Casual Dresses

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.

  • Truly Charming Sleeveless A-Line Mini Dress

    Unlock a truly charming style in this sleeveless mini dress at BBQs to summer picnics! Features a square neckline and adjustable spaghetti straps for the perfect fit. Its A-line silhouette flatters every figure, and the mini-length hem adds flirtatiousness. Complete the look with sunglasses and wedges.

    Fit & Features

    • Woven fabric, minimal stretch
    • Square neckline
    • Adjustable spaghetti straps
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5704

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Remarkable Vibe One Shoulder Printed Mesh Mini Dress

    This mini-length dress features a flattering one-shoulder neckline and a bodycon silhouette. The stretchy mesh-lined fabric boasts a multi-print design that keeps your style fresh. 

    Fit & Features

    • Multi-print, mesh-lined fabric, moderate stretch
    • One-shoulder neckline
    • Shoulder strap
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5701

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feel The Romance Sweetheart Button Lace Trim Maxi Dress

    Instantly feel the romance of this sleeveless maxi dress for a chic and breezy look at showers or parties! It has a sweetheart neckline, adjustable straps, and a ruched bust, so it effortlessly highlights your figure. The button accents and sheer lace trims add delicate touches, while the high waist and flowy maxi silhouette create a flattering and ethereal look. Style this maxi dress with trendy sandals and earrings.

    Fit & Features

    • Airy woven fabric, short woven lining, no stretch
    • Sweetheart neckline
    • Adjustable spaghetti straps
    • Button and sheer lace trim accents
    • Flowy maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5706

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jetset Babe One Shoulder Tropical Maxi Dress

    Jetset off on vacation like a babe in this tropical maxi dress! With a flirty and flattering one-shoulder neckline, ruched seams, and a bodycon silhouette, you'll be turning heads. Plus, the side slit and maxi-length hem add a touch of allure. Complete the look in sandals and sunglasses.

    Fit & Features

    • Tropical palm leaf print, stretchy knit
    • One shoulder neckline
    • Bodycon silhouette
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5702

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Vacation Long Sleeve V-Neck Cutout Mini Dress

    This V-neck mini dress pairs perfectly with your next vacation or pool party! This playful and stylish dress features long sleeves with flare cuffs, a V-neckline with a hoop insert, and cutout details on the bodice and back. Its bodycon fit and mini-length hem will highlight your curves while you explore exotic destinations or the resort bar! Complete the look with sunnies.

    Fit & Features

    • Texture knit fabric, sewn-in knit lining, minimal stretch
    • V-Neckline with hoop insert
    • Cutout bodice and back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5705

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Out Of Town Strapless Floral Crepe Mini Dress

    The perfect floral crepe mini dress to take with you out of town! Boasting a strapless neckline, this mini-length dress has a trendy contrast foldover design and a bodycon silhouette that flatters your curves. Complete the look in sandals and sunnies!

    Fit & Features

    • Floral print, crepe fabric lined with stretchy knit
    • Contrast foldover design
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3364

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Colorful Essence Sleeveless Marble Print Mini Dress

    You'll be the most colorful babe on the scene in this marble print mini dress! Perfect for art gallery openings and date nights, this sleeveless dress boasts a square neckline, adjustable spaghetti straps for a custom fit, and side ruched seams and a bodycon fit to accentuate your curves. Complete the look with a clutch and stiletto heels.

    Fit & Features

    • Marble print, mesh fabric, sewn-in knit lining, moderate stretch
    • Square neckline
    • Adjustable spaghetti straps
    • Ruched side seams
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5691

    Category Name: Casual Dresses

    Price: $42.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Allure One-Shoulder Cutout Waist Knit Midi Dress

    Bring the bold allure to your summer 'fits with this sultry cutout waist midi dress! Made with a lined stretchy ribbed knit fabric, the mid-length dress features a sleeveless one-shoulder neckline and a tank strap with a trendy twisted-back design. The asymmetric goes around the waist, accented with a chic O-ring cutout at the front. The midi-length hem is detailed with a high-cut side slit along the figure-flaunting bodycon silhouette. Style with lace-up sandals for a weekend getaway!

    Fit & Features

    • Stretchy ribbed knit fabric, knit lining
    • One-shoulder neckline, tank strap with twisted-back design
    • Asymmetric waist cutout
    • Front O-ring cutout
    • High side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5697

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stun And Only Mock Neck Floral Mesh Mini Dress

    Leaving people speechless is easy with this floral mesh mini dress! Crafted from a mesh fabric showcasing a cute floral print perfect for mixing it up this season. This dress features sheer fitted long sleeves with slit flare cuffs, a stylish mock neck, and a flattering bodycon fit. The mini-length hem adds a touch of sass to this stunning dress. Complete the look in stiletto heels.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Mock neck
    • Sheer long sleeves with slit flare cuffs
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5698

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    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
  • Walk On The Wild Side Leopard Mesh Mini Dress

    Walk on the wild side in this leopard mesh mini dress perfect for brunch or dates! This daring dress features a flattering square neckline, delicate spaghetti straps, and a surplice bodice for a flattering look. The side ruched seams accentuate your curves, giving you a bodycon fit that will make you stand out in any crowd. And with its mini-length hem and fierce leopard print, this dress is perfect for a night out on the town. Complete the look in platform block heels and earrings!

    Fit & Features

    • Leopard print, stretchy mesh fabric, sewn-in knit lining
    • Spaghetti straps
    • Side ruched seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5696

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Adoring Cutie Sleeveless Lace-Up A-Line Mini Dress

    An attention-worthy A-line mini dress that'll have everyone adoring your cuteness! This square neck dress accentuates your curves while the lace-up back adds a touch of playfulness. The A-line silhouette and mini-length hem are perfect for any occasion. Complete the look in wedges and a clutch!

    Fit & Features

    • Smooth knit fabric lined with stretchy knit
    • Spagehtti straps
    • Square neckline
    • Lace-up
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5689

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Artsy Flair Strapless Cutout Abstract Mini Dress

    Showcase an artsy flair in this abstract mesh mini dress tonight! Featuring a striking strapless neckline, side ruched seams for a flattering fit, and a unique side cutout design, this bodycon mini-length dress is all about highlighting your curvaceous figure. Complete the look with stiletto heels.

    Fit & Features

    • Abstract print, mesh fabric, stretchy knit lining
    • Strapless neckline
    • Side cutout
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5693

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Out Of Office One Shoulder Tropical Maxi Dress

    This tropical maxi dress says it's time for vacation! Switch your email to out of office and enjoy a sunny destination in this sleeveless dress featuring a one-shoulder neckline adorned with a knotted shoulder strap, a flattering mermaid silhouette, and a maxi-length hem. Complete the look with sunglasses and a cocktail in hand!

    Fit & Features

    • Tropical palm leaf print, stretchy knit fabric
    • One-shoulder neckline
    • Knotted shoulder strap
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5695

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Paradise Pick V-Neck Cutout Tropical Maxi Dress

    Enjoy the fun and sun on your paradise vacay in this tropical maxi dress! This flowy maxi silhouette features adjustable spaghetti straps, a flirty V-neckline with a keyhole, and a sultry cutout back. With a front slit, you'll steal the show with every step. Complete the look with sunnies and a straw handbag.

    Fit & Features

    • Tropical print, mesh fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • V-neckline, keyhole
    • Cutout back
    • Front slit
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5692

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Style Cowl Neck Slit Paisley Maxi Dress

    Bask in the aesthetic perfection of this paisley mesh maxi dress whether you're on vacation or having a sunset dinner with friends! This form-hugging dress features a cowl neckline and spaghetti straps, highlighting your figure in all the right ways. The high-side slit and sheer maxi-length hem add a touch of allure to this must-have dress! Complete the look with a necklace and earrings.

    Fit & Features

    • Paisley print, partially lined mesh fabric
    • Cowl neckline
    • Spaghetti straps
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5694

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine And Good Time V-Neck Mermaid Maxi Dress

    This mermaid maxi dress is here for sunshine and good times! Made from textured mesh fabric, this dress will have you feeling so cute. Features a flattering V-neckline, dual spaghetti straps, a crisscross back, and a bust cutout. The mermaid silhouette and high front slit accentuate your curves, while the maxi-length hem adds a touch of chicness. Complete the look with sandals and sunglasses!

    Fit & Features

    • Textured mesh fabric, stretchy knit lining
    • Dual spaghetti straps
    • V-neckline
    • High front slit
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5690

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smooth Silhouette Ruched Bodycon Mini Dress

    Sleek and smooth, this bodycon mini dress serves curves for days! Crafted from a soft double-lined knit fabric that fits like a glove, this dress features a square neckline adorned with adjustable spaghetti straps, side ruched seams to accentuate your figure along the bodycon silhouette, and a flattering mini-length hem. Complete the look with mules and a crop jacket.

    Fit & Features

    • Soft knit fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5683

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Oopsie Daisy Sleeveless A-Line Mini Dress

    Oopsie daisy this sleeveless mini dress must've caught you by a sweet surprise! Crafted from a soft brushed knit fabric with an adorable floral print, this dress is a must-have for spring and summer. Features a flattering V-neckline with an adjustable drawstring tie and an A-line silhouette. Complete the look with a denim jacket and sandals for a casual occasion!

    Fit & Features

    • Floral print, brushed knit fabric lined with knit
    • Adjustable drawstring neckline
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5686

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Alluring Vacay High Slit Tropical Mesh Midi Dress

    Dare to allure on your next vacay in this sultry high slit tropical midi dress! The airy-lined mesh fabric is detailed with a bold all-over tropical palm leaf print to bring those dreamy destination vibes to your look. The mid-length dress features a sleeveless square neckline with pleating, spaghetti straps that lead to an open cross-back strappy design, a high-cut side slit to show off some leg, and a slim-fit silhouette to flaunt your figure. Style with hoop earrings and sandals for a beachy-chic outfit.

    Fit & Features

    • Tropical print
    • Stretchy mesh fabric with knit lining
    • Square neckline
    • Spaghetti straps, open cross-back strappy design
    • High side slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5688

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple Slay Halter Cowl Neck Ribbed Knit Maxi Dress

    This sleek halter cowl neck maxi dress is a simple chic style that will make your casual outfits slay! Made with a lightweight stretchy ribbed knit fabric, it features a sleeveless draped cowl neckline with tie-back halter spaghetti straps, an alluring open back with a lower tie-back strap, and a form-hugging maxi-length silhouette to flaunt your stunning figure. Pair with slip-on sandals for a relaxing weekend getaway.

    Fit & Features

    • Stretchy ribbed knit fabric, partial front knit lining
    • Cowl neckline, halter spaghetti straps
    • Open back, tie-back strap
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5685

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Must-Have Tie Back A-Line Mini Dress

    A must-have tie back A-line mini dress for casual nights out! Featuring chic cap sleeves, a square neckline, a sultry open back with tie closure, and a flattering A-line silhouette with a mini-length hem, this dress will elevate your style game. Complete the look in faux suede heels and a purse!

    Fit & Features

    • Slinky knit fabric lined with stretchy knit
    • Open tie-back design
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5681

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Getaway Bound Tropical Print Woven Maxi Dress

    Jet set to your gorgeous getaway in this tropical woven maxi dress! The lightweight gauze woven fabric features a bold tropical print to bring the allure to your dreamy vacay. The maxi-length dress is shaped with a strapless straight-across neckline with a ruffled fold-over design to add a flirty flair. The fitted high waist seam has an elasticized design for added stretch and a thin tie-front belt with cute tassel accents. The dress flows out to a floor-length hem with an effortless A-line silhouette. Style this maxi dress with strappy sandals.

    Fit & Features

    • Tropical printed gauze woven fabric with short knit lining, minimal stretch
    • Strapless straight neckline with no-slip strip, ruffled fold-over design
    • Fitted elasticized high waist seam
    • Tie-front belt with tassels
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5678

    Category Name: Casual Dresses

    Price: $6.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Oh So Sweet Tie Back A-Line Mini Dress

    You're going to look so sweet in this A-line mini dress for weekend plans! Featuring cap sleeves, a square neckline, and a tie-back design to turn heads. The A-line silhouette and mini-length hem will have you looking effortlessly chic! Complete the look in platform shoes.

    Fit & Features

    • Smooth knit fabric lined with stretchy knit
    • Square neckline
    • Tie back design
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5682

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale