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.
Now Trending
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.
-
Love For Leopard Mesh Mini Dress
Let your wild side come through in this killer mini dress!
Fits & Features
- Adjustable Spaghetti Straps
- Square Neckline & Back
- Mini Length Silhouette I Ruching Along Sides & Center Back
- Leopard Print Throughout With Mesh Overlay I Smooth Knit Lining
- Curve Hugging Fit I Moderate Stretch
- Zipper Not Featured
Style Number/Barcode: 05102-0512
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Floral Fever Midi Dress
Get into that floral fever with this adorable ditsy floral printed midi dress, perf for spring!
Fit & Features
- Ruffle spaghetti straps
- Ruffle square neckline
- High waist seam
- Front slit
- Mid-length, flowy fit
- All over ditsy floral print
- Knit fabric | Moderate stretch
Style Number/Barcode: 05102-0455
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Knits Not You Crossover Mini Dress
Can you handle knit? Because we can't! This fitted dress is more than a 9-5 piece! Style with a blazer, or long duster for the daytime, then once 5 hits ditch the blazer for ur happy hour attire!
Fit & Features
- Cross over neckline
- Sleeveless
- Form fitting silhouette
- Ribbed knit material
- Moderate stretch
- Mini hemline
Style Number/Barcode: 06005-0495
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Can't V Bothered Sweater Dress
Chilly? Never heard of her. Stay stylishly festive and warm in the form-flattering and heavy knit Can't V Bothered sweater dress.
Fits & Features
- V Neckline & Back With Surplice Design
- Roomy, Cuffed Dolman Sleeves
- Bar Strap Accent At Back
- Removable, Waist Tie
- Hem Hits Mid Thigh
- Comfortable Form-Fit I Ample Stretch
Black: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
White & Blue: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06005-0500
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Feline Fierce Sweater Dress
Bold leopard spots and a live-in knit are a must-have combo for the chilly season. Stay stylish and warm in The Feline Fierce sweater dress!
Fits & Features
- Surplice Bodice With V Neck & Back
- Cuffed Long Sleeves
- Knit Composition With Leopard Inspired Print Throughout
- Includes Removable Waist Tie
- Bar Strap Accent At Back
- Mini Length Silhouette
- Form Hugging Fit I Ample Stretch
Brown: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Beige: Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06005-0489
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Long Sleeve Ribbed Mini Dress
Add this staple to your closet to create some seriously fab fall looks!
Fits & Features
- Turtleneck
- Long Sleeves
- Mini Silhouette
- Ribbed Knit
- Form Hugging Fit | Moderate Stretch
- No Zipper
Style Number/Barcode: 06005-0474
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Off Shoulder Knit Mini Dress
There's no such thing as cold weather blues in this number. Snuggle up to this comfy and cute mini dress!
Fits & Features
- Wide, Off Shoulder Neckline
- Cuffed Quarter Length Sleeves
- Elastic Waistband
- Form-Hugging Silhouette I Moderate Stretch
- Knit Composition I Fully Lined At The Skirt
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0511
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Floral Stunner Smocked Mini Dress
You'll be simply stunning in this floral smocked mini dress! It features a slight sweetheart neckline, long sheer chiffon puffed sleeves with smocked hems, and a stretchy smocked dress with a short, mid-thigh length hem with a front drawstring to cinch.Style Number/Barcode: 05102-0510
Category Name: Casual Dresses
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Ready For It Mini Dress
Get ready to have a total trendy look with this cute little mini! It features a slight sweetheart neckline, long sheer chiffon puffed sleeves with smocked cuffs, and a stretchy, smocked dress with a short, mid-thigh length hem with a front drawstring.Style Number/Barcode: 05102-0507
Category Name: Casual Dresses
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Floral Chiffon Blouson Mini Dress
Get an effortlessly beautiful look in this floral printed chiffon blouson dress! The mini features a ruffle mock neckline, long sheer puffed sleeves with elastic cinched wrists, and a stretchy smocked dress with a short hem. The all over floral print gives a pretty touch to the dress.Style Number/Barcode: 05102-0508
Category Name: Casual Dresses
Price: $20.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Classy and Chic Asymmetrical Dress
Tie yourself to a classy and chic look in this stunning mini dress! Pair this beauty with fab pumps and a trendy crossbody to complete the look!
Fit & Features
- Square Neckline
- Spaghetti Straps
- Tie Waist Accent
- Asymmetrical Hem
- Lined Crepe Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0460
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Ruffle Up Chiffon Off Shoulder Mini Dress
Make every walkway your runway in the Ruffle Up Off Shoulder mini dress!
Fits & Features
- Elastic Off Shoulder Neckline
- Long Sleeves
- Ruffle-Trim At Cuffs, Neckline, Waist, And Hem
- Smocked Skirt And Cuffs
- Mini Length Silhouette
- Chiffon Composition
- Form Flattering Fit I Moderate Stretch
Style Number/Barcode: 05102-0506
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
All For Knit Mock Neck Mini Dress
As temperatures drop, you'll want to include a mock neck mini in your wardrobe!
Fits & Features
- Mock Neckline
- Long Fitted Sleeves
- Mini Length Silhouette
- Heavyweight Rib-Knit Fabric
- Form Hugging Fit I Ample Stretch
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0504
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Keepin' Knit Cozy Sweater Dress
Keep it cozy and chic in this knit sweater dress. It features an off the shoulder boat neckline, long sleeves with faux buttoned cuffs, a tie front at the waist, and a short, form-hugging fit. The knit fabric offers plenty of stretch for comfortable wear.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0551
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Ready To Ruche Mini Dress
Get ready to style it up in this adorable ruched mini dress! It features spaghetti straps with a flattering square neckline, front ruched detailing with a tie at the hem, and a mini-length, curve-hugging fit. Pair this dress with some clear slide-on mules and a chic clutch for the perf night-out look.
Fit & Features
- Spaghetti straps, square neckline
- Dart seam detailing
- Back zipper closure
- High waist seam
- Side ruched detailing with tie at the hem
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-3951
Category Name: Casual Dresses
Price: $19.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Picturesque Petals Tiered Ruffle Chiffon Mini Dress
Feel and look picture-perf in this fun floral dress! Pair your look with a denim jacket and some white sneakers!
Fits & Features
-
Adjustable Spaghetti Straps
- V Neckline I Square Sheer Back
- Drawstring Waist
- Mini Length Silhouette I Tiered Ruffle Trim Design
- Floral Chiffon Fabric I Fully Lined
- Zipper Not Featured
Style Number/Barcode: 05102-0503
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Adjustable Spaghetti Straps
-
Vintage Destructed Jersey Knit Mini Dress
Get that vintage edgy vibe going in this jersey knit mini dress.
Fit & Features
- Long fitted sleeves
- Crew neckline with large V cut out
- Slashed distressed detailing
- Large skull and rose graphic with the script "Vintage," "Rock and Roll," and "Live Fast Die Young Festival"
- Short, form hugging fit
- Knit fabric | Plenty of stretch
Style Number/Barcode: 06002-0346
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Bell Sleeve Beauty Floral Mini Dress
You'll be a total beauty in this adorable bell sleeve floral mini dress!
Fit & Features
- Off the shoulder neckline
- Long bell sleeves
- Stretchy smocked bust
- Flowy skirt
- All over floral print
- Knit fabric | Plenty of stretch
Style Number/Barcode: 05102-0502
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Just My Stripe Zebra Sweater Dress
You can never have too many animal prints in your wardrobe!
Fits & Features
- Plunging V Neckline
- Surplice Design At Front & Back
- Bar Strap Accent At Back
- Long Sleeves
- Removable Waist Tie
- Hits Mid-Thigh
- Form Hugging Fit I Ample Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06005-0435
Category Name: Casual Dresses
Price: $4.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Check It Plaid Mini Dress
Check you out! Plaid isn't just the perfect print for flannels.
Fits & Features
- Square Neckline
- Short Sleeves With Puff Shoulders
- Princess Seams
- A-Line Fit
- Mini-Length Silhouette
- Plaid Print Throughout
- Moderate Amount Of Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0501
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Color Block Knit Mini Dress
Keep it chic in stand out color block! This mini dress is perf to pair with your fav booties or strappy heels to easily dress up or down!
Fit & Features
- Mock Neck
- Sleeveless
- Color Block Design
- Ribbed Knit Fabric
- Mini Length Silhouette
- Form Hugging Fit
- Moderate Stretch
Model is 5'4" with 32" bust, 23" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06005-0432
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Charming Ruffles Chiffon Dress
Charm them all with romantic ruffles in this super gorge mini dress!
Fit & Features
- Plunging V-Neckline | Ruffle Trim
- Adjustable Spaghetti Straps | Cross-Back
- Multi-Tiered Ruffle Accents
- Lined Chiffon Fabric
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05102-0498
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Denim Days Button Up Mini Dress
Button up in a denim dress that is part stylish, part edgy! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a button-down front, side pockets, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit. Complete look with mules and hoops.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Button-down front
- Side pockets
- Mini-length silhouette, form-hugging fit
- Denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0499
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Square Neck Floral Mini Dress
Look as beautiful as a bouquet in this springtime dress! It's the perf brunch fit once you accessorize with some nude heels and earrings!
Fits & Features
-
Short, Puff Sleeves
- Elasticized Square Neckline & Cuffs
- Smocked Bodice
- Mini Length Silhouette I A-Line Skirt
- Woven Gauze Composition I Floral Prints
- Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0493
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Short, Puff Sleeves