an island paradise with this vacay ready mini dress! It features a plunging wrap V neckline with a knot accent, long bell sleeves and asymmetrical mini length silhouette. The all over tropical print features palm leaves throughout. Dress is composed of an unlined lightweight woven fabric that offers a relaxed fit with minimal stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0427
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Denim Doll Puff Sleeve Mini Dress
Spring is right around the corner and you'll want to bust out those wedges and sandals to complement this cute denim dress!
Fits & Features
- Puff Shoulder Short Sleeves I Elastic Cuffs
- Sweetheart Neckline
- Square Back I Zipper Closure
- Mini Length Silhouette
- Denim Fabric
- Curve Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0426
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The Essential Sweater Dress
Fall back on this essential sweater dress this season! It features a crew neck, long sleeves with ribbed cuffs and a midi length silhouette that pairs perfectly with booties! Dress is composed of a sweater knit fabric that offers a relaxed fit with a moderate stretch.Style Number/Barcode: 06005-0358
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Leopard Print Surplice Smocked Mini Dress
If you're on the hunt for a fierce print and body-flattering dress, look no further than this!
Fits & Features
- Plunging V Neckline With Surplice Design
- Cuffed Long Sleeves
- Smocked Skirt With Merrow Edge Trim Hem
- Leopard Print Design
- Form Hugging Fit I Plenty Of Stretch At Bottom
- 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: 05102-0428
Category Name: Casual Dresses
Price: $19.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Show 'Em Off Shoulder Smocked Mini Dress
Show off those shoulders in this cute mini dress! For a cute daytime look, pair it with your fave denim jacket and some white sneakers!
Fits & Features
- Off-shoulder neckline, short sleeves
- Keyhole opening with self-ties at front
- Mini length silhouette
- Woven textured fabric, smocked back, ruffle trim detail
- Curve hugging fit, plenty of stretch
Style Number/Barcode: 05102-0472
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Leopard Mesh Mini Dress
Flaunt that trendy leopard print in this fierce mini dress!
Fits & Features
- Elastic Bungee Strap
- Square Neckline & Back
- Mini Length Silhouette I Gathering Detail At Side Seams
- Knit Lining With Leopard Printed Mesh Overlay
- Curve Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0425
Category Name: Casual Dresses
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Walk in the Park Floral Mini Dress
Take a stroll in style wearing this sweet floral dress! Pair it with sandals and a straw bag.
Fit & Features
- Ribbed Fabric
- Off the Shoulder Puff Sleeves
- Tie Front Detail
- Mini Length
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0447
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance