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.

  • 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
  • Floral Bloom Smocked Mini Dress

    Let your style bloom with pretty floral this spring season in this adorable mini dress! The dress keeps it fresh and flirty with a charming floral print. It features a sleeveless bodice with tie shoulder spaghetti straps, a square neckline, a stretchy smocked bust, and a high waist that flows out to a short skirt with an A-line silhouette. Complete your outfit with wedges and a trendy Panama hat for the perfect look.

    Fit & Features

    • Tie shoulder spaghetti straps
    • Square neckline
    • Smocked bust
    • High waist leading to a short skirt
    • A-line silhouette
    • Floral printed woven fabric with a stretchy knit lining
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 05102-0446

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Good To Grow Floral Satin Mini Dress

    Flaunt the florals cause you look good to go! Go for a sultry look by wearing it off the shoulder or wear the short sleeves up. Slip into your favorite heels and you're all set! 

    Fits & Features

    • Short Sleeves I Can Be Worn Off Shoulder 
    • Lace Trim Scoop Neckline I Self Tie At Center Front I Keyhole Opening
    • Empire Waist 
    • Back Zipper With Hook & Eye Closure
    • Mini Length Silhouette
    • Satin-Like Fabric I Floral Print 
    • Form Hugging Fit I Minimal Stretch 

    Style Number/Barcode: 05101-0459

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summer Sweetheart Striped Mini Dress

    Bring the sweet vibes to your summer look with this adorable mini dress. It features a sleeveless square neckline, spaghetti straps, a tie-back detail, and a short, curve-hugging silhouette. The ribbed knit fabric has a cute all-over striped print. Style this dress with casual sneakers.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Tie-back detail
    • Mini-length, form-hugging fit
    • Ribbed knit fabric, striped print
    • Runs true to size

    Style Number/Barcode: 05102-0443

    Category Name: Casual Dresses

    Price: $7.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Support Smocked Skater Dress

    Grow through what you go through. Look and feel uplifted in this cute AF floral dress! Throw on a crop denim jacket and some sneakers for an OOTD! 

    Fits & Features

    • Self Tie Spaghetti Straps 
    • Square Neckline 
    • Smocked Bodice
    • Mini Length I Skater Silhouette 
    • Woven Fabric I Smooth Knit Lining 
    • Ample Stretch 

    Style Number/Barcode: 05102-0444

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Button Up In Denim Frayed Dress

    Button up in this denim dress to make a fun statement bby!

    Fit & Features 

    • Collared Neckline
    • Small Chest Pockets | Button Down Front
    • Short Sleeves 
    • Zipper Front Closure | Side Pockets 
    • Frayed Hem 
    • Medium Wash Denim
    • Relaxed Fit | Slight Stretch 

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

    Style Number/Barcode: 05102-0436

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All That Skater Dress

    There's no denying, carry all that confidence girl in this flirty skater dress! 

    Fit & Features

    • V-Neckline
    • Cross-Back Spaghetti Straps 
    • Ponte-Knit Fabric
    • A-Line Skater Silhouette 
    • Form Hugging Fit
    • Moderate Stretch 

     


    Style Number/Barcode: 05101-0475

    Category Name: Casual Dresses

    Price: $19.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Persuasion Smocked Mini Dress

    Get on this sweet trend this season! Brighten up your closet with pretty florals to make a charming impression! Pair mini dress with your fav wedges to complete the look!

    Fit & Features

    • Square Neckline | Tie Front Accent 
    • Adjustable Spaghetti Straps
    • Smocked Waist and Back 
    • Floral Print 
    • Lined Lightweight Woven Fabric
    • Mini Length Silhouette 
    • Relaxed Fit | Minimal Stretch 

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

     


    Style Number/Barcode: 05102-0445

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Denim Dreamer Tie Front Dress

    Look oh so dreamy in denim in this adorable tie front dress! Perf for a spring day out with your gal pals.

    Fit & Features

    • Collared | Half snap button down front
    • Long sleeves | Single buttons to cuff
    • Two buttoned chest pockets
    • Tie front detail | Front waist cut out
    • Two slanted pockets at the waist | Two back pockets
    • Front button | Hidden zipper closure
    • Short, form hugging fit

    Style Number/Barcode: 05102-0435

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ribbed Knit Ditsy Floral Mini Dress

    Keep it sweet in a ditsy floral dress. Perfect for brunch, this mini dress features a sleeveless bodice with a sweetheart neckline and supportive tank-like straps. The back features an open back with two ribbed bar back straps. The relaxed fit waist leads to a curve-hugging mini-length silhouette. Keep accessories minimal to let the ditsy floral print command attention. 

    Fit & Features

    • Sleeveless bodice
    • Sweetheart neckline
    • Open back with bar straps
    • Ditsy floral print
    • Mini length silhouette 

    Style Number/Barcode: 05102-0439

    Category Name: Casual Dresses

    Price: $13.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Diva Sleeveless Mini Dress

    Dare to impress in denim! This denim mini dress can easily dressed up with the perfect pair of pumps and animal print! 

    Fit & Features

    • Sweetheart Neckline | Padded Cups
    • Adjustable Spaghetti Straps
    • Lace Up Front | Metal Grommets
    • Contrast Stitching 
    • Denim Fabric
    • Form Hugging Fit 
    • Moderate Stretch 

     

     


    Style Number/Barcode: 05102-0437

    Category Name: Casual Dresses

    Price: $14.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Playful Petals Floral Chiffon Off Shoulder Mini Dress

    Let your feminity show and flow in this darling mini dress! 

    Fits & Features 

    • Off Shoulder, Foldover Neckline 
    • Back Zipper With Hook & Eye Closure 
    • Mini Length Silhouette I Detachable Waist Tie I Wrap Skirt 
    • Chiffon Lined Fabric 
    • Moderate Stretch 

    Style Number/Barcode: 05101-0464

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Long Sleeve Ribbed Mini Dress

    It may be cold, but you're heating up in this ribbed mini dress!

    Fits & Features

    • Surplice V Neckline I V Back
    • Fitted Long Sleeves
    • Mini Length Silhouette 
    • Midweight Ribbed Knit Fabric 
    • Curve Hugging Fit I Moderate Stretch 

     

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

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

      Style Number/Barcode: 06005-0361

      Category Name: Casual Dresses

      Price: $6.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Mesh Well Ruched Mini Dress

      A stunning little ruched dress is just what you need to show off those never-ending curves!

      Fits & Features

      • Elastic Cord Straps
      • Square Neckline With Elastic Interior Band 
      • Mini Length Silhouette With Ruching Down The Sides
      • Fully Lined, Mesh Fabric 
      • Curve Hugging Fit | Ample Stretch
      • Zipper Not Included

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

      Style Number/Barcode: 05102-0432

      Category Name: Casual Dresses

      Price: $9.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Ruched Hour Mini Dress

      This fiery number is calling your name. You'll be stopping traffic in this one!

      Fits & Features

      • Dual Shoulder Straps
      • Square Neckline 
      • Ruched Drawstring
      • Form Hugging Fit
      • Moderate Stretch
      • Fully Lined

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

        Style Number/Barcode: 05102-0433

        Category Name: Casual Dresses

        Price: $13.97 $34.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Forever Floral Mesh Burnout Velvet Mini Dress

        Look forever stunning in gorg florals with this adorable little mini dress!

        Fit & Features

        • Spaghetti straps
        • Cowl neckline
        • Short fit
        • Sheer mesh fabric with burnout velvet floral appliques
        • Stretchy knit lining

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

        Style Number/Barcode: 05102-0429

        Category Name: Casual Dresses

        Price: $16.97 $42.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance