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.

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.

Babe In Crochet Skater Dress
This babe is ready for summer in this flirty blue crochet dress! It features a crochet bodice with a plunging V neckline, adjustable shoulder straps that lead to a cute tie back detail, and a flattering wide empire waist panel that leads to a flowy gauze skirt. Includes a knit lining.
Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small.

Style Number/Barcode: 05102-3842

Category Name: Casual Dresses

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Spring Stunner Maxi Dress
Lace up in this pretty dress for those spring time vibes! It features a white hue, a sleeveless bodice, a V neckline, adjustable narrow straps, a tie back accent and a lower back keyhole. The waist features an unlined crochet floral detail and leads to a sweeping maxi floor length skirt. Dress is composed of a combination crochet and linen fabric that 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.

Style Number/Barcode: 05102-0052

Category Name: Casual Dresses

Price: $21.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Romantically Crochet Maxi Dress
Revel in romance this summer in this flowy purple maxi dress! It has a plunging neckline, narrow shoulder straps that lead to an open back paired with crochet panels, a gathered bust, a sheer crochet waist, and a flowy floor length skirt with a short lining. Includes a hidden back zipper closure.
Model is 5'8 with a 32" bust, 23" waist, and 36" hips. She is wearing a size small.

Style Number/Barcode: 05102-3835

Category Name: Casual Dresses

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Why You Linen Skater Dress
No lie, this black button up skater dress will give you a casually classy look this summer! Dress features a V neckline that leads to a row of front buttons, short sleeves, a gathered high waist seam, front pockets, and a comfortable slim fit throughout. Dress is composed of a lined linen fabric with no stretch.
Model is 5'8.5" with a 32" bust, 24" waist, and 35" hips. She is wearing a size small.

Style Number/Barcode: 05102-3832

Category Name: Casual Dresses

Price: $10.00 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Lovely Little Linen Dress
You'll look like a total beauty in this lovely little linen dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline created by a wrap front, a side tie detail, a back zipper and hook and eye closure, and a wrap skater skirt with a faux button down front. The olive green dress is composed of a linen fabric with a short linen lining and offers a flowy fit.
Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

Style Number/Barcode: 05102-3831

Category Name: Casual Dresses

Price: $10.00 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Laced Up In Denim Dress
Lace-up in this trendy denim dress to make a stylish statement! This dress features a sleeveless, plunge v-neck, adjustable spaghetti straps, a trendy lace-up front detail, and a curve hugging, midi silhouette. Complete the look with simple block heels.

Fit & Features
- Sleeveless, plunge v-neck
- Adjustable spaghetti straps
- Back zipper closure
- Lace-up front
- Curve-hugging silhouette
- Midi-length hem
- Denim fabric, moderate stretch, fits true to size
Style Number/Barcode: 05102-0291

Category Name: Casual Dresses

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Just Own Knit Midi Dress
Own this sleek and sexy burgundy midi dress! It features a one shoulder neckline, a belted waist with a large O-ring accent, and a body-hugging fit. Dress is composed of a lined, smooth knit fabric with a moderate stretch.

Style Number/Barcode: 05102-3788

Category Name: Casual Dresses

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Pretty Plaid Knit Mini Dress
You'll be super pretty in plaid in this knit mini dress! It has a sleeveless bodice, adjustable spaghetti straps that lead to a straight across back, a rounded neckline, and a form hugging style. The chic dress is composed of a soft knit fabric that offers plenty of stretch and showcases a glen plaid pattern with a prominent hue of red.
Model is 5'7 with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05102-3761

Category Name: Casual Dresses

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Floral Feels Maxi Dress
Get all those floral feels with this beautiful printed maxi dress! It features a sleeveless bodice, spaghetti straps that cross in the back, a square neckline, a high side slit, and a long, fitted maxi length. The black floral printed dress is composed of a soft knit fabric that offers plenty of form hugging stretch.

Style Number/Barcode: 05102-3749

Category Name: Casual Dresses

Price: $13.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Beautifully Buttoned Skater Dress
Beautifully button up your look with this adorable olive green skater dress! It features flowy short sleeves, a plunging V neckline, a high waistband, an open back with a tie closure with tassel details, a tie back accent, a hidden back zipper and hook and eye closure, and faux buttoned detailing. The dress is composed of a woven gauze fabric with a short lining, pretty pleats, and a flirty, flowy fit.
Model is 5'9" with a 31.5" bust, 24.5" waist and 35.5" hips. She is wearing a size small.

Style Number/Barcode: 05102-3748

Category Name: Casual Dresses

Price: $10.00 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Floral Fusion Midi Dress
Infuse your spring looks with pretty florals! This midi dress features a sleeveless bodice, a V neckline and narrow cross straps. Dress is composed of a smooth slate hued knit fabric adorned with a multi hued floral print. Garment 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: 05102-3743

Category Name: Casual Dresses

Price: $10.00 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral To The Maxi Dress
This gorgeous printed maxi dress is floral to the max! It features an off the shoulder neckline, short flutter sleeves, a square neckline, a stretchy smocked top, a tie front waist, and a high low wrap front. The mauve dress is composed of a woven fabric with a flowy fit.
Model is 5'8" with a 32" bust, 24.5" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05102-3742

Category Name: Casual Dresses

Price: $17.97 $45.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Such A Sweetheart Mini Dress
You're such a sweetheart, and you'll look totally cute in this adorable little black mini dress! It features sheer short ruched sleeves, a low sweetheart neckline with a tie front accent, a smocked back with a hidden zipper and hook and eye closure, and a flirty ruffle hem. The dress is composed of a linen fabric and includes a lining.

Style Number/Barcode: 05102-3720

Category Name: Casual Dresses

Price: $17.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Crochet Cutie Maxi Dress
Keep it cute in crochet! This no fuss maxi dress features a pewter hue, a sleeveless crochet bodice, a V neckline and adjustable narrow straps that lead to an open back design. Her relaxed fit bodice leads to an elongating maxi length skirt. Dress is composed of a lined lightweight woven fabric that offers minimal stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

Style Number/Barcode: 05102-3572

Category Name: Casual Dresses

Price: $10.00 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flowy Vibes Maxi Dress
Get those pretty flowy vibes this spring with this off the shoulder maxi dress! It features short ruffle sleeves, a square neckline, a hidden back zipper and hook and eye closure, a tie front belt, two front slits, and a long maxi length. The mauve dress is composed of a lightweight crepe fabric with a short knit lining.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

Style Number/Barcode: 05102-3571

Category Name: Casual Dresses

Price: $10.00 $45.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish To The Maxi Dress
Be a fab fashionista and stylish to the max in this red maxi dress! It features a sleeveless bodice, a strapless square neckline, a high waist seam, slanted front pockets, pleated details, and a long, maxi fit. The dress is composed of a knit fabric and offers moderate stretch and a flowy, relaxed fit.
Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

Style Number/Barcode: 05102-3557

Category Name: Casual Dresses

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Basic Scoop Mini Dress
Basic never looked so good in this essential mini dress! It features a light blue color, a scoop neckline, tank-like straps and a mini length silhouette. Dress is composed of a double lined smooth knit fabric that offers a form hugging fit with a moderate stretch.
Model is 5'7" with a 34" bust, a 24" waist, and 36" hips. She is wearing a size small.

Style Number/Barcode: 05102-3350

Category Name: Casual Dresses

Price: $13.91 $23.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Basic Essentials Midi Dress
Sometimes less is more! This basic midi length can be kept casual or paired with accessories to dress it up!

Fits & Features
- Tank Shoulder Straps
- Scoop Neckline
- Midi Length Silhouette
- Soft Knit Composition I Fully Lined
- Curve Hugging Fit I Ample Stretch
Black & Ivory: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-3587

Category Name: Casual Dresses

Price: $24.90

Availability: Out of Stock
Product Badge:
- Clearance
On The Button Denim Mini
Streamlined and sweetly sophisticated, this lavender mini draws all eyes to you. Dress features a soft V neckline, button front, and adjustable spaghetti straps. Dress is made from a cotton-denim fabric and has minimal stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05102-0116

Category Name: Casual Dresses

Price: $16.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Second Look Open Back Dress
This LBD is all you need to make them take a second look! It features a sleeveless bodice, a scoop neckline, narrow straps that lead to a cross design, an open back and lattice strap accents. Dress is composed of a knit 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: 05102-0061

Category Name: Casual Dresses

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Button Down In Style Dress
Button down in style in this cute midi dress! The white dress features a square neckline, wide shoulder straps, a button down front, a tie waist belt, side pockets and a center high slit. Dress is composed of an unlined denim-like fabric that offers a form hugging 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: 05102-0059

Category Name: Casual Dresses

Price: $31.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunny Side Up Skater Dress
This mustard yellow skater sundress is a definite must-have for this season! It features a sleeveless bodice, adjustable spaghetti straps, a square neckline, a hidden back zipper and hook and eye closure, a high waist seam, and a wrap skater skirt with a chic side tie. The dress is composed of a woven fabric with no stretch.
Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small.

Style Number/Barcode: 05102-0054

Category Name: Casual Dresses

Price: $10.00 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Buttoned Up In Stripes Dress
Button up in stylish stripes! This pretty dress features a plunging V neckline, kimono sleeves, a cinching tie waist accent and a multi button down front with tortoise shell hued buttons that lead to an A-Line silhouette. The back features a matching plunging V shape, an adjustable bar strap detail and a hidden zipper closure. The all over stripe pattern features blue and white hues. Dress is composed of a lined gauze fabric that offers a relaxed fit with minimal stretch.

Style Number/Barcode: 05102-0040

Category Name: Casual Dresses

Price: $10.00 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Striped With Style Midi Dress
Get all striped with style with this adorable summer ready midi dress! It features a sleeveless bodice, a V neckline created by a wrap front, a partially stretchy and smocked back with a hidden zipper and hook and eye closure, a faux button down front, a waist tie, and a front slit. The mustard yellow dress is composed of lightweight woven fabric with no stretch and a short lining.
Model is 5'8" with a 33" bust, 24" waist and 33.5" hips. She is wearing a size small.

Style Number/Barcode: 05102-0032

Category Name: Casual Dresses

Price: $15.00 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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