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.

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
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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:
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Blossom In Florals Maxi Dress
Let your natural beauty shine through in this pretty maxi dress! It features a taupe hue, a sleeveless bodice, a plunging V neckline, narrow straps that cross at the back and a maxi length skirt with a high side slit. The all over floral print features blue with pink hues that are complemented with a green foliage.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small

Style Number/Barcode: 05102-3930

Category Name: Casual Dresses

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Tied With Style Mini Dress
Make your look all tied together with style with this summer ready mustard yellow mini dress! It features a sleeveless strapless bodice with a square neckline, a tie front belt, side ruched detailing, and a front envelope hem. The dress is composed of a crepe fabric with moderate stretch.
Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.

Style Number/Barcode: 05102-3919

Category Name: Casual Dresses

Price: $9.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Cute As A Button Mini Dress
You'll look cute as a button in this pretty mini dress! The dress features a blue hue, a sleeveless bodice, a square neckline, adjustable narrow shoulder straps, a button down side seam and a mini length silhouette. Dress is composed of a linen fabric that offers a form hugging fit with minimal stretch.
Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

Style Number/Barcode: 05102-3921

Category Name: Casual Dresses

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Button Knit Up Mini Dress
Button up in this adorable mini navy blue dress! It features a sleeveless bodice, spaghetti straps, a scoop neckline, a faux button down front, and a short, fitted look. The dress is composed of a ribbed knit fabric that offers plenty of stretch and a curve hugging style.

Style Number/Barcode: 05102-3915

Category Name: Casual Dresses

Price: $10.00 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Linen Beauty Midi Dress
Be a total beauty in linen with this chic midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline, a faux button down front, a back zipper and hook and eye closure, a back slit, and a full knit lining. The navy blue dress is composed of a woven linen fabric with no stretch.
Model is 5'9" with a 33" bust, 24" waist and 35.5" hips. She is wearing a size small.

Style Number/Barcode: 05102-3913

Category Name: Casual Dresses

Price: $18.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Bohemian Feels Maxi Dress
Get those boho vibes going in this summer ready maxi dress! It features an ivory hue, a sleeveless bodice, a plunging V neckline, sexy waist cut outs and narrow adjustable straps that lead to an open back design. The back features a smocked elastic band and a tie back accent. The waist leads to a sweeping maxi length silhouette accented with a high side slit. The navy blue bohemian design is perfectly complemented with the ivory background. Dress is composed of lightweight woven fabric that offers a relaxed fit with minimal stretch.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small

Style Number/Barcode: 05102-3878

Category Name: Casual Dresses

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Laced In Floral Maxi Dress
Lace yourself up in pretty florals! This blue maxi dress features a sleeveless bodice, a plunging V neckline and narrow straps that lead to an open back with lattice design. The relaxed fit bodice leads to a curve hugging maxi length silhouette. The all over rose print features white and pink hues for a perfectly spring look! Dress is composed of a smooth knit fabric that offers a form hugging fit with 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: 05102-3873

Category Name: Casual Dresses

Price: $10.00 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Flirty In Linen Mini Dress
Make your look fun and flirty with this adorable LBD! It features a sleeveless bodice, thick shoulder straps, a square neckline, a back zipper and hook and eye closure, a high waist seam, a faux button down front, and a flowy skater skirt. The black dress is composed of an unlined slightly sheer linen fabric with no stretch.
Model is 5'9" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

Style Number/Barcode: 05102-3866

Category Name: Casual Dresses

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Bloom With Beauty Maxi Dress
Be a stunning blooming beauty in this floral printed maxi dress!

Fits & Features
- V Neckline
- Spaghetti Straps
- Sheer Lace Back With Zipper I Elastic Back Cut-Out
- High Waist Seam
- Flowy, Maxi Length
- Sheer Chiffon Fabric I Knit Lining
- Relaxed Fit I Minimal Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
*Also available in Plus.
Style Number/Barcode: 05102-3887

Category Name: Casual Dresses

Price: $24.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Walk The Line Skater Dress
Step out and line it out in stripes! This pretty light blue dress features a plunging V neckline, tank-like straps, a cinching tie waist accent and a flaring skater skirt. The all over striped design is all you need for the perfect spring time look! Dress is composed of a linen fabric with a knit lining.
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

Style Number/Barcode: 05102-3843

Category Name: Casual Dresses

Price: $13.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Summer Vibes Gauzy Mini Dress
Feel the heat while keeping it cool in this gauzy olive skater dress. Dress features a deep V at front and back, side bar cutouts, an elasticated waist, and an all-over crinkle effect. Dress is made from a rayon fabric with moderate stretch. Dress is semi-sheer and unlined.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05102-3847

Category Name: Casual Dresses

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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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:
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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:
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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:
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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

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