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.

  • Nothin' But A Sweet Thing Floral Mini Dress

    Honey you ain't nothin' but a sweet thannng when you step out in this floral mini ruched dress. We are already dreaming of that spring wardrobe!

    Fit & Features

    • Modest v-neckline
    • Lace up bust detailing
    • Tank straps | Off- shoulder straps
    • Form fitting silhouette | Mini hemline
    • Brushed knit material
    • Ruched down the center
    • Floral pattern | Slight stretch

    Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small. 

      Style Number/Barcode: 05102-0431

      Category Name: Casual Dresses

      Price: $9.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Carine Metallic Glitter Ruched Mini Dress

      Special Occasion 

      Almost instantly, Carine's glitter metallic shine will draw eyes your way. You'll be loving her figure-flattering fit that'll have you look and feel amazing. Don't forget to include some stiletto heels and earrings to really finish the look! 

      Fits & Features 

      • Adjustable Spaghetti Straps 
      • V Neckline I Padded Bust 
      • Back Zipper With Hook & Eye Closure 
      • Mini Length Silhouette 
      • Ruched Down Center Front, Back & Sides 
      • Smooth Woven Glitter Knit I Fully Lined
      • Form Hugging Fit I Minimal Stretch 

      Special Occasion products cannot be returned to any retail locations.

      Style Number/Barcode: 05001-0326

      Category Name: Casual Dresses

      Price: $36.97 $69.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Basic Buttoned Sweater Dress
      Keep it gorge with buttons this season! The sweater dress features a mock neck, short sleeves, a multi row button detail and a midi length silhouette with a mini side slit. Dress is composed of knit fabric that offers a relaxed fit with a moderate stretch.

      Style Number/Barcode: 06005-0357

      Category Name: Casual Dresses

      Price: $19.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Tropics Vibe Plunging Mini Dress

      Transport to an island paradise with this vacay ready mini dress! It features a plunging wrap V neckline with a knot accent, long bell sleeves and asymmetrical mini length silhouette. The all over tropical print features palm leaves throughout. Dress is composed of an unlined lightweight woven fabric that offers a relaxed fit with minimal stretch. 

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

       

      Style Number/Barcode: 05102-0427

      Category Name: Casual Dresses

      Price: $9.97 $48.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Denim Doll Puff Sleeve Mini Dress

      Spring is right around the corner and you'll want to bust out those wedges and sandals to complement this cute denim dress! 

      Fits & Features

      • Puff Shoulder Short Sleeves I Elastic Cuffs
      • Sweetheart Neckline 
      • Square Back I Zipper Closure 
      • Mini Length Silhouette 
      • Denim Fabric 
      • Curve Hugging Fit I Plenty Of Stretch

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

      Style Number/Barcode: 05102-0426

      Category Name: Casual Dresses

      Price: $9.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • The Essential Sweater Dress
      Fall back on this essential sweater dress this season! It features a crew neck, long sleeves with ribbed cuffs and a midi length silhouette that pairs perfectly with booties! Dress is composed of a sweater knit fabric that offers a relaxed fit with a moderate stretch.

      Style Number/Barcode: 06005-0358

      Category Name: Casual Dresses

      Price: $18.97 $46.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Leopard Print Surplice Smocked Mini Dress

      If you're on the hunt for a fierce print and body-flattering dress, look no further than this!

      Fits & Features

      • Plunging V Neckline With Surplice Design
      • Cuffed Long Sleeves
      • Smocked Skirt With Merrow Edge Trim Hem
      • Leopard Print Design
      • Form Hugging Fit I Plenty Of Stretch At Bottom 
      • Zipper Not Included 

       

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

      Style Number/Barcode: 05102-0428

      Category Name: Casual Dresses

      Price: $19.97 $48.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Show 'Em Off Shoulder Smocked Mini Dress

      Show off those shoulders in this cute mini dress! For a cute daytime look, pair it with your fave denim jacket and some white sneakers! 

      Fits & Features

      • Off-shoulder neckline, short sleeves
      • Keyhole opening with self-ties at front
      • Mini length silhouette 
      • Woven textured fabric, smocked back, ruffle trim detail
      • Curve hugging fit, plenty of stretch 

      Style Number/Barcode: 05102-0472

      Category Name: Casual Dresses

      Price: $9.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Leopard Mesh Mini Dress

      Flaunt that trendy leopard print in this fierce mini dress! 

      Fits & Features

      • Elastic Bungee Strap
      • Square Neckline & Back
      • Mini Length Silhouette I Gathering Detail At Side Seams
      • Knit Lining With Leopard Printed Mesh Overlay 
      • Curve Hugging Fit I Plenty Of Stretch 

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

        Style Number/Barcode: 05102-0425

        Category Name: Casual Dresses

        Price: $12.97 $31.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Walk in the Park Floral Mini Dress

        Take a stroll in style wearing this sweet floral dress! Pair it with sandals and a straw bag.

        Fit & Features

        • Ribbed Fabric
        • Off the Shoulder Puff Sleeves
        • Tie Front Detail
        • Mini Length

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

        Style Number/Barcode: 05101-0447

        Category Name: Casual Dresses

        Price: $9.97 $29.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Sheer I Come Mesh Ruched Midi Dress

        Better fashionably late than never! Make an entrance in this sultry midi. 

        Fits & Features

        • Spaghetti Straps
        • Elastic Square Neckline & Back
        • Ruched Accent Along Sides
        • Midi Length Silhouette
        • Lined, Mesh Fabric 
        • Curve Hugging Fit I Plenty Of Stretch  
        • Zipper Not Included

        Style Number/Barcode: 05102-0423

        Category Name: Casual Dresses

        Price: $14.97 $36.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Keeping It Fierce Snake Mini Dress

        Keep it fierce in snake print! The bodycon features an off the shoulder neckline with ruffled trim, short sleeves, a sweetheart bust, a keyhole with tie front accent, a smocked back and a mini length silhouette. Dress features a snake print to perfectly matching with your favorite solid pieces. Garment is composed of a lined satin fabric that offers a relaxed fit with slight stretch. 

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

         

        Style Number/Barcode: 05102-0421

        Category Name: Casual Dresses

        Price: $9.97 $50.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Turtleneck Ribbed Knit Mini Dress

        Layer away! With a trendy turtleneck and a comfy rib-knit construction, this is the perfect starting piece for your layered looks. 

        Fits & Features 

        • Turtleneck 
        • Long Sleeves With Thumb Holes 
        • Curve-Hugging Fit
        • Plenty Of Stretch
        • Mini Length Silhouette 
        • Zipper Not Included 

         

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

        Style Number/Barcode: 05102-0422

        Category Name: Casual Dresses

        Price: $10.97 $28.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Tropical Print Cowl Neck Maxi Dress

        Head to the tropics in a maxi dress. The vacation-worthy maxi dress features a draped cowl neck, spaghetti straps that lead to a bold open back and an all-over tropical palm leaf print. The relaxed fit waist leads to a sweeping maxi length silhouette that is accented with a daring high slit. Complete your look with clear heels to let the print speak for itself and a floppy hat. 

        Fit & Features 

        • Cowl neck 
        • Spaghetti straps 
        • Open back 
        • High slit, maxi length silhouette 
        • Tropical palm leaf print
        • Smooth knit fabric
        • Form hugging fit, moderate stretch 

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

        Style Number/Barcode: 05101-0446

        Category Name: Casual Dresses

        Price: $9.97 $42.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Flower Up Strapless Skater Dress

        Recharge your wardrobe by adding some bright floral prints! We know you'll be slaying it in the Flower Up skater dress. 

        Fits & Features

        • Elastic, Strapless Neckline 
        • Mini Length Silhouette I Skater Style Skirt 
        • Chiffon Fabric I Floral Print All Over 
        • Ruffle-Trim At Hem & Neckline
        • Form Hugging Fit 

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

        Style Number/Barcode: 05102-0418

        Category Name: Casual Dresses

        Price: $9.97 $36.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Blossom And Bloom Square Neck Skater Dress

        Show that springtime glow in this skater dress! Twirl 'round and 'round and capture everyone's attention with the gorge floral prints! 

        Fits & Features

        • Spaghetti Straps
        • Square Neckline With Center Tie Front 
        • Mini Length Hem I Skater Style Silhouette
        • Smooth Knit Fabric I Floral Print Design 

        Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

        Style Number/Barcode: 05102-0417

        Category Name: Casual Dresses

        Price: $9.97 $35.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • All Over Ruffled Skater Dress

        Get an adorable all over ruffled look in this pretty little skater dress.

        Fits & Features

        • Long Sleeves With Elastic Banded Ruffle Cuffs
        • Deep V Neckline With Ruffle Trim
        • Zipper & Hook And Eye Closure At Back
        • Ruffle Tiered Detailing Along Flowy Skater Skirt
        • Linen Composition
        • No Stretch

        Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

        Style Number/Barcode: 05102-0419

        Category Name: Casual Dresses

        Price: $18.97 $48.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Flirty Fleur Tie Front Mini Dress

        Show off your soft side! Pretty blooms cover this flirty dress! It's the perfect mini for a day with your gals. 

        Fits & Features

        • Spaghetti Straps
        • Square Neckline With Tie Front I Empire Waist
        • Mini Length Silhouette 
        • Knit Fabric I Floral Print 
        • Form Hugging Fit 

        Style Number/Barcode: 05101-0445

        Category Name: Casual Dresses

        Price: $9.97 $34.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Ruched Right In Midi Dress

        Slip right into this curve-flattering midi dress. It features fixed shoulder straps, a scoop neck and back, ruching down the side seams, and a midi-length silhouette. The garment is composed of a sleek and smooth knit, and offers a moderate amount of stretch. Zipper not included. 

        Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small. 

        Style Number/Barcode: 05102-0411

        Category Name: Casual Dresses

        Price: $13.97 $33.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Dreamy In Florals Tie Front Mini Dress

        Bring the spring vibes in this cute and dreamy mini dress! We'd love to see you styling this with a pair of white sneakers or chunky heels! 

        Fits & Features

        • Spaghetti Straps
        • Plunging V Neckline I Bust Tie With Keyhole Opening I Square Back 
        • Mini Length Silhouette 
        • Textured Knit Fabric I Ditsy Floral Print 
        • Form Hugging Fit I Moderate Stretch
        • Zipper Not Included 

        Style Number/Barcode: 05101-0442

        Category Name: Casual Dresses

        Price: $9.97 $33.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • One Shoulder Asymmetrical Ribbed Maxi Dress

        Show off some skin in this cute AF maxi dress! 

        Fits & Features

        • One Shoulder Strap
        • Slanted Neckline 
        • Maxi Length I Sultry Side Slit 
        • Ribbed Knit 
        • Form Hugging I Plenty Of Stretch 

        Style Number/Barcode: 06005-0341

        Category Name: Casual Dresses

        Price: $17.97 $44.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Sleeveless Leopard Chiffon Maxi Dress

        Keep it sassy in spots with this pretty leopard maxi dress! It features a sleeveless bodice, a plunging wrap V neckline, adjustable spaghetti straps that lead to a strappy back design and a relaxed fit bodice that leads to a sweeping maxi length with a ruffled hem. Dress is composed of a semi sheer chiffon fabric that reveals a mini length knit lining. Garment offers a relaxed fit with a minimal stretch. Hidden back zipper closure included.

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

        Style Number/Barcode: 05102-0413

        Category Name: Casual Dresses

        Price: $19.97 $48.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Floral Flirt Skater Dress

        Hey bby! You'll be a total flirt in this pretty floral skater dress! Pair with some strappy sandals and a boho chic panama hat!

        Fit & Features

        • Spaghetti straps | V neck and back
        • Ruched front | Tie closure
        • Small front keyhole cut out
        • High waist
        • Flowy skater skirt
        • Stretchy knit fabric
        • Small all over floral print

        Style Number/Barcode: 05102-0416

        Category Name: Casual Dresses

        Price: $13.97 $35.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Season of Stripes Cutout Gauze Mini Dress

        Keep it sassy in a striped dress this season to keep on-trend! Make a stunning impression for that upcoming date in a dress that features a plunging V-neckline, sexy bar waist cutouts, and a trendy striped design. Complete look with wedges and fringe earrings to channel bohemian vibes. 

        Fit & Features 

        • Sleeveless V-neckline
        • Smocked waist
        • Bar waist cutouts
        • Striped pattern
        • Mini length silhouette
        • Gauze-linen fabric
        • Form hugging fit, 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: 05102-0414

        Category Name: Casual Dresses

        Price: $9.97 $40.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance