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.

  • Ribbed Knit Square Neck Midi Dress

    Can't get enough of knit! Exude your confidence in this form-flattering midi dress.

    Fits & Features

    • Tank-Style Shoulder Straps
    • Square Neck & Back
    • Slit At Center Back
    • Midi Length Silhouette
    • Curve-Hugging Fit 
    • Ample Stretch

     

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

      Style Number/Barcode: 05102-0349

      Category Name: Casual Dresses

      Price: $12.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Ribbed Knit Turtleneck Mini Dress

      Stay comfy and look stylish doing it! This ribbed mini is the perfect foundation for your layered looks. 

      Fits & Features

      • Turtleneck 
      • Quarter-Length Sleeves
      • Mini Length Silhouette That Hits Mid-Thigh
      • Stretchy Ribbed Knit Composition
      • Curve-Hugging Fit I Ample Stretch 

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

      Style Number/Barcode: 05102-0347

      Category Name: Casual Dresses

      Price: $9.97 $25.90

      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
    • Casual Cut Out Mini Dress

      Cute and casual, this mini dress needs to be in your closet! It features an elastic banded off the shoulder square neckline, long fitted sleeves, a front waist cut out, and a short, curve hugging fit. Dress is composed of a ribbed knit fabric with plenty of stretch.

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

      Rust: Model is 5'8" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.

      Style Number/Barcode: 05102-0260

      Category Name: Casual Dresses

      Price: $12.97 $32.90

      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. It features long sleeves with elastic banded ruffle cuffs, a deep V neckline with a ruffle trim, a hidden back zipper and hook and eye closure, ruffle tiered detailing, and a flowy skater skirt. The dress is composed of a linen fabric with no stretch.

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

      Style Number/Barcode: 05102-0321

      Category Name: Casual Dresses

      Price: $18.97 $48.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Get On Knit Long Sleeve Dress

      Get on those basic vibes with this sleek mini dress! It features a turtle neck, fitted long sleeves and rounded mini length silhouette. Dress is composed of a semi-sheer smooth knit fabric that offers a curve hugging fit with 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: 05102-0185

      Category Name: Casual Dresses

      Price: $11.97 $29.90

      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
    • Livin' With Finesse Skater Dress

      Finesse that closet with a perfectly designed skater dress!

      Fits & Features

      • V Neckline
      • Double Spaghetti Straps Leading To Cross Over At Back
      • High Waist Bodice 
      • Mini, A-Line Skirt 
      • Ponte Fabric I Fully Lined
      • Moderate Stretch

      Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.

      Style Number/Barcode: 05101-0147

      Category Name: Casual Dresses

      Price: $14.97 $37.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Loving And Living In Knit Midi Dress

      We love a basic staple midi dress that pair perfectly with booties to channel those fall vibes! The midi dress features a plunging V neckline, long fitted sleeves and a midi length that sits slightly above the knee. Dress is composed of a soft to the touch lined ribbed knit fabric that offers a curve hugging fit with a moderate stretch.

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

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

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

      Style Number/Barcode: 05102-0205

      Category Name: Casual Dresses

      Price: $9.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Ready To Ruche Mini Dress

      Showcase curves in this sultry mini dress! It features a plunging V neckline, fitted long sleeves, a ruched side seam and a mini length silhouette that falls at the mid-thigh length. Dress is composed of a double-lined soft to the touch brushed knit fabric that offers a form hugging fit with a moderate stretch. 

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

      Style Number/Barcode: 05102-0200

      Category Name: Casual Dresses

      Price: $13.97 $33.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Cozy Crush Sweater Dress

      A cozy and crush-worthy sweater dress to include in your winter wardrobe.

      Fits & Features

      • Surplice V Neckline 
      • Long Bishop Sleeves
      • Mid Thigh Length Hem
      • Midweight Rib Knit Fabric 
      • Curve-Hugging Fit 
      • Ample Stretch

      Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.

      Style Number/Barcode: 06005-0231

      Category Name: Casual Dresses

      Price: $9.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Precious In Plaid Mini Dress

      Make your way into the next season with a perfectly plaid mini dress!

      Fits & Features

      • Square Neckline
      • Thick, Tank Strap 
      • Mini Length Silhouette
      • Smooth Poly Material 
      • Curve Hugging Fit I Moderate Stretch 
      • Complete The Look With The Matching Duster (06202-0057)

       

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

      Style Number/Barcode: 05102-0261

      Category Name: Casual Dresses

      Price: $9.97 $31.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Feelin' Sweet Off Shoulder Sweater Dress

      Channel your sweet side when you slip into a flattering off shoulder sweater dress gurl!

      Fit & Features

      • Fold over off shoulder neckline
      • Form fitting silhouette
      • Banded wrist
      • Mini hemline
      • Knit woven material
      • Moderate stretch

      Style Number/Barcode: 06005-0232

      Category Name: Casual Dresses

      Price: $6.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Keepin' Knit Casual Midi Dress

      This knit midi is casual yet oh so cute. It features a sleeveless bodice, adjustable spaghetti straps, a sweetheart neckline with bust stitching, and a mid-length, curve hugging fit with a back slit. The ribbed knit fabric offers plenty of stretch.

      Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.

      Style Number/Barcode: 05102-0202

      Category Name: Casual Dresses

      Price: $12.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • So Into You Faux Suede Mini Dress

      You'll be so into this sleek faux suede mini dress! It features a sleeveless bodice, bungee spaghetti straps that lead to an open lattice back, a square neckline, and a short, curve hugging fit. The faux suede fabric offers plenty of stretch and includes a front knit lining.

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

      Style Number/Barcode: 05102-0274

      Category Name: Casual Dresses

      Price: $12.97 $31.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Off Shoulder Glitter Mini Dress

      Take your look off the charts! Take this mini out on the town when you pair with your favorite pair of heels! 

      Fits & Features

      • Straight Neckline 
      • Off Shoulder Mini Sleeves
      • Mini Length, Curved Hemline
      • Glitter Knit Fabric I Lined
      • Curve-Hugging Fit I Moderate Stretch 
      • Glitter May Transfer 

      Model is 5'8" with a 34" bust, 25" waist and 34" hips. She is wearing a size small.

      Style Number/Barcode: 05103-0318

      Category Name: Casual Dresses

      Price: $9.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Buttoned Beauty Ribbed Mini Dress

      Button up in this cute mini for the perfect day out! It features an off the shoulder neckline, a multi button down front, fitted long sleeves and a mini length silhouette. Dress is composed of a lined ribbed knit fabric that offers a curve hugging fit with a moderate stretch. 

      Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.

       

       

      Style Number/Barcode: 05102-0272

      Category Name: Casual Dresses

      Price: $9.97 $30.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Ribbed Knit Surplice Mini Dress

      Sweater dresses are a must for all things winter wear! This knit mini will become a staple in your winter wardrobe.

      Fit & Features

      • Wrap front V neck and back
      • Back bar detail
      • Long cuffed dolman sleeves
      • High waist seam
      • Short, curve hugging fit
      • Ribbed knit fabric | Plenty of stretch

      Style Number/Barcode: 06005-0222

      Category Name: Casual Dresses

      Price: $6.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Ravishing Ruched Mini Dress

      This dress is a daytime delight. It features ruffled sleeves, a hidden back zipper closure, an adjustable drawstring skirt. It's made of a lightweight linen fabric with zero stretch and full lining.

      Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.

      Style Number/Barcode: 05102-0243

      Category Name: Casual Dresses

      Price: $9.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Casual Vibes Knit Midi Dress

      Get those casual cute vibes in this adorable knit midi! The dress features a V neckline, short sleeves, and a mid-length, curve hugging fit. The ribbed knit fabric offers 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: 05102-0315

      Category Name: Casual Dresses

      Price: $11.97 $28.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Charm Them All Midi Dress

      Charm them all in this casual yet so cute printed midi! The dress features a sleeveless bodice, spaghetti straps, a rounded neckline, and a mid-length, curve hugging fit. The dress is composed of a knit fabric with plenty of stretch.

      Model is 5'9" with a 33" bust, 24" waist and 35.5 hips. She is wearing a size small. 

      Style Number/Barcode: 05102-0252

      Category Name: Casual Dresses

      Price: $9.97 $24.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Stylishly Snapped Sweater Dress
      This stylish sweater dress is ready for all your snaps! It features an off the shoulder square neckline, long fitted sleeves, a side faux snap button down detail leading to a slit, and a curve hugging fit with a slight asymmetrical hem. The dress is composed of a ribbed knit fabric, offering plenty of stretch.

      Style Number/Barcode: 06005-0170

      Category Name: Casual Dresses

      Price: $14.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Keepin' Knit Basic Midi Dress

      Sometimes keeping it basic is the best way to go! This knit midi dress features a sleeveless bodice, tank-like shoulder straps, a scoop neck and back, a side slit, and a mid-length, curve hugging fit. The dress is composed of a stretchy knit fabric.

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

      Style Number/Barcode: 05102-0268

      Category Name: Casual Dresses

      Price: $9.97 $20.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Ruffle It Up Smocked Midi Dress

      Play up your look with this adorable ruffled and smocked midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a square neck and back with a ruffle hem, ruffle tiers, and a stretchy smocked body with a mid-length form hugging fit. Dress is composed of a lightweight woven fabric.

      Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

      Style Number/Barcode: 05102-0341

      Category Name: Casual Dresses

      Price: $9.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance