Casual Dresses

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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!

  • Fab Florals Crochet Waist Maxi Dress

    Impress with florals in a maxi dress that takes you to paradise! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a crochet waist, a floral print, a high side slit, and a maxi length silhouette. The dress is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Crochet waist
    • Floral print
    • High side slit
    • Maxi length silhouette 
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-0196

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Dream Sleeveless Mini Dress

    Dream up the perfect vacation look with a mini dress that channels those vibes! The dress features a sleeveless scoop neckline, adjustable spaghetti straps, lace-up back, a tropical print, 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

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps
    • Lace-up back 
    • Tropical print 
    • Mini length silhouette
    • Smooth knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-0665

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serve Sultry Vibes Halter Cowl Neck Maxi Dress

    Serve sultry vibes only in this sleek knit maxi dress at your next rooftop party. The halter cowl neckline, alluring open back, and curve-hugging mermaid silhouette will steal all the glances.

    Fit & Features

    • Slinky knit fabric, knit lining, high stretch
    • Sleeveless cowl neckline, halter strap
    • Open back
    • Ruching
    • Maxi-length hem
    • Curve-hugging mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4110

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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

    Go with the flow of this gorgeous maxi dress! It features a sleeveless deep V-neckline with a lined crochet lace top, adjustable spaghetti straps, a tie-back detail with a lower back cutout, and a flowy, floor-length skirt with pleated detailing and a relaxed fit. Style this dress with new earrings and strappy sandals for your summer vacay.

    Fit & Features

    • Sleeveless deep V-neckline
    • Lined crochet lace top
    • Adjustable spaghetti straps
    • Tie-back detail, lower back cutout
    • Floor-length skirt, pleated detailing
    • Relaxed fit
    • Gauze fabric
    • Runs true to size

    Style Number/Barcode: 05102-0295

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bombshell Babe Denim Mini Dress

    Yes babe, showcase major bombshell vibes in this stunning denim mini dress! It features a sleeveless mock neckline, tank shoulder straps with frayed detailing, a complete zip front, and a mini-length, curve-hugging silhouette. Style this dress with sneakers to keep it casually cute, or clear heels for an elevated look.

    Fit & Features

    • Sleeveless mock neckline
    • Tank shoulder straps, frayed detailing
    • Complete zip front
    • Short, form-hugging fit
    • Denim fabric
    • Runs true to size

    Style Number/Barcode: 05102-1196

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Getaway Maxi Dress

    This stunning printed maxi dress will have you looking absolutely gorgeous for your next weekend getaway! It features a sleeveless square neckline, spaghetti straps, a flowy, floor-length silhouette, and a sultry thigh-high side slit. The knit fabric has an all-over tropical palm leaf print, making the dress a perf option for a summer vacay. Style it with wedges and a chic pair of sunglasses.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Floor-length silhouette, high side slit
    • Relaxed fit
    • Knit fabric, palm leaf print
    • Runs true to size

    Style Number/Barcode: 05102-0654

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lovely In Linen Sleeveless Skater Dress

    Get a lovely look this season in this flowy linen skater dress! It features a sleeveless bodice, tank shoulder straps, a V-neck and back, a high waist with trendy bar cutouts on each side, and a flirty skater silhouette. Style this dress with sandals for a breezy vacay outfit.

    Fit & Features

    • Tank shoulder straps
    • V-neck and back
    • High waist, bar cutouts on each side
    • Flowy skater silhouette
    • Linen and gauze fabric
    • Runs true to size

    Style Number/Barcode: 05102-0241

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless And Chic Eyelet Mini Dress

    Effortless and chic, this eyelet mini dress is the perfect addition to your summer wardrobe. It features a sleeveless scoop neckline, tank shoulder straps, and a mini-length, curve-hugging silhouette. Style this dress with strappy sandals.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Short, form-hugging fit
    • Sheer eyelet fabric, full lining
    • Runs true to size

    Style Number/Barcode: 05102-1275

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All That Skater Dress

    There's no denying, carry all that confidence girl in this flirty skater dress! 

    Fit & Features

    • V-Neckline
    • Cross-Back Spaghetti Straps 
    • Ponte-Knit Fabric
    • A-Line Skater Silhouette 
    • Form Hugging Fit
    • Moderate Stretch 

     


    Style Number/Barcode: 05101-0475

    Category Name: Casual Dresses

    Price: $19.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • This Moment Floral Lace Skater Dress

    Stand out for those special moments with a skater dress that captivates with stylish details. The dress features a sleeveless V-neckline with a scalloped lace trim, a floral lace bodice, a sheer lace back, and a skater silhouette. The dress is composed of a combination of crepe and lace fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and door knocker earrings. 

    Fit & Features

    • Sleeveless V-neckline 
    • Scalloped lace trim 
    • Floral lace bodice, sheer lace back 
    • Skater silhouette 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0624

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Retro Vibes Tie Dye Mini Dress

    Channel retro vibes with a mini dress that keeps it super cute! The dress features a sleeveless crew neckline, a tie-dye print, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a relaxed fit with a moderate stretch. Complete look with clear mules to let this print take center stage! 

    Fit & Features

    • Sleeveless
    • Crew neckline
    • Tie-dye print
    • Mini length silhouette
    • Brushed knit fabric
    • Relaxed fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1096

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Beauty Tropical Maxi Dress

    Showcase your stunning beauty in this tropical maxi dress on your next weekend getaway! It features a sleeveless V neckline, spaghetti straps that lead to an open back with a strappy design, a high waist, and a floor-length hem with a relaxed fit. The knit fabric has an all-over palm leaf print to bring the vacay vibes. Complete the look with strappy sandals.

    Fit & Features

    • Sleeveless V neckline
    • Spaghetti straps
    • Open back, strappy design
    • High waist
    • Floor-length hem, relaxed fit
    • Knit fabric, palm leaf print
    • Runs true to size

    Style Number/Barcode: 05102-0525

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vintage Racing Sleeveless Mini Dress

    This on-trend vintage-inspired mini dress is perfect for weekend outings with the squad. It features a sleeveless scoop neckline, tank shoulder straps, and a mini-length, curve-hugging silhouette with side drawstrings at the hem. The dress has a cool center car graphic with the script "Vintage Racing." Complete the outfit with edgy combat boots.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Short, form-hugging fit
    • Side drawstrings
    • Car graphic with the script "Vintage Racing"
    • Runs true to size

    Style Number/Barcode: 06002-0803

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lovestruck Butterfly Print Smocked Mini Dress

    Get lovestruck with this pretty butterfly print mini dress that brings the charm! The mini dress features a sleeveless sweetheart neckline with a cute tie-front accent, a cutout at the midriff, adjustable spaghetti straps, a smocked back, and a mini-length silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with mules

    Fit & Features

    • Sleeveless sweetheart neckline 
    • Tie-front accent
    • Adjustable spaghetti straps 
    • Cutout at the midriff 
    • Smocked back
    • Gauze knit fabric, mini length silhouette
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-1230

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Brunch-Ready Floral Midi Dress

    Style this adorable floral midi dress for weekend brunch with the girls! It features a sleeveless square neckline, spaghetti straps, a high waist, ruching, and a mid-length, curve-hugging silhouette. The knit fabric includes a knit lining and offers plenty of stretch. Complete the look with cute sunglasses and chic mules.

    Fit & Features

    • Square neckline
    • Spaghetti straps
    • High waist
    • Ruching
    • Mid-length, form-hugging fit
    • Lined knit fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05101-1045

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Trendsetter Tie-Dye Mini Dress

    Showcase your major trendsetter status in this cute tie-dye mini dress! It features a sleeveless square neckline, spaghetti straps, ruching, and a mini-length, curve-hugging silhouette. Complete the look with sleek hoop earrings and sneakers.

    Fit & Features

    • Square neckline
    • Spaghetti straps
    • Ruching
    • Short, form-hugging fit
    • Knit fabric, plenty of stretch
    • Tie-dye print may vary
    • Runs true to size

    Style Number/Barcode: 05102-2411

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Laid Back Fave Crew Neck Tank Maxi Dress

    Your new laid-back fave tank maxi dress for styling up or down for any occasion! Crafted from rib knit fabric, this crew neck dress offers a form-hugging fit and a maxi-length hem for a flattering silhouette. Complete the look in cute sandals and sunnies!

    Fit & Features

    • Rib-knit stretchy fabric
    • Crew neck
    • Form-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5573

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girl-Next-Door Gingham Mini Dress

    Embrace your girl-next-door vibes with this sweet mini dress! It features a sleeveless square neckline, tie shoulder spaghetti straps, a tie-front detail, and a smocked body with a mini-length, form-hugging silhouette. The woven fabric has a subtle all-over gingham print for a cute look. Complete the outfit with a denim jacket and sneakers.

    Fit & Features

    • Square neckline, ruffle trim
    • Tie shoulder spaghetti straps
    • Tie-front detail
    • Smocked body
    • Short, form-hugging fit
    • Woven fabric, gingham print
    • Runs true to size

    Style Number/Barcode: 05102-1173

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Edgy Destruction American Motorcycle Graphic Tunic

    Channel an edgy look with a tunic that plays up your rocker side! The tunic features a V-neckline, short sleeves, eagle wings graphic, a script that reads: "American Motorcycles", destructed detailing, and a mini length. Complete look with combat boots

    Fit & Features

    • V-neckline 
    • Short sleeves
    • Eagle wings
    • "American Motorcycles" script
    • Destructed detailing 
    • Cotton knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 06002-0801

    Category Name: Casual Dresses

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Taking the Plunge Scoop Neck Midi Dress

    Take the plunge in this stylish midi sweater dress! The dress features a sleeveless scoop neckline, tank shoulder straps, and a bodycon silhouette on rib-knit fabric. Complete the look with mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless scoop neckline
    • Tank-shoulder straps
    • Bodycon silhouette
    • Midi-length hem
    • Rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1233

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Charmer Ditsy Floral Mini Dress

    Charm them all with a mini dress that makes a sweet impression! The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print, 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 square neckline
    • Spaghetti straps
    • Ditsy floral print 
    • Mini-length silhouette
    • Ribbed knit fabric, knit lining
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1895

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Romance Ditsy Floral Mini Dress

    Fall in love with this adorable ditsy floral mini dress that is perfect for summer date nights. It features short puff sleeves, a sweetheart neckline with a center criss-cross bust detail, and a mini-length, curve-hugging silhouette. Complete the outfit with a charm necklace and clear heels.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline
    • Center criss-cross bust detail
    • Short, form-hugging fit
    • Knit fabric, ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-2103

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Center Of Attention Mini Dress

    All eyes will be on you in this casual-chic mini dress. It features a wide sweetheart neckline, short sleeves, seam details that run down the center, ruching, and a mini-length, curve-hugging silhouette. Style this dress with clear heels and a trendy shoulder bag.

    Fit & Features

    • Wide sweetheart neckline
    • Short sleeves
    • Center seam details
    • Ruching
    • Short, form-hugging fit
    • Ribbed knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-0786

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Key To Glam Greek Key Knit Dress

    Unlock your trendy style with a mini dress that stands out on your next date night! The dress features a sleeveless scoop neckline, spaghetti straps, a Greek key-inspired print, 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 clear mules

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Greek key-inspired print
    • Mini length silhouette
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1207

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free