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.

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Everyday Ease: Casual Dresses for Transitional-Weather Plans

From weekend brunches to spontaneous coffee runs, Windsor’s casual dresses deliver easygoing style with just the right amount of polish. These effortlessly chic looks move with you—whether you’re off to the farmers’ market or catching golden hour with friends. Layer your favorite long sleeve to keep the chill out, or pick your Windsor shoes and accessories, and you're ready for the day.

Laid-Back & Versatile

Knit, ribbed, crochet, and sweater dresses bring comfort and style to cooler days. Slip into playful mini dresses, flowy midi styles, or long casual dresses in warm neutrals, jewel tones, and classic plaids. T-shirt and tunic dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.

Chic from Day to Night

Swap sneakers for ankle boots to take your favorite midi dress from errands to evening hangs. A flowy maxi in nuetral or black adds relaxed elegance—just add a faux leather jacket and heeled booties for an effortless finish.

Ready to refresh your everyday looks? Explore Windsor’s full collection of casual dresses online, in-app, or in-store.

What Makes a Dress Casual?

Casual dresses are defined by their effortless styling, comfortable fabrics, and laid-back details. Fabrication plays a key role—soft knits, cotton blends, and breezy silhouettes naturally create an easygoing look. Prints like ditsy florals or neutral-tone patterns, such as snake print, also make great everyday choices. Knit and sweater dresses are perfect for relaxed settings, whether you're heading to work or dressing up for a casual date night.

Styling is just as important in making a dress feel casual. Swap heels for sneakers, lug boots, or strappy sandals to instantly dress down your look. Layering is another effortless way to create a relaxed aesthetic—throw on a denim jacket, cropped sweater, or oversized cardigan for a cool, laid-back vibe. Details like drawstrings, button fronts, and tie accents also add to the casual appeal. Accessories, makeup, and hair styling can further influence the look, so opt for dainty jewelry, natural waves, or a simple ponytail to complete your effortlessly stylish outfit.

How Do I Style a Dress Casually?

Styling a dress casually is all about choosing relaxed layers and accessories that balance comfort with fashion. Denim jackets, graphic tees, scrunchies, crossbody bags, and sneakers all contribute to an effortlessly cool aesthetic. Try pairing a ruched mini dress with a lariat necklace and chunky sneakers for a sporty yet chic look. A basic knit midi dress layered under a cropped denim jacket with slides is perfect for a casual-chic feel.

For road trips or weekend getaways, maxi and midi dresses offer an easy styling solution. Layer a lightweight sweater over a flowy maxi or knot a t-shirt at the waist for a trendy, carefree vibe. Combat boots can add an edgy touch, while simple strappy sandals keep the outfit light and airy. No matter your style, Windsor has a versatile collection of casual dresses and must-have accessories to complete your look. Need styling help? Visit us in-store, and our expert stylists will help you find your perfect outfit!

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
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:
- Ships Free
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:
- Clearance
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:
- Clearance
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:
- Ships Free
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:
- Ships Free
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:
- Ships Free
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:
- Ships Free
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:
- Clearance
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
Out Of Town Striped Mini Dress
Head out of town in this stylish striped mini dress for an effortlessly cute look everywhere! Designed with a trendy twisted bust and a bodycon mini-length silhouette that perfectly flaunts your figure. Style with sandals!

Fit & Features
- Striped pattern, stretchy knit fabric
- Twist sweetheart strapless neckline
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000029

Category Name: Casual Dresses

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
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
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
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:
- Ships Free
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:
- Ships Free
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:
- Ships Free
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
Serving Curves Keyhole Maxi Dress
Serving curves and confidence—this dress eats every time. The keyhole cutout and body-hugging silhouette? A certified head-turner for nights that don’t end early.

Fit & Features
- Stretchy textured knit fabric
- Scoop neckline with spaghetti straps
- Front keyhole cutout at bust
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000166

Category Name: Casual Dresses

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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Casual Dresses