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.

  • 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
  • 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
  • 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
  • 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
  • Ribbed Knit Surplice Mini Dress

    Sweater dresses are a must for all things winter wear! This knit mini will become a staple in your winter wardrobe.

    Fit & Features

    • Wrap front V neck and back
    • Back bar detail
    • Long cuffed dolman sleeves
    • High waist seam
    • Short, curve hugging fit
    • Ribbed knit fabric | Plenty of stretch

    Style Number/Barcode: 06005-0222

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ravishing Ruched Mini Dress

    This dress is a daytime delight. It features ruffled sleeves, a hidden back zipper closure, an adjustable drawstring skirt. It's made of a lightweight linen fabric with zero stretch and full lining.

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

    Style Number/Barcode: 05102-0243

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Vibes Knit Midi Dress

    Get those casual cute vibes in this adorable knit midi! The dress features a V neckline, short sleeves, and a mid-length, curve hugging fit. The ribbed knit fabric 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: 05102-0315

    Category Name: Casual Dresses

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charm Them All Midi Dress

    Charm them all in this casual yet so cute printed midi! The dress features a sleeveless bodice, spaghetti straps, a rounded neckline, and a mid-length, curve hugging fit. The dress is composed of a knit fabric with plenty of stretch.

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

    Style Number/Barcode: 05102-0252

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylishly Snapped Sweater Dress
    This stylish sweater dress is ready for all your snaps! It features an off the shoulder square neckline, long fitted sleeves, a side faux snap button down detail leading to a slit, and a curve hugging fit with a slight asymmetrical hem. The dress is composed of a ribbed knit fabric, offering plenty of stretch.

    Style Number/Barcode: 06005-0170

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

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

    Sometimes keeping it basic is the best way to go! This knit midi dress features a sleeveless bodice, tank-like shoulder straps, a scoop neck and back, a side slit, and a mid-length, curve hugging fit. The dress is composed of a stretchy knit fabric.

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

    Style Number/Barcode: 05102-0268

    Category Name: Casual Dresses

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruffle It Up Smocked Midi Dress

    Play up your look with this adorable ruffled and smocked midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a square neck and back with a ruffle hem, ruffle tiers, and a stretchy smocked body with a mid-length form hugging fit. Dress is composed of a lightweight woven fabric.

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

    Style Number/Barcode: 05102-0341

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic And Spotted Mini Dress

    Get a chic and spotted look in this adorable trendy little mini! The dress features an off the shoulder neckline with short cuffed sleeves with ruffle trim detailing, a front keyhole cut out with a tie closure, a stretchy smocked back, and a short, form hugging fit. The dress is composed of a lightweight woven fabric with a cute all over animal 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: 05102-0342

    Category Name: Casual Dresses

    Price: $19.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Cutout Gauze Knit Skater Dress

    Keep it trendy with a skater dress that keeps it glam for the season! The dress features a plunging V-neckline, waist cutouts with bar straps, and a skater silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.

    Fit & Features

    • Sleeveless V-neckline
    • Waist cutouts with bar straps
    • Skater silhouette
    • Gauze knit fabric
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-0246

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bring Knit On Midi Dress

    Bring on the style with this trendy basic knit midi! The dress features a mock neckline, long fitted sleeves, and a mid-length, curve hugging fit. Garment is composed of a brushed knit fabric with a knit lining, offering plenty of stretch.

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

    Style Number/Barcode: 05102-0178

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweetest Look Floral Off Shoulder High Low Skater Dress

    Enchant everyone with the sweetest of looks! Look flowy and fresh in this captivating dress. Complement your attire with cute earrings and a pair of clear strap mules!

    Fits & Features

    • Off Shoulder Neckline & Sleeves
    • Subtle High Low Hem I Skater Silhouette
    • Smooth Scuba Fabric I Floral Print 
    • Form Hugging Fit I Moderate Stretch
    • 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: 05101-0142

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    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
  • Plant One On Floral Skater Dress

    Featuring pretty floral graphics throughout, this fab floral dress is the perfect partner in crime for all your daytime outings.

    Fits & Features

    • Adjustable spaghetti straps
    • Surplice V neckline
    • Zipper & hook and eye closure at back 
    • Removable waist tie 
    • Wrapped and layered skater skirt
    • Crepe composition I Fully lined
    • Form-fitting, limited stretch

     

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

    Style Number/Barcode: 05102-0223

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flared and Flirty Ponte Skater Dress

    Keep it flared and flirty in this twirl-worthy skater dress! Perfectly pair this dress with a set of fab pumps to make a chic impression! 

    Fit & Features

    • V-Neckline
    • Spaghetti Straps | Cross-At-Back 
    • Princess Seams
    • Skater Silhouette 
    • Ponte Knit Fabric 
    • Form Hugging Fit 
    • Moderate Stretch 

     

    Style Number/Barcode: 05101-0740

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Mock Neck Mini Dress
    Cozy chic, this mock neck mini is perfect for the season. It features long fitted sleeves and a short, curve hugging fit. The ribbed knit fabric offers plenty of stretch.

    Style Number/Barcode: 06005-0216

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Cutie Linen Skater Dress

    Get a casual cute look in this lightweight linen skater dress. It features adjustable spaghetti straps, a lined crochet bodice with a V neckline, an open back with a tie closure, and a flowy, skater silhouette. The gauze and linen fabric has a knit lining. Complete your outfit with adorable wedges and a chic shoulder bag.

    Fit & Features

    • Adjustable spaghetti straps
    • Lined crochet bodice with a V neckline
    • Open back with a tie closure
    • Short skater silhouette
    • Gauze and linen fabric with no stretch
    • Knit lining
    • Runs true to size

    Style Number/Barcode: 05102-0233

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Necessary Basic Midi Dress

    Because we all need this necessary basic midi in our closet! The dress features a sleeveless bodice, spaghetti straps, a square neck and back, and a mid-length, curve hugging fit. The smooth knit fabric offers plenty of stretch for comfortable wear.

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

    Style Number/Barcode: 05102-0256

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Charming And Chic Midi Dress

    This charming and chic midi dress will turn your look into a classic. It features a sleeveless bodice, a high round neckline, a back zipper closure, flattering vertical seam detailing along the bust, and a mid-length, curve hugging fit. The dress is composed of a ponte knit fabric that offers moderate stretch.

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

    Style Number/Barcode: 05102-0190

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pretty And Posh Mini Dress

    Be the it girl of your squad in this pretty and posh mini! The dress features a sleeveless bodice, a rounded neckline, a square back, and a short, form hugging fit. The dress is composed of a stretchy knit fabric with a full knit lining and showcases a trendy all over plaid print.

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

    Style Number/Barcode: 05102-0193

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Cut Out Mini Dress

    This cute and casual cut out mini is perf for your next day out. The dress features an off the shoulder elastic banded square neckline, short sleeves, a trendy front cut out at the waist, and a short, form hugging fit. The dress is composed of a stretchy knit fabric with 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: 05102-0211

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance