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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Fawning Over Florals Mini Dress
We adore this floral mini! Pair this with your fav heels and purse, and you're all ready for date night!
Fits & Features
- Elastic Bungee Cord Straps
- Square Neckline & Back
- Mini Length Silhouette
- Mesh Lined Fabric With Ruching & Floral Prints Throughout
- Curve Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0490
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dreamy Vacay Vibes Maxi Dress
Bring the dreamy vacay vibes to your next getaway in this gorgeous maxi dress. It features a sleeveless V-neckline, adjustable spaghetti straps, a high waist, and a flowy floor-length silhouette with a chic front slit. The mesh fabric has a tropical floral print, making the maxi dress a perf pick for summer. Complete the look with strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Back zipper closure
- High waist
- Flowy floor-length silhouette, front slit
- Mesh fabric, floral print
- Runs true to size
Style Number/Barcode: 05101-0523
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty And Flowy Halter Skater Dress
Showcase your flirty style in this adorable flowy skater dress! It features a sleeveless deep V-neckline, halter straps, dual tie-back accents, a high waist, and a flared-out skater skirt. Complete the look with rhinestone earrings and clear heels.
Fit & Features
- Sleeveless V-neckline
- Halter straps, dual tie-back accents
- High waist
- Flowy skater skirt, fit and flare silhouette
- Chambray fabric
- Runs true to size
Style Number/Barcode: 05102-0488
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Just A Midi Sweater Dress
A perfect addition to your fall and winter wardrobe. Toss on a pair of booties during the day and swap them for heels during a night out! It features a mock neckline with merrow edge trim, raglan long sleeves, and a midi-length silhouette. The form-fitting dress is crafted from a ribbed knit and offers ample stretch.Style Number/Barcode: 06005-0393
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Radiating Ruffles Chiffon Dress
Glow up in this pretty ruffle dress, perfect for brunch with the squad! Pair this airy dress with cute wedges and dainty accessories for a head-turning look!
Fit & Features
- Wrap V Neckline
- Long Bishop Sleeves | Single Button Closure Cuff
- Tie- Waist Belt
- Tiered Ruffle Silhouette
- Lined Chiffon Fabric
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05101-0510
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Snake Print Waffle Knit Mini Dress
Snake print is this season's staple. Pair this comfy knit mini with some edgy booties and your're out the door!
Fit & Features
- Crew neckline
- Long fitted sleeves
- Short, form hugging fit
- Snake print
- Waffle knit fabric
- Plenty of stretch
Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06002-0336
Category Name: Casual Dresses
Price: $16.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Eyelet Puff Sleeves Mini Dress
Do a little spring cleaning with your wardrobe and add this charming mini dress to cart...you know it'll be part of your rotation! We love pairing this look with a denim jacket and some heels!
Fits & Features
- Elastic Puff Shoulder Short Sleeves I Can Be Worn Off Shoulder
- Square Neckline
- Mini Length Silhouette
- Textured Knit Fabric With Eyelet Design I Fully Lined
- Form Hugging Fit I Moderate Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0486
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Free Spirit Knit Skater Dress
Live your best in this season ready skater dress!
Fit & Features
- Plunging V-Neckline
- Halter Neck Tie Straps
- Skater Silhouette
- Fully Lined Gauze-Like Fabric
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05102-0485
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mock Neck Belted Sweater Dress
Look effortless in this one-and-done sweater dress! It features a trendy mock neckline, long sleeves, a removable stylish D-ring belt along the waist, slits at the sides, and a midi-length silhouette. The garment is composed of a ribbed knit and offers a form hugging fit with an ample amount of stretch.
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06005-0391
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek Ya Out Cowl Neck Midi Dress
Girl, look at you! Everyone's eyes will be locked on you in this pretty midi! Slip into some mules and add a panama hat for a chic look!
Fits & Features
- Spaghetti Straps I Strappy Back
- Cowl Neckline
- Midi Length Hem
- Smooth, Satin-Like Fabric
- Relaxed Fit I Minimal Stretch
- Zipper Not Included
Style Number/Barcode: 05102-0484
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fleur Paradise Chiffon Smocked Mini Dress
Slip-on this pretty mini dress and enchant them all with the bold and beautiful floral prints!
Fits & Features
- Ruffle-Trim At Square Neckline, Cuffs & Hem
- Sheer, Roomy Chiffon Long Sleeves I Elastic Cuffs
- Smocked Bodice & Mini Length Silhouette
- Curve Hugging Fit
- Ample Stretch
Style Number/Barcode: 05101-0509
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Dream Corduroy Mini Dress
Keep it dreamy and charming with a pretty floral print! The corduroy fabric on this mini keep this mini feeling luxe and fab!
Fit & Features
- Square Neckline
- Short Sleeves
- Key Hole
- Cross Straps At Back
- Floral Print
- Corduroy Fabric
- Relaxed Fit
Style Number/Barcode: 05102-0481
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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V In The Midi Dress
You'll want to slip right into this cozy and sexy midi dress! Pair with some cute heels and a leather jacket for the perf finishing touches.
Fits & Features
- V Neckline & Back
- Long Fitted Sleeves
- Midi Length Silhouette
- Ribbed Knit Fabric
- Curve Hugging Fit
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 06005-0394
Category Name: Casual Dresses
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Thinking Of You Denim Mini Dress
Leave them thinking of you in this pretty midi dress! The dress features a sleeveless square neckline, adjustable spaghetti straps, a button-down front, a cinching tie waist belt, hidden side pockets, and a mini-length silhouette. The dress is composed of a denim fabric that offers a relaxed fit. Complete look with sandals and a cropped denim jacket.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Button-down front
- Cinching tie waist belt
- Hidden side pockets
- Mini length silhouette
- Denim fabric, form-hugging fit, runs true to size
Style Number/Barcode: 05102-0475
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Headed To The Tropics Mini Dress
Get ready to head to the tropics with this mini dress! The dress features a sleeveless scoop neckline, adjustable spaghetti straps, tropical palm leaf print, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Tropical palm leaf print
- Mini length silhouette
- Lined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0480
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet & Smocked Ditsy Ruffle Midi Dress
Get into the spring vibe with this midi dress on! Easily style it up or down by switching out your white sneakers to heels!
Fits & Features
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Adjustable Spaghetti Straps
- Square Neckline
- Tiered Ruffle Detail
- Midi Length Silhouette
- Ditsy Woven Print
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05101-0501
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Adjustable Spaghetti Straps
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A Splash Of This Tie-Dye Satin Mini Dress
This trendy tie-dye satin mini dress will def expand your color palette babe! With its cowl neckline and slightly flared fit, you'll be serving looks. Perfect for a backyard photo shoot, add some sparkly earrings and slip into a pair of block heels to get the shot.
Fits & Features
- Adjustable spaghetti straps
- Cowl neckline
- Back zipper with hook and eye closure
- Mini length silhouette
- Satin-like fabric with a tie-dye print
- Relaxed fit with minimal stretch
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0476
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Brighter Vibes Lace-Up Chiffon Maxi Dress
Bring on brighter vibes in this maxi dress that brings a burst of color this season. The maxi dress features a plunging v-neckline, sexy waist cutout to show off a hint of skin, a lace-up back, and a high side slit. Complete your look with fab cork wedges and sunnies for those ultimate summer vibes.
Fit & Features
- Sleeveless v-neckline with spaghetti straps
- Waist cutouts
- Lace-up back
- High side slit
- Maxi length silhouette
- Chiffon fabric
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05101-0505
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreaming of Denim Days Dress
We're dreaming of sunny summer days that are perfect for hanging with the squad! Throw this denim mini dress on and pair with clear pumps and dainty pieces for a look that slays!
Fit & Features
- Button Down Collar
- Two Chest Pockets
- Short Roll Up Sleeves
- Tie Front Waist | Waist Cut Out
- Side Pockets
- Single Button | Zipper Closure
- Denim Fabric
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.Style Number/Barcode: 05102-0477
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Girl Next Door Denim Mini Dress
Channel those girl next door vibes with a mini dress that is part casual, part stylish! The dress features a sleeveless square neckline, tank shoulder straps, vertical seams along the body, and a mini center slit at the back. The dress is composed of form-hugging denim fabric. Complete look with clear mules and rhinestone rings.
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Vertical seams
- Mini center slit at back
- Mini length silhouette
- Form hugging denim fabric
- Runs true to size
Style Number/Barcode: 05102-0478
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Denim Diva Zip Front Mini Dress
Stow your jeans and bust out a denim mini dress for the spring szn! Pair this with a lightweight long sleeve and some cute ankle booties!
Fits & Features
- Tank Shoulder Straps
- Scoop Neckline & Back
- Zipper Front I Linear Seam Details
- Mini Length Silhouette
- Denim Composition
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0471
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Crush On You Lace Bust Skater Dress
The lace bodice and flirty skater skirt are a few of the crush-worthy deets of this lovely dress!
Fits & Features
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Adjustable Spaghetti Straps
- Embroidered Lace Design At The Front Bodice I Lightly Padded
- Cut Out At Center Front Waist
- Mini Length Hem I Skater Style Skirt
- Crepe Fabric
- Back Zipper With Hook & Eye Closure
Style Number/Barcode: 05101-0517
Category Name: Casual Dresses
Price: $9.97 $41.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adjustable Spaghetti Straps
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Acid Wash Denim Spaghetti Strap Button Mini Dress
Get drawn to denim dresses this season. Slip into this curve-hugging dress for your next night out with bae. Fitted with a sleeveless sweetheart neckline, adjustable spaghetti straps to avoid wardrobe malfunctions, and corset-like seams that accentuate curves. The real details can be found in the multi-button down accent at the bodice that leads to a mini length silhouette. The light-medium acid wash denim fabric offers a form hugging fit. Complete your look with fab pumps and dainty accessories.
Fit & Features
- Sleeveless sweetheart neckline
- Corset-like seams
- Button-down accent
- Adjustable spaghetti straps
- Mini length silhouette
- Acid wash denim fabric
- Form hugging fit
Style Number/Barcode: 05102-0474
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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What's The Ruche Midi Dress
A look we honestly can't get enough of! Slip into this form-hugging midi dress and show off those never-ending curves!
Fits & Features
- Spaghetti Straps
- Square Neckline
- Midi Length Silhouette
- Woven Fabric I Fully Lined
- Ruching Throughout
- Form Hugging Fit I Curve Hugging Fit
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0463
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance