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.
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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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Go With Florals Mini Dress
Go with florals this season to channel gorge vibes!
Fit & Features
- Scoop Neckline | Spaghetti Straps
- Lattice Back
- Floral Print
- Lined Scuba Knit Fabric
- Form Hugging Fit
- Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0325
Category Name: Casual Dresses
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Asymmetric Ruched Midi Dress
Add some flower power to your look with this bold and beautiful midi dress! Goes amazing with some strappy heels

Fits & Features
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Adjustable Spaghetti Straps That Cross At The Back
- V Neckline | Lined At The Bust
- Midi Length Asymmetric Hemline
- Side Ruching
- Woven Fabric With Floral Prints
- Plenty Of Stretch | Form Hugging Fit
- Zipper Not Featured
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0333
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Adjustable Spaghetti Straps That Cross At The Back
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Pick Of The Bunch Floral Chiffon Skater Dress
It's finally spring and that means adding more floral additions to your wardrobe! Brighten up your look with these fresh prints!
Fits & Features
- Adjustable Shoulder Straps
- V Neckline I Back Zip With Hook & Eye Closure
- Mini Length Hem I Skater Style Silhouette
- Lined Chiffon Fabric I Floral Prints Throughout
- 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: 05101-0313
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Chiffon High Low Dress
We're head over heels in love with fab florals! Bring the charm with this pretty high low dress! Pair with a statement heel and neutrals for a soft glam look!
Fit & Features
- V-Neckline | Spaghetti Straps
- Floral Lace Back | Open Lower Back
- Floral Print
- Lined Chiffon Fabric
- High Low Silhouette
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05101-0314
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Romantic Ruched Knit Maxi Dress
Get a gorgeous look for a romantic date night in this sultry ruched maxi dress. It features spaghetti straps, a square neckline, ruched side detailing, and a maxi length with a high side slit. The knit fabric offers plenty of stretch and provides a curve-hugging fit. Style this dress with a new pair of earrings and strappy heels.
Fit & Features
- Spaghetti straps
- Square neckline
- Ruched side detailing
- Maxi length
- High side slit
- Stretchy knit fabric with a short lining
- Form-hugging fit
Style Number/Barcode: 05102-0331
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Let Beauty Bloom Floral Midi Dress
Let your beauty bloom with a midi dress that is perf for the season! The dress features a sleeveless cowl neckline, adjustable spaghetti straps that lead to a cross-back, a tropical floral print, ruching, and a midi-length silhouette with an asymmetrical hem. Complete look with wedges.
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Cross-back
- Tropical floral print
- Midi length silhouette
- Asymmetrical hem
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0328
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On Your Radar Ruched Maxi Dress
Get on their radar in a sleek maxi dress that shows off curves in all the right places. The maxi dress features a square neckline, sleek spaghetti straps and ruched maxi length silhouette with a high side slit to show off glowing gams. Complete your look with clear heels and statement earrings.
Fit & Features
- Sleeveless square neckline
- Sleek spaghetti straps
- Maxi length silhouette
- Ruched side seams that streamline design
- High side slit
- Smooth knit fabric
- Form hugging fit, moderate stretch
Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0332
Category Name: Casual Dresses
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Island Glam Tropical Maxi Dress
Dazzle with an island-inspired look in this maxi dress that brings those vacay vibes! The dress features a sleeveless V-neckline, spaghetti straps, a tropical floral print, a high side slit, and a maxi length silhouette. Complete look with wedges and a floppy hat.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Tropical floral print
- High side slit
- Maxi length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-0318
Category Name: Casual Dresses
Price: $9.97 $42.90
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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Satin Dreams Midi Dress
We are totally obsessed with satin right now and we are guessing you are too! This midi dress features a v-neckline, thin spaghetti straps that lead to a square back and a hemline that flows into a floor length. Dress is composed of a satin like material that offers a relaxed fit with no stretch.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0325
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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Floral Flaunt Chiffon Skater Dress
Show off those beautiful florals in this enchanting mini dress!
Fits & Features
- Adjustable Spaghetti Straps
- Surplice V Neckline
- Self Ties At Back With Keyhole Opening
- Mini Length I Skater Silhouette
- Lined, Chiffon Fabric I Floral Prints Throughout
- Moderate Stretch
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 05101-0317
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Leopard Cowl Neck Mini Dress
Keep your style untamed in this fierce leopard print mini dress! It features a sleeveless bodice, a cowl neck, adjustable spaghetti straps that leads to a square back and a mini length silhouette. Dress is composed of an unlined lightweight woven fabric with a satin-like sheen that offers a relaxed fit with a minimal stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0326
Category Name: Casual Dresses
Price: $10.97 $28.90
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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Such A Dream Eyelash Knit Mini Dress
Look like a total dream babe in this adorable eyelash knit mini! The soft knit fabric has plenty of stretch for a total comfy form hugging fit.
Fit & Features
- Off the shoulder neckline
- Short sleeves
- Mid-thigh length hem
- Fuzzy eyelash ribbed knit fabric
Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06005-0196
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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V-Neck Ruched Midi Dress
Bring some style to the basic midi with this ruched detail dress! It features long fitted sleeves, a notch front V neckline, ruching along the sides, and a mid-length, curve hugging fit. The dress is composed of a stretchy knit fabric.Style Number/Barcode: 05102-0319
Category Name: Casual Dresses
Price: $9.97 $24.90
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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Turtleneck Long Sleeve Ribbed Knit Mini Dress
Bundle up to this ribbed knit mini for those cool nights. This cozy number features a turtleneck, long sleeves, scalloped hem, and mini length silhouette. The ribbed knit construction offers ample stretch. Zipper not included.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0308
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Snap Snap Slay Ribbed Sweater Dress
Oh snap she came to play! This sexy sweater dress is designed with a mock neckline, long sleeves, and a mid length hem that hits right passed the knee. Dress has a side slit detailing with faux snap buttons that lead down. Composed of a ribbed knit material that offers a form fit with moderate stretch.
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small
Style Number/Barcode: 06005-0193
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Julissa Knot Front Heat Stone Mini Dress
Special Occasion
Sparkle and glitter like the night sky in our statement Julissa!
Fits & Features
- Plunging V Neckline With Twist Front Design
- Adjustable Spaghetti Straps
- Zipper With Hook & Eye Closure At Back
- Ruching Along The Sides & Center Back
- Mini Length Silhouette
- Fully Lined, Mesh Knit Fabric With Heat Stone Embellishments All Over
- Curve Hugging Fit With Ample 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: 05001-0249
Category Name: Casual Dresses
Price: $25.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sophisticated Faux Suede Midi Dress
Keep it sophisticated in statement faux suede! The mini dress features a sleeveless bodice, a scoop neckline, spaghetti straps, vertical princess seams that create an hourglass illusion and a midi length silhouette with a side slit. The back features a sexy keyhole accent to show off more than a hint of skin! Dress is composed of a faux suede fabric that offers a form hugging fit with slight stretch.
Style Number/Barcode: 05101-0276
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Miss Me Mini Dress
Get tied to this cute mini! It features a plunging V neckline with a tie front accent, fitted long sleeves, a sexy mid-drift cut out and a mini length silhouette. Dress is composed of a ribbed knit fabric that offers a curve hugging fit with a moderate stretch.
Model is 5'3" with a 32" bust, 22.5" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0307
Category Name: Casual Dresses
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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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Life's A Beach Mesh Dress
Hit the pool, bask by the beach, or prep to party in this colorful mesh maxi! Dress features a vibrant tropical print in turquoise, blue, and rust, a strapless neckline, dramatic ruffle trim running from bust to hem, a high front slit, and built-in briefs. Dress bodice is semi-sheer and does not include a top. Maxi is made from a mesh blend material with moderate stretch.Style Number/Barcode: 05102-0286
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance