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.

  • Off The Shoulder Ruched Dotted Mini Dress

    Bring the charm in a dotted mini dress to make a flirty impression. The dress features an off the shoulder neckline, sheer long sleeves with a swiss dot pattern and a ruched silhouette throughout. Complete your date night ready look with extra-large hoops and sleek stilettos. 

    Fit & Features

    • Off the shoulder neckline
    • Sweetheart bust with tie front accent
    • Long sheer sleeves with swiss dot pattern
    • Ruched body
    • Mini length silhouette
    • Form hugging fit

     

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

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

    Style Number/Barcode: 05101-0801

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Fun Tie Back Skater Dress

    Look absolutely sweet and chic in this floral skater dress! It's the perfect attire for brunch with your girls or the upcoming baby and bridal showers! 

    Fits & Features

    • Spaghetti Straps
    • Square Neckline 
    • Tie Back I Low Open Back
    • Mini Length Hem I Skater Style Silhouette
    • Knit Fabric I Fully Lined I Floral Print 
    • Moderate Stretch 

    Style Number/Barcode: 05101-0408

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruffled Eyelet Puff Sleeve Mini Dress

    Keep it chic in an eyelet mini dress. This season-ready dress features a sweetheart neckline, a tie front accent, short puff sleeves, and ruched vertical seams that highlight and enhance curves. The relaxed waist leads to a ruffled hem. The dress is composed of a lightweight knit fabric with an eyelet pattern. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete your look with wedges and fringe earrings. 

    Fit & Features

    • Sweetheart neckline
    • Tie front accent 
    • Short puff sleeves
    • Vertical seams
    • Eyelet design
    • Ruffled hem 
    • Lightweight woven fabric, relaxed fit 

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

    Style Number/Barcode: 05102-0734

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Puff Sleeve Ruched Knit Mini Dress

    Keep on trend in a puff sleeve dress. This must-have dress features a sweetheart neckline with ruched detailing, puff sleeves, and a mini length silhouette. The dress is composed of a knit fabric that offers a form hugging fit with a slight stretch. Complete look with a pair of pumps and earrings. 

    Fit & Features 

    • Sweetheart neckline 
    • Ruched detailing at the bust 
    • Short puff sleeves 
    • Knit fabric 
    • Form hugging fit 
    • Moderate stretch 

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

    Style Number/Barcode: 05102-0733

    Category Name: Casual Dresses

    Price: $10.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Persuasion Ruched Mini Dress

    Charm in a floral dress that brings major sweet appeal! Step out for your next lunch date with bae in this head-turning dress. The dress features a plunging v-neckline, quarter sleeves with a ruffled hem, a ruched center that runs bodice through the hem, and a cute floral print! Complete your look with cork wedges and sleek hoops. 

    Fit & Features

    • Plunging v-neckline
    • 3/4 sleeves with ruffled hem
    • Ruched center that runs bodice through the hem
    • Floral print
    • Mini length silhouette with ruffled hem

     

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

    Style Number/Barcode: 05102-0724

    Category Name: Casual Dresses

    Price: $18.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylish In Stripes Tassel Waist Tie Mini Dress

    Leave work looking absolutely stylish in stripes with this cute mini dress! You'll love the cute drawstring tassels that cinch your waist! Slip into a pair of block heels and get your hair up into a high pony for a chic look! 

    Fits & Features

    • V Neckline
    • Button-Front
    • Drawstring Waist With Tassel Detail 
    • Mini Length, Ruffle-Trim Hemline 
    • Drop Shoulder Balloon Sleeves With Elastic Cuffs
    • Woven Fabric With All Over Striped Print 
    • Relax 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: 05102-0732

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spring Simplicity Swiss Dot Babydoll Mini Dress

    Charm them all with this sweet and simple babydoll dress! Put your hair in a cute updo and slip into some block heels for a fabulous spring look! 

    Fits & Features

    • Scoop Neckline
    • Ruffles At Sleeve Openings 
    • Keyhole Opening At The Back I Button Closure
    • Mini Length Hemline
    • Swiss Dot Woven Fabric I Fully Lined I Round Eyelet Design At The Top Front & Along Skirt 
    • Relaxed Fit I Minimal Stretch 

    Style Number/Barcode: 05102-0731

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Florals Smocked Mini Dress

    Charm them all with this sweet and enchanting mini dress! Layer some gorge jewelry and slip into your nude wedges for a fab brunch look! 

    Fits & Features

    • Sweetheart Neckline I Tie At Center Bust
    • Short Sleeves I Ruffle Trim At Cuffs I Off Shoulder Neckline 
    • Fully Smocked Back 
    • Mini Length Silhouette 
    • Woven Fabric I Unlined 
    • Form Hugging Fit I Plenty Of Stretch 

     

     

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

    Style Number/Barcode: 05102-0810

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Thing Chiffon Wrap Mini Dress

    Charm them all, sweet thangggg! They'll be enamored by you in this cute mini dress! Dress up by wearing block heels and adding a cute mini purse! 

    Fits & Features

    • Sheer Flutter Sleeves & Back 
    • Plunging V Neckline 
    • Tie Waist Wrap Design I Belt Loops At Back 
    • Mini Length I Overlap Ruffle-Trim Hem 
    • Chiffon Fabric I Lined 
    • Relax Fit I Minimal Stretch 

    Style Number/Barcode: 05101-0798

    Category Name: Casual Dresses

    Price: $17.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Curves Ahead Sleeveless Ruched Midi Dress

    Showcase curves in a ruched midi dress that elevates your night-out look! The dress features a sleeveless mock neckline, a ruched body, and a midi-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit and a moderate stretch. Complete the look with clear mules.

    Fit & Features

    • Sleeveless mock neckline
    • Ruched body
    • Midi-length silhouette
    • Smooth knit fabric, knit lining
    • Form-hugging fit
    • Moderate stretch
    • Style runs small

    Style Number/Barcode: 05101-0956

    Category Name: Casual Dresses

    Price: $6.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romantic Blooms Floral Chiffon Wrap Mini Dress

    Cupid's got us struck! This romantic airy mini dress is perf for that daytime date you got lined up! Add block heels and a cute cross-body and you'll be all set bb! 

    Fits & Features

    • Sheer Short Sleeves & Back
    • Plunging V Neckline 
    • Tie Waist Wrap Design 
    • Mini Length Silhouette 
    • Chiffon Fabric I Fully Lined I Floral Print 
    • Relax Fit I Minimal Stretch 

    Style Number/Barcode: 05101-0796

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Plaid Moment Ruffled Mini Dress

    Have a major plaid moment in this trendy little mini dress! The ruffle detailing gives off a fun & flirty vibe.

    Fit & Features

    • Adjustable spaghetti straps
    • V neckline
    • Square back
    • Stretchy smocked body
    • Short, tiered ruffled hem
    • All over plaid print

    Style Number/Barcode: 05102-0728

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The One You Need Mini Dress

    Step out in style with this sexy ribbed knit mini dress, perfect for brunch with your besties or a relaxed weekend outing. Its minimalist bodycon silhouette pairs effortlessly with an oversized denim jacket or a fitted blazer for a look that's polished yet effortlessly chic. The dress's flattering V-neckline is ideal for showcasing delicately layered necklaces, adding a sweet and enchanting touch to your ensemble.

     Fit & Features

    • Sleeveless V-neckline
    • Thin bungee straps
    • Strapless bra recommended
    • Mini-length bodycon silhouette
    • Ribbed knit fabric
    • Figure-hugging fit, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-0500

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleeveless Cut Out O-Ring Ribbed Mini Dress

    Step up in a sleeveless ribbed mini dress with sexy cutout details this season. The curve-hugging ribbed dress features a flattering crew neck that leads to a chic O-Ring at the mid-drift accented with waist cut outs for a subtle hint of skin. The back reveals a matching lower back cut out to impress from all angles. The ribbed knit embraces curves while offering a moderate stretch to easily move. Complete this date-night ready look with daring hoops and strappy stilettos. 

    Fit & Features

    • Sleeveless
    • Crew neckline
    • O-Ring at the center, waist cut outs
    • Lower back cut out
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 05102-0723

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Double Take Ribbed Midi Dress

    Make them look twice when you step out in this sexy midi dress!

    Fits & Features

    • Lattice front detail
    • Midi Length I Sultry Side Slit 
    • Ribbed Knit 
    • Form Hugging I Plenty Of Stretch 

    Style Number/Barcode: 06005-0656

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sassy Stripes Midi Dress

    We're feeling sassy in stylish stripes! Take on the season in this chic midi dress, perfect for your next brunch! Pair this piece with wedges and dainty accessories for a complete look!

    Fit & Features

    • Scoop Neckline
    • Spaghetti Straps
    • Cros-Back Straps 
    • Multi-Stripe Pattern
    • Midi Length Silhouette  

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

     

    Style Number/Barcode: 06005-0658

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Button Down Tie Front Midi Dress

    A casual midi dress with chic details! Slip into some mules and you're all set for those daytime festivities with your girls! 

    Fits & Features

    • Bust Tie & Faux Button Front Design 
    • Short Sleeves I Elastic Cuffs & Shoulders 
    • Midi Length Silhouette 
    • Rib Knit Fabric 
    • Form Hugging Fit I Moderate Stretch 
    • Zipper Not Included

    Style Number/Barcode: 05102-0720

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bungee Drawstring Side Seam Knit Mini Dress

    Keep it casual in a knit mini dress. The dress features a round neckline, short sleeves, ruched side seams with bungee straps 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 hoops and heels to dress up this casual dress. 

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Ruched side seams with bungee cords 
    • Mini length silhouette 
    • Curve-hugging fit
    • Moderate stretch 
    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0715

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Swing Into It Ruffle Mini Dress

    Get into the swing of spring by refreshing that wardrobe with this cute mini dress! Slip into some block heels and add a rattan bag for a gorge look! 

    Fits & Features

    • Adjustable Spaghetti Straps 
    • Surplice V Neckline With Snap Button Closure
    • Button Closure At Back I Keyhole Opening I Back Zipper 
    • Ruched Drawstring At The Front 
    • Mini Length Silhouette I Tiered Ruffle-Trim Hem 
    • Woven Fabric I Full Knit Lining
    • Relax Fit I Minimal Stretch 

    Style Number/Barcode: 05102-0718

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Call of The Wild Leopard Ruched Mini Dress

    Channel your instincts in a mini dress that brings the fierce factor! The dress features a sleeveless square neckline, sleek spaghetti straps, and ruched side seams to give curves that cinched effect. Complete your look with sleek hoops and heels. 

    Fit & Features

    • Sleeveless square neckline
    • Sleek spaghetti straps
    • Ruched drawstring side seams
    • Leopard print
    • Mini length silhouette
    • Lined mesh fabric with moderate stretch
    • Form-hugging fit

    Style Number/Barcode: 05103-1734

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Just a Breeze Floral Mini Dress

    You can’t go wrong with a floral mini dress! Style it with wedges and hoops for cute and effortless summer look.

     Fit & Features

    • Off the Shoulder
    • Ditsy Floral Print
    • Mini Length

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

    Style Number/Barcode: 05102-0713

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Give It A Spin Off Shoulder Pleated Skater Dress

    Look chic and cute in this twirl-worthy skater dress! Her best features are def the hidden hand pockets  Make sure you get a pair of block heels to complement this dress! 

    Fits & Features

    • Dual Off Shoulder Bar Straps 
    • V Neckline I Elastic Square Back 
    • Hidden Hand Pockets
    • Mini Length Silhouette I Pleated Skirt I Skater Silhouette
    • Crepe Fabric 
    • Form Hugging Fit I Moderate Stretch 
    • Zipper Not Featured

    Style Number/Barcode: 05101-0783

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Love Chiffon Ruffle Strap Maxi Dress

    Romance is in the air! Take everyone's breath away with this charming maxi dress! 

    Fits & Features

    • Ruffle-Trim Shoulder Straps 
    • Surplice V Neckline I Smocked Back 
    • Adjustable Waist Tie
    • Maxi Length Silhouette I Partial, Mini Length Knit Lining
    • Wrap Skirt Reveals Front Slit 
    • Chiffon Fabric 
    • Moderate Stretch 

    Style Number/Barcode: 05101-0781

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Friday Night Ruched Midi Dress

    Get this dress now so you don’t have to worry about not having anything to wear next Friday! It looks great paired with clear heels and layered gold necklaces.

     Fits & Features

    • Square Neckline
    • Ruched Detailing  
    • Form Hugging Fit

    Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0707

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free