Casual Dresses

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STYLE SPOTLIGHT

Cute Sweater 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!

  • Bold Stunner Cutout Mini Dress

    Create a bold moment in a chic mini dress that stuns! The dress features a scoop neckline, short puff sleeves, dual cutouts at the waist, and an A-line silhouette. The dress is composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch. Complete look with slides and hoops. 

    Fit & Features

    • Scoop neckline
    • Short puff sleeves
    • Dual cutouts at the waist
    • Mini length silhouette
    • Lightweight woven fabric
    • Form hugging fit, runs true to size

    Style Number/Barcode: 05102-4188

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Raise The Stakes High Slit Cutout Dress

    Raise the stakes in a bold maxi dress that dares to stun! The dress features a sleeveless halter neck with a racer bust, a sexy cutout at the midriff, ruching at the waist, and 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 hoops

    Fit & Features

    • Halter neck with racer bust
    • Cutout at the midriff
    • Ruching at waist
    • High side slit
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4108

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Double Take Paisley Cutout Mini Dress

    Make them take a double-take with a sexy mini dress that commands attention on your next GNO! The dress features a trendy paisley print, a halter neck, a twisted neck strap that allows you to customize the coverage of the bodice, cutout at the bodice, ruching, 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

    Fit & Features

    • Paisley print
    • Halter neck
    • Twisted neck strap, allows for adjustable coverage
    • Cutout at the bodice
    • Ruching 
    • Mini length silhouette
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4083

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Passion For Florals Asymmetrical Mini Dress

    Show off your passion for florals with a mini dress that brings the charm! The dress features a sleeveless V-neckline, bungee straps that cross at the back, a floral print, and an asymmetrical 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 clear mules and hoops. 

    Fit & Features

    • Sleeveless V-neckline
    • Bungee straps, cross at back
    • Floral print
    • Asymmetrical mini length silhouette
    • Smooth knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-2205

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Minimal Satin High Slit Mini Dress

    Keep it minimal and sleek with a mini dress that is perf to dress up for your next date night! The dress features a sleeveless V-neckline, adjustable spaghetti straps, and a mini side slit. The dress is composed of a satin fabric that offers a form hugging fit with minimal stretch. Complete look with rhinestone heels and statement earrings. 

    Fit & Features

    • Sleeveless V-neckline 
    • Adjustable spaghetti straps
    • Mini side slit
    • Satin fabric, additional knit lining 
    • Form hugging fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4254

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summertime Beauty Cutout Midi Dress

    Hey beauty! Get a gorgeous look perf for summertime in this stunning midi dress. It features a sleeveless halter neckline, dual waist cutouts, and a mid-length, form-fitting silhouette to hug your curves. Style this dress with strappy sandals.

    Fit & Features

    • Sleeveless halter neckline
    • Dual waist cutouts
    • Mid-length, form-hugging fit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4255

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beach Goddess Crochet Lace-Up Maxi Dress

    She’s giving beach goddess vibes from brunch to golden hour cocktails. This crochet maxi hugs your curves with a bodycon fit and an open lace-up back that’s totally Insta-worthy.

    Fit & Features

    • Crochet lined fabric
    • V-neckline
    • Spaghetti straps
    • Open lace-up back design
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000072

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L

  • Floral Feels Ruffled Mini Dress

    This pretty floral dress has us in our feels, bby! The dress features a floral print, an off-the-shoulder neckline with a ruffled popover, ruffled short sleeves, 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 wedges and a metal cuff. 

    Fit & Features

    • Ditsy floral print
    • Off the shoulder neckline
    • Ruffled popover, ruffled short sleeves
    • Mini length silhouette
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-2096

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Go With The Flow Smocked Maxi Dress

    Go with the flow in a casual maxi dress that keeps your look effortlessly chic! The dress features a sleeveless square neckline, a smocked bodice, halter neck ties, a triple-row bar strap design, and a flowy maxi length silhouette. The dress is composed of a lined gauze fabric that offers a relaxed fit with slight stretch. Complete look with wedges and a floppy hat

    Fit & Features

    • Sleeveless square neckline
    • Smocked bodice
    • Halter neck ties
    • Triple-row bar strap
    • Maxi length silhouette
    • Lined gauze knit fabric
    • Relaxed fit, slight stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1362

    Category Name: Casual Dresses

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Radiance Eyelet Mini Dress

    Radiate in a gorge floral mini dress for your next brunch date! The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of an eyelet knit fabric that offers a form hugging fit with minimal stretch. Complete look with mules and hoops. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ditsy floral print 
    • Mini length silhouette
    • Eyelet knit fabric 
    • Form hugging fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4091

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Crochet Cutie Linen Maxi Dress

    Keep it cute in a crochet maxi dress! The dress features a sleeveless V-neckline, a lined floral lace bodice, adjustable spaghetti straps, an unlined crochet waist, and a flowy maxi-length silhouette. The dress is composed of a linen fabric that offers a relaxed fit with minimal stretch. Complete look with wedges and hoops. 

    Fit & Features

    • Sleeveless V-neckline
    • Lined floral lace bodice
    • Adjustable spaghetti straps
    • Unlined crochet waist
    • Maxi length silhouette
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4184

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Wonder Ruffled Skater Dress

    Make em' awestruck with a pretty mini dress! The dress features a floral print, an off-the-shoulder neckline, ruffled off-the-shoulder straps, a mini tie-front accent at the bust, a smocked bodice, a tie waist belt, and a skater silhouette with a ruffled hem. The dress is composed of a lined chiffon fabric that offers a form hugging fit with minimal stretch. Complete look with wedges and butterfly earrings. 

