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.

  • Look So Sweet Floral Applique Skater Party Dress

    Effortlessly steal the show in this skater party dress at graduations or showers! Made with organza sheer fabric and adorned with delicate floral applique, this dress is sure to turn heads and make you feel like the belle of the ball. Designed with a flattering square neckline and adjustable spaghetti straps, the skater silhouette and short-length hem exude flirty charm so everyone will fall for you! Complete the look in strappy platform heels.

    Fit & Features

    • Floral appliques
    • Sheer organza fabric with woven lining
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3084

    Category Name: Casual Dresses

    Price: $56.90

    Availability: Out of Stock

    Product Badge:
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  • True Devotion Strapless Ruffle Skater Mini Dress

    Express your true devotion to flirty style in this strapless skater dress perfect for strolling a beach city or a brunch! Featuring a flattering strapless neckline with a tie and stretchy elasticized bands for a comfortable, secure fit. The skater silhouette and ruffled mini-length hem add a touch of flirty fun. Complete the look in strappy sandals.

    Fit & Features

    • Cotton woven fabric with non-stretch lining
    • Strapless neckline with tie
    • Skater silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5711

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Upgrading V-Neck Lace Up Bodycon Mini Dress

    Upgrade your style with this sleeveless mini dress for weekend plans! The sleek V-neckline and spaghetti straps accentuate your feminine figure, while the front lace-up and slit add a touch of allure to the mini-length hem. Complete the look with a sleek layered necklace.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Spaghetti straps
    • V-neckline
    • Lace-up front and slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-2004

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    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
  • Strolls In The Sand V-Neck Tropical Skater Mini Dress

    Getaway in this tropical skater mini dress to the beach or on vacay! Featuring adjustable spaghetti straps and a flattering V-neckline, this dress hugs your silhouette with an elasticized waist and side cutouts. Its skater silhouette and mini-length hem make it perfect for any daytime adventure. Complete the look in cute sandals.

    Fit & Features

    • Tropical print, woven fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • V-neckline
    • Elasticized waist with side cutouts
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5656

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Wildflower Hour Lace A-Line Mini Dress

    Flirty meets sultry in one perfect dress. With a draped cowl neck and delicate floral lace, this A-line mini dress hugs every curve, serving up major after-dark romance.

    Fit & Features

    • Floral print, lace fabric lined with stretch knit
    • Cowl neckline, padded bra cups
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • A-line fit, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000477

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • Set To Amaze Mock Neck Abstract Mini Dress

    Everyone will admire your amazing self in this abstract mini dress all over town! Made with a unique abstract print on airy lined mesh fabric, this dress is sure to turn heads. The sleeveless design and mock neckline add a chic touch, while the ruched side seams, bodycon fit, and mini-length hem show off your curves. Complete the look with earrings.

    Fit & Features

    • Abstract print
    • Sheer mesh fabric with knit lining, plenty of stretch
    • Mock neckline
    • Ruching
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5783

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Miami Nights Sleeveless Tropical Slit Maxi Dress

    Turn up the heat in Miami in this tropical maxi dress on vacay! The square neckline and spaghetti straps accentuate your curves in a form-hugging fit while the high side slit adds a touch of sassy sophistication. Let the tropical print and maxi-length hem transport you to a paradise getaway! Complete the look in sandals.

    Fit & Features

    • Tropical print, knit fabric, stretchy short lining
    • Spaghetti straps
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5624

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Darling Appeal Sleeveless Ruffled Midi Dress

    You'll always give off a darling appeal in this sleeveless midi dress for casual occasions! With a classic square neckline and dual spaghetti straps, this dress is perfect for any occasion. The stretchy smocked bodice ensures a comfortable fit while the A-line silhouette and ruffled midi-length hem add a flattering touch. Complete the look in sandals and a crossbody bag.

    Fit & Features

    • Woven fabric, no stretch
    • Square neckline
    • Dual spaghetti straps
    • Stretchy smocked bodice
    • A-Line ruffled silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5457

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    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
  • Casually Flawless Crew Neck Textured Midi Dress

    Getting ready is a breeze with this casual crew neck midi dress for an effortlessly flawless vibe! Featuring classic cap sleeves and a flattering crew neck, this bodycon dress will hug your curves in all the right places down to the alluring midi-length hem on textured mesh fabric. Complete the look in platform sneakers.

    Fit & Features

    • Textured sheer mesh fabric
    • Stretchy slip lining with adjustable spaghetti straps
    • Crew neckline
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5625

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fit To Bloom Scoop Neck Ditsy Floral Midi Dress

    Sweet summer events are calling and this ditsy floral midi dress is here to make you look cute! Adjustable spaghetti straps and a drawstring scoop neckline provide versatile style, while the form-hugging fit and side slit add a touch of sass. Complete the look in high heels.

    Fit & Features

    • Ditsy floral print, bust lining, knit fabric, moderate stretch
    • Spaghetti straps
    • Drawstring adjustable scoop neckline, bust tie
    • Form-hugging fit
    • Side slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5774

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Iconic Occasion Strapless Denim Mini Dress

    Impress with your OOTD in this strapless denim mini dress to channel iconic moments! The strapless neckline flaunts some skin, the flattering bodycon fit with flexible boning hugs your curves, and the mini-length hem adds a touch of playfulness. Complete the look in chic pointed-toe boots and a purse!

    Fit & Features

    • Denim fabric, stretchy knit lining
    • Strapless neckline
    • Back zipper and hook-eye closure
    • Flexible boning
    • Bodycon fit
    • Style runs large

    Style Number/Barcode: 05102-5484

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Set For Cuteness Twist Back Slit Rib Knit Maxi Dress

    You and this maxi dress are set for cuteness all season long! Made with rib knit fabric, this dress is both comfortable and stylish, perfect for any occasion. Featuring a square neckline and shoulder straps, this dress offers a form-hugging fit that will accentuate your curves. The twist-back design adds a trendy touch while the high side slit and maxi-length hem provide an alluring appeal. Complete the look with sandals and sunnies!

    Fit & Features

    • Stretchy rib knit fabric
    • Square neckline
    • Shoulder straps
    • Twist back design
    • High side slit
    • Form-hugging
    • Runs true to size

    Style Number/Barcode: 05102-5577

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Blis Sleeveless Bodycon Knit Midi Dress

    Sit back and watch the compliments roll in when you're seen in this knit midi dress over the weekend! Crafted from a unique knit fabric offering a stretchy knit lining for comfort. It features adjustable spaghetti straps, a square neckline with a flirty bust tie, and a flattering bodycon midi-length silhouette. Complete the look in strappy sandals and a purse.

    Fit & Features

    • Unique knit fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • Square neckline, bust tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5712

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Loving Halter Strappy Floral Mini Dress

    You'll love this floral mini dress all summer for brunch, picnics, and casual parties! Featuring a halter V-neckline with spaghetti strap ties, an open back with spaghetti strap ties, this bodycon dress is perfect for a fun and flirty look. Style this dress with trendy flat sandals.

    Fit & Features

    • Floral print, knit fabric with stretchy knit lining
    • Halter V-neckline with spaghetti strap ties
    • Open back with spaghetti strap ties
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5807

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweeten Up Strappy Back Floral Chiffon Skater Dress

    Sweeten up any moment in this floral chiffon skater dress perfect for celebrations and showers! With a square neckline, spaghetti straps, and a playful strappy back design, this dress is perfect for any occasion. The skater silhouette and ruffled short-length hem add a flirty touch, while the ditsy floral print and chiffon fabric keep it light and whimsical. Complete the look in wedges.

    Fit & Features

    • Ditsy floral print, chiffon fabric lined with stretchy knit
    • Spagehtti straps, square neckline
    • Strappy back design
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5450

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In A Daze Strapless Cutout Striped Knit Mini Dress

    The perfect striped mini dress for summer dazes and effortless styling! Crafted from a stretchy ribbed knit fabric with a trendy striped print, this dress features a strapless straight-across neckline and cutout design at the waist for an alluring vibe. The bodycon fit on the mini-length silhouette will accentuate your gorgeous curves. Style this dress with sunglasses and sandals!

    Fit & Features

    • Striped pattern
    • Stretchy ribbed knit fabric
    • Strapless straight neckline
    • Waist cutout
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1971

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Good Times Bodycon Abstract Print Mini Dress

    A mini dress that calls for good times only at casual parties or weekend plans! Designed with an alluring abstract print on mesh fabric, this dress is both chic and versatile. The sleeveless crew neckline and bodycon silhouette highlight your curves, while the side ruched seams flatter your figure. Complete the look with a mini shoulder bag and heels.

    Fit & Features

    • Abstract print
    • Mesh fabric, sewn-in knit lining, stretchy
    • Side ruched seams
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5606

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Painted Muse Tube Slit Maxi Dress

    Like wearing a work of art, this strapless maxi dress stuns with a marbled print and a curve-hugging silhouette. The sleek side slit adds just the right touch of drama for gallery nights, rooftop hotel bars, or dinner downtown.

    Fit & Features

    • Marbled print stretchy mesh fabric, sewn-in lining
    • Tube strapless neckline
    • High side slit
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000247

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On The Prowl V-Neck Leopard A-Line Mini Dress

    This leopard mini dress calls for a night on the prowl for the best cocktail! Boast a fierce-sultry vibe in this sleeveless dress featuring a flattering V-neckline, adjustable spaghetti straps for the perfect fit, and an A-line silhouette that gracefully shows off your curves along the mini-length hem. Complete the look in an edgy faux leather jacket.

    Fit & Features

    • Leopard print, mesh fabric line with stretchy knit
    • Adjustable spaghetti straps
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5615

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Abstract Beauty Printed Slit Midi Dress

    Embrace your inner beauty in this abstract printed slit midi dress for any casual occasion! Featuring a flattering sleeveless square neckline perfect for layering, delicate spaghetti straps, and a bodycon fit, this dress flatters every figure. The front slit and midi-length hem add a touch of elegance, while the abstract print and mesh fabric create a unique style. Complete the look in mules and a cropped jacket.

    Fit & Features

    • Abstract print, stretchy mesh fabric, sewn-in knit lining
    • Spaghetti straps
    • Bodycon fit
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05102-5736

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vibrant Strapless Butterfly Print Mini Dress

    Set hearts aflutter in this vibrant butterfly print mini dress at parties or concerts! This dress is designed with a retro butterfly print on mesh fabric and boasts a strapless neckline and flattering bodycon fit. The short ruffled hem has a satin bow for added charm to your look! Style with platform shoes.

    Fit & Features

    • Butterfly print, mesh fabric lined with stretchy knit
    • Bodycon fit
    • Ruffled mini-length hem with satin bow
    • Runs short, size up if desired

    Style Number/Barcode: 05102-5775

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale