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.

  • Effortlessly Stunning Crochet Waist Maxi Dress

    You'll look effortlessly stunning in this flowy maxi dress that is perfect for the warmer months. It features spaghetti straps that lead to a cross-back design, a lace top with a V neckline, a sheer crochet high waist, and a flowy floor-length gauze skirt with a side slit. Complete the look with on-trend wedges.

    Fit & Features

    • Spaghetti straps
    • Cross back design
    • Lace top, V neckline
    • Sheer crochet high waist
    • Floor-length gauze skirt, side slit
    • Flowy silhouette
    • Runs true to size

    Style Number/Barcode: 05102-0754

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Button Down Beauty Maxi Dress

    Button-down in a casual maxi dress for a cute day-out outfit the next time you're picking up a must-have iced coffee! This maxi dress features a plunging sweetheart neckline with a tie-front accent, mini cutout at the bodice, and a button-down front with a high center slit. Complete your look with sleek sandals for those low-key vibes. 

    Fit & Features

    • Plunging sweetheart neckline 
    • Tie-front accent with a small cutout at the bodice
    • Adjustable spaghetti straps
    • Multi-button down front
    • High center slit
    • Maxi length silhouette
    • Ribbed knit fabric, form-hugging fit

     

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

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

    Style Number/Barcode: 05102-0746

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Charmer Ditsy Floral Mini Dress

    You'll charm them all in this adorable ditsy floral mini dress! It features a sleeveless sweetheart neckline with a ruffle trim, a tie-front detail, adjustable spaghetti straps, and a mini-length, curve-hugging silhouette. Style this dress with a pair of strappy sandals.

    Fit & Features

    • Sleeveless sweetheart neckline, ruffle trim
    • Tie-front detail
    • Adjustable spaghetti straps
    • Partial smocked back
    • Short, form-hugging fit
    • Chiffon fabric, ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-0757

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keep It Groovy Tie-Dye Maxi Dress

    Keep your summer look groovy and on-trend with this tie-dye maxi dress! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, a high waist seam, and a floor-length silhouette with a thigh-high side slit. Style this dress with strappy sandals for a laid-back vibe.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back design
    • High waist seam
    • Floor-length silhouette, high side slit
    • Relaxed fit
    • Brushed knit fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-0745

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Laid Back Glamour Crochet Knit Midi Dress

    Keep it effortlessly glam with a crochet-knit dress! The dress features a sleeveless V-neckline, a mini side slit, and a midi length silhouette. The dress is composed of a crochet knit fabric that offers a relaxed fit with a moderate stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless V-neckline
    • Mini side slit
    • Midi length silhouette
    • Crochet knit fabric 
    • Relaxed fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0674

    Category Name: Casual Dresses

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Brunch Babe Floral Mini Dress

    We know you love to get cute for brunch with the girls! Style this smocked floral mini dress with white heels and gold accessories.

    Fit & Features

    • Tie front detail
    • Front cut out
    • Stretchy smocked body
    • Short, form hugging fit
    • Ditsy Floral print
    • Adjustable Spaghetti Straps

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

    Style Number/Barcode: 05102-0744

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Babe Sleeveless Midi Dress

    Hey babe, show off your adorable style in this floral midi dress that is perf for spring. It features a sleeveless square neckline, thin ruffle shoulder straps, a fitted bodice, and a flowy mid-length silhouette with a thigh-high slit. Complete the look with hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless square neckline
    • Thin ruffle shoulder straps
    • Fitted bodice
    • Flowy mid-length silhouette
    • High front slit
    • Ditsy floral print
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-0741

    Category Name: Casual Dresses

    Price: $20.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Square Neck Denim Mini Dress

    A casually chic mini dress is a must for any wardrobe! Add a cute cross body purse and slip into some mules for the perf daytime outfit! 

    Fits & Features

    • Square Neckline With Contrast Stitching I Vertical Dart Seams
    • Short Sleeves With Elastic Cuffs
    • Back Zipper With Hook & Eye Closure
    • Mini Length Hem
    • Denim Fabric 
    • Relax Fit I Moderate Stretch 

    Style Number/Barcode: 05102-0738

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flaunt Those Florals Waist Tie Dress

    Work that springtime magic in this pretty and sweet maxi dress! Add a woven bag and wedges for a completed look! 

    Fits & Features

    • Plunging V Neckline 
    • Waist Tie Design 
    • Sleeveless Bodice
    • Maxi Length Silhouette 
    • Woven Fabric I Ditsy Floral Print Design 
    • Relax Fit I Minimal Stretch 

    Style Number/Barcode: 05102-0739

    Category Name: Casual Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Babe In Denim Mini Dress

    Made for a babe like you! Stow away those jeans and rock this denim mini dress. For chillier days, pair it with a long sleeve tee and some matching sneakers! 

    Fits & Features

    • Adjustable Spaghetti Straps
    • Sweetheart Neckline 
    • Linear Seams & Stitching Down Front 
    • Back Zipper With Hook & Eye Closure
    • Mini Length Silhouette
    • Denim Fabric 
    • Form Hugging Fit I Moderate Stretch 

    Style Number/Barcode: 05102-0740

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Take On The Night Chiffon Smocked Mini Dress

    We'd love to see you take on the night in this, gorgeous! Just slip into some strappy heels to really elevate your lewk! 

    Fits & Features

    • Surplice V Neckline 
    • Sheer Long Sleeves 
    • Smocking At The Cuffs & Skirt 
    • Cut Out At Back With Button Closure
    • Mini Length Silhouette I Ruffle Trim Hem 
    • Chiffon Fabric 
    • Form Hugging Fit I Moderate Stretch 

    Style Number/Barcode: 05101-0810

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pop Of Color Block Ditsy Floral Midi Dress

    Give them a pop of color this season in this flowy dress! Add a pair of block heels and cute mini purse for an OOTD! 

    Fits & Features

    • Tank Shoulder Straps
    • Plunging V Neckline & Back 
    • Back Zipper With Hook & Eye Closure
    • Midi Length I Overlapping Ruffle Trim Hem 
    • Woven Fabric With Ditsy Floral Print & Color Block Design I Partial, Mini Length Lining
    • Relax Fit I Minimal Stretch 

    Style Number/Barcode: 05101-0809

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunset Dream Tie Dye Satin Midi Dress

    You'll look like the perf sunset dream in this tie dye midi dess! Pair with some espadrille sandals for a stylish summer time vibe.

    Fit & Features

    • Tie shoulder spaghetti straps
    • Cowl square neckline
    • Flattering horiztonal seam under the bust
    • Back bar detail | Partial open back
    • Flowy mid-length hem
    • Tie dye satin-like fabric | Sheer woven lining

    Style Number/Barcode: 05102-0737

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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