Casual Dresses

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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.

  • Mock Neck Belted Sweater Dress

    Look effortless in this one-and-done sweater dress! It features a trendy mock neckline, long sleeves, a removable stylish D-ring belt along the waist, slits at the sides, and a midi-length silhouette. The garment is composed of a ribbed knit and offers a form hugging fit with an ample amount of stretch. 

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

    Style Number/Barcode: 06005-0391

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bold Beauty Floral Maxi Dress

    Just as bold as it is beautiful, this maxi dress is designed with a statement floral print on a body-skimming silhouette. It's perfect for your next vacation or weekend plans!

    Fit & Features

    • Floral print, mesh fabric, soft stretchy knit lining
    • Strapless neckline
    • Form-hugging bodice
    • Relaxed maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6118

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Just A Midi Sweater Dress
    A perfect addition to your fall and winter wardrobe. Toss on a pair of booties during the day and swap them for heels during a night out! It features a mock neckline with merrow edge trim, raglan long sleeves, and a midi-length silhouette. The form-fitting dress is crafted from a ribbed knit and offers ample stretch. 

    Style Number/Barcode: 06005-0393

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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
  • V Mine Ribbed Knit Midi Dress

    What's not to love about this perfect layering piece? With unlimited styling possibilities, this dress features a v-neckline, long sleeves, and a midi-length silhouette. The garment is composed of a rib-knit construction and offers a form hugging fit with an ample amount of stretch. 

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

    Style Number/Barcode: 05102-0346

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ribbed Knit Cut Out Midi Dress

    Ward off the chill with this cozy for keeps midi-length dress.

    Fits & Features

    • Plunging V Neckline
    • Long Sleeves
    • Large Cut-Out Detail At Back
    • Soft Knit Fabric I Fully Lined
    • Ample Stretch
    • Zipper Not Included

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

    Style Number/Barcode: 05102-0361

    Category Name: Casual Dresses

    Price: $13.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Golden Hour Tropical Floral Mesh Midi Dress

    Make it your moment to glow in this tropical floral midi dress during golden hour! Featuring a strapless neckline and ruched side seams, this dress flatters your silhouette with a form-hugging fit that leads to a flowy sheer hem.

    Fit & Features

    • Tropical floral print, mesh fabric, sewn-in brushed knit lining
    • Strapless neckline
    • Side ruched seams
    • Form-hugging silhouette
    • Sheer flowy midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000024

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Square Neck Long Sleeve Midi Dress

    The pairing possibilities are endless with this simple and chic piece!

    Fits & Features

    • Square Neckline
    • Long Sleeves
    • Midi Length Silhouette
    • Smooth Knit Fabric
    • Form Hugging Fit I Ample 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: 05102-0379

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Mock Neck Mini Dress
    Cozy chic, this mock neck mini is perfect for the season. It features long fitted sleeves and a short, curve hugging fit. The ribbed knit fabric offers plenty of stretch.

    Style Number/Barcode: 06005-0216

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spot On A-Line Midi Dress

    Throw on a cozy knit sweater, add a pair of boots, and your outfit will be looking spot on! Showcasing a smudge spot print, the sleeveless bodice features adjustable shoulder straps and a v-neckline. Decorative buttons trail down the front, leading to a center split. Linen crafted, this dress features an A-line silhouette and offers little to no stretch. Zipper at center back. 

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

    Style Number/Barcode: 05102-0301

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chiffon Floral Surplice Mini Dress

    Look effortlessly chic in this billowy mini dress! With a ditsy floral print throughout, this dress showcases a plunging v-neckline, surplice style middle, and long sleeves with elastic ruffle cuffs. The tiered, shirred, and fully lined skirt features self ties and an adjustable zipper at the side. This chiffon crafted dress offers little to no stretch. 

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

    Style Number/Barcode: 05102-0447

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Turtleneck Long Sleeve Ribbed Knit Mini Dress

    Bundle up to this ribbed knit mini for those cool nights. This cozy number features a turtleneck, long sleeves, scalloped hem, and mini length silhouette. The ribbed knit construction offers ample 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: 05102-0308

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Hiss Me With That Mini Dress

    Sssslither into this sassy number! It features a snake-inspired print, fixed shoulder straps, sweetheart neckline, and mini-length silhouette. Crafted from soft velvet and paired with a soft knit lining, this form-fitting piece extenuates all the right curves. 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: 05102-0364

    Category Name: Casual Dresses

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Long Sleeve Ribbed Mini Dress

    Keep it cozy with this pretty knit dress! It features a plunging V neckline, long puff sleeves and a mini length silhouette. Dress is composed of a ribbed knit fabric that offers a form hugging fit. 

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

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

    Style Number/Barcode: 05102-0365

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Here To Be Loved V-Neck Eyelet Skater Mini Dress

    Layered or worn solo, this stunning skater dress features a forever flattering mini-length silhouette and an adorable eyelet pattern for the perfect femme finish.

    Fit & Features

    • Eyelet woven fabric, stretchy knit lining
    • V-neckline, bust tie
    • Adjustable spaghetti straps
    • Stretchy smocked bodice
    • Skater silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3950

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Satin Leopard Print Mini Dress

    On the hunt for the perfect mini? Look no further than this sassy satin number. Featuring adjustable spaghetti straps and a square neckline, it also showcases a tonal leopard print and a daring slit at front. Fully lined, it offers minimal stretch and a zipper at the back.

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

    Style Number/Barcode: 05102-0359

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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
  • Smocked Off The Shoulder Mini Dress

    Radiate in this sweet smocked piece! This linen dress features an off the shoulder design with ruffle trim, billowy sleeves with elastic cuffs, smocking at the midsection, and a pleated hem. It showcases a mini-length silhouette with a form hugging fit. Does not include zipper and has a moderate stretch. 

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

    Style Number/Barcode: 05102-0375

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    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
  • Poised In Plaid Sleeveless Mini Dress

    Keep it poised with trendy plaid! The mini dress features a sleeveless bodice, a square neckline, tank-like straps and a mini length silhouette that hugs curves all over. The all over plaid season is perfect to stay on trend this season! Dress is composed of a knit fabric.

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

     

    Style Number/Barcode: 05102-0363

    Category Name: Casual Dresses

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirty Bloom Floral Ruffle Skater Dress

    Serving soft-girl romance with a side of sass, this floral halter mini dress is made for twirls and double takes. Wear it when you want compliments on repeat.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch, floral print
    • Sleeveless V-neckline
    • Tie-back halter straps, partially open back
    • Ruching, drop waist
    • Tiered ruffled design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000297

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • Long Sleeve Ribbed Knit Midi Dress

    Keep it cozy and chic this season with a basic midi! This must have features a turtleneck, long sleeves and a midi length silhouette. Dress is composed of ribbed knit fabric that offers a form hugging fit with a moderate stretch. 

     

     

    Style Number/Barcode: 05102-0344

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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