Casual Dresses

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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.

  • Floral Flair Smocked Mini Dress

    Bring some flair to your fall look with this floral smocked mini! The dress features a slight sweetheart neckline, long sleeves with smocked cuffs, and a short hem with a drawstring at the front. Dress is composed of a smocked woven fabric that offers plenty of stretch and a curve hugging fit.

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

    Style Number/Barcode: 05102-0393

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Out In The Town Lace-Up Skater Dress

    Playful and daring, this skater dress showcases your best self with a lace-up back design and flowy short-length hem. 

    Fit & Features

    • Eyelet fabric
    • Scoop neckline
    • Adjustable spaghetti straps
    • Lace-up back design
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000013

    Category Name: Casual Dresses

    Price: $33.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charming Ruffles Floral Mini Dress

    Charm them all in ruffles and florals!

    Fits & Features

    • Sweetheart Neckline With Tie Front Accent I Square Back
    • Adjustable, Ruffle Trim Spaghetti Straps
    • Multi-Tiered, Ruffle Mini-Length Silhouette
    • Lined Chiffon Fabric With Dainty Floral Print Against Solid Background
    • Relaxed Fit With Slight Stretch

     

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

    Style Number/Barcode: 05101-0426

    Category Name: Casual Dresses

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Comfy Cozy Slim Hoodie Tunic

    Get all those comfy cozy feels in this slim fit hoodie tunic! It features a drawstring hood, long sleeves, a front kangaroo pocket, and a mid-thigh length, relaxed and comfortable fit. The knit fabric offers moderate stretch.

    Style Number/Barcode: 06002-0245

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Loving And Living In Knit Midi Dress

    We love a basic staple midi dress that pair perfectly with booties to channel those fall vibes! The midi dress features a plunging V neckline, long fitted sleeves and a midi length that sits slightly above the knee. Dress is composed of a soft to the touch lined ribbed knit fabric that offers a curve hugging fit with a moderate stretch.

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

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

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

    Style Number/Barcode: 05102-0205

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Get On Knit Long Sleeve Dress

    Get on those basic vibes with this sleek mini dress! It features a turtle neck, fitted long sleeves and rounded mini length silhouette. Dress is composed of a semi-sheer smooth knit fabric that offers a curve hugging fit with 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: 05102-0185

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ready To Ruche Mini Dress

    Showcase curves in this sultry mini dress! It features a plunging V neckline, fitted long sleeves, a ruched side seam and a mini length silhouette that falls at the mid-thigh length. Dress is composed of a double-lined soft to the touch brushed knit fabric that offers a form hugging fit with a moderate stretch. 

    Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small

    Style Number/Barcode: 05102-0200

    Category Name: Casual Dresses

    Price: $13.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • V-Neck Ruched Midi Dress
    Bring some style to the basic midi with this ruched detail dress! It features long fitted sleeves, a notch front V neckline, ruching along the sides, and a mid-length, curve hugging fit. The dress is composed of a stretchy knit fabric.

    Style Number/Barcode: 05102-0319

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Off Shoulder Glitter Mini Dress

    Take your look off the charts! Take this mini out on the town when you pair with your favorite pair of heels! 

    Fits & Features

    • Straight Neckline 
    • Off Shoulder Mini Sleeves
    • Mini Length, Curved Hemline
    • Glitter Knit Fabric I Lined
    • Curve-Hugging Fit I Moderate Stretch 
    • Glitter May Transfer 

    Model is 5'8" with a 34" bust, 25" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05103-0318

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sultry And Fierce Satin Mini Dress
    Sultry and oh so fierce, this satin mini is the one for you. It features a sleeveless bodice, bungee spaghetti straps, a square neck and back, and a short, curve huggng fit. The dress is composed of a smooth satin-like fabric with plenty of stretch.

    Style Number/Barcode: 05102-0376

    Category Name: Casual Dresses

    Price: $10.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Such A Sweetie Open Back Gingham Ruffle Skater Dress

    Please, please, please envision how sweet you'll look in this gingham ruffle skater dress! Boasting a head-turning open back and flattering mini-length hem perf for pairing with boots!

    Fit & Features

    • Gingham print, woven fabric
    • Sweetheart neckline, lace trim, bust tie
    • Spaghetti straps
    • Open back with spaghetti strap tie
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6102

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Miss Me Mini Dress

    Get tied to this cute mini! It features a plunging V neckline with a tie front accent, fitted long sleeves, a sexy mid-drift cut out and a mini length silhouette. Dress is composed of a ribbed knit fabric that offers a curve hugging fit with a moderate stretch.

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

    Style Number/Barcode: 05102-0307

    Category Name: Casual Dresses

    Price: $13.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Into You Faux Suede Mini Dress

    You'll be so into this sleek faux suede mini dress! It features a sleeveless bodice, bungee spaghetti straps that lead to an open lattice back, a square neckline, and a short, curve hugging fit. The faux suede fabric offers plenty of stretch and includes a front knit lining.

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

    Style Number/Barcode: 05102-0274

    Category Name: Casual Dresses

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wrap Around My Heart Dress

    You're looking like hot stuff this evening, babes! This dress has a wrap bodice with a deep V neckline, spaghetti straps, and ruching on the side. A wrap skirt creates an asymmetrical hemline for a party perfect ensemble. Dress is composed of an unlined crepe fabric that offers a moderate stretch.

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

    Style Number/Barcode: 05103-3609

    Category Name: Casual Dresses

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simply Stated Sleeveless Midi Dress

    Simple and sleek is the statement you want to make! This dress features a sleeveless bodice, a scoop neckline, tank-like straps and a curve hugging midi length silhouette with side slit. Dress is composed of a 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: 05102-0270

    Category Name: Casual Dresses

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • A Casual Slay Long Sleeve Mini Dress

    Oh you know, just a casual slay. This dress has all the features that we are obsessed with! A deep v neckline, an empire waist, matching buttons down the center, and long sleeves that are balloon style which adds a bohemian flare. Dress is composed of a linen material offers no stretch, and showcases a striking snake skin pattern. Lined at the skirt.

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

     

    Style Number/Barcode: 05103-0473

    Category Name: Casual Dresses

    Price: $20.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keepin' Knit Casual Midi Dress

    This knit midi is casual yet oh so cute. It features a sleeveless bodice, adjustable spaghetti straps, a sweetheart neckline with bust stitching, and a mid-length, curve hugging fit with a back slit. The ribbed knit fabric offers plenty of stretch.

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

    Style Number/Barcode: 05102-0202

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Precious In Plaid Mini Dress

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

    Fits & Features

    • Square Neckline
    • Thick, Tank Strap 
    • Mini Length Silhouette
    • Smooth Poly Material 
    • Curve Hugging Fit I Moderate Stretch 
    • Complete The Look With The Matching Duster (06202-0057)

     

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

    Style Number/Barcode: 05102-0261

    Category Name: Casual Dresses

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Katelyn Ruched Midi Dress

    Chic and fab, the Katelyn ruched midi dress is a new go-to. She features a sleeveless bodice, a Y neck with halter straps, a knot detail, and a front keyhole cut out, and a square back with a zipper closure. Her high waist band leads to a curve hugging skirt with ruched side details and a mid-length hem. The dress is composed of a stretchy knit fabric with a pretty sheen.

    Model is 5'8" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small. 

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0238

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Satin Dreams Midi Dress

    We are totally obsessed with satin right now and we are guessing you are too! This midi dress features a v-neckline, thin spaghetti straps that lead to a square back and a hemline that flows into a floor length. Dress is composed of a satin like material that offers a relaxed fit with no stretch.

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

    Style Number/Barcode: 05102-0325

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish In Spots Tunic
    Spotted! A stylish tunic perfect for transitioning to the fall season. It features a sleeveless bodice, spaghetti straps that tie at the neck and lead to a square back, a wrap front creating a V neckline, a hidden side zipper and hook and eye closure, a trendy twist front detail, and a short hem. The tunic is composed of a lightweight woven fabric with no stretch and includes a woven lining.

    Style Number/Barcode: 06003-0397

    Category Name: Casual Dresses

    Price: $4.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Classic Basic Mini

    We are loving a mini dress with a square neckline! This basic mini is composed of a fully lined ribbed knit material that offers moderate stretch and a form fitting silhouette. The spaghetti straps are bungee style. The skinny straps are flattering and offer stretch as well. This look says it all! Throw on some heels and throw your hair up for a sexy effortless look!

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

    Style Number/Barcode: 06002-0152

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Buttoned Beauty Ribbed Mini Dress

    Button up in this cute mini for the perfect day out! It features an off the shoulder neckline, a multi button down front, fitted long sleeves and a mini length silhouette. Dress is composed of a lined ribbed knit fabric that offers a curve hugging fit with a 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: 05102-0272

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Picture Perfect Color Block Midi Dress

    For a picture-perfect look you'll be reaching for this color block midi dress for any casual plans! The strapless fitted bodice accentuates your silhouette while the flowy midi-length hem creates an elegant movement as you walk. Plus, keep your hands warm in the convenient hidden side pockets!

    Fit & Features

    • Woven cotton-blend fabric, stretchy knit lining
    • Strapless color block fitted bodice
    • Hidden side pockets
    • Back zipper and hook-eye closure
    • Flowy midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6109

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free