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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Polly Formal High Slit Dress
Special OccasionBring the glamour in the ever so lovely Polly dress! She features a vibrant yellow hue, a sleeveless bodice, a plunging V neckline, padded cups, princess seams and adjustable narrow straps. Her slim fit bodice leads to an elongating sweeping floor length A-Line skirt that is accented with a high side slit to show off your heel game! She offers a form hugging fit with minimal stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-0089
Category Name: Casual Dresses
Price: $9.97 $89.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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Spotted With Sass Cowl Neck Mini Dress
We are lovin' a cowl neck mini dress, no matter what the season! Pair with a leather jacket and boots on a chilly night, or simply pair with ur fave mules!
Fit & Features
- Cowl neckline | Spaghetti straps
- Form fitting silhouette
- Side slits | Mini hemline
- Spotted leopard print pattern
- Minimal stretch | Knit woven material
Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.Style Number/Barcode: 05102-0388
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Forever Floral Mesh Burnout Velvet Mini Dress
Look forever stunning in gorg florals with this adorable little mini dress!
Fit & Features
- Spaghetti straps
- Cowl neckline
- Short fit
- Sheer mesh fabric with burnout velvet floral appliques
- Stretchy knit lining
Style Number/Barcode: 05102-0429
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bring That Floral Flair Midi Dress
Girl, bring that floral flair in this adorable printed midi dress!
Fit & Features
- Spaghetti straps
- V neckline
- Padded bust
- High waist seam
- Mid-length, curve hugging fit
- Scuba knit fabric | Plenty of stretch
Style Number/Barcode: 05101-0308
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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
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Casual Chick Mock Neck Mini Dress
Pair this basic necessity with some thigh-high boots, take cover with your fave jacket, and you're all ready for a night out!
Fits & Features
- Mock Neckline
- Long, Balloon Sleeves With Elastic Cuffs
- Mini Length Silhouette
- Lightweight Ribbed Fabric I Best Paired With Tonal Shaper
- Curve Hugging Fit I Ample Stretch
Style Number/Barcode: 05102-0559
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ready To Ruffle Chiffon Mini Dress
You'll be mesmerizing them in this dreamy mini dress! It's the perfect romantic look for date night!
Fits & Features
- V Neckline
- Sheer Long Sleeves I Elasticized Cuffs
- 3 Button Detail At Nape Of Neck I Cut Out At Back I Hidden Zipper
- Elasticized, Smock Midsection
- Mini Length, Skater Skirt
- Lined Chiffon Fabric I Ruffle Detail Throughout
- Form-Fitting I Minimal Stretch
Style Number/Barcode: 05101-0312
Category Name: Casual Dresses
Price: $18.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Knit Mini Tie-Waist Sweater Dress
Keep it cute and cozy in a soft sweater dress that has an effortlessly classy finish!
Fit & Features
- High neckline
- Long flared sleeves
- Long hemline
- High waist slits
- Tie waist
- Knit material | Moderate stretch
Style Number/Barcode: 06005-0588
Category Name: Casual Dresses
Price: $21.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Snake Print Waffle Knit Mini Dress
Snake print is this season's staple. Pair this comfy knit mini with some edgy booties and your're out the door!
Fit & Features
- Crew neckline
- Long fitted sleeves
- Short, form hugging fit
- Snake print
- Waffle knit fabric
- Plenty of stretch
Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06002-0336
Category Name: Casual Dresses
Price: $16.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Warming Sign Midi Sweater Dress
All signs are pointing to *add to cart* with this cozy midi dress!
Fits & Features
- Off Shoulder Neckline
- Cuffed, Roomy Blouson Sleeves
- Midi Length Silhouette I Side Slit
- Midweight Ribbed Knit
- Comfortable Relax Fit I Plenty Of Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0558
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Precious In Plaid Duster
Make your way into the next season with a perfectly plaid duster!
Fits & Features
- Drape Open Front
- Fitted Long Sleeves
- Long Hem That Hits Mid Thigh
- Smooth Poly Material
- Plenty Of Stretch
- Complete The Look With The Matching Dress (05102-0261)
Model is 5'3" with a 32" bust, 22.5" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06202-0057
Category Name: Casual Dresses
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Easy Does Knit Midi Dress
Let your outfit do all the talking for you! Heat up your wardrobe with this knit midi
Fits & Features
- Scoop Neck
- Fitted Long Sleeves
- Faux Button Down Front
- Midi Length Silhouette I Front Slit
- Ribbed Knit I 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: 05102-0442
Category Name: Casual Dresses
Price: $12.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cut to the Chase Belted Denim Mini Dress
No time for small talk. This bodycon mini gets straight to the point with daring front cutouts, a plunge halter neckline, and belted straps that hit different.
Fit & Features
- Denim fabric, slight stretch
- Plunge halter neckline, dual button closures on the strap
- Front cutouts with belted straps
- Back zipper and hook-eye closure
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000195
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Florals Blouson Mini Dress
Look fresh and effortlessly in this flirty mini dress! A perf day-time look for coffee dates or brunch with your girls!
Fits & Features
- Sweetheart Neckline With Twist At Center Front
- Cut Out Underneath Bust
- Unlined, Sheer Fitted Long Sleeves I Smocked Cuffs
- Back Zipper
- Flowy, Mini Length Skirt With Drawstrings At The Side
- Relax Fit I Minimal Stretch
Style Number/Barcode: 05102-0556
Category Name: Casual Dresses
Price: $18.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cable Knit Off Shoulder Sweater Dress
Cozy AF! Maximize the styling potential of this mini sweater dress!
Fits & Features
- Off Shoulder Neckline Design
- Long Sleeves WIth Elasticized Cuffs
- Mini Length Silhouette
- Lined, Knit Fabric I Cable Knit Design
- Form Hugging Fit I Ample Stretch
Style Number/Barcode: 05102-0553
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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
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Stripe Right Mock Neck Mini Dress
We're crushing on stripes and lovin' the mock neck on this mini. Toss on a leather jacket and a pair of white sneakers, and you're all ready to mingle!
Fits & Features
- Mock Neckline
- Fitted Long Sleeves
- Mini Length Silhouette
- Ribbed Knit With An All Over Stripe Print
- Bodycon Fit I Plenty Of Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0320
Category Name: Casual Dresses
Price: $9.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sea Salt Vibes Halter Crochet Midi Dress
Your next vacay is calling, and this crochet midi dress will set the vibes! Embrace the sand and sun in this stylish dress designed with a flattering high neckline and form-hugging fit.
Fit & Features
- Crochet knit fabric, stretchy knit lining
- High halter neckline, spaghetti strap ties
- Form-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000028
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Danya Scuba Floral A-Line Dress
Special Occasion
Sway and sashay your way around the dance floor with our beautiful Danya! Her delicate floral prints add a flirty feminine touch.
Fits & Features
- Spaghetti Straps
- Plunging V Neckline I Princess Seams
- Zipper With Hook & Eye Closure At The Back
- A-Line, Floor Length Hem I High Slit At The Front
- Smooth Scuba Knit Fabric With Floral Prints Throughout
- Form-Hugging Fit I Moderate Stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-0355
Category Name: Casual Dresses
Price: $19.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feline This Leopard Midi Dress
Lovin' that look, girl! You're going to be feeling this mini dress as soon as you slip it on!
Fits & Features
- Adjustable Spaghetti Straps
- Cowl Neckline I Square Back
- Zipper With Hook & Eye Closure At Back
- Midi Length Silhouette With Front Slit
- Unlined, Satin-Like Fabric I Tonal Leopard Print Throughout
- Relax Fit I Minimal Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0401
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Knit Girl Mock Neck Sweater Dress
When cozy meets chic. This midi is just what you need for that winter wardrobe!
Fits & Features
- Mock Neckline
- Fitted Long Sleeves
- Midi Length Silhouette
- Ribbed Knit
- Bodycon Fit I Ample Stretch
- Zipper Not Included
Style Number/Barcode: 06005-0569
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feelin' Sweet Off Shoulder Sweater Dress
Channel your sweet side when you slip into a flattering off shoulder sweater dress gurl!
Fit & Features
- Fold over off shoulder neckline
- Form fitting silhouette
- Banded wrist
- Mini hemline
- Knit woven material
- Moderate stretch
Style Number/Barcode: 06005-0232
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rianna One Shoulder Heat Stone Dress
Special Occasion
Light up the night with dazzling heat stones as you wow in our Rianna dress!
Fit & Features
- One Shoulder Neckline
- Ruched Side Seam
- Heat Stones
- Lined Mesh
- Midi Silhouette
- Form Hugging Fit
- Moderate Stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0268
Category Name: Casual Dresses
Price: $24.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance