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.

  • Meow Or Never Leopard Midi Dress

    Move fast girl. Snag this purr-fect midi before it's too late!

    Fits & Features

    • Spaghetti Straps That Cross At The Back
    • Self Ties & Keyhole Opening At Back
    • Draped Cowl Neckline
    • Front Slit At Midi Length Silhouette
    • Stretchy Polyester Composition I Form Hugging Fit

     

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

     

    Style Number/Barcode: 05102-0408

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ribbed Knit Off Shoulder Mini Dress

    Slip into this adorable ribbed knit mini dress!

    Fits & Features

    • Elastic, Off Shoulder Neckline 
    • Unlined Long Sleeves 
    • Fold-Over, Overlay At Center Front
    • Mini Length Silhouette
    • Fully Lined, Ribbed Knit Composition I Slub Print Throughout 
    • Curve Hugging Fit I Moderate Stretch

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

    Style Number/Barcode: 05102-0407

    Category Name: Casual Dresses

    Price: $10.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wild Feline Leopard & Tiger Ruched Midi Dress

    Spotted: The purrrrrrfect midi dress! Shake up your look and add some animal print in your wardrobe. 

    Fits & Features

    • Bungee Spaghetti Straps
    • Elastic Square Neckline
    • Ruched Design 
    • Mixed Leopard & Tiger Inspired Print
    • Midi Length Silhouette
    • Mesh Composition I Fully Lined
    • Little Stretch

     

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

      Style Number/Barcode: 05102-0406

      Category Name: Casual Dresses

      Price: $13.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Simply Perfect Knit Mini Dress

      Get a simply perfect 'fit with this basic knit mini dress! With its fitted long sleeves and curve-hugging silhouette, this stretchy knit dress is oh-so-flattering. A definite for your next date night, keep it casual with a pair of chunky sneakers or glam it up with some bold block heels.

      Fit & Features

      • Crew neckline
      • Long fitted sleeves
      • Short, form-hugging fit
      • Ribbed knit fabric
      • Plenty of stretch

      Style Number/Barcode: 06002-0519

      Category Name: Casual Dresses

      Price: $6.97 $26.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Floral Feeling Chiffon Off Shoulder Mini Dress

      Bloom, baby! Look absolutely stunning in this floral mini dress!

      Fits & Features

      • Adjustable Shoulder Straps 
      • Off Shoulder Neckline & Sleeves
      • Layered Ruffles Along Neckline & Hem 
      • Mini Length Silhouette
      • Chiffon Fabric I Lining
      • Form Hugging Fit I Minimal Stretch

      Style Number/Barcode: 05101-0434

      Category Name: Casual Dresses

      Price: $9.97 $30.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Snake It To The Top Mini Dress

      This ssstylish fierce mini dress is bound to be at the top of your wardrobe rotation!

      Fits & Features

      • High Neckline
      • Sleeveless Bodice
      • Mini Length Silhouette
      • Knit Composition With Snake Print Design
      • Fully Lined
      • Form Fitting I Ample Stretch

       

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

      Style Number/Barcode: 05102-0399

      Category Name: Casual Dresses

      Price: $12.97 $31.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Feline This Leopard Midi Dress

      Lovin' that look, girl! You're going to be feeling this mini dress as soon as you slip it on! 

      Fits & Features

      • Adjustable Spaghetti Straps
      • Cowl Neckline I Square Back
      • Zipper With Hook & Eye Closure At Back
      • Midi Length Silhouette With Front Slit 
      • Unlined, Satin-Like Fabric I Tonal Leopard Print Throughout 
      • Relax Fit I Minimal Stretch

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

      Style Number/Barcode: 05102-0401

      Category Name: Casual Dresses

      Price: $9.97 $38.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Feline Good Leopard Print Mesh Mini Dress

      Whether you are out on a date night, or out with the gals you'll be feelin' good in this feline inspired leopard print mesh mini dress! Dress up with heels and hoops, or dress down with booties and a leather jacket!

      Fit & Features

      • Spaghetti straps
      • Square neck and back
      • Ruched side detailing
      • Short, curve hugging fit
      • Sheer mesh leopard printed fabric
      • Knit lining | Plenty of stretch
      • Leopard print pattern

      Style Number/Barcode: 05102-0402

      Category Name: Casual Dresses

      Price: $9.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Smooth Like Satin Mini Dress

      It's the perfect combo of sleek & sweet. Combat the chilly temps by throwing on a knit turtleneck underneath or a chunky sweater over.

      Fits & Features

      • Elastic Cord Straps
      • Elastic Square Neckline With Vertical Darts At The Bust
      • Mini Length Silhouette 
      • Fully Lined, Satin Fabric 
      • Curve Hugging Fit I Minimal Stretch 
      • Zipper Not Included 

      Style Number/Barcode: 05102-0405

      Category Name: Casual Dresses

      Price: $9.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • She's A Plaid Girl Mini Dress

      It's true. Plaid girls have more fun.

      Fits & Features 

      • Square Neckline 
      • Bungee Spaghetti Straps 
      • Mini Length Silhouette
      • Textured Knit Composition I Velvet Plaid Print Throughout
      • Curve Hugging Fit I Moderate Stretch 
      • Zipper Not Included 

       

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

      Style Number/Barcode: 05102-0400

      Category Name: Casual Dresses

      Price: $10.97 $28.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Beautifully Buttoned Ribbed Sweater Dress
      Button up in this casually chic sweater dress to impress this season! It features a wrap V-neckline, long sleeves, a multi-button down accent on the left seam and a mini length silhouette. Dress is composed of an unlined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Zipper not included.

      Style Number/Barcode: 06005-0322

      Category Name: Casual Dresses

      Price: $13.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Long Sleeve Ribbed Mini Dress

      Keep it cozy with this pretty knit dress! It features a plunging V neckline, long puff sleeves and a mini length silhouette. Dress is composed of a ribbed knit fabric that offers a form hugging fit. 

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

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

      Style Number/Barcode: 05102-0365

      Category Name: Casual Dresses

      Price: $9.97 $28.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Cool Cat Leopard Off Shoulder Mini Dress

      Leopard prints FTW. You'll be having a moment everywhere you go in the Cool Cat off shoulder mini dress!

      Fits & Features

      • Smocked Off Shoulder Neckline 
      • Roomy Cuffed Long Sleeves
      • Elastic, Smocked Skirt
      • Subtly Pleated, Mini-Length Hemline
      • Form-Hugging Fit WIth Plenty Of Stretch

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

        Style Number/Barcode: 05102-0397

        Category Name: Casual Dresses

        Price: $9.97 $48.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Leopard Print Wrap Front Midi Dress

        You're quite the fierce fashionista, so this leopard print midi suits you! The dress features a sleeveless bodice, adjustable spaghetti straps, a wrap front V neckline, a V back with a hidden zipper closure, a high waist seam with a wrap front skirt with a faux tie detail, and a mid-length, flowy fit. Dress is comosed of a sheer textured woven fabric with a short woven lining.

        Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

        Style Number/Barcode: 05102-0396

        Category Name: Casual Dresses

        Price: $19.97 $48.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Long Sleeve Knit Midi Dress

        Keep it basic this season! The midi dress features a V neckline, fitted long sleeves vertical stripes and a midi length silhouette that rests slightly above the knee. Dress is composed of a lined knit fabric with a form hugging fit with a slight stretch. Zipper not included. 

        Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

        Style Number/Barcode: 05102-0395

        Category Name: Casual Dresses

        Price: $14.97 $36.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Charming Ruffles Floral Mini Dress

        Charm them all in ruffles and florals!

        Fits & Features

        • Sweetheart Neckline With Tie Front Accent I Square Back
        • Adjustable, Ruffle Trim Spaghetti Straps
        • Multi-Tiered, Ruffle Mini-Length Silhouette
        • Lined Chiffon Fabric With Dainty Floral Print Against Solid Background
        • Relaxed Fit With Slight Stretch

         

        Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small. 

        Style Number/Barcode: 05101-0426

        Category Name: Casual Dresses

        Price: $18.97 $46.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Floral Flair Smocked Mini Dress

        Bring some flair to your fall look with this floral smocked mini! The dress features a slight sweetheart neckline, long sleeves with smocked cuffs, and a short hem with a drawstring at the front. Dress is composed of a smocked woven fabric that offers plenty of stretch and a curve hugging fit.

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

        Style Number/Barcode: 05102-0393

        Category Name: Casual Dresses

        Price: $9.97 $49.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Puff Sleeve Floral Mini Dress

        Puff sleeves are so of the moment. Pair that with spring time florals and you've got yourself an adorably trendy fit! Pair this mini dress with some cute clear mules and wear either off the shoulder or on.

        Fit & Features

        • Short puff sleeves | Merrow edge trim
        • Square neckline | Faux tie front detail
        • High elastic banded waist
        • Ruched side detailing
        • Short, form hugging fit
        • Small floral print
        • Brushed knit fabric | Plenty of stretch

        Model is 5'6.5" with 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

        Style Number/Barcode: 05101-0420

        Category Name: Casual Dresses

        Price: $9.97 $29.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Fab In Floral Brushed Knit Maxi Dress

        Walk right in like you own the place! This maxi dress features romantic florals throughout and a flowy, trailing skirt. Wear some bold earrings and block heels for a perfect 'fit! 

        Fits & Features

        • Spaghetti Straps
        • Square Neckline | Elastic Back
        • Maxi Length Silhouette | Dual Front Slit
        • Brushed Knit Fabric 
        • Form Hugging Fit | Plenty Of Stretch 
        • Zipper Not Featured 

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

        Style Number/Barcode: 05101-0409

        Category Name: Casual Dresses

        Price: $9.97 $37.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Spring It On Floral Mini Dress

        Bring on the sunny, spring weather! Look fresh in florals with the Spring It On mini dress! Wear your sleeves up or soak up some vitamin C by wearing it off the shoulder! 

        Fits & Features 

        • Short Sleeves With Elastic Shoulders & Cuffs I Can Be Worn Off Shoulder
        • V Neckline I Square Back 
        • Keyhole Opening With Adjustable Ties 
        • Mini Length Silhouette 
        • Stretchy Woven Textured Mesh I Floral Prints
        • Form Hugging Fit I Moderate Stretch 

        Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small. 

        Style Number/Barcode: 05102-0392

        Category Name: Casual Dresses

        Price: $12.97 $32.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Bring The Romance Off Shoulder Long Sleeve Skater Dress

        Date night calls for a sweet and pretty look! Style with some soft curls, a cute crossbody, and sparkly finishing touches and you'll be ready for the night! 

        Fits & Features

        • Elasticized, Off Shoulder Neckline I Tie At Center Front 
        • Off Shoulder Long Sleeves I Elastic Cuffs 
        • Crochet Waist Design 
        • Mini Length, Skater Style Skirt 
        • Brushed Knit Design I Floral Print 
        • Plenty Of Stretch 

        Style Number/Barcode: 05101-0401

        Category Name: Casual Dresses

        Price: $9.97 $30.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Long Sleeve Ribbed Midi Dress

        We're totally loving knit this season girl! Create some seriously cute looks with a basic midi dress! 

        Fit & Features

        • Off The Shoulder Neckline 
        • V-Neck Bust
        • Fitted Long Sleeves
        • Ribbed 
        • Knit
        • Form Hugging Fit
        • Moderate Stretch 

         

        Style Number/Barcode: 05102-0391

        Category Name: Casual Dresses

        Price: $11.97 $29.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Flow With The Floral Skater Dress

        Go with the flow of this pretty floral skater dress! Pair with some everyday sandals for an effortless, spring ready vibe.

        Fit & Features

        • Off the shoulder elastic banded neckline
        • Three quarter length flowy sleeves
        • High waist seam
        • Skater skirt
        • Sheer chiffon fabric | Knit lining
        • Rose print

        Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.

        Style Number/Barcode: 05101-0410

        Category Name: Casual Dresses

        Price: $9.97 $38.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Sassy Snaps Ribbed Midi Dress

        Keep it sassy as you snap into this must have! The dress features a crew neck, fitted long sleeves, a curve hugging midi length silhouette and a multi row snap button detail on the left side seam. Dress is composed of an unlined ribbed knit fabric that offers a moderate stretch.

        Model is 5'3" with a 32" bust, 22.5" waist and 34" hips. She is wearing a size small.

         

        Style Number/Barcode: 06005-0304

        Category Name: Casual Dresses

        Price: $17.97 $44.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance