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.

  • Friendly Flirt Eyelet Mini Dress

    Catch yourself a cutie-looking flirty in this eyelet mini dress featuring short puff sleeves, a sweetheart neck, a ruched bust with a tie front, a corset-seam bodice, and a bodycon silhouette. The dress is composed of stretchy eyelet lace fabric with a knit lining. Complete the look with a dainty choker and earrings set.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neck
    • Ruched bust, tie front
    • Corset-seam bodice
    • Bodycon silhouette, mini-length hem
    • Eyelet lace, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4978

    Category Name: Casual Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Just Spotted Leopard Lace-Up Midi Dress

    Just spotted, you in this effortlessly fierce leopard print midi dress! It features a sleeveless V-neckline with a twisted bust accent, spaghetti straps that lace up in the back, and a flattering A-line silhouette with a flowy hem. Complete the look with a sleek choker for lunch with friends!

    Fit & Features

    • Sleeveless V-neckline, twisted bust accent
    • Spaghetti straps, lace-up back
    • A-line silhouette
    • Flowy midi-length hem
    • Leopard print, breezy woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4976

    Category Name: Casual Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Style Eyelet Knit Mini Dress

    Show off the sweetest style in this adorable eyelet knit mini dress. It features a sleeveless sweetheart neckline with a knot-front design at the bust, spaghetti straps, a mini-length hem, a form-hugging fit, and a dainty floral eyelet pattern. The lined knit fabric offers plenty of stretch. Complete your look with espadrille sandals for a weekend date.

    Fit & Features

    • Sleeveless sweetheart neckline, knot-front design
    • Spaghetti straps
    • Mini-length hem
    • Form-hugging fit
    • Floral eyelet pattern
    • Lined knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4969

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Looks Mesh V-Neck Babydoll Dress

    Showcase a dreamy look in this mesh babydoll dress perfect for date nights or parties! It features a sleeveless V-neckline, adjustable spaghetti straps, ruched bust seams, and a flattering babydoll style silhouette with a mini-length hem. Complete the look in sleek hoop earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Ruched bust seams
    • Babydoll style silhouette
    • Mini-length hem
    • Airy mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4971

    Category Name: Casual Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Like A Day Dream Eyelet Lace Dress

    Look like a daydream come true in this eyelet lace mini dress for your next date! It features adorable puff sleeves with ruffle trim, a sweetheart neck, a ruched bust seam, and a bodycon silhouette with a flirty tiered ruffle hem. Complete the look in cute stiletto heels.

    Fit & Features

    • Puff short sleeves, ruffle trim
    • Sweetheart neck
    • Ruched bust seam
    • Bodycon silhouette
    • Tiered ruffle mini-length hem
    • Eyelet lace fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2184

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay In Bali One-Shoulder Maxi Dress

    Vacation in sultry style wearing this maxi dress! Serve major looks on the island in this dress featuring a sleeveless one-shoulder neckline, a tank strap with a hoop insert, and a form-hugging slim silhouette with a high side slit and ruched seam on textured knit fabric. Complete the look in chic sandals.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Tank strap, hoop insert
    • Form-hugging, slim silhouette
    • High side slit, side ruched seam
    • Maxi-length hem
    • Textured knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4970

    Category Name: Casual Dresses

    Price: $5.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Language Of Romance Lace Babydoll Dress

    This lace babydoll dress speaks your language for romance! Let this short dress sweep you off your feet for wedding showers, graduations, or birthday brunches! It features three-quarter-length puff sleeves, a square neck, a stretchy smocked back, and an empire waist seam that flares out into the flowy hem. Complete the look in new sandals and a clutch!

    Fit & Features

    • Three-quarter-length puff sleeves
    • Square neck
    • Stretchy smocked back
    • Empire waist, fit and flare silhouette
    • Flowy short-length hem
    • Lace overlay, chiffon lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4973

    Category Name: Casual Dresses

    Price: $5.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Somewhere Tropical V-Neck Midi Dress

    You deserve to go somewhere tropical with this midi dress as your inspiration! It features a sleeveless V-neckline, spaghetti straps, a curve-hugging silhouette, and a flirty slit hem. The dress is composed of a palm-printed stretchy knit fabric. Complete the look in strappy-heeled sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Curve-hugging silhouette
    • Slit midi-length hem
    • Palm print, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4966

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • 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
  • Dream Escape Tropical Midi Dress

    Pack right for your dream escape with this tropical print midi dress perfect for a dinner with a beachside view! It features a sleeveless V-neckline, adjustable spaghetti straps that crisscross in the back, a bodycon fit, and a ruched side seam to accentuate your curves atop a sultry slit. The smooth knit fabric features a gorgeous tropical floral print that will give off major vacay vibes. Complete the look with sleek earrings and a choker necklace.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, crisscross back
    • Bodycon silhouette
    • Side ruched seam, slit accent
    • Asymmetric midi-length hem
    • Tropical floral print, knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4957

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Palms Tropical One-Shoulder Dress

    This tropical mini dress will put you in vacay mode! Flaunt some skin in this sleeveless one-shoulder dress featuring a sleek bungee spaghetti strap, side ruched seams to accentuate your curves, and a bodycon fit. The dress is designed with a palm leaf print on stretchy knit-lined fabric. Complete your getaway look in platform wedges.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Bungee spaghetti strap
    • Side ruched seams
    • Bodycon fit, mini-length hem
    • Palm leaf print
    • Lined stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4956

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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
  • 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
  • Just Peachy Keen Off-The-Shoulder Midi Dress

    Look and feel peachy keen in this cute swiss dot midi dress perfect for strolls downtown or grabbing brunch! It features an off-the-shoulder neckline with adorable flutter short-sleeve cuffs, a stretchy smocked bodice, and a flowy hem with a front-slit accent. Complete the look in sleek hoop earrings and sandals.

    Fit & Features

    • Off-the-shoulder neckline
    • Flutter short-sleeve cuffs
    • Stretchy smocked bodice
    • Flowy midi-length hem, front slit accent
    • Swiss dot woven fabric, mini-length woven lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4953

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Mart Chiffon Skater Dress

    Always look like you've just come from somewhere with flowers! This breezy ditsy floral skater dress embodies every girl's favorite thing about spring. It features sheer 3/4 length sleeves with elastic cuffs, a sweetheart neck with a bust tie and keyhole, a smocked back, and a flowy fit and flare short-length hem. Complete the look in platform wedges.

    Fit & Features

    • Sheer 3/4 length sleeves, elastic cuffs
    • Sweetheart neck, bust tie, and keyhole
    • Smocked back
    • Skater silhouette, short-length hem
    • Ditsy floral print
    • Chiffon fabric with lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2161

    Category Name: Casual Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Pretty Chiffon Midi Dress

    Showcase your effortless beauty in this airy, lightweight chiffon midi dress. It features a sweetheart neckline with a ruched bodice, long sheer peasant sleeves, a stretchy smocked back design, a fitted high waist seam, a midi-length hem with a high front slit, and a flowy, A-line silhouette. Style with clear mules for a weekend brunch date.

    Fit & Features

    • Sweetheart neckline, ruched bodice
    • Long sheer peasant sleeves, elastic cinched hems
    • Stretchy smocked back design
    • Fitted high waist seam
    • Midi-length hem, high front slit, A-line silhouette
    • Sheer chiffon fabric, partial knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4954

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flower Power Lace-Up Mini Dress

    Keep your spring look on point with this cute and casual floral mini dress! It features a sleeveless scoop neckline, spaghetti straps, a lace-up back with tie closure, a bodycon silhouette, and a charming flower print on stretchy knit fabric. Complete the look with sandals for a day date!

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Lace-up back with tie closure
    • Bodycon silhouette, mini-length hem
    • Flower print
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4955

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Playful Spirit Chiffon Skater Dress

    Play up your flirty side in this adorable chiffon skater dress featuring sheer peasant sleeves, a square neckline, an open-back with tie closure, and a short-length hem. Complete the look in platform heels for a dressy event!

    Fit & Features

    • Sheer peasant sleeves
    • Square neckline
    • Open-back with tie closure
    • Skater silhouette
    • Short-length hem
    • Airy chiffon fabric, woven lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-2162

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Seasonal Surprise Color Block Dress

    Mix it up this season! Step out in this trendy color block mini dress featuring fitted long sleeves, a scoop neck, and a bodycon silhouette on stretchy rib-knit fabric. Style with over-the-knee boots to complete the look!

    Fit & Features

    • Fitted long sleeves
    • Scoop neck
    • Bodycon silhouette
    • Mini-length hem
    • Color block pattern
    • Rib-knit fabric, double-lined, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4952

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pick Me Floral Lace-Up Maxi Dress

    This floral maxi dress will be the first pick in your closet! It features a sleeveless V-neckline with a knotted bust, spaghetti straps that creates the open lace-up back design, and a flowy slim silhouette. Complete the look in cute new sandals for a baby shower or casual lunch out!

    Fit & Features

    • Sleeveless V-neckline, knotted bust
    • Spaghetti straps
    • Lace-up open back
    • Flowy slim silhouette
    • Maxi-length hem
    • Floral print, breezy woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4947

    Category Name: Casual Dresses

    Price: $5.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Slay Tropical Print Midi Dress

    Slay your vacay look with this curve-hugging tropical print midi dress! It features a sleeveless V-neckline, spaghetti straps, a ruched side seam, a midi-length asymmetric hem creating a chic side slit, and a bodycon silhouette. The all-over tropical palm leaf print will really bring those vacay vibes. Complete the look with clear mules.

    Fit & Features

    • Sleeveless V-neckline, spaghetti straps, bust lining
    • Ruched side seam
    • Midi-length asymmetric hem, side slit
    • Bodycon silhouette
    • Tropical palm leaf print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4948

    Category Name: Casual Dresses

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Made You Flirt Lace Skater Dress

    Make your crush flirt with how cute you'll be looking in this lace eyelet short dress perfect for birthday brunches or parties! Featuring a sleeveless scoop neck, ruffled straps, a ruched bust, and a fit-and-flare skater silhouette. Style with a chic bracelet and heels to complete the look.

    Fit & Features

    • Sleeveless scoop neck, ruffled straps
    • Ruched bust
    • Fit and flare skater silhouette
    • Short-length hem
    • Lace eyelet fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2155

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • What A Sight Eyelet Lace Lace-Up Dress

    You'll be quite a dreamy sight in this eyelet lace skater dress! Perfect for wedding showers, grabbing lunch with the girls, or backyard parties. It features adorable puff short sleeves, a sweetheart neck with an underbust seam, an open lace-up back, and a flattering short-length silhouette. Complete the look in strappy block heels.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neck, underbust seam
    • Open lace-up back
    • Skater silhouette
    • Short-length hem
    • Eyelet lace cotton fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4946

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale