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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Got A Flair For It Ruffle Hem Mini Dress
Add some flair to your movement with this ruffle mini dress! Pair with some block heels and hoop earrings!
Fits & Features
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Spaghetti Straps
- Square Neckline I Princess Seams
- Back Zipper With Hook & Eye Closure
- Side Ruching
- Mini Length Silhouette I Ruffle Trim Hemline
- Smooth Textured Woven Fabric
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0697
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spaghetti Straps
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Be Amazed Ruched Off Shoulder Mini Dress
Not your typical LBD. They're going to be amazed once they see you strutting in with this mini dress! Dust your neckline with some sparkling rhinestone accents to go for that extra glow!
Fits & Features
- Off Shoulder Neckline I Elastic Interior Band
- Fitted Long Sleeves
- Drawstring Bust
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette I Mesh Lined Fabric
- Ruching Throughout I Ruffle Trim Neckline & Hem
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05101-0767
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Leopard Love Lace Up Front Mini Dress
We've all got love for leopard print in our wardrobe! Make your presence be known in this fierce mini dress!
Fits & Features
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Sheer Roomy Long Sleeves
- Ruffle-Trim At Sweetheart Neckline & Shoulders
- Lace-Up Front
- Back Zipper With Hook & Eye Closure
- Mini Length Hemline I Adjustable Dual Drawstrings At The Front
- Woven Lined Fabric
- Minimal Stretch
Style Number/Barcode: 05101-0768
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sheer Roomy Long Sleeves
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Dreamy Meadow Chiffon Ruffle Maxi Dress
Look like a dreamy meadow in this flowy and sweet midi dress! Slip into some block heels and you'll be ready for your spring soiree!
Fits & Features
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Adjustable Spaghetti Straps
- Surplice V Neckline I V Back
- Back Zipper
- Maxi Length Silhouette I Ruffle-Trim Hem I Partial Lining
- Adjustable Drawstring & Ruching At Front Side
- Chiffon Fabric I Floral & Botanical Prints
- Minimal Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05101-0769
Category Name: Casual Dresses
Price: $21.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Adjustable Spaghetti Straps
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Center Of Attention Ruched Mini Dress
Be the center of attention in this sultry mini dress! Pair with some booties or heels for a chic look!
Fits & Features
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V Neckline
- Roomy Sheer Long Sleeves
- Elastic Shoulder & Cuffs
- Adjustable Drawstring Center Front
- Mini Length Silhouette
- Mesh Lined Fabric
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0696
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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V Neckline
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Purrfectly Fierce Smocked Mini Dress
Look purrfectly fierce in this so of the moment leopard printed mini dress! Its smocked detailing will flatter your curves.
Fit & Features
- Strapless sweetheart neckline
- Tie front detail
- Front cut out
- Stretchy smocked body
- Short, form hugging fit
- Leopard print
Style Number/Barcode: 05102-0682
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ribbed Knit Crew Neck Bodycon Mini Dress
Keep it casually chic in a mini dress that is a total must-have! The short dress features a crew neckline with a racerback design, a mini-length hem, and is composed of a form-hugging ribbed knit fabric. Put your hair in an updo and style with strappy mules for a cute look!
Fit & Features
- Crew neckline
- Sleeveless bodice
- Racerback design
- Mini-length hem
- Ribbed knit fabric, fully lined
- Form-hugging fit, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-0689
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Burst Ruffle Mini Dress
Burst into the season with fab florals bby! Pair this charming print with fab wedges and pop of color to complete a brunch-ready look!
Fit & Features
- Sweetheart Neckline | Drawstring
- Short Puff Sleeves
- Mid-Drift Cut Out
- Ruched Side Seam | Drawstring
- Floral Print
- Lined Chiffon
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 05102-0676
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Smocked Sweetheart Gingham Mini Dress
Yes girl, it's the perfect daytime date dress! Perfectly pair the look with some clean white sneakers or heeled sandals!
Fits & Features
- Elastic Sweetheart Neckline & Cuffs
- Tie Design & Cut Out At The Bust
- Woven Short Sleeves I Can Be Worn Off Shoulder
- Smocking Throughout
- Mini Length Hemline With Ruffle Trim
- Gingham Print Design
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0688
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Friday Night Ruched Midi Dress
Get this dress now so you don’t have to worry about not having anything to wear next Friday! It looks great paired with clear heels and layered gold necklaces.
Fits & Features
- Square Neckline
- Ruched Detailing
- Form Hugging Fit
Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0692
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Effortless Beauty Eyelet Mini Dress
You've got that effortless beauty babe! Wear this gorg eyelet mini dress and have the perfect spring time look!
Fit & Features
- Adjustable spaghetti straps
- Wrap front V neckline
- Hidden back zipper | Hook and eye closure
- Side tie detail
- Wrap front skirt
- Eyelet detail woven fabric | No stretch
Style Number/Barcode: 05102-0686
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Breeze On By A-Line Mini Dress
Breeze right through the crowd (and catch some glances doing it!) in this simply chic mini dress! Elevate your look adding some dainty jewels and a pair of strappy mules!
Fits & Features
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Surplice v neckline
- Short sleeves
- Mini length hem, A-line silhouette
- Smooth, stretchy knit fabric
- Form hugging fit, plenty of stretch
- Zipper not included
Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0687
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Surplice v neckline
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You're The One Bodycon Midi Dress
There's truly no one like you bb girl! With a statement single strap and a figure-hugging fit, you'll be feeling fierce in this basic ribbed dress!
Fits & Features
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One Shoulder Strap
- Slanted Neckline
- Midi Length Hem
- Ribbed Knit Fabric
- Figure Hugging I Moderate Stretch
Style Number/Barcode: 05102-0685
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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One Shoulder Strap
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Carmela Metallic Shine Party Dress
Special Occasion
You'll be leading the dance floor in our sparkling Carmela! Twist, twirl, and bust a move in her flowy skater skirt while showcasing all the shine from every angle. Style her up with some rhinestone heels and a pair of earrings to match!
Fits & Features
- Adjustable Spaghetti Straps
- V Neckline I Padded Bust I Mesh Inset
- Mini Length Hem I Skater Silhouette
- Mesh Inset At Back With Triple Row Detail I Back Zipper With Hook & Eye Closure
- Mesh Lined Metallic Threaded Fabric I Fully Lined
- Form Hugging Fit I Moderate Stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0417
Category Name: Casual Dresses
Price: $31.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blissful In Lace Maxi Dress
This gorge lace maxi dress will have you looking and feeling blissful! Don't forget to pair this dress with a fab mini purse and block heels!
Fits & Features
- Crew Neckline I Button Nape & Keyhole Opening At Back
- Sheer Fitted Long Sleeves I Smocked Cuffs
- Sheer Partially Lined Bodice
- Maxi Length Hem
- Lace Fabric I Mini-Length Lining
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05101-0760
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
- Crew Neckline I Button Nape & Keyhole Opening At Back
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Too Dot To Handle Polka Dot Midi Dress
Bb girl, you're sizzling in this dress! Add a pair of cute booties and a faux leather jacket to complement this 'fit!
Fits & Features
- Adjustable Spaghetti Straps
- Surplice V Neckline
- Side Zipper WIth Hook & Eye Closure
- Midi Length Silhouette With Front Slit
- Textured Knit Fabric I Polka Dot Design I Unlined
- Relax Fit I Minimal Stretch
- Zipper Not Featured
Style Number/Barcode: 05101-0761
Category Name: Casual Dresses
Price: $14.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simply Chic Wrap Front Romper
Simple & chic is your go-to style. This wrap front romper is perf for a daytime look paired with some gold hoops and cute wedges.
Fit & Features
- Short sleeves
- Hidden back zipper | Hook and eye closure
- Wrap front V neckline
- Button closure
- Wrap overlay
- Flowy shorts
- Woven fabric with a short lining | No stretch
Style Number/Barcode: 06303-0068
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Total Sweetheart Floral Mini Dress
Showcase your sweet style in this adorable floral printed mini dress! It features short sleeves, a V neckline, ruching at the bust with a front drawstring, a small cutout under the bust, and a short, form-hugging silhouette. The unlined knit fabric offers plenty of stretch. Complete your look with dainty earrings and a cute crossbody purse.
Fit & Features
- Short sleeves
- V neckline
- Ruching at the bust with a front drawstring
- Small cutout under the bust
- Ruching down the sides
- Mini-length, form-hugging fit
- Unlined knit fabric with plenty of stretch
- Floral print
- Runs true to size
Style Number/Barcode: 05102-0679
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lovely In Linen Smocked Mini Dress
Look oh so lovely in linen in this perf springtime mini! The smocked detailing make it all the more flattering!
Fit & Features
- Long sleeves | Smocked cuffs
- Square neck | Eyelet trim detail
- Front tie | Keyhole cut out
- Stretchy smocked skirt
- Short, ruffle hem
- Linen fabric
Style Number/Barcode: 05102-0681
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pretty In Plaid Mini Dress
Keep it pretty in plaid with this brunch ready mini dress! This season-ready dress only needs a pair of wedges and a pop of jewel tones for a complete look!
Fit & Features
- Square Neckline
- 3/4 Puff Sleeves
- Plaid Print
- Lined Lightweight Fabric
- Mini Length Silhouette
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05102-0680
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Day Dreamin’ Eyelet Mini Dress
Get ready for a sweet summer day in this eyelet dress. Pair it with wedges and a cute mini bag.
Fits & Features
- All Over Eyelet Pattern
- Puff Sleeves
- Lace Up Detailing
- Ruffle Hem
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0678
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flower Power Puff Sleeve Mini Dress
Take on the floral trend with this gorg puff sleeve printed mini! Pair the dress with some espadrille platform sandals and a cute woven bag!
Fit & Features
- Short puff sleeves | Elastic banded cuffs
- Sweetheart neckline
- Back zipper | Hook and eye closure
- Front center ruched detailing
- Short ruffle hem
- Sheer floral printed woven fabric
- Knit lining
Style Number/Barcode: 05101-0756
Category Name: Casual Dresses
Price: $17.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tortoise O-Ring Ribbed Knit Midi Dress
Casual and cute, you'll be loving the O-ring belt around this chic midi dress! We love to see you rockin' this with some white sneakers and a faux leather jacket!
Fits & Features
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Spaghetti Straps
- Scoop Neckline I Square Back
- Tortoise O-Ring Waist Belt
- Midi Length Silhouette
- Ribbed Knit Fabric I Fully Lined
- Form Hugging Fit I Plenty Of Stretch
- Zipper Not Featured
Style Number/Barcode: 05102-0673
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spaghetti Straps
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All About It Ribbed Knit Mini Dress
We're all about our basic essentials and this mini dress is a must! Pair it with some white sneakers for a daytime look or throw on a faux leather jacket and some thigh-high boots for a PM 'fit!
Fits & Features
- Scoop Neckline & Back
- Mini Length Silhouette
- Double Layered Ribbed Knit
- Form Hugging Fit
- Plenty Of Stretch
Style Number/Barcode: 05102-0668
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free