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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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
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Simply Chic A-Line Smocked Dress
Keep it simply chic with a dress that says it all!
Fit & Features
- Elastic Square Neckline
- Tie Front Accent
- Long Sleeve | Elastic Cuffs
- Smocked Waist
- A-Line Silhouette
- Lined Lightweight Woven Fabric
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 05102-0465
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sprung On Florals Chiffon Midi Dress
Get sprung over florals this spring! This midi dress is the perfect all occasion piece, whether your going to a shower, a bbq, or brunch, this dress is perf!
Fit & Features
- Scoop drawstring neckline
- Adjustable spaghetti straps
- Milkmaid style bodice
- Fully lined
- Chiffon | Minimal stretch
- Ditsy floral print
- Bust tie detailing | Hidden zipper closure at side
- Mini length
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0467
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Groovy Baby Tie Dye Mesh Mini Dress
Show them how you groove in this tie-dye mini! We'd love to see you step out in this with a white pair of booties bb girl!
Fits & Features
- Spaghetti Straps Cross & Tie At Back
- V Neckline
- Mini Length Silhouette
- Fully Lined Mesh Fabric I Tie Dye Print
- Ruching Throughout
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0466
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Scoop Neck Floral Mesh Mini Dress
Look fine in florals and strut your stuff in this fab mini dress!
Fits & Features
- Elastic Bungee Cord Straps
- Scoop Neckline I Square Back
- Mini Length Silhouette I Gathering Detail At Low Side Seams
- Knit Lining With Floral Printed Mesh Overlay
- Curve Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0469
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spring Fling Floral Chiffon Ruffle Dress
Embrace the florals and ruffles in this romantic mini dress! It features peasant long sleeves, a plunge v-neckline, and a babydoll style silhouette with flirty ruffle trim on floral chiffon-lined fabric. Complete the look in a boho ring set.
Fits & Features
- Plunging V Neckline
- Sheer Roomy Long Sleeves I Elastic Cuffs
- Back Zipper With Hook & Eye Closure
- Dual Buton Detail At Nape Of Neck I Cut Out At Back
- Mini Length Hemline
- Lined Chiffon Fabric With Floral Print I Ruffle-Trim Detail
- Minimal Stretch
Style Number/Barcode: 05102-0470
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Scuba Lace Back Mini Dress
Look your freshest in this pretty dress!
Fits & Features
- Spaghetti Straps I Lace Back With Zipper
- Plunging V Neckline
- Mini Length Silhouette
- Scuba Fabric With All Over Floral Prints
- Curve Hugging Fit I Moderate Stretch
Style Number/Barcode: 05101-0495
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Romantic Floral Ruched Mini Dress
Make your look a romantic one with a touch of sexy when you slip into a curve flattering ruched mini dress!
Fit & features
- Square neckline I Back zipper with hook & eye closure
- Adjustable spaghetti straps
- Form fitting silhouette
- Ruched detailing throughout
- Mesh lined fabric | Moderate stretch
- Mini Hemline
- Romantic floral pattern
Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.Style Number/Barcode: 05102-0464
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ribbed Knit Mock Neck Mini Dress
The everyday sweater dress you need in your life. Add to cart!
Fit & Features
- Mock neckline
- Long fitted sleeves
- Short, curve hugging fit
- Ribbed knit fabric | Knit lining
- Plenty of stretch
Style Number/Barcode: 06002-0329
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Double Take Glitter Mini Dress
You're going to be making an entrance AND an exit with this fiery number!
Fits & Features
- Square Neckline I Back
- Bungee Cord Straps
- Mini Length Silhouette
- Textured Glitter Knit I Fully Lined
- Curve Hugging Fit I Moderate Stretch
Style Number/Barcode: 05103-0594
Category Name: Casual Dresses
Price: $17.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Full Bloom Satin Cowl Mini Dress
Spring is just around the corner! Can you believe it? We are ready, satin dresses all season, it's a trend that isn't going away any time soon!
Fit & Features
- Spaghetti straps that cross and tie at the back
- Cowl neckline
- Mini hemline
- Composed of satin | Minimal stretch
- Printed floral design
- Low back
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0458
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Romantic Floral Ruffled Chiffon Skater Dress
Get an effortlessly romantic look for a daytime date with this floral chiffon skater dress. It features ruffle detail shoulder straps, a wrap-front V neckline, a backless design with a thin tie-back accent, a high waist with a tie-front, and a flowy skater silhouette with tiered ruffle detailing. Complete the outfit with hoop earrings and a new purse.
Fit & Features
- Ruffle detail shoulder straps
- Wrap-front V neckline
- Open-back design, zipper closure, tie-back closure
- High waist, tie-front
- Short skater silhouette, ruffle details
- Floral chiffon fabric
- Runs true to size
Style Number/Barcode: 05102-0454
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fresh Start Floral Off Shoulder Dress
Spring is here and it's time for a fresh start on that wardrobe! Wear this gorgeous chiffon dress out for all those sunny affairs!
Fits & Features
- Off Shoulder Elastic Neckline & Long Sleeves
- Elastic Cuffs
- Mini Length Silhouette
- Chiffon Fabric | Full Knit Lining
- Floral Print Design
- Moderate Stretch
Style Number/Barcode: 05102-0450
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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A Floral Moment Woven Mini Dress
Have a major floral moment in this adorable woven mini dress! It features a sleeveless sweetheart neckline with ruching at the bust, thin ruffle-detail shoulder straps, a smocked back, and a short, curve-hugging silhouette. The all-over ditsy floral print is perf for summer. Style this dress with casual sneakers.
Fit & Features
- Sleeveless sweetheart neckline, ruching at the bust
- Thin ruffle-detail shoulder straps
- Smocked back
- Mini-length, form-hugging fit
- Woven fabric, ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-0451
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale