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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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
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In Check Plaid Mini Dress
Get your look in check with this cute plaid mini dress!
Fits & Features
- Narrow Spaghetti Strap
- Scoop Neckline I Square Back
- Mini Length Silhouette
- Fully Lined, Textured Knit Fabric I Plaid Print Throughout
- Bodycon Fit I Moderate Stretch
- Zipper Not Included
Style Number/Barcode: 05102-0554
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance