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.

  • 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
  • Fab Florals Crochet Waist Maxi Dress

    Impress with florals in a maxi dress that takes you to paradise! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a crochet waist, a floral print, a high side slit, and a maxi length silhouette. The dress is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Crochet waist
    • Floral print
    • High side slit
    • Maxi length silhouette 
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-0196

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet And Smocked Floral Mini Dress

    Bring a sweet vibe to your spring style with this adorable floral mini dress! It features an off-the-shoulder square neckline, short ruffle sleeves, and a curve-hugging, mini-length silhouette with a smocked design. Complete the look with hoop earrings and new heels.

    Fit & Features

    • Off-the-shoulder square neckline
    • Short ruffle sleeves
    • Short, form-hugging fit
    • Floral print
    • Chiffon fabric, smocked design
    • Runs true to size

    Style Number/Barcode: 05102-0339

    Category Name: Casual Dresses

    Price: $20.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Chiffon Long Sleeve Skater Dress

    We're falling for this floral look! It's the perf dress for that special outing you got lined up 

    Fits & Features

    • Surplice V Neckline
    • Cuffed & Unlined, Sheer Long Sleeves 
    • Zipper At Back 
    • Mini Length | Flowy Skater Skirt 
    • Lined, Chiffon Fabric 
    • Minimal Stretch
    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0192

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Still Got Knit Mini Dress

    Flaunt your love for knit with this casual mini dress! It features a turtle neck, long fitted sleeves and a curve hugging mini length silhouette that rests at the mid-thigh level. Dress is composed of a cable-knit fabric that offers a relaxed fit with 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: 05102-0186

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Alluring Tropical Floral Maxi Dress

    Create a stylish and alluring look for your next vacay in this gorgeous maxi dress! It features a sleeveless V-neckline, spaghetti straps that lead to a lace-up back design, a high waist, a floor-length hem with a chic side slit, and a flowy, relaxed fit. The knit fabric has an all-over tropical floral print, making this dress a perf pick for summer. Complete the outfit with strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Lace-up back design
    • High waist
    • Floor-length hem, side slit, relaxed fit
    • Knit fabric, tropical floral print
    • Runs true to size

    Style Number/Barcode: 05102-0195

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • That's My Stripe Crepe Triangle Waist Cut Out Mini Dress

    This striped crepe waist cut out mini dress will be just your type! Featuring a sultry cutout, a streamlined silhouette, and trendy stripes, this dress checks all the boxes. Opt for some booties and statement earrings to go with this look for a night out.

    Fits & Features

    • Spaghetti straps
    • V Neckline and vertical dart seams 
    • Square back with no zipper
    • Triangular waist cut out
    • Mini length silhouette 
    • Crepe fabric 
    • Form-hugging fit with moderate stretch

    Style Number/Barcode: 05103-0292

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Tropical Surplice Wrap Maxi Dress

    Wrap yourself in a floral maxi dress. Bring the vacation vibes this season in this dress that features an all-over tropical floral print, a sleeveless surplice wrap neckline, and spaghetti straps. The relaxed fit waist leads to a carefree maxi length silhouette. The dress is composed of a lightweight smooth knit fabric that offers a form hugging fit. Complete your outfit with dainty bracelets and face-framing sunglasses.

    Fit & Features

    • Sleeveless
    • Wrap v-neckline
    • Spaghetti straps
    • Tropical floral print
    • Maxi length silhouette
    • Smooth knit 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: 05102-0194

    Category Name: Casual Dresses

    Price: $21.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral The Right Reasons High Neck

    Brunch? Wedding guest? Winery? This floral mini dress is perfect for all these special occasions!

    Fits & Features

    • Adjustable Spaghetti Straps 
    • Lace Zipper Back 
    • High Neckline 
    • Mini Length Silhouette | Skater Skirt
    • Smooth Scuba Fabric With Floral Prints 
    • Form Hugging Fit | Moderate Stretch 
    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0168

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • City Slicker Satin Mini Dress

    A sleek mini, inspired by the trendy city girl in mind! 

    Fits & Features

    • Cowl Neckline
    • Adjustable Self Tie Shoulder Straps
    • Square Back
    • Satin-Like Composition I Fully Lined
    • Mini Length Silhouette
    • Form-Flattering Fit I Minimal Stretch 

     Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0350

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance