Casual Dresses

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STYLE SPOTLIGHT

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Everyday Ease: Casual Dresses for Cool-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.

Laid-Back & Versatile

Knit, ribbed, and sweater dresses bring comfort and style to crisp fall 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 burgundy 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!

  • Steal The Spotlight Leopard Slit Midi Dress

    Steal the spotlight looking so fierce in this leopard midi dress! It features a sleeveless V-neckline, spaghetti straps, a flowy midi-length hem, and a front slit perfect for showing off some skin. Style with a pair of strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Midi-length hem, flowy silhouette
    • Front slit
    • Leopard print
    • Crepe knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4306

    Category Name: Casual Dresses

    Price: $19.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual-Chic Moment Mini Dress

    Have a stylish casual-chic moment in this ribbed knit mini dress. It features a crew neckline, long fitted sleeves, a trendy wrap tie-front design, and a short, form-hugging silhouette. Complete the look with heeled booties.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Wrap tie-front design
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4298

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Classic Chic Shirt Dress

    This classic chic mini shirt dress is everything you need and more. It features a collar, a plunging V neckline with lace-up ties, long sleeves with buttons to cuff, a high waist seam, and a mini-length silhouette. The dress is composed of a woven fabric with no stretch. Complete look with thigh-high boots and a cabby hat. 

    Fit & Features

    • Collar, V-neckline
    • Lace-up front 
    • Long sleeves, buttoned cuffs
    • High waist seam 
    • Mini length silhouette
    • Woven fabric 
    • Form hugging fit, minimal stretch, runs true to size 

    Style Number/Barcode: 05101-1464

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sporty Babe Hooded Mini Dress

    Achieve that trendy sporty babe look with this casual ribbed knit mini dress. It features a hoodie, a high neckline with front drawstrings, long sleeves, ruched side detailing, and a short, curve-hugging silhouette. Style this dress with cute sneakers.

    Fit & Features

    • Hoodie
    • High neckline, front adjustable drawstrings
    • Long fitted sleeves
    • Ruched sides, adjustable drawstrings
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4324

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Embrace The Chill Mock Neck Sweater Tunic

    Embrace the chill in style! This sweater tunic features a sleeveless, mock neck design on a form-fitting silhouette and mini-length hem. Composed of a soft eyelash knit fabric with a moderate stretch. Complete the look in an oversized blazer.

    Fit & Features

    • Sleeveless, mock neck
    • Form-fitting silhouette
    • Mini-length hem
    • Soft eyelash knit fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1113

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Born to Be Bold Lace Leopard Maxi Dress

    This curve-hugging maxi brings the heat with sultry lace, sheer mesh, and sky-high slits—made for nights when playing it safe isn't on the mood board!

    Fit & Features

    • Leopard print, mesh fabric, stretchy knit lining
    • Lace sweetheart neckline, lace bust, lace shoulder straps
    • High side slits
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000265

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L, XS, XL

  • Wild At Heart Brushed Knit Leopard Mini Dress

    Showcase your wild side in a mini dress that makes a fierce impression! The dress features a leopard print, a crew neckline, long sleeves, ruched drawstrings, and a mini-length silhouette with a rounded hem. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a moto and ankle booties. 

    Fit & Features

    • Crew neckline
    • Long sleeves
    • Ruched drawstrings
    • Leopard print
    • Mini length silhouette
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4263

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Everyday Plaid Mini Dress

    Create an elevated everyday outfit with this chic plaid mini dress! It features an on-trend square neckline, long sleeves, and a short, form-hugging fit. Style this dress with an oversized faux leather blazer and ankle booties.

    Fit & Features

    • Square neckline
    • Long fitted sleeves
    • Mini-length, form-fitting silhouette
    • Plaid print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4228

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Twist Long Sleeve Midi Dress

    The twist back on this midi dress is pretty chic! It features long sleeves, a crew neckline, and a form-fitting silhouette. The dress is composed of a ribbed knit fabric with a moderate stretch. Perfect for styling with suede booties and a statement bracelet.

    Fit & Features

    • Long fitted sleeves
    • Crew neckline
    • Twisted open back detail
    • Midi-length hem
    • Form-fitting silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1075

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Moves Ruched Mini Dress

    Make chic moves in this curve-hugging mini dress! It features a trendy mock neckline, long sleeves, a sultry cutout above the bust, ruched detailing down the sides, and a short, form-fitting silhouette. Style this dress with sleek hoop earrings.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Cutout above the bust
    • Ruching down the sides
    • Mini-length, form-fitting silhouette
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4144

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fiercely Bold Dragon Graphic Mini Dress

    Keep it fiercely bold with a mini dress that slays! The dress features a V-neckline, slashed detailing, an image of a dragon, text that reads: "Free Soul", long sleeves, and a mini-length silhouette. The dress is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a moto jacket and booties.  

    Fit & Features

    • V-neckline
    • Slashed distressing 
    • Image of dragon 
    • "Free Soul" in black text
    • Long sleeves
    • Mini length silhouette
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 06002-1048

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Totally Tie-Dye Mock Neck Dress

    You'll tie-dye for this mock neck dress featuring long sleeves and a mini-length hem. The dress is composed of a ribbed knit fabric with a moderate stretch. Style with edgy booties.

    Fit & Features

    • Long fitted sleeves
    • Mock neckline
    • Tie-dye pattern
    • Bodycon silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4206

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Silhouette Ribbed Knit Mini Dress

    Create a chic silhouette in this curve-hugging mini dress! It features a wrap front and back design with a V-front and back, long fitted sleeves, a high waist seam, and a mini-length fit. The ribbed knit fabric offers plenty of stretch. Style this dress with cute mules.

    Fit & Features

    • Wrap front and back, V-front and back
    • Long fitted sleeves
    • High waist seam
    • Short, form-fitting silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-0993

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Back To Basics Turtleneck Mini Dress

    Your head-to-toe look needs this turtleneck dress as a base for creating fab looks! It features fitted long sleeves and a short-length hem. This dress is composed of crepe-lined fabric with a moderate stretch. Style with a duster coat. 

    Fit & Features

    • Fitted long sleeves
    • Turtleneck design
    • Bodycon silhouette
    • Short-length hem
    • Crepe-lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4299

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rocker Babe Slashed Mini Dress

    Rock on babe in a tee that shows off your edgy side! The mini dress features a crew neckline, short sleeves, a bold rock-inspired graphic, a slashed design at the back, and a mini-length silhouette. The dress is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with combat boots and a swag chain belt. 

    Fit & Features 

    • Crew neckline 
    • Short sleeves
    • Rock-inspired graphic 
    • Slashed design at back 
    • Mini length silhouette
    • Cotton knit fabric 
    • Form hugging fit, moderate stretch, runs true to size 

    Style Number/Barcode: 06002-1027

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Basic Mock Neck Mini Dress

    This mini dress is the perfect day-to-night style! It features long sleeves, a mock neckline, and a bodycon silhouette designed to accentuate your curves. Complete the look with a necklace.

    Fit & Features

    • Long fitted sleeves
    • Mock neckline
    • Bodycon silhouette
    • Mini-length hem 
    • Runs true to size

    Style Number/Barcode: 05102-4281

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shirr Thing Long Sleeve Mini Dress

    This mini dress is sure to be a hit for your closet! It features long fitted sleeves, a mock neck, and a side shirring detail that shapes the high-low short hem. The brushed knit fabric offers a moderate stretch. Style with an oversized jacket.

    Fit & Features

    • Long sleeves
    • Mock neck
    • Side shirring detail
    • Bodycon silhouette
    • High-low mini hem
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4139

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daring Chic Cutout Mini Dress
    Dare to go bold with a dress that is anything but basic! The dress features a collared neckline, a multi-button down front, long sleeves, dual waist cutouts, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear heels and a crossbody

     

    Fit & Features

    • Collared neckline
    • Multi-button down front
    • Long sleeves
    • Dual waist cutouts
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4276

    Category Name: Casual Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Casual Slay Ruched Midi Dress

    You'll casually slay in this basic chic midi dress with elevated details. It features a mock neckline, long fitted sleeves, a curve-hugging silhouette, and a front slit with ruching. Style this dress with trendy clear mules.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Form-fitting silhouette
    • Front slit, ruching
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4284

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Eyes On You High Slit Maxi Dress

    Giving "I didn’t come to play, I came to slay" energy. With a draped neckline, leggy side slit, and flattering ruching—this dress is a total scene-stealer from cocktail hour to afterparty.

    Fit & Features

    • Soft knit fabric with stretch, full knit lining
    • Draped cowl neckline with adjustable spaghetti straps
    • Side slit
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000059

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Totally Fab Ribbed Mini Dress

    Keep your look totally fab in a mini dress that keeps it effortlessly chic! The dress features a sleeveless V-neckline, bungee spaghetti straps, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless V-neckline 
    • Bungee spaghetti straps
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06002-1050

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Sultry And Stunning Mini Dress

    You'll look simply sultry and stunning in this lightweight knit mini dress! It features a strappy cross-front design with a V-neckline, long fitted sleeves, an open back with a strappy cross-back design, and a short, curve-hugging fit. Style this dress with clear mules.

    Fit & Features

    • Front and back cross-strap designs
    • V-neckline
    • Open back
    • Long fitted sleeves
    • Mini-length, form-fitting silhouette
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4289

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Ribbed Knit High Slit Midi Dress

    Channel effortless style while looking chic in a knit dress! The dress features a mock neck, long sleeves, an asymmetrical high side slit, and a midi-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with ankle booties and a moto jacket.

    Fit & Features

    • Mock neck 
    • Long fitted sleeves
    • Asymmetrical high side slit
    • Midi-length silhouette
    • Ribbed knit fabric
    • Form-hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 06005-1174

    Category Name: Casual Dresses

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Drawn To Glam Ruched Mini Dress

    Get drawn to this fab dress that creates a head-turning moment. The dress features a mock neck, long sleeves, a ruched drawstring, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and dainty rings.

    Fit & Features

    • Mock neck 
    • Long fitted sleeves
    • Ruched drawstring
    • Mini-length silhouette
    • Smooth knit fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size 

    Style Number/Barcode: 05102-4230

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale