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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Bad Bee Mini Dress
You're the baddest B in this simple dress. This piece features a crew neckline, short sleeves, and a bodycon fit throughout. It's made of a rib knit fabric that's perfect for dressing up or down.
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06002-0164
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Don't You Want Me Dress
They're gonna want you AND your dress! This tank dress features adjustable shoulder straps with a back tie closure and ruched sides. It's structured with a bodycon fit and hits at the mid-thigh. Fully lined and made of a comfy, textured jersey knit fabric for dressing up or down.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0258
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Simple And Stunning Midi Dress
Simply stunning is what you are in this trendy knit midi dress.
Fits & Features
- Bungee Spaghetti Straps
- Square Neckline
- Curve-Hugging Fit
- Midi Length Silhouette
- Soft Brushed Knit Composition | Fully Lined
- Offers Plenty Of Stretch
Hunter & Mauve: Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Black: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0175
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Talk That Talk Tank Dress
You're a bad gal, bb! Catch some eyes in this simple-yet-sexy tank dress. Including a racerback neckline that flows into a midi length, this spaghetti tank dress features a smooth, stretchy fabric that hugs your body with every move.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0183
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Over You Sleeveless Midi Dress
Show us who is boss in sleek midi! This mid length dress features a crew neckline, and a sleeveless bodice. Hem is tailored to a mid calf length, and dress is composed of a ponte material that offers moderate stretch. Throw on some heels and walk the walk!
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0189
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Into The Florals Dress
Immerse yourself in all the floral print you can take! This flower bomb features a cowl neck, adjustable narrow straps that create an X back, and a slim fit. Dress is composed of a casual knit fabric with a lightweight feel that offers plenty of stretch. Dress is unlined.Style Number/Barcode: 05102-3105
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Meow You're Talking Leopard Mini Dress
Satin and leopard? Matchmade in heaven. Show your sleek and wild side in the Meow You're Talking mini dress!
Fits & Features
- Cowl Neckline
- Spaghetti Straps
- Adjustable Tie At Back I Low Open Back
- Satin-Like Composition I Minimal Stretch
- Mini Length Silhouette
- 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: 05102-0338
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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What's Knot To Like Mini Dress
Take your look to the next level with this pretty mini dress! It features an off the shoulder neckline, fitted long sleeves, a cinching tie waist belt with loops and an asymmetrical mini length silhouette with a ruched detailing. Dress is composed of a lined crepe fabric that offers a curve hugging fit with a moderate stretch. Zipper not included.
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0336
Category Name: Casual Dresses
Price: $12.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Vintage Motors Slashed Mini Dress
Give your look some serious edge with this mini dress! It features a round neckline, long fitted sleeves and a mini length silhouette with slashed distressed detailing. The graphic at the center of the bodice features a motorcycle with wings and a graphic that reads: " Superior Motorcycle Vintage Garments." Mini dress is composed of a cotton-blend fabric that offers a curve hugging fit with a moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06002-0242
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Classic Basic Mini
We are loving a mini dress with a square neckline! This basic mini is composed of a fully lined ribbed knit material that offers moderate stretch and a form fitting silhouette. The spaghetti straps are bungee style. The skinny straps are flattering and offer stretch as well. This look says it all! Throw on some heels and throw your hair up for a sexy effortless look!
Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06002-0152
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Forever Reckless Lace Up Tunic
You're a free spirit and you do what you want! This lace up tunic features short sleeves, a mid-thigh length, and a center script reading "Forever Reckless" in a bold contrasting print. The knit fabric offers moderate stretch and a relaxed fit.
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06002-0224
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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