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.

  • Read All About It Newspaper Bodycon Mini Dress

    Extra, extra read all about how fine you'll look in this newspaper print mini dress! This dress features a sweetheart neckline with lace trim and adjustable spaghetti straps for a perfect fit. The built-in padded underwire bust ensures support while the bodycon fit and mini-length hem create a flattering silhouette. Complete the look in a crop denim jacket.

    Fit & Features

    • Newspaper print, knit fabric with stretchy lining
    • Adjustable spaghetti straps
    • Sweetheart neckline with lace trim
    • Back zipper and hook-eye closure
    • Built-in padded underwire bust
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5578

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Attention Getter Strapless Newspaper Print Mini Dress

    Capture attention with all eyes on you in this fab newspaper print mini dress! The textured lined woven fabric features a newspaper print with rose print accents for that trendy-girl vibe. The strapless straight-across neckline is detailed with an eyelet lace and thin velvet ribbon trim, tying at the center. The bodice features a bust seam outline with ruching to accentuate your figure. The flexible side boning adds structure, while the hidden back zipper offers effortless styling. The form-hugging fit on the mini-length hem will flaunt your stunning curves. Style with a layered choker necklace.

    Fit & Features

    • Non-stretch textured lined woven fabric, rose newspaper print
    • Strapless straight neckline with no-slip strip
    • Eyelet lace and velvet ribbon trim, tie-front, bust seam outline with ruching
    • Flexible side boning, hidden back zipper with hook and eye closure
    • Form-hugging fit
    • Strapless or sticky bra recommended
    • Runs true to size 

    Style Number/Barcode: 05102-5644

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Lovely In Lace Ruffled Puff Sleeve Mini Dress

    You'll be looking oh-so-lovely in this adorable ruffled puff sleeve mini dress! The sheer floral lace fabric gives that dainty-chic vibe, while the partial knit lining provides coverage. The mini-length dress features a square neckline and sheer short puff sleeves with the cutest ruffle trim, a small bust cutout with a sleek ribbon tie-front design, and a flattering empire waist seam. The flowy A-line silhouette adds that effortless flair. Style this short dress with heeled mules for date night.

    Fit & Features

    • Sheer floral lace fabric with knit lining, minimal stretch
    • Square neckline, ruffle trim
    • Sheer short puff sleeves, ruffle trim
    • Bust cutout, tie-front design
    • Empire waist seam, hidden side zipper closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3338

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Ocean Breeze Cowl Neck Low Back Tropical Maxi Dress

    Relax poolside with a drink in hand and this tropical mesh maxi dress on! Featuring a playful cowl neckline, adjustable spaghetti straps, and a low back with criss-cross straps for a touch of intrigue. Its curve-hugging silhouette and maxi-length hem will make you feel like a tropical goddess on vacation! Complete the look in sunnies and sandals!

    Fit & Features

    • Tropical palm print, mesh fabric lined with stretchy knit
    • Cowl neckline
    • Adjustable spaghetti straps
    • Low back with criss-cross straps
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5645

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Babe With Taste Buckle Strap Pleated Mini Dress

    Let everyone know you're a babe with taste in this pleated mini dress! Made from a twill woven fabric for structure and has a stretchy knit lining for coverage. With a square neckline and seam detailing, this dress exudes style. The adjustable buckle shoulder straps provide a customizable fit, while the fitted bodice and pleated mini-length hem flatter your figure. Complete the look with sunglasses and a purse!

    Fit & Features

    • Twill woven fabric, stretchy knit lining
    • Square neckline
    • Back zipper closure
    • Adjustable buckle shoulder straps
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5629

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Tuscan Charm Strapless Slit Eyelet Maxi Dress

    You'll be so charming in Tuscan wearing this eyelet maxi dress as the stunning new bride or chic traveler! The eyelet fabric adds a touch of delicacy, making it the perfect dress for any occasion. With a form-hugging fit and a high-side slit, this dress exudes confidence and elegance! Complete the look with earrings.

    Fit & Features

    • Eyelet fabric, sewn-knit lining, minimal stretch
    • Strapless neckline
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5637

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artsy Scene Mock Neck Abstract Mini Dress

    Indulge in the artsy scene in this mock neck abstract mini dress for downtown art walks! This sleeveless dress boasts a figure-flattering bodycon silhouette with side ruching, while the mini-length hem adds a flirty touch. The abstract print adds a bold and unique touch to this must-have dress. Complete the look in edgy boots and a shoulder bag.

    Fit & Features

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

    Style Number/Barcode: 05102-5630

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Everyday Beauty Sleeveless A-Line Mini Dress

    This sleeveless mini dress features a crew neckline, a flattering A-line silhouette, and a front slit accent. The soft rib knit fabric offers plenty of stretch and comfort.

    Fit & Features

    • Rib knit fabric, moderate stretch
    • Crew neckline
    • Front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5631

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Eye-Catching Vibes Cut Out Bodycon Mini Dress

    Keep every eye on you in this bodycon mini dress for flawless vibes at parties! Made from a brushed soft knit double-lined fabric, this dress offers ultimate comfort and style. Featuring a square neckline, spaghetti straps, and a bodycon fit, this dress will enhance your curves and make you stand out. The side cut out and ruched seams add an edgy touch, while the mini-length hem flaunts your figure. Complete the look in sandals and earrings.

    Fit & Features

    • Brushed knit soft double-lined fabric, stretchy
    • Spagehtti straps
    • Side cut out, side ruched seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5640

    Category Name: Casual Dresses

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • In The Mood Scoop Neck Lace A-Line Mini Dress

    Get in the mood to romance your look with this lace A-line mini dress perfect for a dressy soiree! This fun and flirty lace A-line mini features a scoop neckline and adjustable spaghetti straps for a perfect fit while the mini-length hem adds a touch of flirty. Complete the look with the matching bolero. 

    Shop Matching Bolero: In The Mood Long Sleeve Lace Bolero

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Scoop neckline
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3332

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • Bold Allure Abstract Print Mesh Midi Dress

    Show up and stun in this airy mesh midi dress accented with a trendy abstract print for a bold allure. The dress features a crew neckline, short cap sleeves, and a form-hugging silhouette to highlight your curves.

    Fit & Features

    • Abstract printed sheer mesh fabric with partial knit lining, plenty of stretch
    • Lettuce edge hems
    • Crew neckline
    • Short cap sleeves
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5628

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • 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
  • Always Eye-Catching Halter Ruffle Chiffon Mini Dress

    You'll look positively eye-catching in this floral mini dress at weddings or garden parties! The halter crew neckline and open back ooze elegance, while the ruffled bodycon silhouette flatters your curves. With a mini-length hem, this dress is perfect for any occasion. Complete the look with earrings.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Halter crew neckline, spaghetti strap tie
    • Open back
    • Ruffled bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5627

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Delightful View Collared Scenic Waist Skater Dress

    You'll be such a delightful view in this collared skater dress strolling the streets of Silicy or downtown! Featuring long sleeves with buttoned cuffs and a collared V-neckline, hidden front hook and eye fasteners provide a seamless look, and a scenic printed waist and short skater silhouette add a touch of charm. Complete the look in heels and a crossbody purse.

    Fit & Features

    • Gauze woven fabric with lining, no stretch
    • Collared V-neckline
    • Hidden front hook and eye fasteners
    • Scenic printed waist
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5638

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charmed Sweetness Lace-Up Floral Skater Dress

    Charm everyone with your sweetness in this floral skater dress with a flirty lace-up back and a ruffled short hem perfect for any weekend plans.

    Fit & Features

    • Floral print, woven fabric, bust lining
    • V-neckline, wide shoulder straps, padded bra cups
    • Lace-up back
    • Ruffled skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5622

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    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
  • Social Butterfly Square Neck Floral Mini Dress

    A dreamy butterfly floral mini dress perfect for social girlies! The mini-length dress features a square neckline that showcases a ribbon trim for romance, adjustable spaghetti straps to get a perfect fit, front metal closures, and a form-hugging silhouette that will flatter your figure. Complete the look in lace-up stiletto heels and a purse for a date!

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Butterfly floral print
    • Adjustable spaghetti straps
    • Ribbon trim, front metal closures
    • Back zipper and hook-eye closure
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5623

    Category Name: Casual Dresses

    Price: $5.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Arrived In Style Strapless Knit Mini Dress

    Arrive in this stylish strapless mini dress for brunch or parties! The contrasting folded neckline adds a touch of boldness while the slim-fit silhouette shows off your curves perfectly on the smooth knit fabric. The mini-length hem features a subtle A-line fit. Complete the look in platform heels.

    Fit & Features

    • Smooth knit fabric lined with stretchy knit
    • Strapless folded contrast neckline
    • Slim-fit silhouette
    • Mini-length A-line hem
    • Runs true to size

    Style Number/Barcode: 05102-5621

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    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
  • Adorably Chic Bow-Detailed Ruffled Mesh Mini Dress

    This bow-detailed ruffled mesh mini dress is so adorably chic and perfect for date nights or parties! Made with an airy sheer mesh fabric with a full-length knit lining, this dress gives those effortless breezy vibes. The sleeveless square neckline shapes the bodice, and the adjustable spaghetti straps offer a customized fit. The dress features a ruffled tiered silhouette for the cutest look, detailed with dainty bow accents. The tiers have elastic seams for stretch. The flowy A-line fit on the mini-length hem will give your 'fit a feminine touch. Style with lace-up heels.

    Fit & Features

    • Non-stretch sheer mesh fabric, stretchy knit lining
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Ruffled tiered silhouette with bow accents
    • Elastic seams for stretch
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5618

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leave An Impression Twist Cutout Knit Midi Dress

    Leaving an impression will be easy with this sleeveless knit midi dress! Perfect for vacation or a weekend spent at the beach, this dress features a flattering scoop neckline, spaghetti straps, a head-turning twist cutout back design, a bodycon fit, and a sultry side slit along the midi-length hem. Complete the look in strappy espadrille wedges.

    Fit & Features

    • Knit fabric, moderate stretch
    • Scoop neckline
    • Spaghetti straps
    • Twist back cutout
    • Side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1950

    Category Name: Casual Dresses

    Price: $17.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Blooming Bouquet Sleeveless Floral Mesh Mini Dress

    Get ready to bloom in this floral mesh mini dress at a girl's brunch or evening soiree! The sleeveless crew neckline and bodycon silhouette highlight your curves, while the bold floral print and mesh fabric add a touch of feminine charm. Complete the look in simple stiletto heels.

    Fit & Features

    • Blooming floral print
    • Sheer mesh fabric with knit lining, plenty of stretch
    • Crew neckline
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5612

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale