Casual Dresses

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Cute Sweater Dresses

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Everyday Ease: Casual Dresses for Transitional-Weather Plans

From weekend brunches to spontaneous coffee runs, Windsor’s casual dresses deliver easygoing style with just the right amount of polish. These effortlessly chic looks move with you—whether you’re off to the farmers’ market or catching golden hour with friends. Layer your favorite long sleeve to keep the chill out, or pick your Windsor shoes and accessories, and you're ready for the day.

Laid-Back & Versatile

Knit, ribbed, crochet, and sweater dresses bring comfort and style to cooler days. Slip into playful mini dresses, flowy midi styles, or long casual dresses in warm neutrals, jewel tones, and classic plaids. T-shirt and tunic dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.

Chic from Day to Night

Swap sneakers for ankle boots to take your favorite midi dress from errands to evening hangs. A flowy maxi in nuetral or black adds relaxed elegance—just add a faux leather jacket and heeled booties for an effortless finish.

Ready to refresh your everyday looks? Explore Windsor’s full collection of casual dresses online, in-app, or in-store.

What Makes a Dress Casual?

Casual dresses are defined by their effortless styling, comfortable fabrics, and laid-back details. Fabrication plays a key role—soft knits, cotton blends, and breezy silhouettes naturally create an easygoing look. Prints like ditsy florals or neutral-tone patterns, such as snake print, also make great everyday choices. Knit and sweater dresses are perfect for relaxed settings, whether you're heading to work or dressing up for a casual date night.

Styling is just as important in making a dress feel casual. Swap heels for sneakers, lug boots, or strappy sandals to instantly dress down your look. Layering is another effortless way to create a relaxed aesthetic—throw on a denim jacket, cropped sweater, or oversized cardigan for a cool, laid-back vibe. Details like drawstrings, button fronts, and tie accents also add to the casual appeal. Accessories, makeup, and hair styling can further influence the look, so opt for dainty jewelry, natural waves, or a simple ponytail to complete your effortlessly stylish outfit.

How Do I Style a Dress Casually?

Styling a dress casually is all about choosing relaxed layers and accessories that balance comfort with fashion. Denim jackets, graphic tees, scrunchies, crossbody bags, and sneakers all contribute to an effortlessly cool aesthetic. Try pairing a ruched mini dress with a lariat necklace and chunky sneakers for a sporty yet chic look. A basic knit midi dress layered under a cropped denim jacket with slides is perfect for a casual-chic feel.

For road trips or weekend getaways, maxi and midi dresses offer an easy styling solution. Layer a lightweight sweater over a flowy maxi or knot a t-shirt at the waist for a trendy, carefree vibe. Combat boots can add an edgy touch, while simple strappy sandals keep the outfit light and airy. No matter your style, Windsor has a versatile collection of casual dresses and must-have accessories to complete your look. Need styling help? Visit us in-store, and our expert stylists will help you find your perfect outfit!

  • Knot Front Open Waist Mini Dress

    Slay any occasion in this mini dress! She features a crew neckline, fitted long sleeves, a decorative twist front, and an open cut-out at the midsection. Crafted from a poly-rib textured knit, she offers a curve-hugging fit with an ample amount of stretch to move and groove. 

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

    Style Number/Barcode: 06005-0404

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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