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.

  • Flowy Feels Paisley Maxi Dress

    You'll love the flowy fit of this paisley maxi dress, perfect for the warmer months! It features a sleeveless cowl neckline, spaghetti straps, a maxi-length hem, and a thigh-high front slit. The smooth and stretchy knit fabric features a trendy paisley print pattern. Complete the look with strappy sandals.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Maxi-length hem, high front slit
    • Flowy silhouette
    • Paisley print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4967

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So In Love Floral A-Line Midi Dress

    You'll fall so in love with this floral midi dress to wear for day dates! It features a sleeveless square neckline, elastic ruched straps with lettuce-edge trim, an A-line silhouette, and a flirty front slit. The dress has a dainty rose floral print on stretchy knit-lined fabric. Complete the look in heeled sandals.

    Fit & Features

    • Sleeveless square neckline
    • Elastic ruched straps
    • Lettuce-edge trim
    • A-line silhouette
    • Front slit, midi-length hem
    • Dainty rose floral print, stretchy knit-lined fabric
    • Runs true to size

    Style Number/Barcode: 05102-4921

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trip To The Tropics Printed Midi Dress

    You'll look like you're ready to whisk away on a tropical vacay in this printed midi dress! It features a sleeveless V-neckline, spaghetti straps, a midi-length hem, a hip-hugging fit and an A-line silhouette, a thigh-high front slit, and an eye-catching tropical palm leaf print. Style with trendy wedges.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Midi-length hem, hip-hugging fit, A-line silhouette
    • High front slit
    • Tropical palm leaf print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4979

    Category Name: Casual Dresses

    Price: $19.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Let's Go Party Marble Mesh Mini Dress

    You'll be ready to live it up this festival season in this trendy marble mesh mini dress! It features a sleeveless square neckline, spaghetti straps, an alluring open back with a lace-up strappy design, a mini-length hem with a curve-hugging bodycon silhouette, and a fab marble swirl printed design. The lined mesh fabric offers plenty of stretch. Complete your party look with a faux leather jacket.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Open back, lace-up strappy design, tie closure
    • Mini-length hem, bodycon silhouette
    • Marble swirl print
    • Sheer mesh fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4960

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fiercely Stylish Leopard Print Maxi Dress

    Keep it fiercely stylish with a maxi dress that brings a chic flair! The lightweight knit dress features a sleeveless V-neckline, spaghetti straps, a maxi-length, flowy, A-line silhouette, a sultry thigh-high front slit, and a trendy leopard print pattern. Complete the look with clear mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Maxi-length A-line silhouette
    • High front slit
    • Leopard print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4968

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spice It Up Cutout Midi Dress

    Serving sultry vibes with zero effort required. This knit midi hugs in all the right places with a bold cutout back and leg slit that was made for double takes.

    Fit & Features

    • Textured knit fabric with stretch
    • V-neckline, tank shoulder straps
    • Open back cutout with racer strap detail
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000109

    Category Name: Casual Dresses

    Price: $12.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On The Go Crew Neck Slit Midi Dress

    The perfect casual midi dress to look stylish while on the go! It features cap short sleeves, a crew neck, a bodycon silhouette, a side ruched drawstring, and a flirty slit along the hem. The dress is composed of a super soft brushed knit fabric with plenty of stretch. Style with cute slide sandals and a tote bag! 

    Fit & Features

    • Cap short sleeves
    • Crew neck
    • Bodycon silhouette
    • Side ruched drawstring, slit accent
    • Midi-length hem
    • Soft brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4872

    Category Name: Casual Dresses

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Charm Tie-Front Midi Dress

    Make them all fall for your stylish charm in this adorable midi dress! It features a sleeveless V-neckline with a cute tie-front detail, spaghetti straps, a midi-length hem with a high front slit for a subtle sultry vibe, and a slim-fit silhouette. The lightweight knit fabric has plenty of stretch. Pair with hoop earrings and block heels for a date night.

    Fit & Features

    • Sleeveless V-neckline, tie-front detail
    • Spaghetti straps
    • Midi-length hem, high front slit
    • Slim-fit silhouette
    • Lightweight knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4864

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Irresistible Mesh Midi Dress

    You'll be a vision in this simply irresistible mesh midi dress perfect for an engagement party or cocktail soiree! It features a sleeveless plunge v-neck, adjustable straps, a back slit accent, and ruched seams that accentuate your curves along the bodycon silhouette. Complete the look in stiletto heels.

    Fit & Features

    • Sleeveless plunge v-neck
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Ruched seams, back slit accent
    • Bodycon, midi-length hem
    • Mesh fabric, sewn-in knit lining, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05101-1857

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blooming Beauty Floral Midi Dress

    Bloom with beauty in this gorgeous floral midi dress perfect for the season! It features a sleeveless square neckline, spaghetti straps, a knot-front design at the waist with ruching, a midi-length hem with a chic high front slit, and a curve-hugging fit. The stretchy knit fabric showcases a stunning bold floral print. Style with platform heels for a bridal shower.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps, square back
    • High waist seam, knot-front design, ruching
    • Midi-length hem, high front slit
    • Form-hugging fit
    • Bold floral print, knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1678

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Staple Wrap-Front Mini Dress

    Update your wardrobe with this cute and casual mini dress that is a stylish staple! It features a crew neckline, short sleeves, a trendy wrap-front design at the waist with a tie closure, a form-hugging fit, and a mini-length hem. The soft brushed knit fabric offers plenty of stretch for comfort. Complete the look with ankle booties.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Wrap-front design at the waist, tie closure
    • Form-fitting silhouette
    • Mini-length hem
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5007

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Prowlin' Cutie Leopard Crepe A-Line Dress

    Look cute for your daytime prowls in this leopard print crepe dress! It features long bell sleeves, a scoop neck with a ruched tie-front bust, halter straps with self-tie closure, and a flattering A-line silhouette and dual side slit accents. Complete the look in sassy sandals!

    Fit & Features

    • Long bell sleeves
    • Scoop neck, ruched tie-front bust
    • Halter straps, self-tie closure
    • A-line silhouette
    • Short-length hem with dual side slit accents
    • Leopard print, crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4959

    Category Name: Casual Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple Chic Style Satin Mini Dress

    The simple chic style of this satin mini dress is perf for the babe who loves a classic look. It features a sleeveless V-neckline, bungee spaghetti straps, a fitted A-line silhouette, and a mini-length hem with an alluring front slit. The lightweight satin-knit fabric offers a moderate stretch. Complete the outfit with strappy heels.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Fitted A-line silhouette
    • Mini-length hem
    • Front slit
    • Satin-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1965

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfectly Striped Shirt Skater Dress

    Step out in this perfectly striped shirt dress to look cute for picnics in the park, family gatherings, or graduations! It features long sleeves with buttoned cuffs, a collar v-neckline, a corset-seam illusion waist, a cutout lace-up back design, and a short skater silhouette. Complete the look with teardrop earrings.

    Fit & Features

    • Long sleeves, buttoned cuffs
    • Collar v-neckline
    • Corset-seam illusion waist
    • Cutout lace-up back design
    • Skater silhouette, short-length hem
    • Striped print, poplin non-stretch woven fabric
    • Runs true to size

    Style Number/Barcode: 05102-5048

    Category Name: Casual Dresses

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Moves Long Sleeve Bodycon Mini Dress

    Showcase your silhouette in this chic bodycon mini dress! It features a V-neckline, long fitted sleeves, ruched detailing at the shoulders, a mini-length hem, and a curve-hugging fit. The smooth knit fabric offers plenty of stretch. Style with clear lucite heels.

    Fit & Features

    • V-neckline
    • Long fitted sleeves
    • Ruching at the shoulders
    • Mini-length hem
    • Fitted bodycon silhouette
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05103-4835

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance For One Rose Tie-Front Dress

    Romance yourself! Look sweet in this rose print casual dress on a day date or brunch. It features a sleeveless sweetheart neck, spaghetti straps, bust tie-front, and keyhole, side ruched seams to accentuate your figure along the mini, bodycon silhouette. Style with a denim jacket to complete the look!

    Fit & Features

    • Sleeveless sweetheart neck, spaghetti straps
    • Bust tie-front and keyhole
    • Side ruched seams
    • Bodycon silhouette, mini-length hem
    • Ditsy rose print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4929

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Beauty Floral Mini Dress

    Radiate effortless beauty in this gorg floral mini dress! It features a square neckline, sheer long peasant sleeves to add a chic flair, all-over ruching, a mini-length hem with a form-hugging fit, and an all-over blooming floral print. The sheer chiffon fabric includes a partial knit lining down the body of the dress. Style with dainty duster earrings and a pair of neutral heels.

    Fit & Features

    • Square neckline
    • Sheer long peasant sleeves, elastic cinched hems
    • All-over ruching, back zipper, hook and eye closure
    • Mini-length hem, form-hugging fit
    • Floral print
    • Sheer chiffon fabric, partial knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1860

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tie Dye Over Bodycon Mini Dress

    You'll tie-dye over this casual mini dress to add some color to your closet for warmer seasons ahead! It features a square neck, bungee spaghetti straps, and side ruched seams that accentuate your curves along the bodycon silhouette. The dress is composed of stretchy mesh fabric with a sewn-in knit lining. Complete the look in a cropped denim jacket and sneakers.

    Fit & Features

    • Sleeveless, square neck
    • Bungee spaghetti straps
    • Side ruched seams, bodycon silhouette
    • Mini-length hem
    • Tie-dye pattern, mesh fabric, sewn-in knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4931

    Category Name: Casual Dresses

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Staple Long Sleeve Midi Dress

    This long sleeve midi dress is such a stylish staple! Featuring a square neckline with a chic center cutout at the bust, long fitted sleeves, a midi-length hem with a front slit, and a form-hugging fit, this crepe dress can be styled up or down. Pair with strappy mules for a date night.

    Fit & Features

    • Square neckline
    • Small bust cutout
    • Long fitted sleeves
    • Midi-length hem, front slit
    • Form-hugging fit
    • Crepe fabric, short knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5529

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Paradise Halter Open Back Slit Midi Dress

    Own the spotlight on vacation in this midi dress! Featuring a bold halter neckline and an sexy open back, this dress exudes allure, while the bodycon silhouette and slit add a flattering look.

    Fit & Features

    • Slinky knit fabric, smooth stretchy knit lining
    • Halter cowl neckline, beaded spaghetti strap tie
    • Open back with spaghetti strap tie
    • Bodycon silhouette
    • Slit accent, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000283

    Category Name: Casual Dresses

    Price: $32.00 $45.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED, BROWN

    Available Size: XS, S, M

    Product Badge:
    • Sale
  • True Colors Marble Print Mini Dress

    Show your true colors of style in this marble print dress perfect for casual plans! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, and a mini-length hem. Style with trendy heels and a denim jacket to complete the look!

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Marble print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5000

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Extra Flair Floral Skater Dress

    You'll be a darling delight in this short skater dress perfect for parties and ceremonies! It features three-quarter-length puff sleeves, a square neck, a smocked back, and a fit and flare silhouette. The dress is composed of a floral burnout woven fabric with a chiffon lining and no stretch. Style with earrings and a choker to complete the look!

    Fit & Features

    • Three-quarter-length puff sleeves
    • Square neck
    • Smocked back
    • Fit and flare skater silhouette
    • Short-length hem
    • Floral burnout woven fabric, chiffon lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2211

    Category Name: Casual Dresses

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Into Floral Chiffon Skater Dress

    Transition your winter blues into fresh spring florals! This breezy chiffon skater dress is perfect for dressy brunches or engagement parties. It features a surplice V-neckline, sheer peasant sleeves, a tie-back belted waist, and a tiered ruffle short-length hem with an adorable ditsy floral print. Complete the look in lace-up heels.

    Fit & Features

    • Surplice V-neckline
    • Sheer peasant sleeves 
    • Tie-back belted waist, back zipper and hook-eye closure
    • Skater, fit and flare silhouette
    • Tiered ruffle short-length hem
    • Ditsy floral print, chiffon fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1711

    Category Name: Casual Dresses

    Price: $5.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Babe Cutout Sweater Dress

    You'll be such a trendy babe in this adorable cutout sweater dress! Featuring a sleeveless high neckline with a racerback design, a front keyhole cutout at the bust, alluring side cutouts at the waist, a midi-length hem, and a curve-hugging silhouette, this dress is a perfect pick for a night out with the girls. Style with platform heels and a chic handbag.

    Fit & Features

    • Sleeveless high neckline, racerback design
    • Front keyhole cutout at the bust
    • Dual side cutouts at the waist
    • Midi-length hem, curve-hugging fit
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1633

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance