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!

  • 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
  • Picturesque Cutie Corset Lace-Up A-Line Midi Dress

    Create a cute picturesque 'fit in this corset A-line midi dress! The corset bodice and lace-up back add a touch of allure to the sweet silhouette.

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Sweetheart neckline, tie-front detail
    • Thin adjustable straps
    • Corset bodice, lace-up back
    • High waist seam
    • Midi-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3069

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Plant One On Floral Skater Dress

    Featuring pretty floral graphics throughout, this fab floral dress is the perfect partner in crime for all your daytime outings.

    Fits & Features

    • Adjustable spaghetti straps
    • Surplice V neckline
    • Zipper & hook and eye closure at back 
    • Removable waist tie 
    • Wrapped and layered skater skirt
    • Crepe composition I Fully lined
    • Form-fitting, limited stretch

     

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

    Style Number/Barcode: 05102-0223

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Prettiest Pick Sweetheart Ruched Mini Dress

    Girl, this dress is the right pick for that girl's brunch you got planned! Add a pair of statement-making earrings and some cute strappy heels.

    Fits & Features

    • Off Shoulder Sleeves I Elastic Shoulders & Back
    • Lace-Up Design At Center Front Bodice 
    • Ruching Throughout
    • Mini Length Silhouette
    • Woven Fabric With Mesh Lining
    • Ruffle-Trim At The Cuffs & Hem
    • Minimal Stretch 

    Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small.

      Style Number/Barcode: 05102-0604

      Category Name: Casual Dresses

      Price: $9.97 $48.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Easy Does It Puff Sleeve Ruched Mini Dress

      Fall for this sweet mini dress that'll have you ready for the warmer days ahead! Pair with slip-on mules and a cute mini purse for the perf daytime OOTD!

      Fits & Features

      • Surplice V Neckline
      • Puff, Short Sleeves 
      • Mini Length Silhouette
      • Ruching Along The Sides 
      • Brushed Knit Fabric 
      • Form Hugging Fit I Plenty Of Stretch 

      Style Number/Barcode: 05102-0663

      Category Name: Casual Dresses

      Price: $9.97 $31.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Off Shoulder Ruffle Mini Dress

      Pretty layered ruffles and a sweetheart neckline are just a few of the fab details on this cute mini dress! 

      Fits & Features

      • Off Shoulder Short Sleeves With Puff & Ruffle Accents 
      • Sweetheart Neckline With No-Slip Interior Strip I Padded Bust 
      • Back Zip With Hook & Eye Closure 
      • Cut Out At The Center Waist 
      • Mini Length I Ruched Skirt I Layered Ruffle Hem
      • Woven Fabric I Fully Lined  
      • Minimal Stretch

       

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

      White Dress: Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

      Style Number/Barcode: 05101-0753

      Category Name: Casual Dresses

      Price: $19.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Pretty In Plaid Mini Dress

      Keep it pretty in plaid with this brunch ready mini dress! This season-ready dress only needs a pair of wedges and a pop of jewel tones for a complete look! 

      Fit & Features 

      • Square Neckline
      • 3/4 Puff Sleeves
      • Plaid Print 
      • Lined Lightweight Fabric
      • Mini Length Silhouette 
      • Relaxed Fit 
      • Minimal Stretch 

       


      Style Number/Barcode: 05102-0680

      Category Name: Casual Dresses

      Price: $9.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Floral Moment Maxi Dress

      Create a charming moment in florals in this sweet maxi dress! Perfect for brunch when paired with fab heels and a neutral handbag! 

      Fit & Features

      • Wrap V-Neckline 
      • Spaghetti Straps
      • Elastic Waist 
      • Floral Print
      • Maxi Silhouette 
      • Lined Knit Fabric | Mini Skirt Length Lining
      • Relaxed Fit | Moderate Stretch 

       

       

      Style Number/Barcode: 05101-0530

      Category Name: Casual Dresses

      Price: $14.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Floral Moment Asymmetrical High Slit Midi Dress

      Make a fab impression in a floral dress, perfect for a first date. The midi dress features a gorgeous floral print, a wrap V-neckline for a flattering fit, and an asymmetrical high slit. Complete your look with strappy heels and hoop earrings to complement this fab print. 

      Fit & Features

      • Sleeveless, v-neck, spaghetti straps
      • Bodycon silhouette
      • Asymmetrical high slit
      • Midi-length hem
      • Floral print, knit fabric, moderate stretch
      • Fits true to size

      Style Number/Barcode: 05102-0562

      Category Name: Casual Dresses

      Price: $9.97 $35.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Zipper Key Hole Ribbed Knit Mini Dress

      This ribbed mini dress features a zippered keyhole that adds an element of sexiness! We love to see you pairing this look with some booties or heels! 

      Fits & Features

      • Ribbed Crew Neck 
      • Front Zipper Opens To Keyhole Cut Out 
      • Mini Length Silhouette
      • Ribbed Fabric
      • Form Hugging Fit I Plenty Of Stretch 

      Style Number/Barcode: 05102-0574

      Category Name: Casual Dresses

      Price: $10.97 $28.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Floral Bliss Smocked Mini Dress

      Bring out the floral prints and wave those gloomy winter-blues goodbye! Radiate that early springtime energy in this cute mini dress! 

      Fits & Features 

      • Adjustable Spaghetti Straps 
      • Lettuce Edge Trim At Square Neckline & Hem 
      • Smocking Throughout 
      • Mini Length Silhouette 
      • Curve Hugging Fit 
      • Ample Stretch 

      Style Number/Barcode: 05102-0519

      Category Name: Casual Dresses

      Price: $19.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Sleeveless Bodycon Denim Midi Dress

      Make a denim dress a work from home must. The bodycon dress features a sleeveless bodice with a square neckline, thick shoulder straps that offer plenty of support, and vertical seams that lead to a midi length silhouette. The dress is composed of denim fabric that offers a form hugging fit that enhances curves. Dress up this midi with colorful pumps and statement earrings.

      Fit & Features

      • Sleeveless square neckline
      • Thick shoulder straps
      • Front vertical seams that lead from bust to hem
      • Midi length silhouette
      • Denim fabric
      • Form hugging fit 

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

      Style Number/Barcode: 05102-0192

      Category Name: Casual Dresses

      Price: $9.97 $30.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Sweet Romance Chiffon Floral Mini Dress

      It's a match babe! Add this dreamy dress to cart and you'll be sweeping them off their feet! 

      Fits & Features 

      • Sweetheart Neckline I Lace-Up Bodice 
      • Square Back With Zipper & Hook And Eye Closure 
      • Sheer Long Sleeves I Elastic Cuffs
      • Mini Length Silhouette With Self Ties At The Front
      • Ruffle-Trim  At Shoulders, Neckline, Hem 
      • Lined Chiffon Fabric With Romantic Floral Print
      • Form Flattering Fit I Minimal Stretch 

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

      Style Number/Barcode: 05101-0707

      Category Name: Casual Dresses

      Price: $9.97 $52.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Tropical Moment Sleeveless Asymmetrical Ruched Midi Dress

      Create a tropical moment in a midi dress that brings the color this season. This vacation-ready dress features a sleeveless bodice, a plunging V-neckline and adjustable spaghetti straps that lead to an X-back design. The relaxed fit waist leads to a midi length silhouette with a ruched side seam and an asymmetrical high slit to show off a hint of skin. The all-over tropical print features bright hues that perfectly contrast the dark background. The dress is composed of a smooth knit fabric that offers a form-hugging fit. Complete your look with a pair of heels and golden hoop earrings

      Fit & Features

      • Plunging V-neckline
      • Adjustable spaghetti straps
      • X-back 
      • Midi length silhouette 
      • Tropical print
      • Asymmetrical high side slit
      • Form hugging fit

      Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.

      Style Number/Barcode: 05102-0231

      Category Name: Casual Dresses

      Price: $9.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Off Shoulder Puff Sleeve Mini Dress

      With puff sleeves and an off-shoulder neckline, you'll be making a trendy and stylish statement in this romantic little number! 

      Fits & Features 

      • Off Shoulder Neckline I No-Slip Interior Slip 
      • Puff Long Sleeves With Ruffle Accents At The Cuffs & Shoulders
      • Smocked Back I Zipper With Hook & Eye Closure
      • Mini Length Silhouette 
      • Woven Fabric I Smooth Knit Lining 
      • Ties At The Hem 
      • Relaxed Fit I Minimal Stretch 

      Style Number/Barcode: 05102-0596

      Category Name: Casual Dresses

      Price: $9.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Bungee Drawstring Side Seam Knit Mini Dress

      Keep it casual in a knit mini dress. The dress features a round neckline, short sleeves, ruched side seams with bungee straps and a mini length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with hoops and heels to dress up this casual dress. 

      Fit & Features

      • Crew neckline
      • Short sleeves
      • Ruched side seams with bungee cords 
      • Mini length silhouette 
      • Curve-hugging fit
      • Moderate stretch 
      Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small. 

      Style Number/Barcode: 05102-0715

      Category Name: Casual Dresses

      Price: $10.97 $26.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Simple Staple Ribbed Knit Bodycon Mini Dress

      Comfy and chic, this knit bodycon mini dress is the simple staple you need in your closet! Made with a stretchy ribbed knit fabric, it features a sleeveless scoop neckline, spaghetti straps, and a form-hugging fit to flaunt your curves along the bodycon silhouette. Style this mini-length dress with a denim jacket and sneakers for a cute and casual vibe.

      Fit & Features

      • Stretchy ribbed knit fabric
      • Scoop neckline
      • Spaghetti straps
      • Bodycon fit
      • Runs true to size

      Style Number/Barcode: 06005-1937

      Category Name: Casual Dresses

      Price: $12.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • High Slit Floral Knit Maxi Dress

      Upgrade your dress with a floral print. The floral maxi dress features a sleeveless bodice, a plunging V-neckline, and spaghetti straps that lead to a partially open back with a square neck. The relaxed fit waist leads to a curve-hugging maxi length silhouette that is accented with a high side slit to reveal a hint of leg. The dress is composed of a smooth knit fabric that offers a form hugging fit.  Complete your brunch-ready look with statement heels and extra-large hoops

      Fit & Features

      • Sleeveless v-neckline 
      • Spaghetti straps
      • Partially open back
      • Floral print 
      • Maxi length silhouette
      • High side slit 
      • Knit fabric 

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

      Style Number/Barcode: 05101-0645

      Category Name: Casual Dresses

      Price: $21.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Speechless Strapless Floral Ruffle Mini Dress

      Leave everyone speechless when you stroll in wearing this floral mini dress at parties or brunch! The strapless neckline and stretchy smocked bodice provide a comfortable and flattering fit, while the dainty floral print and embroidery add a touch of whimsy. Complete the look with sunnies.

      Fit & Features

      • Dainty floral print and embroidery
      • Woven fabric, some stretch
      • Fitted silhouette
      • Ruffled mini-length hem
      • Runs true to size

      Style Number/Barcode: 05102-5456

      Category Name: Casual Dresses

      Price: $9.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Ribbed Knit Ditsy Floral Mini Dress

      Keep it sweet in a ditsy floral dress. Perfect for brunch, this mini dress features a sleeveless bodice with a sweetheart neckline and supportive tank-like straps. The back features an open back with two ribbed bar back straps. The relaxed fit waist leads to a curve-hugging mini-length silhouette. Keep accessories minimal to let the ditsy floral print command attention. 

      Fit & Features

      • Sleeveless bodice
      • Sweetheart neckline
      • Open back with bar straps
      • Ditsy floral print
      • Mini length silhouette 

      Style Number/Barcode: 05102-0439

      Category Name: Casual Dresses

      Price: $13.97 $26.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Sleeveless V Neck Ruffled Floral Mini Dress

      Get frilly in a ruffled floral dress. Celebrate with your squad in a floral mini dress that features a sleeveless bodice, a plunging V neckline, and spaghetti straps. The relaxed fit waist leads to a mini-length silhouette with a frilly ruffled hem. The all-over floral print features bright hues that contrast with the dark background. Complete your look with wedges and sunglasses.

      Fit & Features

      • Sleeveless V neckline
      • Spaghetti straps
      • Floral print 
      • Mini-length silhouette
      • Ruffled hem
      • Lightweight knit fabric with a moderate stretch
      • Runs true to size

      Style Number/Barcode: 05102-0517

      Category Name: Casual Dresses

      Price: $6.97 $26.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Sleeveless Crossback Floral Ruffled Mini Dress

      Get crossed up in a floral mini dress. Make a statement this season in a mini dress that features a charming floral print, a scoop neckline, and spaghetti straps. The back features an open back design with cross-strap ties. The relaxed fit waist features a ruffled hem and leads to a mini length silhouette with matching ruffled hem. The dress is composed of a lightweight woven fabric that offers a relaxed fit with a slight stretch.  Complete your look with neutral-hued wedges and a floppy hat

      Fit & Features

      • Sleeveless scoop neckline
      • Spaghetti straps
      • Floral print 
      • X-back 
      • Ruffles 
      • Mini length silhouette
      • Lightweight woven fabric, slight stretch 

      Style Number/Barcode: 05102-0581

      Category Name: Casual Dresses

      Price: $15.97 $30.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Sleek Sleeveless Square Neck Ribbed Knit Midi Dress

      Keep it sleek in this simple and stylish ribbed midi dress. Go for a minimal vibe with this dress that features a square neckline, spaghetti straps, and a high side slit to showcase some leg. The dress features a relaxed fit waist that leads to an at-the-knee midi-length silhouette. The dress is composed of a curve-hugging ribbed knit fabric that offers a moderate stretch. Complete look with strappy stilettos and extra-large hoops to dress up this minimal piece.

      Fit & Features

      • Sleeveless square neckline
      • Spaghetti straps 
      • High side slit
      • Midi-length silhouette
      • Ribbed knit fabric
      • Curve-hugging fit, moderate stretch
      • Runs true to size

      Style Number/Barcode: 05102-0706

      Category Name: Casual Dresses

      Price: $9.97 $26.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Bloom With Beauty Maxi Dress

      Be a stunning blooming beauty in this floral printed maxi dress!

      Fits & Features

      • V Neckline
      • Spaghetti Straps
      • Sheer Lace Back With Zipper I Elastic Back Cut-Out 
      • High Waist Seam
      • Flowy, Maxi Length 
      • Sheer Chiffon Fabric I Knit Lining
      • Relaxed Fit I Minimal Stretch 

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

      *Also available in Plus.

      Style Number/Barcode: 05102-3887

      Category Name: Casual Dresses

      Price: $24.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale