Casual Dresses

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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!

  • Effortless Flowy A-Line Mini Dress

    Get an effortless look in this flowy boho-chic mini dress. It features a sleeveless subtle square neckline, adjustable spaghetti straps that lead to a cross-back design, a short A-line silhouette, and a drop hem with a cute ruffle detail. Style this dress with your fave pair of wedges.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Cross-back design
    • Mini-length, A-line silhouette
    • Drop hem, ruffle detail
    • Double-lined gauze fabric
    • Runs true to size

    Style Number/Barcode: 05102-3099

    Category Name: Casual Dresses

    Price: $20.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trend Moment Lace-Up Bodycon Midi Dress

    Have your trending moment in this midi dress! It's designed to hug your curves in a bodycon silhouette while the front lace-up adds a playful touch to your day or night look.

    Fit & Features

    • Knit fabric with moderate stretch
    • Square neckline
    • Lace-up front bust
    • Spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6072

    Category Name: Casual Dresses

    Price: $9.97

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M

  • Sporty-Chic Knit Mini Dress

    Get a sporty-chic style with this adorable knit mini dress. It features a collared V-neckline with a zip-front, short sleeves, and a mini-length, curve-hugging silhouette. The lined knit fabric offers plenty of stretch. Complete the look with trendy mules.

    Fit & Features

    • Collared V-neckline, zip-front
    • Short sleeves
    • Mini-length hem
    • Form-hugging fit
    • Lined knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4152

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Denim Dreams Lace-Up Mini Dress

    Keep it dreamy with a denim mini dress that elevates your look! The dress features a sleeveless scoop neckline, spaghetti straps that lead to a lace-up back, vertical seams, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Lace-up back, lower back zipper and hook and eye closure
    • Vertical seams
    • Mini-length silhouette
    • Denim fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4089

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ravishing Florals Ruched Mini Dress

    Stun with ravishing florals in a pretty mini dress! The dress features a sleeveless V-neckline, adjustable spaghetti straps, dual ruching that runs from the bodice to hem, a ditsy floral print, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Dual ruching
    • Ditsy floral print
    • Mini length silhouette
    • Lined mesh fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4151

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sweet Ruffled Cutout Skater Dress

    Keep it so sweet with a charming ruffled skater dress! The dress features an off-the-shoulder neckline, a smocked bodice with a ruched drawstring, long sleeves, a sexy cutout at the midriff, and a tiered ruffled skater silhouette. The dress is composed of a lightweight gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with sandals

    Fit & Features

    • Off-the-shoulder neckline 
    • Smocked bodice with a ruched drawstring
    • Long sleeves, elastic cinched hems
    • Cutout at the midriff 
    • Tiered ruffle skater skirt
    • Gauze knit fabric, relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2486

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Vibes Off-The-Shoulder Floral Mini Dress

    Bring those sweet vibes with a pretty mini dress that is perf for your next date night! The dress features a ditsy floral print, an off-the-shoulder neckline, a sweetheart bust with a mini tie-front, short puff sleeves, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.

    Fit & Features

    • Off-the-shoulder neckline
    • Sweetheart bust, mini tie-front 
    • Short puff sleeves, ruffled hems
    • Mini-length silhouette
    • Brushed knit fabric, side ruched detailing
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4154

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless And Pretty A-Line Mini Dress

    You'll look so effortlessly pretty in this adorable mini dress that is perf for a weekend brunch. It features a square neckline, a low square back design, short puff sleeves, a flattering high waist, and a short tiered skirt with an A-line silhouette. Style this dress with hoop earrings and cute wedges.

    Fit & Features

    • Square neckline
    • Low square back
    • Short puff sleeves, cinched hems
    • High waist
    • Mini-length A-line silhouette, tiered design
    • Cotton fabric
    • Runs true to size

    Style Number/Barcode: 05102-4296

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Glam Ribbed Knit Maxi Dress

    Keep it casually glam with a maxi dress that is perf to dress up or down for brunch! The dress features a sleeveless V-neckline, a cute tie-front, adjustable spaghetti straps, a button-down front, and a maxi-length silhouette accented with a high center slit. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges and a floppy hat.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, tie-front 
    • Button-down front
    • Maxi-length silhouette, high center slit
    • Ribbed knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1347

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hooked In Denim Mini Dress

    Get hooked in with this cute mini dress that is part glam, part casual! The dress features a strapless sweetheart neckline, hook and eye front closures, corset seams, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.

    Fit & Features

    • Strapless sweetheart neckline
    • Hook and eye front closures
    • Corset seams
    • Mini-length silhouette
    • Denim knit fabric
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4081

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • What's The Scoop Ribbed Knit Mini Dress

    Serve up a stylish look with a pretty mini dress! The dress features a sleeveless scoop neckline, a tie-front at the bust, bungee spaghetti straps, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with plenty of stretch. Complete look with mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Tie-front at the bust
    • Bungee spaghetti straps
    • Mini-length silhouette
    • Ribbed knit fabric 
    • Form-hugging fit, plenty of stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4162

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Boho Vibes Maxi Dress

    Bring on the stunning boho vibes with this effortlessly chic maxi dress. It features a sleeveless V-neckline, spaghetti straps, a tie-front bust with a sexy waist cutout, and a curve-hugging floor-length silhouette with a sultry thigh-high side slit. Style this dress with trendy earrings and cute mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Tie-front bust, waist cutout
    • Floor-length, form-hugging fit
    • High side slit
    • Knit fabric, paisley print
    • Runs true to size

    Style Number/Barcode: 05102-4159

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cut Above The Rest Ribbed Knit Mini Dress

    Step into a league of your own with a ribbed knit mini dress! The dress features a one-shoulder neckline, an asymmetrical midriff cutout, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging with a moderate stretch. Complete look with mules

    Fit & Features

    • One-shoulder neckline
    • Asymmetrical midriff cutout 
    • Mini length silhouette
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-1212

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Girly Vibes Gingham Babydoll Dress

    Keep it super girly with a pretty babydoll dress that brings those good vibes this season! The dress features a sweetheart neckline, quarter-length balloon sleeves, a gingham print, and flared mini-length silhouette with a ruffled hem. The dress is composed of cotton knit fabric that offers a relaxed fit with a moderate stretch. Complete look with sandals

    Fit & Features 

    • Sweetheart neckline
    • Quarter-length balloon sleeves
    • Gingham print
    • Ruffles
    • Mini length silhouette
    • Cotton knit fabric, additional knit lining
    • Relaxed fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-3064

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Sunsets Maxi Dress

    Your dream vacation is calling! Pack this stunning tropical floral printed maxi dress for a gorgeous look. It features an off-the-shoulder square neckline, a fitted smocked bodice, short ruffled sleeves, a tie-front accent to highlight the waist, and a flowy, floor-length silhouette with a wrap-front design. Style this dress with sleek hoop earrings and strappy sandals.

    Fit & Features

    • Off-the-shoulder square neckline
    • Fitted smocked bodice
    • Short ruffled sleeves
    • Tie-front detail
    • Flowy, floor-length silhouette, wrap-front design
    • Woven fabric, tropical floral print
    • Runs true to size

    Style Number/Barcode: 05102-4068

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Barely Blushing Floral Mini Dress

    Soft girl, but make it sultry. This floral mini dress clings in all the right ways, with delicate straps and a dreamy texture that feels flirty but effortless!

    Fit & Features

    • Floral print, burnout texture, mesh fabric, stretchy knit lining
    • Scoop neckline
    • Adjustable spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000165

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Keepin' It Cute And Casual Denim Dress

    Keep your everyday look cute and casual in this must-have denim dress! It features a sleeveless square neckline, thin shoulder straps, a complete button-down front, and a short, curve-hugging silhouette. Style this dress with sneakers and chic shades.

    Fit & Features

    • Sleeveless square neckline
    • Thin shoulder straps
    • Complete button-down front
    • Mini-length, form-hugging fit
    • Denim fabric
    • Runs true to size

    Style Number/Barcode: 05102-0500

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wrapped In Florals Chiffon Skater Dress

    Wrap yourself in a fab floral dress this season for your next brunch! The dress features a floral print, plunging V-neckline, ruffled cap sleeves, an open back with a tie-back strap, and a skater silhouette with an asymmetrical ruffled trim. The dress is composed of a semi-sheer chiffon fabric that offers a form hugging fit with minimal stretch. Complete look with sandals and duster earrings. 

    Fit & Features

    • Wrap V-neckline
    • Ruffled cap sleeves
    • Open back with tie back ties
    • Skater silhouette
    • Ruffle trim
    • Floral print
    • Form hugging fit, minimal stretch, runs true to size

    Style Number/Barcode: 05101-1103

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Getaway Mesh Mini Dress

    Get ready for your island getaway in this adorable mesh mini dress! It features a sleeveless square neckline, adjustable spaghetti straps, ruched detailing, a short, curve-hugging silhouette, and an all-over tropical palm leaf print. Style this dress with strappy sandals.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Ruching
    • Mini-length, form-hugging fit
    • Sheer mesh fabric, tropical palm leaf print, knit lining
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4133

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Eyes On Me Floral Eyelet Maxi Dress

    Draw all eyes on you in this bold maxi dress! The dress features a vibrant floral print, an eyelet pattern, a sleeveless V-neckline, spaghetti straps, dual waist cutouts, and a maxi-length silhouette with a flared hem. The dress is composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch. Includes a mini skirt-length knit lining. Complete look with sandals and hoops. 

    Fit & Features

    • Floral print 
    • Sleeveless V-neckline, spaghetti straps
    • Dual waist cutouts
    • Eyelets
    • Maxi length silhouette
    • Lightweight woven fabric, mini skirt knit lining
    • Form hugging fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-4123

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Sunsets Asymmetrical Midi Dress

    Take in those tropical vibes with a midi dress that will have you vacay-ready! The dress features a tropical palm leaf print, a sleeveless scoop neckline, adjustable spaghetti straps that cross at the back, and an asymmetrical hem. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with hoops and sandals

    Fit & Features

    • Tropical palm leaf print
    • Sleeveless scoop neckline
    • Adjustable spaghetti straps, cross at back 
    • Midi length silhouette
    • Asymmetrical hem 
    • Smooth knit fabric, form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4111

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fabulous Floral Puff Sleeve Mini Dress

    Keep your look fresh and fab in this adorable floral printed mini dress! It features a sweetheart neckline with a tie at the bust, short puff sleeves, and a short, curve-hugging silhouette. Style this dress with strappy sandals and chic sunnies.

    Fit & Features

    • Sweetheart neckline, tie at the bust
    • Short puff sleeves, elastic cinched hems
    • Mini-length, form-hugging fit
    • Brushed knit fabric, plenty of stretch
    • Ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-4125

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Carefree Bohemian Chic Cutout Maxi Dress

    Channel a carefree vibe with a maxi dress that is so bohemian chic! The dress features a bohemian print, a sleeveless V-neckline, spaghetti straps, dual cutouts at the waist, and a maxi-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit. Complete look with sandals and tassel earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Dual cutouts at the waist
    • Knit fabric, bohemian print
    • Maxi-length silhouette
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4063

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Dream Lace-Up Maxi Dress

    Get carried away in this tropical maxi dress that will have you ready for that cabana life! The dress features a tropical floral print, a sleeveless V-neckline, a double row of spaghetti straps that cross at the back, a lace-up back, and a maxi-length silhouette with a high side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and hoops. 

    Fit & Features

    • Tropical floral print
    • Sleeveless V-neckline
    • Double-row of spaghetti straps, cross at back
    • Lace-up back
    • High side slit
    • Maxi length silhouette
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-2104

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free