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.

  • 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
    • Flow On Chiffon Mini Dress

      Let the good times flow in this pretty mini dress!

      Fits & Features

      • Elastic Square Neckline With Self Ties At Center Front 
      • Unlined, Cuffed Long Sleeves
      • Ruffle-Trim At Mini Length Hem 
      • Smocked Skirt 
      • Chiffon Composition I Fully Lined 
      • Form Flattering Fit I Moderate Stretch

       

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

      Style Number/Barcode: 05102-0448

      Category Name: Casual Dresses

      Price: $9.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Chiffon Floral Surplice Mini Dress

      Look effortlessly chic in this billowy mini dress! With a ditsy floral print throughout, this dress showcases a plunging v-neckline, surplice style middle, and long sleeves with elastic ruffle cuffs. The tiered, shirred, and fully lined skirt features self ties and an adjustable zipper at the side. This chiffon crafted dress offers little to no stretch. 

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

      Style Number/Barcode: 05102-0447

      Category Name: Casual Dresses

      Price: $9.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Chiffon Sweetheart Smocked Mini Dress

      Whether you're brunching with your girls or got a date scheduled, finding the right dress can be difficult. Look no further, this pretty chiffon mini dress is your perfect go-to! 

      Fits & Features 

      • Sweetheart Neckline
      • Puff Accent Shoulders I Long Sleeves
      • Empire Waist
      • Smocked Skirt & Cuffs
      • Fully Lined I Chiffon Composition 
      • Mini Length, Ruffle Trim Hemline
      • Zipper Not Included 

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

      Style Number/Barcode: 05102-0449

      Category Name: Casual Dresses

      Price: $9.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Brunch Babe Smocked Floral Dress

      This adorable floral dress will have you looking so cute for brunch with the girls! It features a sleeveless bodice with tie shoulder spaghetti straps, a square neckline, a stretchy smocked bust, and a high waist with a flowy short skirt with an A-line silhouette. The floral printed dress is composed of a lightweight woven fabric with a stretchy skirt lining. Style this dress with a denim jacket and wedges.

      Fit & Features

      • Tie shoulder spaghetti straps
      • Square neckline
      • Stretchy smocked bust
      • High waist leading to a flowy short skirt
      • A-line silhouette
      • Floral-printed woven fabric
      • Stretchy knit skirt lining
      • Runs true to size

      Style Number/Barcode: 05102-0441

      Category Name: Casual Dresses

      Price: $20.97 $35.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Flirty Florals Ruffled Chiffon Mini Dress

      Bring the charm in a ruffled mini dress that makes a sweet impression! The dress features a plunging V-neckline, adjustable cross-straps, a floral print, tiered ruffles, and a mini-length silhouette. The dress is composed of a sheer lined chiffon fabric that offers a form-hugging fit that offers a minimal stretch. Complete your look with wedges and a floppy hat for a brunch-worthy outfit.

      Fit & Features

      • Sleeveless V-neckline
      • Adjustable cross-straps 
      • Floral print, back zipper closure
      • Tiered ruffles
      • Mini length silhouette
      • Chiffon fabric, knit lining
      • Fits true to size

      Style Number/Barcode: 05101-0463

      Category Name: Casual Dresses

      Price: $9.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Scooped In Style Sleeveless Cutout Ribbed Maxi Dress

      Serve up a stylish look in a maxi dress that slays girl! Step out in this dress that features a sleeveless bodice, a scoop neckline with tank-like straps, a sexy mid-drift cutout to show off a hint of skin, and a maxi length silhouette with twist front accent to reveal a mini length skirt. Complete outfit with wedges and fringe earrings. 

      Fit & Features 

      • Sleeveless scoop neckline
      • Tank-like straps
      • Mid-drift cutout
      • Maxi length silhouette overlay with twist front accent 
      • Mini length skirt 
      • Ribbed knit fabric 
      • Form hugging fit

       

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

      Style Number/Barcode: 05101-0462

      Category Name: Casual Dresses

      Price: $14.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Precious In Plaid Duster

      Make your way into the next season with a perfectly plaid duster!

      Fits & Features

      • Drape Open Front 
      • Fitted Long Sleeves
      • Long Hem That Hits Mid Thigh 
      • Smooth Poly Material 
      • Plenty Of Stretch
      • Complete The Look With The Matching Dress (05102-0261) 

       

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

      Style Number/Barcode: 06202-0057

      Category Name: Casual Dresses

      Price: $12.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Easy Does Knit Midi Dress

      Let your outfit do all the talking for you! Heat up your wardrobe with this knit midi 

      Fits & Features

      • Scoop Neck
      • Fitted Long Sleeves 
      • Faux Button Down Front 
      • Midi Length Silhouette I Front Slit 
      • Ribbed Knit I Plenty Of Stretch 

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

      Style Number/Barcode: 05102-0442

      Category Name: Casual Dresses

      Price: $12.97 $33.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Take a Trip Tropical Mini Dress

      You’ll be ready for date night on the beach in this tropical print mini dress. Style it with clear heels and hoops for an effortless look.

      Fits & Features

      • V-Neckline
      • Spaghetti Straps
      • Asymmetrical Hem

      Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.

      Style Number/Barcode: 05102-0440

      Category Name: Casual Dresses

      Price: $9.97 $33.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance