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.

  • Off Shoulder Knit Mini Dress

    There's no such thing as cold weather blues in this number. Snuggle up to this comfy and cute mini dress!

    Fits & Features 

    • Wide, Off Shoulder Neckline
    • Cuffed Quarter Length Sleeves
    • Elastic Waistband
    • Form-Hugging Silhouette I Moderate Stretch
    • Knit Composition I Fully Lined At The Skirt  

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small

    Style Number/Barcode: 05102-0511

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Stunner Smocked Mini Dress
    You'll be simply stunning in this floral smocked mini dress! It features a slight sweetheart neckline, long sheer chiffon puffed sleeves with smocked hems, and a stretchy smocked dress with a short, mid-thigh length hem with a front drawstring to cinch.

    Style Number/Barcode: 05102-0510

    Category Name: Casual Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ready For It Mini Dress
    Get ready to have a total trendy look with this cute little mini! It features a slight sweetheart neckline, long sheer chiffon puffed sleeves with smocked cuffs, and a stretchy, smocked dress with a short, mid-thigh length hem with a front drawstring.

    Style Number/Barcode: 05102-0507

    Category Name: Casual Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Chiffon Blouson Mini Dress
    Get an effortlessly beautiful look in this floral printed chiffon blouson dress! The mini features a ruffle mock neckline, long sheer puffed sleeves with elastic cinched wrists, and a stretchy smocked dress with a short hem. The all over floral print gives a pretty touch to the dress.

    Style Number/Barcode: 05102-0508

    Category Name: Casual Dresses

    Price: $20.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Classy and Chic Asymmetrical Dress

    Tie yourself to a classy and chic look in this stunning mini dress! Pair this beauty with fab pumps and a trendy crossbody to complete the look!

    Fit & Features 

    • Square Neckline 
    • Spaghetti Straps 
    • Tie Waist Accent 
    • Asymmetrical Hem 
    • Lined Crepe Fabric 
    • Form Hugging Fit 
    • Moderate Stretch 

    Style Number/Barcode: 05102-0460

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruffle Up Chiffon Off Shoulder Mini Dress

    Make every walkway your runway in the Ruffle Up Off Shoulder mini dress! 

    Fits & Features

    • Elastic Off Shoulder Neckline
    • Long Sleeves 
    • Ruffle-Trim At Cuffs, Neckline, Waist, And Hem
    • Smocked Skirt And Cuffs
    • Mini Length Silhouette
    • Chiffon Composition
    • Form Flattering Fit I Moderate Stretch

    Style Number/Barcode: 05102-0506

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • All For Knit Mock Neck Mini Dress

    As temperatures drop, you'll want to include a mock neck mini in your wardrobe!

    Fits & Features

    • Mock Neckline
    • Long Fitted Sleeves
    • Mini Length Silhouette
    • Heavyweight Rib-Knit Fabric
    • Form Hugging Fit I Ample Stretch 

    Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0504

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keepin' Knit Cozy Sweater Dress

    Keep it cozy and chic in this knit sweater dress. It features an off the shoulder boat neckline, long sleeves with faux buttoned cuffs, a tie front at the waist, and a short, form-hugging fit. The knit fabric offers plenty of stretch for comfortable wear.

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small

    Style Number/Barcode: 05102-0551

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ready To Ruche Mini Dress

    Get ready to style it up in this adorable ruched mini dress! It features spaghetti straps with a flattering square neckline, front ruched detailing with a tie at the hem, and a mini-length, curve-hugging fit. Pair this dress with some clear slide-on mules and a chic clutch for the perf night-out look.

    Fit & Features

    • Spaghetti straps, square neckline
    • Dart seam detailing
    • Back zipper closure
    • High waist seam
    • Side ruched detailing with tie at the hem
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-3951

    Category Name: Casual Dresses

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picturesque Petals Tiered Ruffle Chiffon Mini Dress

    Feel and look picture-perf in this fun floral dress! Pair your look with a denim jacket and some white sneakers! 

    Fits & Features

    • Adjustable Spaghetti Straps
    • V Neckline I Square Sheer Back 
    • Drawstring Waist 
    • Mini Length Silhouette I Tiered Ruffle Trim Design 
    • Floral Chiffon Fabric I Fully Lined 
    • Zipper Not Featured

    Style Number/Barcode: 05102-0503

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vintage Destructed Jersey Knit Mini Dress

    Get that vintage edgy vibe going in this jersey knit mini dress.

    Fit & Features

    • Long fitted sleeves
    • Crew neckline with large V cut out
    • Slashed distressed detailing
    • Large skull and rose graphic with the script "Vintage," "Rock and Roll," and "Live Fast Die Young Festival"
    • Short, form hugging fit
    • Knit fabric | Plenty of stretch

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

      Style Number/Barcode: 06002-0346

      Category Name: Casual Dresses

      Price: $9.97 $24.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Bell Sleeve Beauty Floral Mini Dress

      You'll be a total beauty in this adorable bell sleeve floral mini dress!

      Fit & Features

      • Off the shoulder neckline
      • Long bell sleeves
      • Stretchy smocked bust
      • Flowy skirt
      • All over floral print
      • Knit fabric | Plenty of stretch

      Style Number/Barcode: 05102-0502

      Category Name: Casual Dresses

      Price: $9.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Just My Stripe Zebra Sweater Dress

      You can never have too many animal prints in your wardrobe!

      Fits & Features

      • Plunging V Neckline
      • Surplice Design At Front & Back
      • Bar Strap Accent At Back 
      • Long Sleeves
      • Removable Waist Tie
      • Hits Mid-Thigh
      • Form Hugging Fit I Ample Stretch

      Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

       

      Style Number/Barcode: 06005-0435

      Category Name: Casual Dresses

      Price: $4.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Check It Plaid Mini Dress

      Check you out! Plaid isn't just the perfect print for flannels. 

      Fits & Features

      • Square Neckline
      • Short Sleeves With Puff Shoulders
      • Princess Seams
      • A-Line Fit
      • Mini-Length Silhouette
      • Plaid Print Throughout
      • Moderate Amount Of Stretch 

      Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

      Style Number/Barcode: 05102-0501

      Category Name: Casual Dresses

      Price: $9.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Color Block Knit Mini Dress

      Keep it chic in stand out color block! This mini dress is perf to pair with your fav booties or strappy heels to easily dress up or down! 

      Fit & Features 

      • Mock Neck 
      • Sleeveless 
      • Color Block Design 
      • Ribbed Knit Fabric
      • Mini Length Silhouette 
      • Form Hugging Fit 
      • Moderate Stretch 

       Model is 5'4" with 32" bust, 23" waist and 38" hips. She is wearing a size small.     

      Style Number/Barcode: 06005-0432

      Category Name: Casual Dresses

      Price: $17.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Charming Ruffles Chiffon Dress

      Charm them all with romantic ruffles in this super gorge mini dress!

      Fit & Features

      • Plunging V-Neckline | Ruffle Trim
      • Adjustable Spaghetti Straps | Cross-Back 
      • Multi-Tiered Ruffle Accents 
      • Lined Chiffon Fabric
      • Relaxed Fit 
      • Minimal Stretch 


      Style Number/Barcode: 05102-0498

      Category Name: Casual Dresses

      Price: $9.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Denim Days Button Up Mini Dress

      Button up in a denim dress that is part stylish, part edgy! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a button-down front, side pockets, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit. Complete look with mules and hoops.

      Fit & Features

      • Sleeveless V-neckline
      • Adjustable spaghetti straps
      • Button-down front
      • Side pockets
      • Mini-length silhouette, form-hugging fit
      • Denim fabric, moderate stretch
      • Runs true to size

      Style Number/Barcode: 05102-0499

      Category Name: Casual Dresses

      Price: $9.97 $38.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Square Neck Floral Mini Dress

      Look as beautiful as a bouquet in this springtime dress! It's the perf brunch fit once you accessorize with some nude heels and earrings! 

      Fits & Features

      • Short, Puff Sleeves
      • Elasticized Square Neckline & Cuffs
      • Smocked Bodice 
      • Mini Length Silhouette I A-Line Skirt
      • Woven Gauze Composition I Floral Prints 
      • Moderate Stretch 

      Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

      Style Number/Barcode: 05102-0493

      Category Name: Casual Dresses

      Price: $9.97 $38.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Keepin' It Cute And Casual Denim Dress

      Keep your everyday look cute and casual in this must-have denim dress! It features a sleeveless square neckline, thin shoulder straps, a complete button-down front, and a short, curve-hugging silhouette. Style this dress with sneakers and chic shades.

      Fit & Features

      • Sleeveless square neckline
      • Thin shoulder straps
      • Complete button-down front
      • Mini-length, form-hugging fit
      • Denim fabric
      • Runs true to size

      Style Number/Barcode: 05102-0500

      Category Name: Casual Dresses

      Price: $6.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Adore You Floral High Slit Maxi Dress

      Feel adored in a floral dress that brings some serious butterflies this season. The dress features a gorgeous floral print, a flattering cowl neckline, and a maxi length silhouette that is accented a high side slit. Complete your date-night ready outfit with sleek hoop earrings and strappy heels that mesmerize. 

      Fit & Features

      • Sleeveless bodice
      • Cowl neckline
      • Spaghetti straps that cross at the back
      • Floral print
      • Maxi length silhouette
      • High side slit
      • Smooth knit fabric, form-hugging fit

       

      Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.

      Style Number/Barcode: 05101-0529

      Category Name: Casual Dresses

      Price: $9.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Floral Ditsy Smocked Tie Front Mini Dress

      Spring into a smocked disty mini dress to keep on trend this season. This flirty piece features a sweetheart neckline, a tie front with a small keyhole at the bust, and an all-over floral ditsy print. The relaxed fit bodice leads to a curve-hugging mini-length silhouette. The dress is composed of a smocked knit fabric that offers a moderate stretch. Complete your look with hoop earrings and minimal heels. 

      Fit & Features

      • Sweetheart neckline
      • Keyhole at bust
      • Floral ditsy print
      • Smoked fabric
      • Form-hugging fit
      • Moderate stretch 

      Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

      Style Number/Barcode: 05102-0497

      Category Name: Casual Dresses

      Price: $9.97 $35.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Groovy Gal Tie Dye Mini Dress

      Give your wardrobe a splash of color with this groovy mini dress! Amp up your look by pairing this with a mini backpack and some platform sneakers!

      Fits & Features

      • Spaghetti Straps
      • Scoop Neckline I Square, Elastic Back 
      • Mini Length Silhouette 
      • Brush Knit Fabric I Tie Dye Design 
      • Form Hugging Fit I Plenty Of Stretch

      Style Number/Barcode: 05102-0495

      Category Name: Casual Dresses

      Price: $9.97 $25.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Floral Moment Maxi Dress

      Create a charming moment in florals in this sweet maxi dress! Perfect for brunch when paired with fab heels and a neutral handbag! 

      Fit & Features

      • Wrap V-Neckline 
      • Spaghetti Straps
      • Elastic Waist 
      • Floral Print
      • Maxi Silhouette 
      • Lined Knit Fabric | Mini Skirt Length Lining
      • Relaxed Fit | Moderate Stretch 

       

       

      Style Number/Barcode: 05101-0530

      Category Name: Casual Dresses

      Price: $14.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Summer Sweetheart Smocked Mini Dress

      You'll be a total summer sweetheart in this adorable mini dress! It features a sleeveless square neckline with a ruffle trim, a tie-front bust detail, tie-shoulder spaghetti straps, a smocked body, and a mini-length, curve-hugging silhouette. Style this dress with casual sandals.

      Fit & Features

      • Sleeveless square neckline, ruffle trim
      • Tie-front bust detail
      • Tie-shoulder spaghetti straps
      • Smocked body
      • Short, form-hugging fit
      • Woven fabric
      • Runs true to size

      Style Number/Barcode: 05102-0496

      Category Name: Casual Dresses

      Price: $19.97 $35.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free