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.

  • Thinking Of You Denim Mini Dress

    Leave them thinking of you in this pretty midi dress! The dress features a sleeveless square neckline, adjustable spaghetti straps, a button-down front, a cinching tie waist belt, hidden side pockets, and a mini-length silhouette. The dress is composed of a denim fabric that offers a relaxed fit. Complete look with sandals and a cropped denim jacket. 

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Button-down front 
    • Cinching tie waist belt 
    • Hidden side pockets
    • Mini length silhouette
    • Denim fabric, form-hugging fit, runs true to size

    Style Number/Barcode: 05102-0475

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Headed To The Tropics Mini Dress

    Get ready to head to the tropics with this mini dress! The dress features a sleeveless scoop neckline, adjustable spaghetti straps, tropical palm leaf print, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules. 

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps
    • Tropical palm leaf print
    • Mini length silhouette 
    • Lined mesh fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0480

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet & Smocked Ditsy Ruffle Midi Dress

    Get into the spring vibe with this midi dress on! Easily style it up or down by switching out your white sneakers to heels! 

    Fits & Features

    • Adjustable Spaghetti Straps
    • Square Neckline 
    • Tiered Ruffle Detail 
    • Midi Length Silhouette 
    • Ditsy Woven Print 
    • Form Hugging Fit I Plenty Of Stretch 

    Style Number/Barcode: 05101-0501

    Category Name: Casual Dresses

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • A Splash Of This Tie-Dye Satin Mini Dress

    This trendy tie-dye satin mini dress will def expand your color palette babe! With its cowl neckline and slightly flared fit, you'll be serving looks. Perfect for a backyard photo shoot, add some sparkly earrings and slip into a pair of block heels to get the shot.

    Fits & Features

    • Adjustable spaghetti straps
    • Cowl neckline
    • Back zipper with hook and eye closure
    • Mini length silhouette
    • Satin-like fabric with a tie-dye print
    • Relaxed fit with minimal stretch

     

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

    Style Number/Barcode: 05102-0476

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Brighter Vibes Lace-Up Chiffon Maxi Dress

    Bring on brighter vibes in this maxi dress that brings a burst of color this season. The maxi dress features a plunging v-neckline, sexy waist cutout to show off a hint of skin, a lace-up back, and a high side slit. Complete your look with fab cork wedges and sunnies for those ultimate summer vibes. 

    Fit & Features

    • Sleeveless v-neckline with spaghetti straps
    • Waist cutouts
    • Lace-up back 
    • High side slit
    • Maxi length silhouette
    • Chiffon fabric 


    Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0505

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreaming of Denim Days Dress

    We're dreaming of sunny summer days that are perfect for hanging with the squad! Throw this denim mini dress on and pair with clear pumps and dainty pieces for a look that slays!

    Fit & Features

    • Button Down Collar 
    • Two Chest Pockets
    • Short Roll Up Sleeves
    • Tie Front Waist | Waist Cut Out
    • Side Pockets
    • Single Button | Zipper Closure
    • Denim Fabric 


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

    Style Number/Barcode: 05102-0477

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girl Next Door Denim Mini Dress

    Channel those girl next door vibes with a mini dress that is part casual, part stylish! The dress features a sleeveless square neckline, tank shoulder straps, vertical seams along the body, and a mini center slit at the back. The dress is composed of form-hugging denim fabric. Complete look with clear mules and rhinestone rings. 

    Fit & Features 

    • Sleeveless square neckline
    • Tank shoulder straps
    • Vertical seams 
    • Mini center slit at back
    • Mini length silhouette
    • Form hugging denim fabric
    • Runs true to size

    Style Number/Barcode: 05102-0478

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Diva Zip Front Mini Dress

    Stow your jeans and bust out a denim mini dress for the spring szn! Pair this with a lightweight long sleeve and some cute ankle booties! 

    Fits & Features

    • Tank Shoulder Straps
    • Scoop Neckline & Back
    • Zipper Front I Linear Seam Details 
    • Mini Length Silhouette
    • Denim Composition
    • Form Hugging Fit I Moderate Stretch

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

      Style Number/Barcode: 05102-0471

      Category Name: Casual Dresses

      Price: $9.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Crush On You Lace Bust Skater Dress

      The lace bodice and flirty skater skirt are a few of the crush-worthy deets of this lovely dress!

      Fits & Features 

      • Adjustable Spaghetti Straps 
      • Embroidered Lace Design At The Front Bodice I Lightly Padded
      • Cut Out At Center Front Waist 
      • Mini Length Hem I Skater Style Skirt 
      • Crepe Fabric 
      • Back Zipper With Hook & Eye Closure 

      Style Number/Barcode: 05101-0517

      Category Name: Casual Dresses

      Price: $9.97 $41.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Acid Wash Denim Spaghetti Strap Button Mini Dress

      Get drawn to denim dresses this season. Slip into this curve-hugging dress for your next night out with bae. Fitted with a sleeveless sweetheart neckline, adjustable spaghetti straps to avoid wardrobe malfunctions, and corset-like seams that accentuate curves. The real details can be found in the multi-button down accent at the bodice that leads to a mini length silhouette. The light-medium acid wash denim fabric offers a form hugging fit. Complete your look with fab pumps and dainty accessories.

      Fit & Features

      • Sleeveless sweetheart neckline
      • Corset-like seams
      • Button-down accent 
      • Adjustable spaghetti straps 
      • Mini length silhouette
      • Acid wash denim fabric 
      • Form hugging fit

      Style Number/Barcode: 05102-0474

      Category Name: Casual Dresses

      Price: $15.97 $39.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • What's The Ruche Midi Dress

      A look we honestly can't get enough of! Slip into this form-hugging midi dress and show off those never-ending curves!

      Fits & Features

      • Spaghetti Straps
      • Square Neckline
      • Midi Length Silhouette
      • Woven Fabric I Fully Lined
      • Ruching Throughout 
      • Form Hugging Fit I Curve Hugging Fit 

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

      Style Number/Barcode: 05102-0463

      Category Name: Casual Dresses

      Price: $9.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Simply Chic A-Line Smocked Dress

      Keep it simply chic with a dress that says it all! 

      Fit & Features

      • Elastic Square Neckline
      • Tie Front Accent 
      • Long Sleeve | Elastic Cuffs
      • Smocked Waist 
      • A-Line Silhouette
      • Lined Lightweight Woven Fabric
      • Relaxed Fit | Minimal Stretch  


      Style Number/Barcode: 05102-0465

      Category Name: Casual Dresses

      Price: $12.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Sprung On Florals Chiffon Midi Dress

      Get sprung over florals this spring! This midi dress is the perfect all occasion piece, whether your going to a shower, a bbq, or brunch, this dress is perf! 

      Fit & Features

      • Scoop drawstring neckline
      • Adjustable spaghetti straps
      • Milkmaid style bodice
      • Fully lined
      • Chiffon | Minimal stretch
      • Ditsy floral print
      • Bust tie detailing | Hidden zipper closure at side
      • Mini length

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

      Style Number/Barcode: 05102-0467

      Category Name: Casual Dresses

      Price: $13.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Groovy Baby Tie Dye Mesh Mini Dress

      Show them how you groove in this tie-dye mini! We'd love to see you step out in this with a white pair of booties bb girl! 

      Fits & Features 

      • Spaghetti Straps Cross & Tie At Back 
      • V Neckline 
      • Mini Length Silhouette 
      • Fully Lined Mesh Fabric I Tie Dye Print 
      • Ruching Throughout
      • Form Hugging Fit I Plenty Of Stretch 

      Style Number/Barcode: 05102-0466

      Category Name: Casual Dresses

      Price: $11.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Scoop Neck Floral Mesh Mini Dress

      Look fine in florals and strut your stuff in this fab mini dress! 

      Fits & Features

      • Elastic Bungee Cord Straps
      • Scoop Neckline I Square Back 
      • Mini Length Silhouette I Gathering Detail At Low Side Seams 
      • Knit Lining With Floral Printed Mesh Overlay 
      • Curve Hugging Fit I Moderate Stretch

      Style Number/Barcode: 05102-0469

      Category Name: Casual Dresses

      Price: $9.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Spring Fling Floral Chiffon Ruffle Dress

      Embrace the florals and ruffles in this romantic mini dress! It features peasant long sleeves, a plunge v-neckline, and a babydoll style silhouette with flirty ruffle trim on floral chiffon-lined fabric. Complete the look in a boho ring set.

      Fits & Features

      • Plunging V Neckline
      • Sheer Roomy Long Sleeves I Elastic Cuffs
      • Back Zipper With Hook & Eye Closure 
      • Dual Buton Detail At Nape Of Neck I Cut Out At Back 
      • Mini Length Hemline 
      • Lined Chiffon Fabric With Floral Print I Ruffle-Trim Detail
      • Minimal Stretch 

      Style Number/Barcode: 05102-0470

      Category Name: Casual Dresses

      Price: $9.97 $45.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Floral Scuba Lace Back Mini Dress

      Look your freshest in this pretty dress! 

      Fits & Features

      • Spaghetti Straps I Lace Back With Zipper 
      • Plunging V Neckline 
      • Mini Length Silhouette 
      • Scuba Fabric With All Over Floral Prints 
      • Curve Hugging Fit I Moderate Stretch 

      Style Number/Barcode: 05101-0495

      Category Name: Casual Dresses

      Price: $9.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Romantic Floral Ruched Mini Dress

      Make your look a romantic one with a touch of sexy when you slip into a curve flattering ruched mini dress!

      Fit & features

      • Square neckline I Back zipper with hook & eye closure
      • Adjustable spaghetti straps
      • Form fitting silhouette
      • Ruched detailing throughout
      • Mesh lined fabric | Moderate stretch
      • Mini Hemline
      • Romantic floral pattern

      Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.  

      Style Number/Barcode: 05102-0464

      Category Name: Casual Dresses

      Price: $9.97 $35.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Ribbed Knit Mock Neck Mini Dress

      The everyday sweater dress you need in your life. Add to cart!

      Fit & Features

      • Mock neckline
      • Long fitted sleeves
      • Short, curve hugging fit
      • Ribbed knit fabric | Knit lining
      • Plenty of stretch

      Style Number/Barcode: 06002-0329

      Category Name: Casual Dresses

      Price: $6.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Double Take Glitter Mini Dress

      You're going to be making an entrance AND an exit with this fiery number!

      Fits & Features

      • Square Neckline I Back
      • Bungee Cord Straps
      • Mini Length Silhouette
      • Textured Glitter Knit I Fully Lined
      • Curve Hugging Fit I Moderate Stretch 

      Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.

        Style Number/Barcode: 05103-0594

        Category Name: Casual Dresses

        Price: $17.97 $45.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Full Bloom Satin Cowl Mini Dress

        Spring is just around the corner! Can you believe it? We are ready, satin dresses all season, it's a trend that isn't going away any time soon!

        Fit & Features

        • Spaghetti straps that cross and tie at the back
        • Cowl neckline
        • Mini hemline
        • Composed of satin | Minimal stretch
        • Printed floral design
        • Low back

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

        Style Number/Barcode: 05102-0458

        Category Name: Casual Dresses

        Price: $9.97 $42.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Romantic Floral Ruffled Chiffon Skater Dress

        Get an effortlessly romantic look for a daytime date with this floral chiffon skater dress. It features ruffle detail shoulder straps, a wrap-front V neckline, a backless design with a thin tie-back accent, a high waist with a tie-front, and a flowy skater silhouette with tiered ruffle detailing. Complete the outfit with hoop earrings and a new purse.

        Fit & Features

        • Ruffle detail shoulder straps
        • Wrap-front V neckline
        • Open-back design, zipper closure, tie-back closure
        • High waist, tie-front
        • Short skater silhouette, ruffle details
        • Floral chiffon fabric
        • Runs true to size

        Style Number/Barcode: 05102-0454

        Category Name: Casual Dresses

        Price: $9.97 $42.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Fresh Start Floral Off Shoulder Dress

        Spring is here and it's time for a fresh start on that wardrobe! Wear this gorgeous chiffon dress out for all those sunny affairs! 

        Fits & Features

        • Off Shoulder Elastic Neckline & Long Sleeves
        • Elastic Cuffs 
        • Mini Length Silhouette 
        • Chiffon Fabric | Full Knit Lining 
        • Floral Print Design 
        • Moderate Stretch 

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

        Style Number/Barcode: 05102-0450

        Category Name: Casual Dresses

        Price: $9.97 $30.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • A Floral Moment Woven Mini Dress

        Have a major floral moment in this adorable woven mini dress! It features a sleeveless sweetheart neckline with ruching at the bust, thin ruffle-detail shoulder straps, a smocked back, and a short, curve-hugging silhouette. The all-over ditsy floral print is perf for summer. Style this dress with casual sneakers.

        Fit & Features

        • Sleeveless sweetheart neckline, ruching at the bust
        • Thin ruffle-detail shoulder straps
        • Smocked back
        • Mini-length, form-hugging fit
        • Woven fabric, ditsy floral print
        • Runs true to size

        Style Number/Barcode: 05102-0451

        Category Name: Casual Dresses

        Price: $9.97 $35.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale