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.

  • 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
  • A Bold Move Mini Dress

    Make a major bold move and absolutely stun in this vibrant mini dress! The bright coral hue is perf for spring break!

    Fit & Features

    • Bungee spaghetti straps
    • Square neckline
    • Dart seam detailing
    • High waist | Front cut out
    • Short, ruffle hem
    • Form hugging fit
    • Crepe fabric | Moderate stretch

    Style Number/Barcode: 05101-0780

    Category Name: Casual Dresses

    Price: $13.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleek Sleeveless Square Neck Ribbed Knit Midi Dress

    Keep it sleek in this simple and stylish ribbed midi dress. Go for a minimal vibe with this dress that features a square neckline, spaghetti straps, and a high side slit to showcase some leg. The dress features a relaxed fit waist that leads to an at-the-knee midi-length silhouette. The dress is composed of a curve-hugging ribbed knit fabric that offers a moderate stretch. Complete look with strappy stilettos and extra-large hoops to dress up this minimal piece.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps 
    • High side slit
    • Midi-length silhouette
    • Ribbed knit fabric
    • Curve-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-0706

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild In Lace Leopard Dress

    Unlock your wild side in this fierce mini dress! Pair this bold print with sleek hoops and stilettos for stand out lewk! 

    Fit & Features 

    • V-Neckline | Lace Trim 
    • Spaghetti Straps 
    • Side Slit | Lace Trim 
    • Leopard Print 
    • Lined Smooth Knit Fabric
    • Relaxed Fit 
    • Moderate Stretch 

     

    Style Number/Barcode: 05102-0710

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feeling Floral Eyelet Mini Dress

    We’re always in the mood for a little floral print! Pair this mini dress with sandals and layered dainty jewelry.

    Fit & Features

    • All Over Eyelet Design
    • 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: 05102-0709

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spot Me Woven Ruffle Mini Dress

    Get spotted in this chic & stylish woven LBD, perf paired with some strappy sandals and a denim jacket.

    Fit & Features

    • Short sheer sleeves
    • Wrap front V neckline
    • Sheer back | Hidden zipper closure
    • High waist
    • Front ruched detailing | Faux drawstring
    • Short, ruffle hem
    • Sheer swiss dot woven fabric | Stretchy knit lining

    Style Number/Barcode: 05101-0775

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Got A Flair For It Ruffle Hem Mini Dress

    Add some flair to your movement with this ruffle mini dress! Pair with some block heels and hoop earrings!

    Fits & Features

    • Spaghetti Straps
    • Square Neckline I Princess Seams 
    • Back Zipper With Hook & Eye Closure 
    • Side Ruching 
    • Mini Length Silhouette I Ruffle Trim Hemline 
    • Smooth Textured Woven Fabric 
    • Form Hugging Fit I Moderate Stretch 

    Style Number/Barcode: 05102-0698

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Falling For Florals Mini Dress

    Fall for this pretty print this season as you charm them all! Pair this beauty with fab pumps and butterfly accessories for an unforgettable look! 

    Fit & Features 

    • Sweetheart Neckline with Built-In Boning 
    • Lace-Up Bodice 
    • Adjustable Spaghetti Straps 
    • Floral Print 
    • Lined Lightweight Woven Fabric 
    • Mini Skirt Length Knit Lining
    • Relaxed Fit | Minimal Stretch  

     


    Style Number/Barcode: 05102-0700

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Daisy Days Smocked Mini Dress

    Keep it fab in florals this season with this charming mini dress! Pair with wedges and a cute tote for the perf lewk honey! 

    Fit & Features 

    • Square Neckline | Smocked Trim
    • Inset | Tie at Bust 
    • Spaghetti Tie Straps 
    • Daisy Floral Print
    • Smocked 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: 05102-0684

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Felt Cute Button Off Shoulder Mini Dress

    Felt cute, probably leaving on! Show off those curves in this sweet mini! Opt for some strappy mules and a pair of chic earrings for an adorable attire! 

    Fits & Features

    • Off Shoulder Design I Short Sleeves
    • V Neckline 
    • Snap Button-Front 
    • Ribbed Knit Fabric 
    • Mini Length Hem 
    • Figure Hugging I Plenty Of Stretch 

    Style Number/Barcode: 06005-0636

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleeveless Ruched Midi Dress

    Yessssss girl! She's classy and curvy. Up your midi game with this form-hugging dress! Pair it with your fav block heels.

    Fits & Features

    • Crew Neckline
    • Dual Button Closure At Nape I Keyhole Opening
    • Midi Length Silhouette
    • Ruching Throughout 
    • Smooth Jersey Knit Fabric I Fully LIned
    • Form Hugging Fit I Moderate Stretch 
    • Zipper Not Featured

    Style Number/Barcode: 05102-0699

    Category Name: Casual Dresses

    Price: $13.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free