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.

  • Artful Drama Floral Open Back Maxi Dress

    Serve artful drama in this halter maxi dress featuring a draped cowl neckline, sultry open back, and a watercolor-inspired floral print. Made for cocktail receptions, weddings, and statement entrances into parties.

    Fit & Features

    • Watercolor floral print, mesh-lined fabric, stretchy
    • Cowl halter neckline, tie closure
    • Open back with tie closure
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000690

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fall In Love Floral Eyelet A-Line Mini Dress

    A flirty floral mini dress to attend parties, brunch, and day dates! This sleeveless dress boasts a classy V-neckline and a flattering a-line silhouette on pretty eyelet woven fabric with a dainty floral print. Pair with mules.

    Fit & Features

    • Dainty floral print
    • Eyelet woven fabric lined with stretchy knit
    • V-neckline, adjustable spaghetti straps
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6038

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweeter Than Pie Scoop Neck Gingham Mini Dress

    So on trend and sweeter than pie, this gingham mini dress is essential for spring-to-summer fun! This mini-length dress is made from woven fabric and features a charming gingham print that exudes effortless style.  The scoop neckline and tank shoulder straps flatter your figure, while the form-hugging fit accentuates your curves. Complete the look in cute sandals and a mini purse!

    Fit & Features

    • Gingham print, woven fabric, slight stretch
    • Back zipper closure
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5568

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Days Floral Chiffon Skater Dress

    Swing into the sunnier days ahead in this floral chiffon dress! It features a sleeveless square neck, adjustable spaghetti straps, a stretchy smocked bodice, and a tiered ruffle short-length skater silhouette. Complete the look in cute espadrille wedges for a family picnic!

    Fit & Features

    • Sleeveless square neck, adjustable spaghetti straps
    • Stretchy smocked bodice
    • Skater silhouette, tiered ruffles
    • Short-length hem
    • Floral print, airy chiffon, knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4936

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blissful Cutie Floral Bodycon Midi Dress

    Enter a state of blissful cuteness in this floral midi dress boasting a flattering bodycon fit perfect for layering with denim jacket.

    Fit & Features

    • Eyelet knit stretchy fabric, sewn-in knit lining
    • Strapless neckline
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6044

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Subtle Charm V-Neck Ruffled Floral Skater Dress

    Embrace your inner charm in this floral skater dress at showers or birthdays! The flattering V-neckline and adjustable spaghetti straps provide a perfect fit, while the tiered ruffled skater silhouette adds a touch of feminine flair. With its tie-back design, short-length hem and beautiful floral print, this dress will make you feel effortlessly stylish. Complete the look in mules and earrings!

    Fit & Features

    • Ditsy floral print
    • Chiffon fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Tie-back design
    • Tiered ruffled skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3022

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Style Leopard And Floral Print Mini Dress

    Create a weekend look exuding trendy style with this multi-print mini dress! The stretchy sheer mesh fabric is detailed with a leopard and rose print for a sweet and sassy vibe. The short dress features a sleeveless V-neckline accented with a dainty sheer lace trim, spaghetti straps, and a flowy A-line silhouette with a mini-length hem. Style with cowgirl boots!

    Fit & Features

    • Leopard and rose-print
    • Stretchy sheer mesh fabric with knit lining
    • V-neckline with sheer lace trim
    • Spaghetti straps
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5764

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Exquisite Charm A-Line Floral Mini Dress

    The perfect floral mini dress pick for your weekend plans! Showcasing a flattering sweetheart ruffle neckline and a-line silhouette, this dress will capture your heart. Pair with heels.

    Fit & Features

    • Ditsy floral print, cotton knit fabric lined 
    • Strapless sweetheart ruffle neckline
    • Padded bra cups
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6033

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bright Beauty Halter Cutout Tropical Maxi Dress

    You'll look bright and beautiful in this tropical maxi dress on vacation or at a weekend pool party! The halter neckline with a spaghetti strap tie highlights your shoulders, while the U-ring insert adds some structure. The cutout back with smocked detail flatters your figure along the flowy maxi-length silhouette. Complete the look with sunglasses and sandals for a chic vibe!

    Fit & Features

    • Tropical print, chiffon fabric, short stretchy knit lining
    • Halter neckline with spaghetti strap tie, U-ring insert
    • Cutout back with smocking
    • Flowy maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5791

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Unforgettably Bold Abstract Mesh Mini Dress

    Bold and unforgettable—this halter mini dress brings the heat with a plunging neckline and layered ruffle skirt in a fiery abstract print.

    Fit & Features

    • Abstract print, mesh-lined fabric, moderate stretch
    • Halter plunge neckline, tie closure
    • A-line form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000243

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fabulous Destination Tropical Cowl Neck Maxi Dress

    Look fabulous heading to your destination in this tropical maxi dress for the cutest look on the island or beach resort! The cowl neckline creates a flattering drape and spaghetti strap tie while the low cowl back adds a touch of allure. The flowy maxi silhouette will make you feel like you're on a tropical escape! Complete the look in sunnies.

    Fit & Features

    • Tropical palm print, stretchy knit fabric
    • Cowl neckline
    • Low cowl back, spaghetti strap tie
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5727

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Note To Self Ribbed Knit A-Line Mini Dress

    Note to self, this sleeveless mini dress is a must-have for every day! Perfect for any occasion, this stretchy ribbed knit dress will surely become a staple in your wardrobe. It features a crew neckline with tank straps and a flattering A-line silhouette with a flirty front slit on the mini-length hem. Complete the look with an oversized blazer and a sleek necklace.

    Fit & Features

    • Soft and stretchy ribbed knit fabric
    • Crew neckline
    • Tank shoulder straps
    • Front slit
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5632

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Look Ditsy Floral Ruched Knit Mini Dress

    Create the cutest look for your weekend plans in this floral ruched knit mini dress! The adorable ditsy floral print on the soft and stretchy brushed knit fabric will give your casual look a flirtatious vibe! The short dress features a sleeveless square neckline with tie-shoulder spaghetti straps for a trendy detail and customized fit. The ruching down the side seams will show off your curves on the bodycon silhouette. Style this dress with hoop earrings and strappy mules for brunch with your girls!

    Fit & Features

    • Ditsy floral print
    • Stretchy brushed knit fabric
    • Sleeveless square neckline
    • Tie-shoulder spaghetti straps
    • Ruched side seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5533

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Striking Impression Sleeveless Slit Mesh Maxi Dress

    Impress with your striking style in this sleeveless mesh maxi dress perfect for dressy occasions! This dress will show off your curves with a square neckline, adjustable spaghetti straps, and a form-hugging fit. The sheer slit maxi-length hem adds a touch of elegance and allure. Complete the look with strappy stiletto heels.

    Fit & Features

    • Sheer mesh fabric, partial knit lining
    • Square neckline
    • Adjustable spaghetti straps
    • Form-hugging fit
    • Sheer slit mesh maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5583

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Darling Ditsy Floral V-Neck Mini Dress

    This ditsy floral mini dress will have you dreaming of sunshine days! Flaunt your figure with the bodycon fit of this dress showcasing a flattering V-neckline, dainty spaghetti straps, a tie-front bust for added detail, and a mini-length hem on ditsy floral print mesh fabric. Complete the look in sandals and a mini tote bag.

    Fit & Features

    • Ditsy floral print
    • Mesh fabric lined with stretchy knit
    • Spaghetti straps
    • Slit accent
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5571

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Days Square Neck Tie-Back Skater Short Dress

    Sunny days pair perfectly with this skater short dress for casual occasions or day dates! Made from lightweight cotton, this dress boasts a square neckline and elasticized cap sleeves for a perfectly feminine touch. The smocked bodice and tie-back waist ensure a flattering fit, while the tiered skater silhouette adds a playful flair. Complete the look with sandals, sunglasses, and a purse for a cute style!

    Fit & Features

    • Lightweight cotton fabric with woven lining
    • Stretchy smocked bodice
    • Tie-back waist
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5417

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Impressive Blossom Strapless Floral Maxi Dress

    Impress in this floral maxi dress showcasing a sleek strapless neckline and a column silhouette that flatters your figure. Style the dress with a choker.

    Fit & Features

    • Statement floral print
    • Mesh fabric lined with soft, stretch knit
    • Column silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5953

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's Stylish Mock Neck Cable Knit Midi Dress

    A stylish sleeveless midi dress featuring a mock neck, a flattering form-hugging fit, and a side slit for movement. Complete the look with strappy heels.

    Fit & Features

    • Cable knit fabric, stretchy knit lining
    • Mock neck
    • Side slit
    • Form-hugging fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5897

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute In Plaid Strapless Plaid A-Line Mini Dress

    Look and feel cute in this plaid strapless dress with a flattering A-line silhouette and a mini-length hem. Complete the look with a choker necklace.

    Fit & Features

    • Plaid print, woven fabric, woven lining
    • Strapless neckline
    • Back zipper closure
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5980

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Currently In Paradise V-Neck Tropical Midi Dress

    This tropical midi dress will be with you paradise for a stylishly chic vacation! Featuring a V-neckline adorned with spaghetti straps and a tie-back design, it's the perfect form-hugging dress for any island adventure. With a side slit and midi-length hem, you'll be sure to turn heads! Complete the look in wedge sandals and earrings.

    Fit & Features

    • Tropical print, stretchy knit fabric, sewn-in knit lining
    • Spaghetti straps
    • V-Neckline
    • Tie-back design
    • Side slit
    • Form-hugging
    • Runs true to size

    Style Number/Barcode: 05102-5633

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Ways V-Neck Floral Crepe A-Line Dress

    All eyes and hearts will be on you in this floral crepe mini dress all season! With puff sleeves and a mini-length hem, this dress is perfect for a playful day out. The A-line silhouette will flatter your figure, making you stand out in style. Complete the look in wedge sandals.

    Fit & Features

    • Floral print, crepe fabric, moderate stretch
    • V-neckline
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5700

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fabulous Icon Sleeveless Ribbed Knit Midi Dress

    An iconic knit midi dress that can go from day to night! Crafted from soft and stretchy ribbed knit fabric, this sleeveless dress offers a stylish square neckline, a flattering underbust seam, and a bodycon silhouette that will hug your curves in all the right places. Complete the look with a moto jacket and stiletto heels for a chic style.

    Fit & Features

    • Soft, stretchy ribbed knit fabric
    • Square neckline
    • Underbust seam
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-1853

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fun In Floral Lace Mini Dress

    So fun in floral print, this lace dress is featured in a form-hugging A-line silhouette and playful mini-length hem. Pair with cute wedge sandals for a cute summer look!

    Fit & Features

    • Floral print, lace fabric, stretchy knit lining
    • Square neck with bust tie
    • Adjustable spaghetti straps
    • Form-hugging A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6015

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Charmer Basic Rib Knit Maxi Dress

    A basic maxi dress that brings everyday charm! This long rib knit dress features a square neckline, spaghetti straps, and a flattering bodycon silhouette, you'll love this maxi dress for any occasion. Complete the look in a cute crop jacket and your favorite sneakers! 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Maxi-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5522

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale