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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Everyday Ease: Casual Dresses for Transitional-Weather Plans
From weekend brunches to spontaneous coffee runs, Windsor’s casual dresses deliver easygoing style with just the right amount of polish. These effortlessly chic looks move with you—whether you’re off to the farmers’ market or catching golden hour with friends. Layer your favorite long sleeve to keep the chill out, or pick your Windsor shoes and accessories, and you're ready for the day.
Laid-Back & Versatile
Knit, ribbed, crochet, and sweater dresses bring comfort and style to cooler days. Slip into playful mini dresses, flowy midi styles, or long casual dresses in warm neutrals, jewel tones, and classic plaids. T-shirt and tunic dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.
Chic from Day to Night
Swap sneakers for ankle boots to take your favorite midi dress from errands to evening hangs. A flowy maxi in nuetral or black adds relaxed elegance—just add a faux leather jacket and heeled booties for an effortless finish.
Ready to refresh your everyday looks? Explore Windsor’s full collection of casual dresses online, in-app, or in-store.
What Makes a Dress Casual?
Casual dresses are defined by their effortless styling, comfortable fabrics, and laid-back details. Fabrication plays a key role—soft knits, cotton blends, and breezy silhouettes naturally create an easygoing look. Prints like ditsy florals or neutral-tone patterns, such as snake print, also make great everyday choices. Knit and sweater dresses are perfect for relaxed settings, whether you're heading to work or dressing up for a casual date night.
Styling is just as important in making a dress feel casual. Swap heels for sneakers, lug boots, or strappy sandals to instantly dress down your look. Layering is another effortless way to create a relaxed aesthetic—throw on a denim jacket, cropped sweater, or oversized cardigan for a cool, laid-back vibe. Details like drawstrings, button fronts, and tie accents also add to the casual appeal. Accessories, makeup, and hair styling can further influence the look, so opt for dainty jewelry, natural waves, or a simple ponytail to complete your effortlessly stylish outfit.
How Do I Style a Dress Casually?
Styling a dress casually is all about choosing relaxed layers and accessories that balance comfort with fashion. Denim jackets, graphic tees, scrunchies, crossbody bags, and sneakers all contribute to an effortlessly cool aesthetic. Try pairing a ruched mini dress with a lariat necklace and chunky sneakers for a sporty yet chic look. A basic knit midi dress layered under a cropped denim jacket with slides is perfect for a casual-chic feel.
For road trips or weekend getaways, maxi and midi dresses offer an easy styling solution. Layer a lightweight sweater over a flowy maxi or knot a t-shirt at the waist for a trendy, carefree vibe. Combat boots can add an edgy touch, while simple strappy sandals keep the outfit light and airy. No matter your style, Windsor has a versatile collection of casual dresses and must-have accessories to complete your look. Need styling help? Visit us in-store, and our expert stylists will help you find your perfect outfit!
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Sun Rays Tropical V-Neck Babydoll Mini Dress
Flaunt beachy perfection in this tropical babydoll dress with a strappy tie-back that turns heads with every wear! Style with sandals for a cute vacation look.
Fit & Features
- Tropical print, woven fabric, bust knit lining
- V-neckline, twisted bust
- Spaghetti straps
- Strappy tie-back design
- Babydoll silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000042
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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