Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, or keep it flowy with midi and maxi silhouettes. Mesh details add a little edge, while sleeveless minis and long-sleeve staples cover every season. Whether you’re layering up for a chill weekend or slipping into something light for a last-minute dinner date, these casual dresses are made to move with your mood—and 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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She's A Plaid Girl Mini Dress
It's true. Plaid girls have more fun.
Fits & Features
- Square Neckline
- Bungee Spaghetti Straps
- Mini Length Silhouette
- Textured Knit Composition I Velvet Plaid Print Throughout
- Curve Hugging Fit I Moderate Stretch
- Zipper Not Included
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0400
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Clad In Plaid Scoop Neck Mini Dress
Look pretty in plaid! Give your flannels a break and rock this cozy plaid mini dress.
Fits & Features
- Scoop Neckline
- Cap Sleeves
- Dart Detail At The Bust
- Plaid Print
- Mini Length Silhouette
- Form Hugging Fit
- Moderate Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0378
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stylishly Sweet Smocked Tube Skater Dress
Stylishly sweet, this smocked tube skater dress is perfect for weekend brunch! It features a strapless straight neckline, a V-shaped waist, and a short A-line silhouette for that flirty flair.
Fit & Features
- Poplin cotton-blend woven fabric, stretchy knit lining
- Strapless straight-across neckline
- Stretchy smocked bodice
- V-shaped waist
- Pleating
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000049
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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
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Chiffon Sweetheart Smocked Mini Dress
Whether you're brunching with your girls or got a date scheduled, finding the right dress can be difficult. Look no further, this pretty chiffon mini dress is your perfect go-to!
Fits & Features
- Sweetheart Neckline
- Puff Accent Shoulders I Long Sleeves
- Empire Waist
- Smocked Skirt & Cuffs
- Fully Lined I Chiffon Composition
- Mini Length, Ruffle Trim Hemline
- Zipper Not Included
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0449
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Too Fab Knit Mini Dress
You'll be simply too fab in this hot little mini! The dress features a sleeveless bodice, bungee spaghetti straps, a square neck and back, and a short, curve-hugging fit. The double-lined knit fabric offers plenty of stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0548
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ribbed Knit Square Neck Midi Dress
Can't get enough of knit! Exude your confidence in this form-flattering midi dress.
Fits & Features
- Tank-Style Shoulder Straps
- Square Neck & Back
- Slit At Center Back
- Midi Length Silhouette
- Curve-Hugging Fit
- Ample Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0349
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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
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Leopard Print Surplice Smocked Mini Dress
If you're on the hunt for a fierce print and body-flattering dress, look no further than this!
Fits & Features
- Plunging V Neckline With Surplice Design
- Cuffed Long Sleeves
- Smocked Skirt With Merrow Edge Trim Hem
- Leopard Print Design
- Form Hugging Fit I Plenty Of Stretch At Bottom
- Zipper Not Included
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0428
Category Name: Casual Dresses
Price: $19.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Meow Or Never Leopard Midi Dress
Move fast girl. Snag this purr-fect midi before it's too late!
Fits & Features
- Spaghetti Straps That Cross At The Back
- Self Ties & Keyhole Opening At Back
- Draped Cowl Neckline
- Front Slit At Midi Length Silhouette
- Stretchy Polyester Composition I Form Hugging Fit
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0408
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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
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Wild Feline Leopard & Tiger Ruched Midi Dress
Spotted: The purrrrrrfect midi dress! Shake up your look and add some animal print in your wardrobe.
Fits & Features
- Bungee Spaghetti Straps
- Elastic Square Neckline
- Ruched Design
- Mixed Leopard & Tiger Inspired Print
- Midi Length Silhouette
- Mesh Composition I Fully Lined
- Little Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0406
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Turtleneck Ribbed Knit Mini Dress
Layer away! With a trendy turtleneck and a comfy rib-knit construction, this is the perfect starting piece for your layered looks.
Fits & Features
- Turtleneck
- Long Sleeves With Thumb Holes
- Curve-Hugging Fit
- Plenty Of Stretch
- Mini Length Silhouette
- Zipper Not Included
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0422
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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
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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
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Saddle Up Cow Print Denim Mini Dress
Serving western attitude with a side of yeehaw chaos. This cow-print mini dress brings the edge with a snap-front design and pockets for full rodeo realness.
Fit & Features
- Cow print, cotton denim fabric, no stretch
- Sleeveless V-neckline
- Button front closures
- Two front pockets
- Curve-hugging fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000230
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Satin Snake Print Mini Dress
Sleek with a chic snake print, this satin mini is a trendy find. The dress features a sleeveless bodice, bungee spaghetti straps, a square neck and back, and a short, curve hugging fit. The satin-like fabric has moderate stretch.Style Number/Barcode: 05102-0383
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Snake It To The Top Mini Dress
This ssstylish fierce mini dress is bound to be at the top of your wardrobe rotation!
Fits & Features
- High Neckline
- Sleeveless Bodice
- Mini Length Silhouette
- Knit Composition With Snake Print Design
- Fully Lined
- Form Fitting I Ample Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0399
Category Name: Casual Dresses
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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
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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
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On A Roll Long Sleeve Mini Dress
Look cozy and chic in the On A Roll mini dress! Pairs well with your fave boots and denim jacket.
Fits & Features- Turtleneck
- Long Sleeves
- Curve-Hugging Fit
- Mini Length, Scalloped Hemline
- Fully Lined
- Zipper Not Included
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0372
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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
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V Neck Front Knot Midi Dress
Toss on some heels and you've got yourself a look! This dress features a V-neckline and decorative center front knot, short sleeves, and a midi-length silhouette with front slit. Composed of a stretchy and smooth textured knit, it offers a form hugging fit and ample stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0369
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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