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.

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.

Spiced Up Knit Midi Dress
Spice up your wardrobe in this season appropriate copper midi dress! This cozy sweater dress features an off the shoulder neckline, long fitted sleeves, a comfortable slim fit, and a flatter midi length. Dress is composed of a ribbed knit fabric that offers plenty of stretch.

Style Number/Barcode: 06005-5987

Category Name: Casual Dresses

Price: $15.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Pop Of Stripes Knit Dress
Accentuate those curves with a flattering pop of stripes! This black knit mini dress features an off the shoulder neckline, short sleeves, horizontal pink and white stripes across the bust and hips, and a comfortable slim fit. Dress is composed of a casual knit fabric with plenty of stretch.
Model is 5'7" with a 34" bust, a 24" waist, and 36" hips. She is wearing a size small.

Style Number/Barcode: 06005-0006

Category Name: Casual Dresses

Price: $36.90

Availability: Out of Stock
Product Badge:
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Rock N' Roll Vintage Tunic
Channel your inner rocker with this vintage-inspired tunic! It features a round neckline, a multi strap distressed inset, short sleeves, a contrasting guitar graphic with a block script that reads: "Rock & Rock: Live Fast Die Young" and a distressed detailing throughout. Tunic is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch.

Style Number/Barcode: 06002-0004

Category Name: Casual Dresses

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Can't Relate Henley Mini Dress
Basic? Sorry can't relate. Stand out in this natural mini dress that features a sleeveless bodice, a sweetheart neckline, a multi button down front with wooden buttons, wide shoulder straps and a mini length silhouette. Dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

Style Number/Barcode: 06001-1279

Category Name: Casual Dresses

Price: $22.00 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Flawless Style Knit Off-The-Shoulder Long Sleeve Mini Dress
Show off your stunning curves in this form-hugging mini dress made with pointelle knit fabric with plenty of stretch. It features a chic off-the-shoulder neckline with a fold-over design, long fitted sleeves, and ruched side seams along the short bodycon silhouette.

Fit & Features
- Pointelle knit fabric with knit lining, plenty of stretch
- Off-the-shoulder neckline with fold-over design
- Unlined long fitted sleeves
- Ruched side and back seams
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5917

Category Name: Casual Dresses

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glow Getter Strapless Cutout Mini Dress
Catch flights and compliments. This strapless mini hugs you in all the right places with a ruched bust ring detail and cheeky cutout that turns the charm up. Brunch, beach, or bae date—it’s a serve every time.

Fit & Features
- Rib knit stretchy fabric
- Strapless sweetheart tube neckline with hardware trim
- Cutout accent
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000033

Category Name: Casual Dresses

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Spotted In Style Mini Dress
Spotted! You'll be stylin' from head to toe in this fab mini dress. It features a sleeveless bodice, thin shoulder straps, a V neckline, a sultry front waist cut out with a bar accent, and a short, form hugging fit. The leopard print dress is composed of a ponte knit fabric 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: 05103-3445

Category Name: Casual Dresses

Price: $13.44 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Ruched And Ready Mini Dress
Get ready to go out with the squad in this must have LBD! The black dress features a sleeveless bodice, a square neckline, narrow shoulder straps and a mini length silhouette. The body features ruched detailing throughout to showcase curves! Dress is composed of a lined mesh fabric that offers a moderate stretch.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small

Style Number/Barcode: 05103-0177

Category Name: Casual Dresses

Price: $9.97 $40.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Triple Threat Rhinestone Bodycon Dress
No one can mess with this ivory triple threat dress! They won't be able to take their eyes off you with this piece's side cut outs and three sparkling rhinestone bars. Dress has a deep V neckline with a lightly padded bust, narrow cord straps, an invisible back zipper, and princess seams for a longer and leaner illusion. Garment is composed of a thick crepe fabric that offers a moderate stretch. Includes a full lining.

Style Number/Barcode: 05103-2906

Category Name: Casual Dresses

Price: $17.97 $43.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Eyes On Me Mini Dress
Demand attention in this Insta-worthy day dress! It features a flirty off-the-shoulder neckline paired with short sleeves. Dress has a round hemline and is composed of a textured knit fabric that offers plenty of stretch.
Model is 5'6" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05103-2257

Category Name: Casual Dresses

Price: $19.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Nautical By Nature Mini Dress
This navy blue and white mini dress is a little naughty, but still sweet! It features a white, sleeveless knit bodice with a V neckline and adjustable shoulder straps. Her A-line skirt has a high paper bag waist with a tie belt, a double row of large buttons on the front, and side pockets.
Model is 5'6.5 with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

Style Number/Barcode: 05102-4049

Category Name: Casual Dresses

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Twist In Florals Maxi Dress
Give your look a pretty twist in this navy maxi dress! It features a sleeveless bodice, a plunging V neckline, narrow shoulder straps and an open back with tie strap accent. The slim fit bodice leads to a curve hugging maxi length silhouette accented with a high side slit. The all over floral print features pink hues to contrast with the navy background. Dress is composed of a lightweight woven fabric that offers a form hugging fit with a minimal stretch.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small

Style Number/Barcode: 05102-4015

Category Name: Casual Dresses

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Full Scoop Tank Mini Dress
Get the full scoop in this casual cutie! This black knit dress features a scoop neckline, tank-style straps, white stripes running down the sides, and a mini length. Dress is pullover with plenty of stretch.
Model is 5'9" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

Style Number/Barcode: 05102-4036

Category Name: Casual Dresses

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Buttoned And Striped Maxi Dress
Give yourself a cute and casual look with this buttoned and striped maxi dress! It features a sleeveless bodice, spaghetti straps, a scoop neckline, a faux button down front, and a front slit. The black and white dress is composed of a knit fabric with 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: 05102-4028

Category Name: Casual Dresses

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Casual Cutie Linen Maxi Dress
Go for casual and cute in this taupe dress! It features a V neckline, adjustable narrow straps and a maxi length silhouette with hidden side pockets. Dress is composed of a double lined linen knit fabric that offers a relaxed fit with minimal stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05102-3966

Category Name: Casual Dresses

Price: $15.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Plus Crochet In Color Dress
This cute crochet dress is perfect for a day out! It features a V neckline, adjustable spaghetti straps that create an X back, a sheer crochet waist, and a short flared skirt with a full lining.

Style Number/Barcode: 15102-0017

Category Name: Casual Dresses

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Lovely Little Floral Dress
Look oh so lovely in this little floral printed mini dress! It features a sleeveless bodice, spaghetti straps, a square neckline, a lettuce edge trim, and a short, form hugging fit. The natural hued dress is composed of a smocked and stretchy linen fabric and showcases an adorable all over ditsy floral print.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05102-3979

Category Name: Casual Dresses

Price: $13.94 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Sculpted Chic Ribbed Knit Midi Dress
The ribbed knit dress features a sweetheart neckline with a twist accent at the bust, long sleeves, and a midi-length hem. Channel a casual vibe with chunky sneakers.

Fit & Features
- Ribbed knit fabrication
- Sweetheart neckline with twist accent
- Long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5962

Category Name: Casual Dresses

Price: $18.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Blooming Beauty Mini Dress
Have a cute brunch with your bffs as you bloom with beauty in this floral mini dress! It features an off the shoulder neckline with an overlay, a high waist seam, and a subtle ruffled seam at the hem. The black dress is composed of an unlined lightweight, flowy linen fabric with no stretch and showcases a pretty pink floral print.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

Style Number/Barcode: 05102-3981

Category Name: Casual Dresses

Price: $10.00 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Groovy Gal Striped Cutout Mini Dress
When your dress is the moment, this one’s got that groovy energy! The bold bell sleeves and plunging neckline were made for concerts, bright lights, and dance floors.

Fit & Features
- Striped texture knit fabric, soft stretchy knit lining
- Plunging V-neckline with half hoop insert
- Bell long sleeve
- Side cutouts and open back
- Bodycon silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000118

Category Name: Casual Dresses

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Back In Basics Mini Dress
Fall back on basics for an effortlessly trendy look! This ivory mini dress features a sleeveless strapless bodice, a square neckline, and a short, curve hugging fit. The basic dress is composed of a sheer knit fabric with a full knit lining and 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: 05102-3971

Category Name: Casual Dresses

Price: $10.00 $27.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fiercely Wild Mini Dress
You're fiercely wild, so you need a dress to match! This mini dress features a sleeveless bodice, spaghetti straps, a scoop neckline, and a short, flattering fit. The dress is composed of a lined knit fabric and offers plenty of stretch and a curve hugging style. Zipper not included.

Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.

Style Number/Barcode: 05102-3946

Category Name: Casual Dresses

Price: $9.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Denim For Days Mini Dress
We're living for denim this season! Slay any day in this cute denim dress that features a scoop neckline, adjustable narrow straps and a matching scoop back. The curve hugging mini length silhouette features faded accents to create a pretty contrast! Dress is composed of a double lined denim fabric that offers a moderate stretch.
Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.

Style Number/Barcode: 05102-3952

Category Name: Casual Dresses

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Casually Chic Maxi Dress
This black maxi dress is the perfect base piece to dress up or down for a casually chic look! Dress features a scoop neckline, adjustable spaghetti straps, and a comfortable slim fit. Dress includes a full lining and is composed of a soft, lightweight knit fabric that offers a moderate stretch.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05102-3931

Category Name: Casual Dresses

Price: $11.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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