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.

  • Carmela Metallic Shine Party Dress

    Special Occasion

    You'll be leading the dance floor in our sparkling Carmela! Twist, twirl, and bust a move in her flowy skater skirt while showcasing all the shine from every angle. Style her up with some rhinestone heels and a pair of earrings to match! 

    Fits & Features

    • Adjustable Spaghetti Straps 
    • V Neckline I Padded Bust I Mesh Inset 
    • Mini Length Hem I Skater Silhouette 
    • Mesh Inset At Back With Triple Row Detail I Back Zipper With Hook & Eye Closure 
    • Mesh Lined Metallic Threaded Fabric I Fully Lined
    • Form Hugging Fit I Moderate Stretch

     

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0417

    Category Name: Casual Dresses

    Price: $31.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blissful In Lace Maxi Dress

    This gorge lace maxi dress will have you looking and feeling blissful! Don't forget to pair this dress with a fab mini purse and block heels!

    Fits & Features

    • Crew Neckline I Button Nape & Keyhole Opening At Back
    • Sheer Fitted Long Sleeves I Smocked Cuffs 
    • Sheer Partially Lined Bodice 
    • Maxi Length Hem 
    • Lace Fabric I Mini-Length Lining 
    • Form Hugging Fit I Plenty Of Stretch 

    Style Number/Barcode: 05101-0760

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Too Dot To Handle Polka Dot Midi Dress

    Bb girl, you're sizzling in this dress! Add a pair of cute booties and a faux leather jacket to complement this 'fit! 

    Fits & Features

    • Adjustable Spaghetti Straps
    • Surplice V Neckline 
    • Side Zipper WIth Hook & Eye Closure 
    • Midi Length Silhouette With Front Slit 
    • Textured Knit Fabric I Polka Dot Design I Unlined
    • Relax Fit I Minimal Stretch 
    • Zipper Not Featured

    Style Number/Barcode: 05101-0761

    Category Name: Casual Dresses

    Price: $14.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Chic Wrap Front Romper

    Simple & chic is your go-to style. This wrap front romper is perf for a daytime look paired with some gold hoops and cute wedges.

    Fit & Features

    • Short sleeves
    • Hidden back zipper | Hook and eye closure
    • Wrap front V neckline
    • Button closure
    • Wrap overlay
    • Flowy shorts
    • Woven fabric with a short lining | No stretch

    Style Number/Barcode: 06303-0068

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Total Sweetheart Floral Mini Dress

    Showcase your sweet style in this adorable floral printed mini dress! It features short sleeves, a V neckline, ruching at the bust with a front drawstring, a small cutout under the bust, and a short, form-hugging silhouette. The unlined knit fabric offers plenty of stretch. Complete your look with dainty earrings and a cute crossbody purse.

    Fit & Features

    • Short sleeves
    • V neckline
    • Ruching at the bust with a front drawstring
    • Small cutout under the bust
    • Ruching down the sides
    • Mini-length, form-hugging fit
    • Unlined knit fabric with plenty of stretch
    • Floral print
    • Runs true to size

    Style Number/Barcode: 05102-0679

    Category Name: Casual Dresses

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lovely In Linen Smocked Mini Dress

    Look oh so lovely in linen in this perf springtime mini! The smocked detailing make it all the more flattering!

    Fit & Features

    • Long sleeves | Smocked cuffs
    • Square neck | Eyelet trim detail
    • Front tie | Keyhole cut out
    • Stretchy smocked skirt
    • Short, ruffle hem
    • Linen fabric

    Style Number/Barcode: 05102-0681

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pretty In Plaid Mini Dress

    Keep it pretty in plaid with this brunch ready mini dress! This season-ready dress only needs a pair of wedges and a pop of jewel tones for a complete look! 

    Fit & Features 

    • Square Neckline
    • 3/4 Puff Sleeves
    • Plaid Print 
    • Lined Lightweight Fabric
    • Mini Length Silhouette 
    • Relaxed Fit 
    • Minimal Stretch 

     


    Style Number/Barcode: 05102-0680

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Day Dreamin’ Eyelet Mini Dress

    Get ready for a sweet summer day in this eyelet dress. Pair it with wedges and a cute mini bag.

     Fits & Features

    • All Over Eyelet Pattern
    • Puff Sleeves
    • Lace Up Detailing
    • Ruffle Hem  

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

    Style Number/Barcode: 05102-0678

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flower Power Puff Sleeve Mini Dress

    Take on the floral trend with this gorg puff sleeve printed mini! Pair the dress with some espadrille platform sandals and a cute woven bag!

    Fit & Features

    • Short puff sleeves | Elastic banded cuffs
    •  Sweetheart neckline
    • Back zipper | Hook and eye closure
    • Front center ruched detailing
    • Short ruffle hem
    • Sheer floral printed woven fabric
    • Knit lining

    Style Number/Barcode: 05101-0756

    Category Name: Casual Dresses

    Price: $17.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tortoise O-Ring Ribbed Knit Midi Dress

    Casual and cute, you'll be loving the O-ring belt around this chic midi dress! We love to see you rockin' this with some white sneakers and a faux leather jacket! 

    Fits & Features

    • Spaghetti Straps
    • Scoop Neckline I Square Back
    • Tortoise O-Ring Waist Belt  
    • Midi Length Silhouette 
    • Ribbed Knit Fabric I Fully Lined 
    • Form Hugging Fit I Plenty Of Stretch 
    • Zipper Not Featured

    Style Number/Barcode: 05102-0673

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All About It Ribbed Knit Mini Dress

    We're all about our basic essentials and this mini dress is a must! Pair it with some white sneakers for a daytime look or throw on a faux leather jacket and some thigh-high boots for a PM 'fit!

    Fits & Features

    • Scoop Neckline & Back 
    • Mini Length Silhouette
    • Double Layered Ribbed Knit 
    • Form Hugging Fit 
    • Plenty Of Stretch 

    Style Number/Barcode: 05102-0668

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Vibes Skater Dress

    Give off major flirty vibes and capture some hearts in this adorable double layered skater dress! Keep it casual with some white sneakers or dress it up with some wedges!

    Fit & Features

    • Adjustable spaghetti straps
    • Square neckline
    • Open back | Tie closure
    • High waistband
    • Double layered skater skirt
    • Flowy fit
    • Woven fabric

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

      Style Number/Barcode: 05101-0747

      Category Name: Casual Dresses

      Price: $9.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Tropical Dream Sleeveless Mini Dress

      Dream up the perfect vacation look with a mini dress that channels those vibes! The dress features a sleeveless scoop neckline, adjustable spaghetti straps, lace-up back, a tropical print, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges. 

      Fit & Features

      • Sleeveless scoop neckline
      • Adjustable spaghetti straps
      • Lace-up back 
      • Tropical print 
      • Mini length silhouette
      • Smooth knit fabric 
      • Form hugging fit, moderate stretch, runs true to size

      Style Number/Barcode: 05102-0665

      Category Name: Casual Dresses

      Price: $9.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Drawn To You Ruched Mini Dress

      Get drawn into this fab mini dress that is perf for your next date night with bae! The dress features a sleeveless sweetheart neckline, a small keyhole with a ruched drawstring, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules. 

      Fit & Features

      • Sleeveless sweetheart neckline
      • Keyhole
      • Ruched drawstring
      • Mini length silhouette
      • Knit fabric
      • Form hugging fit, moderate stretch 
      • Runs true to size

      Style Number/Barcode: 05102-0664

      Category Name: Casual Dresses

      Price: $6.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Easy Does It Puff Sleeve Ruched Mini Dress

      Fall for this sweet mini dress that'll have you ready for the warmer days ahead! Pair with slip-on mules and a cute mini purse for the perf daytime OOTD!

      Fits & Features

      • Surplice V Neckline
      • Puff, Short Sleeves 
      • Mini Length Silhouette
      • Ruching Along The Sides 
      • Brushed Knit Fabric 
      • Form Hugging Fit I Plenty Of Stretch 

      Style Number/Barcode: 05102-0663

      Category Name: Casual Dresses

      Price: $9.97 $31.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • On My Level Ruched Mini Dress

      GIRLLL, they'll want to get on your level as soon as they see you in this! Slip into some pumps to really elevate your look! 

      Fits & Features

      • Elastic Spaghetti Straps 
      • Scoop Neckline
      • Mini Length Silhouette
      • Ruching All Over 
      • Form Hugging Fit I Plenty Of Stretch 
      • Zipper Not Included 

      Style Number/Barcode: 05102-0661

      Category Name: Casual Dresses

      Price: $9.97 $31.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Oh So Dainty Ruffle Trim Off Shoulder Ruched Mini Dress

      Step right into sunnier days with this charming mini dress! Opt for block heels and a cute mini purse for an eyecatching ensemble! 

      Fits & Features

      • Ruffle Trim Off Shoulder Design 
      • Tie Front 
      • Ruching Throughout
      • Mini Length Hem I Full Knit Lining
      • Form Hugging Fit I Plenty Of Stretch 

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

      Style Number/Barcode: 05102-0657

      Category Name: Casual Dresses

      Price: $9.97 $30.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Ribbed Cut Out Sweater Dress

      Can't decide what to wear in-between that winter and spring transition? This sleeveless sweater dress is the perf mid-point!  Style this look up with some booties or chic mules! 

      Fits & Features

      • Crew Neckline 
      • Cut Out Design At Center Front Reveals Plunging V 
      • Sleeveless Bodice
      • Mini Length Silhouette 
      • Ribbed Knit Fabric 
      • Form Hugging Fit I Plenty Of Stretch

      Style Number/Barcode: 06005-0613

      Category Name: Casual Dresses

      Price: $11.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Own Knit Open Back Midi Dress

      Own your look bb! You know how to werk it, especially in this sultry open back knit midi dress!

      Fit & Features

      • Mock neckline
      • Long fitted sleeves
      • Open back | Twist back detail | Lower back cut out
      • Curve hugging fit
      • Ribbed knit fabric | Plenty of stretch

      Style Number/Barcode: 05102-0656

      Category Name: Casual Dresses

      Price: $9.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Gorgeous Getaway Maxi Dress

      This stunning printed maxi dress will have you looking absolutely gorgeous for your next weekend getaway! It features a sleeveless square neckline, spaghetti straps, a flowy, floor-length silhouette, and a sultry thigh-high side slit. The knit fabric has an all-over tropical palm leaf print, making the dress a perf option for a summer vacay. Style it with wedges and a chic pair of sunglasses.

      Fit & Features

      • Sleeveless square neckline
      • Spaghetti straps
      • Floor-length silhouette, high side slit
      • Relaxed fit
      • Knit fabric, palm leaf print
      • Runs true to size

      Style Number/Barcode: 05102-0654

      Category Name: Casual Dresses

      Price: $6.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Flirty and Frilly Skater Lace Dress

      Keep it flirty and fab in this twirl-worthy skater dress! Pair this must-have dress with pumps and dainty pieces to complete your look!

      Fit & Features 

      • Sweetheart Neckline
      • Floral Lace Bodice 
      • Adjustable Spaghetti Straps 
      • Lattice Back 
      • Skater Silhouette
      • Lined Crepe Fabric 
      • Relaxed Fit | Moderate Stretch 

      Style Number/Barcode: 05101-0738

      Category Name: Casual Dresses

      Price: $9.97 $46.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Floral Smocked Ruffle Mini Dress

      This smocked and ruffled floral mini dress is a major yes. Add to cart and pair with some strappy heels for a nice daytime look!

      Fit & Features

      • Puff shoulders
      • Long sleeves | Smocked detail | Ruffle hems
      • Square neckline | Ruffle trim
      • Stretchy smocked bodice
      • Ruffle details
      • Short tiered ruffle hem
      • Floral print

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

      Style Number/Barcode: 05102-0649

      Category Name: Casual Dresses

      Price: $9.97 $46.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Zip Up Chic Mini Dress

      Zip up into this chic LBD! Perf for a casual night out with the girls when you want to feel a little dressier than jeans!

      Fit & Features

      • Collared
      • Short sleeves
      • Half zip up front
      • Short, form hugging fit
      • Stretchy knit fabric

      Style Number/Barcode: 05102-0650

      Category Name: Casual Dresses

      Price: $9.97 $28.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Dreamy In Denim Button Front Mini Dress

      Look ever so dreamy in denim in this spring ready mini dress! Pair with some wedges and trendy sunnies and you'll be ready to go!

      Fit & Features

      • Long sleeves | Single buttons to cuff | Puff shoulders
      • Sweetheart neckline | Bust seam detailing
      • Partial stretchy smocked back
      • Button down front
      • Slanted front pockets
      • Short, form-fitting style
      • Jean fabric | Moderate stretch

      Style Number/Barcode: 05102-0653

      Category Name: Casual Dresses

      Price: $9.97 $45.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free