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.

  • Hear Meow-Out Leopard Midi Dress

    Fiercely command a room with this bold mini dress! They'll be listening to every fashion tip you got 

    Fits & Features

    • Adjustable Spaghetti Straps Cross At Back 
    • Cowl Neckline I Back Zip 
    • Midi Length Silhouette I Side Slit 
    • Woven Fabric I Leopard-Inspired Print 
    • Relax Fit I Minimal Stretch

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

    Style Number/Barcode: 05102-0371

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Hiss Me With That Mini Dress

    Sssslither into this sassy number! It features a snake-inspired print, fixed shoulder straps, sweetheart neckline, and mini-length silhouette. Crafted from soft velvet and paired with a soft knit lining, this form-fitting piece extenuates all the right curves. Zipper not included. 

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

    Style Number/Barcode: 05102-0364

    Category Name: Casual Dresses

    Price: $11.97 $28.90

    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
  • Poised In Plaid Sleeveless Mini Dress

    Keep it poised with trendy plaid! The mini dress features a sleeveless bodice, a square neckline, tank-like straps and a mini length silhouette that hugs curves all over. The all over plaid season is perfect to stay on trend this season! Dress is composed of a knit fabric.

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

     

    Style Number/Barcode: 05102-0363

    Category Name: Casual Dresses

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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
  • Ribbed Knit Cut Out Midi Dress

    Ward off the chill with this cozy for keeps midi-length dress.

    Fits & Features

    • Plunging V Neckline
    • Long Sleeves
    • Large Cut-Out Detail At Back
    • Soft Knit Fabric I Fully Lined
    • Ample 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: 05102-0361

    Category Name: Casual Dresses

    Price: $13.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Dreaming Satin Midi Dress

    We're dreaming of romance in this floral beauty! This midi dress perfectly pairs with stilettos and clutch for the perfect date night look!

    Fit & Features

    • V-Neckline
    • Adjustable Spaghetti Straps | Cross-Back
    • Floral Print 
    • Lined Satin Fabric 
    • Midi Length Silhouette 
    • Front Slit
    • Relaxed Fit | Minimal Stretch 

     

     

    Style Number/Barcode: 05101-0367

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Satin Leopard Print Mini Dress

    On the hunt for the perfect mini? Look no further than this sassy satin number. Featuring adjustable spaghetti straps and a square neckline, it also showcases a tonal leopard print and a daring slit at front. Fully lined, it offers minimal stretch and a zipper at the back.

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

    Style Number/Barcode: 05102-0359

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylishly Destructed Tunic

    This tunic is destructed with all the style! It features a crew neckline, long fitted sleeves, a short hem, and distressed slit detailing on the top and toward the hem. Tunic is composed of a cotten blend 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: 06002-0276

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Viper Vixen Knot Mini Dress

    Vamp it out girl with statement snake print in this trendy mini dress! It features a deep V neckline with a knot front detail, long fitted sleeves, and a curve-hugging, mini length silhouette with a wrap skirt detail. Pair this dress with strappy heels and a faux leather jacket.

    Fit & Features 

    • Plunging V neckline
    • Knot bodice
    • Long fitted sleeves
    • Snake print
    • Mini length silhouette
    • Form-hugging fit
    • Smooth knit fabric with moderate stretch

    Style Number/Barcode: 05102-0357

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Plus Crochet In Color Dress

    This cute crochet dress is perfect for a day out! It features a V neckline, adjustable spaghetti straps that create an X back, a sheer crochet waist, and a short flared skirt with a full lining. 

    Style Number/Barcode: 15102-0018

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleeveless Velvet Leopard Mini Dress

    Stay on trend with fierce animal print!

    Fits & Features

    • Square neckline
    • Corded straps
    • Mini length silhouette
    • Velvet composition I Fully lined
    • Form hugging fit with slight stretch 
    • Zipper not included

     

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

    Style Number/Barcode: 05102-0356

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tropical Moment Sleeveless Asymmetrical Ruched Midi Dress

    Create a tropical moment in a midi dress that brings the color this season. This vacation-ready dress features a sleeveless bodice, a plunging V-neckline and adjustable spaghetti straps that lead to an X-back design. The relaxed fit waist leads to a midi length silhouette with a ruched side seam and an asymmetrical high slit to show off a hint of skin. The all-over tropical print features bright hues that perfectly contrast the dark background. The dress is composed of a smooth knit fabric that offers a form-hugging fit. Complete your look with a pair of heels and golden hoop earrings. 

    Fit & Features

    • Plunging V-neckline
    • Adjustable spaghetti straps
    • X-back 
    • Midi length silhouette 
    • Tropical print
    • Asymmetrical high side slit
    • Form hugging fit

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

    Style Number/Barcode: 05102-0231

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Knits An Essential Off Shoulder Maxi Dress

    Sure it's winter, but it doesn't mean you have to stash away your dresses. Toss on a leather jacket, add a scarf, grab your fave bag, and you're all ready to go girlie!

    Fits & Features

    • Off Shoulder Neckline
    • Fitted Long Sleeves
    • Ruching Down The Side Seams
    • Maxi Length Silhouette I Slit At The Side
    • Ribbed Knit Composition
    • Curve Hugging Fit I Ample Stretch

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

    Style Number/Barcode: 05102-0354

    Category Name: Casual Dresses

    Price: $12.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Basic Ribbed Knit Midi Dress

    Dress up down or up with a basic midi this season girl! The dress features a mock neck, long sleeves and a midi length silhouette with a high side slit. Dress is composed of ribbed knit fabric that offers a form hugging fit with plenty of stretch. Perfect to pair with booties! 

    Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0276

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Major Flirt Ditsy Floral Skater Dress

    You'll be a major flirt in this adorable ditsy floral dress! It features tie-shoulder spaghetti straps, a V neck and back, a high waist seam, and a flowy skater silhouette. The floral printed knit fabric offers plenty of stretch. Complete your outfit with gold hoop earrings and strappy sandals.

    Fit & Features

    • Tie-shoulder spaghetti straps
    • V neck and back
    • Elastic high waist seam
    • Short skater silhouette
    • Ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-0222

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Plant One On Floral Maxi Dress

    Flaunt your florals in this gorge maxi dress! It's the perfect dress for the winery or as a wedding guest! 

    Fits & Features

    • Spaghetti Straps
    • V-Neckline
    • Maxi Length Silhouette With Gathering & Slit Detail At Side  
    • Smooth Jersey Knit Fabric I Floral Prints Throughout 
    • Curve Hugging Fit 
    • Ample Stretch

    Model is 5'4" with a 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0251

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The Fuzz Sweater Dress
    Mini dresses are all the fuzz! Featuring a crew neckline, long sleeves and a ribbed design. Hem of dress hits mid thigh and dress is composed of an eyelash knit material that offers moderate stretch. Perfect for the winter season!

    Style Number/Barcode: 06005-0152

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tropical Ruffled Chiffon Skater Dress

    Bring the charm in a ruffled dress that gets those tropical island vibes just right! This vacay-approved dress features a tropical palm-leaf print, a plunging V neckline, ruffled shoulder straps, a cinching tie waist belt, and a flirty skater silhouette. Complete the outfit with pretty wedge heels and fringe earrings.

    Fit & Features

    • Tropical palm-leaf print
    • Plunging V neckline
    • Ruffled shoulder straps
    • Tie waist belt 
    • Open back with tie back ties
    • Lower back zipper and hook and eye closure
    • Skater silhouette 
    • Sheer chiffon fabric with a woven lining
    • Runs true to size

    Style Number/Barcode: 05102-0264

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Small Town Girl Eyelet Mini Dress

    Whether you're a small town girl, or a city babe, this sweet mini dress is a day out go-to! Slip on and head out to brunch babe!

    Fit & Features

    • Square neckline
    • Adjustable Spaghetti straps | Sleeveless
    • Mini hemline
    • Zipper closure center back
    • Eyelet linen material
    • Minimal stretch
     Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0213

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Ribbed Knit Midi Dress

    Dress up down or up with a basic midi this season girl! The dress features a mock neck, long sleeves and a midi length silhouette with a high side slit. Dress is composed of ribbed knit fabric that offers a form hugging fit with plenty of stretch. Perfect to pair with booties! 

    Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0275

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleeveless Bodycon Denim Midi Dress

    Make a denim dress a work from home must. The bodycon dress features a sleeveless bodice with a square neckline, thick shoulder straps that offer plenty of support, and vertical seams that lead to a midi length silhouette. The dress is composed of denim fabric that offers a form hugging fit that enhances curves. Dress up this midi with colorful pumps and statement earrings.

    Fit & Features

    • Sleeveless square neckline
    • Thick shoulder straps
    • Front vertical seams that lead from bust to hem
    • Midi length silhouette
    • Denim fabric
    • Form hugging fit 

    Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0192

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold In Blooms Deep V Midi Dress

    Girl, you are so fab in florals! You'll love sauntering around in the Bold In Blooms mini dress! 

    Fits & Features

    • Dual Spaghetti Straps | Cross At Back
    • Plunging V Neckline | Padded Bust 
    • Back Zipper With Hook & Eye Closue
    • Midi Length Silhouette | Slit At Center Back
    • Smooth Scuba Fabric | Floral Prints Throughout 
    • Curve Hugging Fit 

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

    Style Number/Barcode: 05101-0193

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flower Of Love Scuba Mini Dress

    Brighten up your wardrobe with bold and beautiful floral prints! It's the perf dress for your wedding guest attire!

    Fits & Features

    • Wire V Neckline I Vertical Darts At The Bust
    • High Waist Seam
    • Mini Length Silhouette
    • Smooth Scuba Fabric 
    • Form Hugging Fit I Moderate Stretch 

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

    Style Number/Barcode: 05101-0191

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance