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!

  • 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
  • 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
  • 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
  • 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: 05102-0275

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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
  • 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
  • Long Sleeve Knit Midi Dress

    Keep it basic this season! The midi dress features a V neckline, fitted long sleeves vertical stripes and a midi length silhouette that rests slightly above the knee. Dress is composed of a lined knit fabric with a form hugging fit with a slight stretch. Zipper not included. 

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

    Style Number/Barcode: 05102-0395

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Beautifully Buttoned Ribbed Sweater Dress
    Button up in this casually chic sweater dress to impress this season! It features a wrap V-neckline, long sleeves, a multi-button down accent on the left seam and a mini length silhouette. Dress is composed of an unlined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Zipper not included.

    Style Number/Barcode: 06005-0322

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Off Shoulder Sweater Dress

    It's sweater time! We love a good sweater dress, just slip it on and you are ready! Designed with an off shoulder fold over neckline, long sleeves, and a form fitting silhouette. Dress is composed of a soft knit woven fabric that offers moderate stretch.

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

    Style Number/Barcode: 06005-0068

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Own The Room Striped Knit Midi Tube Dress

    Hot girl summer just got a little hotter. This striped midi tube dress hugs you in all the right places with a soft, textured knit that moves with you.

    Fit & Features

    • Striped textured cotton-blend knit fabric, lightweight knit lining
    • Moderate stretch
    • Strapless straight-across neckline
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000019

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Leopard Cowl Neck Mini Dress

    Keep your style untamed in this fierce leopard print mini dress! It features a sleeveless bodice, a cowl neck, adjustable spaghetti straps that leads to a square back and a mini length silhouette. Dress is composed of an unlined lightweight woven fabric with a satin-like sheen that offers a relaxed fit with a minimal stretch.

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

    Style Number/Barcode: 05102-0326

    Category Name: Casual Dresses

    Price: $10.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylishly Destructed Tunic

    This tunic is destructed with all the style! It features a crew neckline, long fitted sleeves, a short hem, and distressed slit detailing on the top and toward the hem. Tunic is composed of a cotten blend fabric that offers moderate stretch.

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

    Style Number/Barcode: 06002-0276

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sultry Sweater Dress

    Keep it classy in a sweater dress! This dress features a v neckline, and long sleeves that puff at the wrist with the help of a thick wristband. Bodice meets skirt high waist with a belt that ties at the side. Back of the garment has a tie detail below the neck.The hem of this dress hits mid thigh, and dress is composed of a knit material that offers a comfortable form fit with 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: 06005-0076

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Forever Reckless Lace Up Tunic

    You're a free spirit and you do what you want! This lace up tunic features short sleeves, a mid-thigh length, and a center script reading "Forever Reckless" in a bold contrasting print. The knit fabric offers moderate stretch and a relaxed fit.

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

    Style Number/Barcode: 06002-0224

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Hot In The Tropics Tropical Bodycon Mini Dress

    Walk around looking hot in this tropical bodycon mini dress while on a resort vacation or island destination! 

    Fit & Features

    • Tropical palm print, knit fabric, stretchy knit lining
    • Scoop neckline
    • Spagehtti straps
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000101

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vintage Motors Slashed Mini Dress

    Give your look some serious edge with this mini dress! It features a round neckline, long fitted sleeves and a mini length silhouette with slashed distressed detailing. The graphic at the center of the bodice features a motorcycle with wings and a graphic that reads: " Superior Motorcycle Vintage Garments." Mini dress is composed of a cotton-blend fabric that offers a curve hugging fit with a moderate stretch.

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

     

    Style Number/Barcode: 06002-0242

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • What's Knot To Like Mini Dress

    Take your look to the next level with this pretty mini dress! It features an off the shoulder neckline, fitted long sleeves, a cinching tie waist belt with loops and an asymmetrical mini length silhouette with a ruched detailing. Dress is composed of a lined crepe fabric that offers a curve hugging fit with a moderate stretch. Zipper not included.  

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

    Style Number/Barcode: 05102-0336

    Category Name: Casual Dresses

    Price: $12.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sophisticated Faux Suede Midi Dress

    Keep it sophisticated in statement faux suede! The mini dress features a sleeveless bodice, a scoop neckline, spaghetti straps, vertical princess seams that create an hourglass illusion and a midi length silhouette with a side slit. The back features a sexy keyhole accent to show off more than a hint of skin! Dress is composed of a faux suede fabric that offers a form hugging fit with slight stretch.

     

    Style Number/Barcode: 05101-0276

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sassy Snaps Ribbed Midi Dress

    Keep it sassy as you snap into this must have! The dress features a crew neck, fitted long sleeves, a curve hugging midi length silhouette and a multi row snap button detail on the left side seam. Dress is composed of an unlined ribbed knit fabric that offers a moderate stretch.

    Model is 5'3" with a 32" bust, 22.5" waist and 34" hips. She is wearing a size small.

     

    Style Number/Barcode: 06005-0304

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Leopard Print Wrap Front Midi Dress

    You're quite the fierce fashionista, so this leopard print midi suits you! The dress features a sleeveless bodice, adjustable spaghetti straps, a wrap front V neckline, a V back with a hidden zipper closure, a high waist seam with a wrap front skirt with a faux tie detail, and a mid-length, flowy fit. Dress is comosed of a sheer textured woven fabric with a short woven lining.

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

    Style Number/Barcode: 05102-0396

    Category Name: Casual Dresses

    Price: $19.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Plaid Knit Mini Dress
    Pretty plaid is the way to go! This knit mini dress features a sleeveless bodice, spaghetti straps, a scoop neck, a square back, and a short, curve hugging fit. The dress offers plenty of stretch and includes a knit lining.

    Style Number/Barcode: 05102-0302

    Category Name: Casual Dresses

    Price: $12.97 $31.90

    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 Eyes on You Lace Low Back Midi Dress

    Soft girl era, but make it spicy. With a sheer midi hem, sultry low back, and flirty side slit, this is the “accidentally iconic” dress for nights out, beach dates, or brunches.

    Fit & Features

    • Stretch lace knit fabric, partially lined
    • V-neckline, spaghetti straps
    • Low back cut
    • Curve-hugging silhouette
    • Sheer midi hem, side slit
    • Runs true to size

    Style Number/Barcode: 05102-000222

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Knit Open Back Tunic

    Keep it casual cutie with pretty knits! The tunic features a turtle neck, long sleeves with ribbed cuff, a partial open back and a short form hugging fit. Tunic is composed of knit fabric that offers 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: 06005-0053

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance