Casual Dresses

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Casual Dresses Made for Everyday Fall Plans

Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.

Easy Prints, Textures & Layers for the Season

Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.

What Makes a Dress Casual?

A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.

How Do You Transition a Casual Dress From Summer to Fall?

Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.

Which Fabrics Work Best for Everyday Dresses?

Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.

How Can You Style One Casual Dress for Different Plans?

Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.

  • 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:
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  • 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
  • Sweet As Honey Strapless Floral Skater Dress

    Look and feel oh-so-sweet in this strapless floral skater dress with a flirty ruffled hem perfect for day dates or parties!

    Fit & Features

    • Floral print, woven fabric, stretchy knit lining
    • Strapless neckline
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3881

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free