    Fit & Features

    • Floral print
    • Off the shoulder neckline with ruffled shoulder straps
    • Smocked bodice, mini-tie front 
    • Tie waist belt
    • Skater silhouette
    • Chiffon fabric
    • Form hugging fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-4227

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picture Perfect Knit Mini Dress

    Create a picture-perfect moment in a cute mini dress! The dress features a scoop neckline, spaghetti straps, an exposed seam pattern, 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 heels and hoops

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Exposed seam pattern
    • Mini length silhouette
    • Smooth knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 05102-4180

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keep It Trendy Cutout Mini Dress

    Keep your look trendy and chic in this ribbed knit mini dress that is a summer staple! It features a sleeveless crew neckline, a front O-ring accent, dual waist cutouts, and a short, curve-hugging silhouette. Style this dress with sneakers for everyday wear, or cute mules for date night.

    Fit & Features

    • Sleeveless crew neckline
    • Front O-ring detail
    • Dual waist cutouts
    • Mini-length, form-hugging fit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4115

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simple And Sexy High-Slit Midi Dress

    Simple and sexy, this ribbed cotton midi dress can be dressed up or down. It features a sleeveless crew neckline, tank shoulder straps that lead to a cross-back design, a high side slit, and a mid-length, curve-hugging silhouette. Style this dress with sandals to keep it casual, or heels for a chic vibe.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Open back, cross-back design
    • High side slit
    • Mid-length, form-hugging fit
    • Ribbed cotton fabric, lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4213

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Chic Smocked Maxi Dress

    Capture those effortlessly chic vibes in this maxi dress! The dress features a square neckline, short sleeves, and a smocked bodice. The maxi length silhouette features a button-down center and a mini skirt length lining. The dress is composed of a smocked knit fabric and lightweight woven fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and a floppy hat

    Fit & Features

    • Square neckline, short sleeves
    • Smocked bodice
    • Button-down center
    • Maxi length silhouette
    • Mini skirt length knit lining
    • Smocked knit, lightweight woven fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4113

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Romance Asymmetrical Mini Dress

    Fall in love with this dreamy tropical printed mini dress that is a must-have for summer vacays. It features a sleeveless V-neckline, adjustable spaghetti straps, side ruched detailing, and a mini-length, curve-hugging silhouette with a trendy asymmetrical hem. Style this dress with cute mules.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Side ruched detailing
    • Short, form-hugging fit
    • Asymmetrical hem
    • Brushed knit fabric, plenty of stretch, tropical palm leaf print
    • Runs true to size

    Style Number/Barcode: 05102-1857

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Eyes On Me Eyelet Mini Dress

    Draw all eyes on you in this pretty mini dress! The dress features a sleeveless square neckline, spaghetti straps, a ruched mini length with drawstring, and an eyelet pattern throughout. The dress is composed of a lined lightweight woven fabric that offers a form hugging fit with minimal stretch. Complete look with block heels and a straw tote

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruched drawstring
    • Eyelet pattern
    • Mini length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 05102-1381

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Put A Ring On It Cutout Mini Dress

    Put a ring on this cute mini dress that is a must for your next night out! The dress features a plunging sleeveless V-neckline, dual cutouts at the waist, an O-Ring at the center of the bodice, 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

    Fit & Features

    • Sleeveless V-neckline
    • Cutouts at the waist
    • O-Ring
    • Mini length silhouette
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-2139

    Category Name: Casual Dresses

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Vibes Sleeveless Mini Dress

    Showcase a gorgeous glow in this sunset-hued tie-dye mini dress! It features a sleeveless scoop neckline, tank shoulder straps, and a short, curve-hugging silhouette. The brushed knit fabric offers plenty of stretch. Style this dress with a denim jacket and sneakers for a casual look.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Mini-length, form-hugging fit
    • Brushed knit fabric, plenty of stretch
    • Tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-1483

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sheer Appeal High Slit Halter Dress

    Bring some serious sheer appeal with a maxi dress that wows! The dress features a halter neck with a plunging keyhole, halter neck tie, and a maxi-length silhouette with a high side slit. The dress is composed of a sheer mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and a chic updo. 

    Fit & Features

    • Halter neck 
    • Plunging keyhole 
    • Halter neck tie
    • Maxi length silhouette
    • High side slit
    • Mesh fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-1203

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get It Girl Belted Skater Dress

    Get a bold style in this belted skater dress! The fitted waist belt and seam details accentuate your silhouette, while the pleated skirt adds movement.

    Fit & Features

    • Twill stretch fabric, stretchy knit lining
    • Strapless neckline with grommet trim
    • Back zipper and hook-eye closure
    • Seam detailing
    • Belted waist
    • Skater silhouette, pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000105

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Color Burst Tie Dye Mini Dress

    Add a burst of color to your look with this fab mini dress! The dress features a tie-dye print, sleeveless square neckline, bungee straps that cross at the back, lace-up straps, 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 clear heels

    Fit & Features

    • Sleeveless square neckline
    • Bungee straps, cross at the back 
    • Lace-up straps 
    • Mini length silhouette
    • Tie-dye print
    • Smooth knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4114

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The One Eyelet Mini Dress

    This eyelet dress is the one for you, babe! The dress features an eyelet pattern, a scoop neckline with a tie-bust accent, spaghetti straps, ruffle trim at the bodice, and a mini-length silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges

    Fit & Features

    • Sleeveless scoop neckline, tie-bust accent
    • Spaghetti straps
    • Ruffle trim at bodice
    • Mini length silhouette
    • Eyelet pattern
    • Lightweight woven fabric, lined knit fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-4122

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale