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.

  • Sultry Sweater Dress

    Keep it classy in a sweater dress! This dress features a v neckline, and long sleeves that puff at the wrist with the help of a thick wristband. Bodice meets skirt high waist with a belt that ties at the side. Back of the garment has a tie detail below the neck.The hem of this dress hits mid thigh, and dress is composed of a knit material that offers a comfortable form fit with moderate stretch.

    Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06005-0076

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Off Shoulder Sweater Dress

    It's sweater time! We love a good sweater dress, just slip it on and you are ready! Designed with an off shoulder fold over neckline, long sleeves, and a form fitting silhouette. Dress is composed of a soft knit woven fabric that offers moderate stretch.

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

    Style Number/Barcode: 06005-0068

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Casual Knit Open Back Tunic

    Keep it casual cutie with pretty knits! The tunic features a turtle neck, long sleeves with ribbed cuff, a partial open back and a short form hugging fit. Tunic is composed of knit fabric that offers a moderate stretch. 

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

    Style Number/Barcode: 06005-0053

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Mod Mini Belted Dress

    Get retro glam in this sunny, striking mini! Dress has a body con cut and features thick, tank-style straps, a square neckline, seam detail at bust, an attached fabric belt with oversize buckle, and a pencil skirt. Dress is lined, slips on, and is made from a woven crepe material with a fair amount of stretch.

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

    Style Number/Barcode: 05102-0171

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fine In Florals High Neck Maxi Dress

    Florals are DEF your color, bb girl! Show off your curves in our Fine In Florals maxi dress! 

    Fits & Features

    • Spaghetti Straps That Cross & Lace-Up At The Back 
    • High Neckline 
    • Maxi Length Silhouette 
    • Dual Side Slits 
    • Smooth Jersey Knit Fabric 
    • Form Hugging Fit I Ample Stretch 

    Style Number/Barcode: 05102-0277

    Category Name: Casual Dresses

    Price: $20.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild Child Bodycon Mini Dress

    Stay fierce in a dress as wild as you! This bodycon features elasticized spaghetti straps and a square neckline. Cut to a flirty mini length, this piece is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Dress also includes a knit lining.

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

    Style Number/Barcode: 05102-0152

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Daring In Denim Mini Dress

    We dare you to be bold in this hot denim mini! The dress features a sleeveless strapless square neckline, double vertical seam detailing down the front and back, and a short, raw hem. The dress is composed of a jean fabric that offers moderate stretch and a curve hugging fit.

    Model is 5'9" with a 33" bust, 24" waist and 35.5 hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0162

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ready To Ruffle Mini Dress
    You'll be ready to ruffle in this flirty little mini dress! It features a sleeveless bodice, a V neckline with an adorable tie closure followed by a front cut out, button detailing starting at the waist, a hidden back zipper and hook and eye closure, and a cute tiered ruffle hem. The dress is composed of a linen fabric with no stretch.

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

    Style Number/Barcode: 05102-0149

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortless Beauty Eyelet Mini Dress
    Showcase your effortless beauty in this beyond gorgeous eyelet mini dress! It features a square neck and back, short sleeves with ruffle detailing, a hidden back zipper and hook and eye closure, mini side cut outs at the waist seam, and a short, mid-thigh length. The dress is composed of a woven fabric with a full lining and has no stretch.

    Style Number/Barcode: 05102-0150

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On Knit Mini Dress
    You're always on it when it comes to style, and this basic knit mini will make for such a cute 'fit. The dress features a sleeveless bodice, tank-like shoulder straps, a square neck and back, and a short, form hugging fit. The dress is composed of a soft knit that offers plenty of stretch.

    Style Number/Barcode: 05102-0095

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Darling In Denim Mini Dress

    This darling denim mini is the new dress you need! It features a sleeveless, sweetheart neckline with a built-in padded bust, adjustable spaghetti straps, piping detailing down the front, and a short, curve-hugging fit. Complete the look in PVC strap mules.

    Fit & Features

    • Sleeveless, sweetheart neckline, built-in padded bust
    • Adjustable spaghetti straps
    • Back zipper closure
    • Piping detail down the front and back
    • Short, curve-hugging fit
    • Denim fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-0120

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Walk The Mock Neck Mini Dress

    Talk the talk and walk the walk in this must have mini dress! It features a sleek, form hugging silhouette with a mock neck, long sleeves with thumb-hole slits, and a mini length. Brushed knit offers plenty of stretch.

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

    Style Number/Barcode: 05102-0123

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylish And Sultry Mini Dress

    You're a stylish girl who likes her look to be a little sultry too! This ribbed knit mini dress features long fitted sleeves, a wired sweetheart neckline with padded cups and a small front cut out, and a short, form hugging fit. The dress offers 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: 05102-0103

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirty In Floral Skater Dress

    Create an efforteless flirty look in pretty florals! This skater dress' flowy feel has a flattering figure.

    Fit & Features

    • Adjustable spaghett straps
    • Wrap front V neckline
    • Square back | Zipper and hook and eye closure
    • High waist seam
    • Flowy layered skater skirt | Knit lining
    • All over floral print
    • Sheer chiffon fabric | No stretch

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

    Style Number/Barcode: 05101-0114

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Stunner Ruched Maxi Dress

    You'll be quite the stunner in this floral ruched maxi dress! Its stretchy knit fabric will hug and flatter your curves beautifully!

    Fit & Features

    • Spaghetti straps | Cross back
    • V neckline
    • Center ruched detailing
    • Front slit
    • Stretchy knit fabric
    • Floral print

    Style Number/Barcode: 05101-0073

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Persuasion Sweetheart Midi Dress

    We think we are in love with florals! Fall for this sweet trend in this charming midi dress! Pair with clear heels for a brunch-ready outfit!

    Fit & Features

    • Sweetheart Neckline | Padded Cups
    • Spaghetti Straps 
    • Floral Print 
    • Lined Scuba Knit Fabric 
    • Midi Length Silhouette 
    • Form Hugging Fit 
    • Moderate Stretch 

     


    Style Number/Barcode: 05101-0066

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Getaway Girl Floral Smocked Tube Maxi Dress

    Girl, you'll look stunning on your weekend getaway in this floral tube maxi dress! It features a strapless square neckline, a smocked bodice, and a flowy maxi-length silhouette with a ruffle bottom hem. Don't forget to add a pair of wedges and a wide brim hat to your cart as well!

    Fit & Features

    • Strapless square neckline
    • Stretchy smocked bodice 
    • Maxi-length silhouette, mini-length lining
    • Ruffle bottom hem
    • Floral printed woven fabric
    • No stretch
    • Runs true to size

    Style Number/Barcode: 05101-0033

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chiffon Tropical Floral Maxi Dress

    You are bronzed and ready for vacay in this goddess-like tropical maxi dress!

    Fit & Features

    • V-neckline
    • Spaghetti straps
    • Drop shoulder detailing
    • Long maxi hemline
    • Chiffon material | Minimal stretch
    • Tropical floral pattern

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

    Style Number/Barcode: 05101-0036

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Budding Love Floral Mini Dress

    Show your love for florals in this pretty mini dress! It's the prettiest pick for a wedding guest look! 

    Fits & Features

    • Adjustable Spaghetti Straps 
    • Sweetheart Neckline I No-Slip Interior Strip 
    • Back Zipper With Hook & Eye Closure
    • Mini Length Silhouette
    • Lined, Smooth Scuba Fabric With Floral Prints Throughout 
    • Curve Hugging Fit I Moderate Stretch

     

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

      Style Number/Barcode: 05101-0007

      Category Name: Casual Dresses

      Price: $9.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • New Leaf Linen Mini Dress

      A lovely leaf print lends this green and white linen mini its easy sweetness. Dress features adjustable tie straps, a seamed bodice with ruffle trim and back zip, and a slight A-line skirt with ruffle hem. Dress is lined and made from a lightweight cotton blend with little to no stretch.

      Style Number/Barcode: 05102-0266

      Category Name: Casual Dresses

      Price: $9.97 $46.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Make It Snappy Dress
      Time to flaunt those curves and make it snappy girl! This white toned dress features adjustable spaghetti straps that lead to a square back. The dress has a form fitting silhouette and an a-symmetrical hem at the hip with a gold button detail and a small slit. This ensemble is composed of a ribbed knit material that offers moderate stretch.

      Style Number/Barcode: 06005-0129

      Category Name: Casual Dresses

      Price: $14.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Oh Snap Button Midi Dress
      Be all over everyone's snaps in this midi dress! It has a scoop neckline, tank-style straps, and a row of faux snap buttons down the side of the skirt that leads to a side slit. Sweater dress has a comfortable slim fit and is composed of a ribbed knit fabric with 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: 06005-6308

      Category Name: Casual Dresses

      Price: $39.90

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Plus From The Block Midi Dress
      Where you from Lil' Mama? This cute dress has a flattering V neckline paired with thin straps and a sexy, bodycon fit with a small back slit. The garment is composed of a crepe fabric that offers a moderate stretch and is detailed with a multi-color block design.

      Model is 5'9" with a 44" bust, 37" waist and 47" hips. She is wearing a size 1X

      Style Number/Barcode: 15102-0028

      Category Name: Casual Dresses

      Price: $13.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Plus Basic Essentials Midi Dress

      Sometimes less is more! This basic red midi dress can be kept casual or paired with accessories to dress it up! Throw on your favorite sunnies or wide brimmed hat to achieve beach worthy vibes! This dress features a scoop neckline, narrow shoulder straps and a soft to the touch fabric feel creating a curve hugging fit with plenty of stretch. 

      Style Number/Barcode: 15102-0020

      Category Name: Casual Dresses

      Price: $13.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance