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.

  • Not Your Angel Mesh Mini Dress

    You're no one's angel. Make their jaw drop in this mesh mini dress featuring a sleeveless, square neck, spaghetti straps, bodycon silhouette, front ruched seams, and an angel multi-print design. Complete the look in large hoops for a party.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Front ruched seams
    • Bodycon silhouette
    • Angel multi-print 
    • Mesh-lined fabric
    • Fits true to size

    Style Number/Barcode: 05102-4617

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lily Girl A-Line Mini Dress

    A girl like you will love this floral mini dress for a sweet summer vibe! It features a sleeveless V-neck, spaghetti straps that lace up on the open-back design, a bodycon A-line silhouette, and a front slit accent. Complete the look in wedges.

    Fit & Features

    • Sleeveless, V-neck, spaghetti straps
    • Open-back with lace-up design
    • Bodycon A-line silhouette
    • Front slit accent
    • Mini-length hem
    • Floral print, knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4618

    Category Name: Casual Dresses

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picture Perfect Marble Print Dress

    This marble print mini dress is picture-perfect for snapping an insta-worthy shot! It features a sleeveless, square neck, spaghetti straps, side ruched seams, and a form-hugging fit on stretchy-lined knit fabric. Complete the look in sleek hoop earrings.

    Fit & Features

    • Sleeveless, square neck
    • Spaghetti straps
    • Side ruched seams
    • Form-hugging fit
    • Lined knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4611

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Striped Sensation Ruche Mini Dress

    You'll be such a sensation in this striped mini dress featuring a sleeveless square neck, spaghetti straps, and ruched side ties on ribbed knit fabric offering a form-hugging fit and a moderate stretch. Complete your casual look in a denim jacket and tennis shoes.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Ruched side ties
    • Form-hugging fit
    • Mini-length hem
    • Striped print, ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4614

    Category Name: Casual Dresses

    Price: $9.97 $23.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Moments Twist Front Midi Dress

    This midi dress deserves a moment of admiration! It features a sleeveless, v-neck, tank straps, a sultry twisted bust with cutout detail, and a bodycon silhouette on stretchy rib-knit fabric. Complete the look in strappy heels for date night.

    Fit & Features

    • Sleeveless, v-neck, tank straps
    • Sultry twisted bust, cutout detail
    • Bodycon silhouette
    • Midi-length hem
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4610

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sun's Out Halter Button Mini Dress

    Sun's out, shoulders out! This halter mini dress is perfect for a sunny day out and about. It features a sleeveless bodice, collared neckline, a partial open-back, button-down front, and a bodycon silhouette on sweater rib-knit fabric. Complete the look in a dainty ring set. 

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Sleeveless, halter collared neckline
    • Partial open-back
    • Button-down front
    • Bodycon silhouette
    • Mini-length hem
    • Sweater rib-knit 
    • Runs true to size

    Style Number/Barcode: 06005-1463

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Leave Em' Breathless Sweater Dress

    Leave your crush breathless when they see you in this spicy sweater mini dress! It features an off-the-shoulder neckline, long sleeves, a cutout bust, and a bodycon silhouette. Complete the look in thigh-high boots for everyday slay! 

    Shop More Sweater Styles: The Sweater Collection

    Fit & Features

    • Off-the-shoulder neckline
    • Long sleeves
    • Cutout bust
    • Bodycon silhouette
    • Mini-length hem
    • Ribbed-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1456

    Category Name: Casual Dresses

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Silhouette Midi Sweater Dress

    This curve-hugging sweater dress was made for sunset happy hour! It features a sleeveless V-neckline with a twist-front design, a center cutout under the bust, tank shoulder straps, and a midi-length, form-fitting silhouette with a chic high side slit. Style with classic hoop earrings and clear mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless V-neckline, twist-front accent
    • Center cutout under the bust
    • Tank shoulder straps
    • Midi-length hem, form-fitting silhouette, high side slit
    • Ribbed sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1462

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Live Fast Graphic Halter Tunic

    A biker babe like you is in need of this graphic tunic! It features a sleeveless, halter neck with tie closure and a front lace-up cutout with graphic detail that reads, "Live Fast/Born To Ride" on a fitted, short-length hem. Complete the look in sleek booties.

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • Front lace-up cutout
    • Graphic detail that reads, "Live Fast/Born To Ride"
    • Fitted, short-length hem
    • Cotton fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1294

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Soiree Puff Sleeve Mini Dress

    Heading to an afternoon soiree? This floral mini dress is perfect! It features adorable short puff sleeves, a sweetheart neckline, a front bust tie with a keyhole accent, and a bodycon silhouette. Complete the look with a crossbody bag.

    Fit & Features

    • Short puff sleeves, elasticized hems
    • Sweetheart neckline
    • Front bust tie, keyhole accent
    • Bodycon silhouette
    • Mini-length hem
    • Floral pattern
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4608

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachside Beauty Floral Mini Dress

    You'll be a total beachside beauty on your summer vacay in this floral mini dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, dual front verticals seams with ruched detailing, and a short, curve-hugging silhouette. The lined mesh fabric features an all-over tropical floral print. Complete the look with espadrille sandals.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Dual front vertical seams, ruched detailing
    • Mini-length, form-fitting, bodycon silhouette
    • Tropical floral print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4609

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Set The Style Marble Print Dress

    Set the style you desire! This marble print mini dress features side ruched drawstrings that let you customize the length depending on your preference, a square neck, spaghetti straps, and a form-hugging fit. Complete the look in strappy heeled mules. 

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Side ruched customizable drawstrings
    • Marble print 
    • Form-hugging fit
    • Soft knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4605

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Good Marbles Lace-Up Mini Dress

    Turn your day into a fashion slay! Stay trending in this sleeveless mini dress featuring a square neck, spaghetti straps that lace up on the open back, and Venecia marble print on stretch-knit fabric that offers a form-hugging fit. Complete the look in doorknocker earrings.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Open-back, lace-up design
    • Form-hugging fit
    • Mini-length hem
    • Venecia marble print, stretch knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4607

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Poised And Chic Sweater Dress

    Keep it poised and chic with a sweater dress that is perf for every day! The dress features a sleeveless collared neckline, a button-down front, and a bodycon fit through the hip and thigh. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules and hair clips.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features 

    • Sleeveless collared neckline
    • Button-down front 
    • Bodycon fit
    • Short-length hem 
    • Ribbed knit fabric
    • Form-hugging fit, moderate stretch 
    • Runs true to size  

    Style Number/Barcode: 06005-1451

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Occasion Ruched Side Mini Dress

    Your next daytime occasion calls for this floral mini dress featuring a sleeveless, square neck, spaghetti straps, and side ruched seams that accentuate your curves on the soft-knit fabric. Complete the look with a cropped jacket.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Floral print
    • Soft-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4606

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Knit Your Average Sweater Dress

    Level up in this curve-flaunting sweater dress featuring a sleeveless, scoop neckline, spaghetti straps, a bodycon silhouette, and a mini-length hem on ribbed knit fabric with plenty of stretch. Complete the look in a crop cardigan and booties.

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Sleeveless, scoop neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Ribbed knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1450

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feel The Heat V-Neck Midi Dress

    Sizzle and stun in this midi dress perf to bring up the temps! It features a sleeveless plunge V-neckline with a center O-ring insert, cutout bodice, form-fitting silhouette, and a side slit accent. Complete the look in lucite mules for a night out.

    Fit & Features

    • Sleeveless, plunge V-neck
    • Center O-ring
    • Cutout bodice
    • Form-fitting silhouette
    • Side slit accent, midi-length hem
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1448

    Category Name: Casual Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flatter Me Cutout Maxi Dress

    You won't need anyone flattering you in this sexy maxi dress! Featuring a sleeveless, scoop neck, spaghetti straps, a cutout bodice, partial open-back, a form-fitting silhouette, and a sultry slit perfect for showcasing heels.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Cutout bodice
    • Partial open-back
    • Form-fitting silhouette
    • Front slit
    • Maxi-length hem
    • Slinky knit fabric, moderate stretch, fits true to size

    Style Number/Barcode: 05102-4603

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fine Lines Chambray Skater Dress

    Flirty and fine! Look and feel effortlessly cute in this chambray striped skater dress featuring a sleeveless, v-neck, ruffled trim, and a babydoll-style seam that leads to the flowy short-length hem. Complete the look in braid strap mules.

    Fit & Features

    • Sleeveless, v-neck, ruffled trim
    • Babydoll-style seam
    • Flowy short-length hem
    • Chambray striped fabric, lining, no stretch
    • Back keyhole accent, button closure
    • Fits true to size

    Style Number/Barcode: 05102-4602

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Have We Met Lace-Up Mini Dress

    Say hello to your new fave mini dress for day-to-night soirees! Featuring a sleeveless, square neck, spaghetti straps, high waist seam, side ruched seams, and an open-back with lace-up closure. Composed of brushed soft and stretchy knit fabric that hugs your curves like an hourglass. Finish the look in a sleek cropped jacket.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • High waist seam
    • Side ruched seams
    • Open-back, lace-up closure
    • Bodycon silhouette, mini-length hem
    • Brushed soft and stretchy knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4593

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple Smooth Knit Mini Dress

    Style up this simple smooth knit mini dress for adorable date looks! It features a sleeveless square neckline, spaghetti straps, ruching down the side seams, a wrap-front design, and a short, curve-hugging, bodycon silhouette. Complete the outfit with strappy mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching down the side seams
    • Wrap-front
    • Mini-length hem, bodycon silhouette
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4594

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral State Scoop Neck Mini Dress

    Got a floral state of mind? Then this mini dress is just what you need! It features a sleeveless, scoop neck, spaghetti straps, and ruched bust seam that leads to a bodycon silhouette. Complete the look in chic wedges for a cute picnic date.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Ruched bust seam
    • Bodycon silhouette
    • Mini-length hem
    • Floral print
    • Stretchy rib-knit fabric, lined
    • Fits true to size

    Style Number/Barcode: 05102-4601

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • You'll Be Back Twist Bodycon Dress

    You'll be back wearing this sultry bodycon dress on repeat! It features a sleeveless square neckline, sleek spaghetti straps, a mini-length hem, and an open back with dual twist accents that add sultry detail to your look. Style with a necklace and heels for a daytime party.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Open-back, dual twist accents
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4592

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Splash Of Style Twist Mini Dress

    Your summer closet could use this stylish swirl print mini dress perfect for adding in brighter hues! It features a sleeveless, v-neck atop a twisted bust, spaghetti straps, bodycon silhouette, and side ruched seams to accentuate your natural curves. Complete the look in stiletto heels for a dinner with friends.

    Fit & Features

    • Sleeveless, v-neck, twisted bust, spaghetti straps
    • Bodycon silhouette
    • Side ruched seams
    • Mini-length hem
    • Swirl print
    • Stretchy soft knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4596

    Category Name: Casual Dresses

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale