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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Keepin' It Cute And Casual Denim Dress
Keep your everyday look cute and casual in this must-have denim dress! It features a sleeveless square neckline, thin shoulder straps, a complete button-down front, and a short, curve-hugging silhouette. Style this dress with sneakers and chic shades.
Fit & Features
- Sleeveless square neckline
- Thin shoulder straps
- Complete button-down front
- Mini-length, form-hugging fit
- Denim fabric
- Runs true to size
Style Number/Barcode: 05102-0500
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adore You Floral High Slit Maxi Dress
Feel adored in a floral dress that brings some serious butterflies this season. The dress features a gorgeous floral print, a flattering cowl neckline, and a maxi length silhouette that is accented a high side slit. Complete your date-night ready outfit with sleek hoop earrings and strappy heels that mesmerize.
Fit & Features
- Sleeveless bodice
- Cowl neckline
- Spaghetti straps that cross at the back
- Floral print
- Maxi length silhouette
- High side slit
- Smooth knit fabric, form-hugging fit
Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.
Style Number/Barcode: 05101-0529
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Ditsy Smocked Tie Front Mini Dress
Spring into a smocked disty mini dress to keep on trend this season. This flirty piece features a sweetheart neckline, a tie front with a small keyhole at the bust, and an all-over floral ditsy print. The relaxed fit bodice leads to a curve-hugging mini-length silhouette. The dress is composed of a smocked knit fabric that offers a moderate stretch. Complete your look with hoop earrings and minimal heels.
Fit & Features
- Sweetheart neckline
- Keyhole at bust
- Floral ditsy print
- Smoked fabric
- Form-hugging fit
- Moderate stretch
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0497
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Groovy Gal Tie Dye Mini Dress
Give your wardrobe a splash of color with this groovy mini dress! Amp up your look by pairing this with a mini backpack and some platform sneakers!
Fits & Features
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Spaghetti Straps
- Scoop Neckline I Square, Elastic Back
- Mini Length Silhouette
- Brush Knit Fabric I Tie Dye Design
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0495
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spaghetti Straps
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Floral Moment Maxi Dress
Create a charming moment in florals in this sweet maxi dress! Perfect for brunch when paired with fab heels and a neutral handbag!
Fit & Features
- Wrap V-Neckline
- Spaghetti Straps
- Elastic Waist
- Floral Print
- Maxi Silhouette
- Lined Knit Fabric | Mini Skirt Length Lining
- Relaxed Fit | Moderate Stretch
Style Number/Barcode: 05101-0530
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 Smocked Mini Dress
You'll be a total summer sweetheart in this adorable mini dress! It features a sleeveless square neckline with a ruffle trim, a tie-front bust detail, tie-shoulder spaghetti straps, a smocked body, and a mini-length, curve-hugging silhouette. Style this dress with casual sandals.
Fit & Features
- Sleeveless square neckline, ruffle trim
- Tie-front bust detail
- Tie-shoulder spaghetti straps
- Smocked body
- Short, form-hugging fit
- Woven fabric
- Runs true to size
Style Number/Barcode: 05102-0496
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Petals Tie Waist Skater Dress
Hey doll! Showcase your pretty self in this adorable floral printed skater dress! Paired with some wedges, you'll be ready for a perf spring day.
Fit & Features
- Adjustable spaghetti straps
- Wrap front V neckline
- High rise elastic banded waist
- Tie front detail
- Flowy skater skirt
- Lightweight floral printed woven fabric
- Stretchy knit lining
Style Number/Barcode: 05102-0494
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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A Classic Ribbed Midi Dress
Look like an instant classic with this curve-hugging sweater dress! The ribbed fabric creates an instant hour-glass illusion!
Fit & Features
- Off The Shoulder Neckline
- Long Sleeves
- Ribbed Knit Fabric
- Midi Silhouette
- Form Hugging Fit
- Moderate Stretch
Model is 5'9" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06005-0417
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Knot Front Open Waist Mini Dress
Slay any occasion in this mini dress! She features a crew neckline, fitted long sleeves, a decorative twist front, and an open cut-out at the midsection. Crafted from a poly-rib textured knit, she offers a curve-hugging fit with an ample amount of stretch to move and groove.
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06005-0404
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Forever In Love Floral Dress
Be forever in love with florals in this beyond gorg printed dress! Its flowy feel adds a major flirty vibe.
Fit & Features
- Long loose sleeves with single buttons to cuff
- Wrap front V neckline
- Back zipper | Hook and eye closure
- High waist | Tie back detail
- Wrap front tiered skirt
- Sheer floral printed chiffon fabric | Knit lining
Model is 5'9" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0527
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cat Touch This Satin Leopard Mini Dress
You can look, but you can't touch. Slay it in this feisty mini dress!
Fits & Features
- Self Tie Spaghetti Straps
- Square Neckline & Back
- All Over Smocked Design
- Mini Length Silhouette
- Satin-Like Fabric
- Curve Hugging Fit I Ample Stretch
Style Number/Barcode: 05102-0492
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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