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!

  • Floral Stunner Puff Sleeve Mini Dress

    You'll be a total stylish stunner in this adorable floral mini dress! It features short puff sleeves, a square neckline with a front keyhole cut out and tie at the bust, and a short, curve-hugging silhouette. The all-over floral print makes the dress a perfect option for brunch dates and shopping trips with your girls. Complete the look with a pair of cute wedges.

    Fit & Features

    • Short puff sleeves, elasticized hems
    • Elastic square neckline
    • Front keyhole cut out and tie at the bust
    • Back zipper, hook and eye closure
    • Mini-length, form-hugging fit, moderate stretch 
    • Floral print
    • Smooth knit fabric, fully lined
    • Runs true to size

    Style Number/Barcode: 05102-4339

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Casual-Chic Moment Maxi Dress

    Have a major casual-chic moment in this must-have maxi dress! It features short sleeves, a V neckline, and a flowy silhouette with a rounded hem and side slits. Tie the front hem in a knot to add a trendy detail. Pair this maxi dress with adorable new sandals for a laidback look.

    Fit & Features

    • Short sleeves
    • V neckline
    • Flowy silhouette
    • Rounded hem and side slits
    • Knit fabric with plenty of stretch

    Style Number/Barcode: 05102-1072

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Button Down Chic Ribbed Mini Dress

    Button-down in this chic mini dress that is perf for grabbing coffee with your bestie. The dress features an off the shoulder neckline, long sleeves with lettuce-edge trim, a faux button-down front, 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 wedges.

    Fit & Features

    • Off the shoulder neckline
    • Long sleeves with lettuce-edge trim
    • Faux button down front
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit
    • Moderate stretch  

    Style Number/Barcode: 06005-0896

    Category Name: Casual Dresses

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wrapped In Lace Ruched Mini Dress

    Wrap yourself in an elegant lace mini dress that brings the sophistication. The dress features a sleeveless v-neckline, adjustable spaghetti straps, a ruched body, and a mini length silhouette with a ruffled hem. The dress is composed of a lined floral lace fabric that offers a form hugging fit with minimal stretch. Complete look with wedges for a pretty brunch outfit.

    Fit & Features

    • Sleeveless v-neckline
    • Adjustable spaghetti straps
    • Ruched body
    • Mini length silhouette with ruffled hem
    • Lined floral lace fabric
    • Form hugging fit
    • Minimal stretch 

    Style Number/Barcode: 05102-0750

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Level Up Ruched Knit Midi Dress

    Level up your basic look with this trendy ruched knit midi dress. It features a sleeveless bodice, bungee spaghetti straps, a square neckline, all-over ruched detailing, and a mid-length, curve-hugging silhouette. The soft brushed knit fabric includes a lining and offers plenty of stretch for comfortable wear. Complete your outfit with a layered necklace and sleek heels.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Strapless bra recommended
    • All-over ruched detailing
    • Mid-length, form-fitting style
    • Lined-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4437

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Preppy Vibes Collared Mini Dress

    Add some stylish preppy vibes to your look in this trendy mini dress! It features a collared neckline with a partial button-down front, short sleeves, and a mini-length, curve-hugging silhouette. The black sweater knit fabric showcases light brown striped detailing at the waist, a light brown collar and button-down front, and light brown hems at the sleeves. Complete your outfit with chunky sneakers and sleek hoop earrings.

    Fit & Features

    • Collared neckline
    • Partial button-down front
    • Short sleeves
    • Mini-length
    • Form-hugging fit
    • Sweater knit fabric with plenty of stretch
    • Striped detailing at the waist

    Style Number/Barcode: 06005-0938

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance In Ruffles Mini Dress

    Fall for romantic ruffles as they fall for you in this sweet mini dress! It features short sheer puff sleeves and ruched, lined mesh fabric with a form-hugging fit. Dress up with some fab heels for a night out with your girls, or keep it chill with some chunky sneakers for a day date.

    Fit & Features

    • Square neckline 
    • Puff sleeves with a ruffled trim 
    • Ruched 
    • Lined mesh fabric
    • Rounded hem 
    • Form-hugging fit 
    • Moderate stretch

    Style Number/Barcode: 05103-0755

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Laced Up In Denim Dress

    Lace-up in this trendy denim dress to make a stylish statement! This dress features a sleeveless, plunge v-neck, adjustable spaghetti straps, a trendy lace-up front detail, and a curve hugging, midi silhouette. Complete the look with simple block heels.

    Fit & Features

    • Sleeveless, plunge v-neck
    • Adjustable spaghetti straps
    • Back zipper closure
    • Lace-up front
    • Curve-hugging silhouette
    • Midi-length hem 
    • Denim fabric, moderate stretch, fits true to size

    Style Number/Barcode: 05102-0291

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

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

    Capture hearts in this flirty ditsy floral printed mini dress that is perfect for spring! It features short puff sleeves, a sweetheart neckline with a tie-front detail, and a mini-length, curve-hugging silhouette. The dress is composed of a lightweight, stretchy knit fabric with no lining. Style this floral dress with cute wedges for brunch with the girls.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline
    • Tie-front at the bust
    • Short, form-hugging fit
    • Ditsy floral print
    • Stretchy unlined knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1078

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Eyes On You Lace-Up Slit Maxi Dress

    Not just a dress—this is the moment. From date nights to rooftop dinner parties, this linen maxi dress boasts a cutout bodice and leg-baring slit that does all the flirting for you!

    Fit & Features

    • Gauze linen-blend woven fabric, stretchy knit lining
    • Halter neckline, spaghetti strap ties
    • Lace-up back
    • Cutout accents
    • High front slit
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000053

    Category Name: Casual Dresses

    Price: $19.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Florals Ruffled Chiffon Mini Dress

    Bring the charm in a ruffled mini dress that makes a sweet impression! The dress features a plunging V-neckline, adjustable cross-straps, a floral print, tiered ruffles, and a mini-length silhouette. The dress is composed of a sheer lined chiffon fabric that offers a form-hugging fit that offers a minimal stretch. Complete your look with wedges and a floppy hat for a brunch-worthy outfit.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable cross-straps 
    • Floral print, back zipper closure
    • Tiered ruffles
    • Mini length silhouette
    • Chiffon fabric, knit lining
    • Fits true to size

    Style Number/Barcode: 05101-0463

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Stylish Snake Print Ruched Mini Dress

    Keep it so stylish in a snake print mini dress that slays your night out outfits. The mini dress features a sleeveless crew neckline, a trendy snake print, ruched side seams, 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

    • Crew neckline
    • Sleeveless 
    • Snake print
    • Ruched side seams
    • Brushed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-1077

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ready to Slay Ruched Mini Dress

    Babe, you'll be ready to slay in this sleek mini dress! Perfect for date night or a GNI, style this chic must-have with lucite heels and a sleek satin clutch. The dress features a  sleeveless crew neckline, a ruched drawstring at the side seam, and a mini-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch.

    Fit & Features

    • Crew neckline
    • Sleeveless
    • Ruched drawstring
    • Mini-length silhouette
    • Smooth knit fabric
    • Form-hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05103-3744

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On Vacay V-Neck Floral Maxi Dress

    Look a daydream come true in this floral maxi dress while on vacay! Designed with a bold floral print on a sultry form-hugging silhouette.

    Fit & Features

    • Floral print, mesh-lined fabric
    • V-neckline
    • Spaghetti straps
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4076

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Mesh Mini Dress

    Keep it Stunning in a chic mini dress, babe! The dress features a sleeveless square neckline, bungee-corded straps, and a curve-hugging mini-length silhouette. Complete the look with chic mules.

    Fit & Features

    • Sleeveless square neckline
    • Corded shoulder straps 
    • Mini-length silhouette
    • Sheer mesh fabric, full knit lining
    • Form-hugging fit
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-0976

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wrap Me In Glam Ribbed Mini Dress

    Wrap yourself in this glam sweater knit dress that brings the charm. The dress features an off-the-shoulder neckline, long sleeves, a gorge tie waist ribbon, 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 your look with mules and a trendy crossbody.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Off-the-shoulder neckline 
    • Long fitted sleeves
    • Tie waist ribbon 
    • Mini-length silhouette
    • Ribbed knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-0881

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keeping Knit Trendy Ribbed Mini Dress

    Keep it trendy in a ribbed mini dress that is perfect for nails those casual vibes! The dress features a square neckline, long sleeves, and a mini length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit that offers a moderate stretch. Complete your look with chunky sneakers

    Fit & Features

    • Square neckline
    • Long sleeves
    • Mini length silhouette 
    • Ribbed knit fabric 
    • Form hugging fit
    • Moderate stretch
    • Double lined

    Style Number/Barcode: 05102-0940

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Majorly Chic Turtleneck Midi Dress

    Give your workwear look a majorly chic vibe when you wear this must-have midi dress! It features a sleeveless bodice, a trendy turtleneck, and a mid-length, curve-hugging silhouette. Layer on an oversized blazer and style with strappy heels for the perfect outfit for the office.

    Fit & Features

    • Sleeveless bodice
    • Turtleneck
    • Mid-length
    • Form-hugging fit, moderate stretch 
    • Viscose crepe fabric
    • Double-lined

    Style Number/Barcode: 05102-0911

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rose Darling Floral and Lace Mini Dress

    Let this flirty dress showcase your sweet and sultry side for date night! The dress features a sleeveless sweetheart neckline with lace trim, sleek spaghetti straps, a disty floral print, and a stunning matching lace trim at the hem. Complete your night out look with a moto jacket and mules.

    Fit & Features

    • Sleeveless sweetheart neckline with lace trim
    • Sleek spaghetti straps
    • Ditsy floral print
    • Mini length silhouette
    • Lace hem
    • Smooth knit fabric with a knit lining
    • Form-hugging fit, moderate stretch 

    Style Number/Barcode: 05101-0940

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rose Darling Sweetheart Neck Mini Dress

    Enchant in this gorg mini dress that will make hearts flutter! The dress features a sweet ditsy rose print, a sweetheart neckline, a tie-front at the bust, 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. Style dress with dainty heart charm necklaces and mules for the perfect brunch date with bae.

    Fit & Features

    • Sweetheart neckline
    • Tie-front at the bust
    • Short sleeves
    • Ditsy floral print
    • Mini-length silhouette, form-hugging fit
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-0775

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heart Of Glam Ruched Midi Dress

    Bring the romantic vibes in this casually-chic midi dress! It features a sleeveless bodice with a square neckline, bungee spaghetti straps, a square back, ruched detailing, and a mid-length, curve-hugging silhouette. Pair this dress with strappy heels and a sleek clutch to complete your look.

    Fit & Features

    • Bungee spaghetti straps
    • Square neckline
    • Square back
    • Ruched detailing
    • Mid-length, form-hugging fit
    • Lined knit fabric with plenty of stretch

     

    SHOP ALL HEART OF GLAM COLLECTION

    Style Number/Barcode: 05102-1104

    Category Name: Casual Dresses

    Price: $14.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Edgy Babe Ribbed Knit Mini Dress

    Hey babe! Showcase an effortlessly edgy style in this ribbed knit mini dress. It features a crew neckline, a chest cut out right above the bust, long fitted sleeves, and a mini length, curve-hugging silhouette. Pair this dress with combat booties for the perf look.

    Fit & Features

    • Crew neckline
    • Chest cut out
    • Long fitted sleeves
    • Short, form-hugging fit
    • Ribbed knit fabric

    Style Number/Barcode: 05102-1006

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beautiful Bloom Ruched Midi Dress

    Showcase your beauty in this stylish floral printed midi dress! It features spaghetti straps, a square neck and back, ruched detailing, and a mid-length, curve-hugging fit. Pair this dress with strappy heels and a rhinestone necklace for a romantic date night.

    Fit & Features

    • Spaghetti straps
    • Square neck and back
    • Ruched detailing
    • Mid-length
    • Form-hugging silhouette
    • Floral print
    • Knit fabric with plenty of stretch

    Style Number/Barcode: 05101-0949

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All Dolled Up Ribbed Knit Mini Dress

    Get dolled up in a dress that is oh so stylish! Perf for date night, the dress features a mock neck, long Dolman sleeves, 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 thigh-high boots and hoops. 

    Fit & Features

    • Mock neck 
    • Long Dolman sleeves
    • Mini length silhouette 
    • Ribbed knit fabric 
    • Form hugging fit 
    • Moderate stretch 

    Style Number/Barcode: 06005-0823

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale