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!

  • Still Got Knit Mini Dress

    Flaunt your love for knit with this casual mini dress! It features a turtle neck, long fitted sleeves and a curve hugging mini length silhouette that rests at the mid-thigh level. Dress is composed of a cable-knit fabric that offers a relaxed 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: 05102-0186

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Flair Smocked Mini Dress

    Bring some flair to your fall look with this floral smocked mini! The dress features a slight sweetheart neckline, long sleeves with smocked cuffs, and a short hem with a drawstring at the front. Dress is composed of a smocked woven fabric that offers plenty of stretch and a curve hugging fit.

    Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0393

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Out In The Town Lace-Up Skater Dress

    Playful and daring, this skater dress showcases your best self with a lace-up back design and flowy short-length hem. 

    Fit & Features

    • Eyelet fabric
    • Scoop neckline
    • Adjustable spaghetti straps
    • Lace-up back design
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000013

    Category Name: Casual Dresses

    Price: $33.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charming Ruffles Floral Mini Dress

    Charm them all in ruffles and florals!

    Fits & Features

    • Sweetheart Neckline With Tie Front Accent I Square Back
    • Adjustable, Ruffle Trim Spaghetti Straps
    • Multi-Tiered, Ruffle Mini-Length Silhouette
    • Lined Chiffon Fabric With Dainty Floral Print Against Solid Background
    • Relaxed Fit With Slight Stretch

     

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

    Style Number/Barcode: 05101-0426

    Category Name: Casual Dresses

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Comfy Cozy Slim Hoodie Tunic

    Get all those comfy cozy feels in this slim fit hoodie tunic! It features a drawstring hood, long sleeves, a front kangaroo pocket, and a mid-thigh length, relaxed and comfortable fit. The knit fabric offers moderate stretch.

    Style Number/Barcode: 06002-0245

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    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
  • 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
  • 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
  • V-Neck Ruched Midi Dress
    Bring some style to the basic midi with this ruched detail dress! It features long fitted sleeves, a notch front V neckline, ruching along the sides, and a mid-length, curve hugging fit. The dress is composed of a stretchy knit fabric.

    Style Number/Barcode: 05102-0319

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    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
  • Sultry And Fierce Satin Mini Dress
    Sultry and oh so fierce, this satin mini is the one for you. It features a sleeveless bodice, bungee spaghetti straps, a square neck and back, and a short, curve huggng fit. The dress is composed of a smooth satin-like fabric with plenty of stretch.

    Style Number/Barcode: 05102-0376

    Category Name: Casual Dresses

    Price: $10.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Such A Sweetie Open Back Gingham Ruffle Skater Dress

    Please, please, please envision how sweet you'll look in this gingham ruffle skater dress! Boasting a head-turning open back and flattering mini-length hem perf for pairing with boots!

    Fit & Features

    • Gingham print, woven fabric
    • Sweetheart neckline, lace trim, bust tie
    • Spaghetti straps
    • Open back with spaghetti strap tie
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6102

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Miss Me Mini Dress

    Get tied to this cute mini! It features a plunging V neckline with a tie front accent, fitted long sleeves, a sexy mid-drift cut out and a mini length silhouette. Dress is composed of a ribbed knit fabric that offers a curve hugging fit with 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: 05102-0307

    Category Name: Casual Dresses

    Price: $13.97 $35.90

    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
  • Wrap Around My Heart Dress

    You're looking like hot stuff this evening, babes! This dress has a wrap bodice with a deep V neckline, spaghetti straps, and ruching on the side. A wrap skirt creates an asymmetrical hemline for a party perfect ensemble. Dress is composed of an unlined crepe fabric that offers 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: 05103-3609

    Category Name: Casual Dresses

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simply Stated Sleeveless Midi Dress

    Simple and sleek is the statement you want to make! This dress features a sleeveless bodice, a scoop neckline, tank-like straps and a curve hugging midi length silhouette with side slit. Dress is composed of a 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: 05102-0270

    Category Name: Casual Dresses

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • A Casual Slay Long Sleeve Mini Dress

    Oh you know, just a casual slay. This dress has all the features that we are obsessed with! A deep v neckline, an empire waist, matching buttons down the center, and long sleeves that are balloon style which adds a bohemian flare. Dress is composed of a linen material offers no stretch, and showcases a striking snake skin pattern. Lined at the skirt.

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

     

    Style Number/Barcode: 05103-0473

    Category Name: Casual Dresses

    Price: $20.97 $52.90

    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
  • 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
  • Katelyn Ruched Midi Dress

    Chic and fab, the Katelyn ruched midi dress is a new go-to. She features a sleeveless bodice, a Y neck with halter straps, a knot detail, and a front keyhole cut out, and a square back with a zipper closure. Her high waist band leads to a curve hugging skirt with ruched side details and a mid-length hem. The dress is composed of a stretchy knit fabric with a pretty sheen.

    Model is 5'8" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small. 

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0238

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Satin Dreams Midi Dress

    We are totally obsessed with satin right now and we are guessing you are too! This midi dress features a v-neckline, thin spaghetti straps that lead to a square back and a hemline that flows into a floor length. Dress is composed of a satin like material that offers a relaxed fit 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: 05102-0325

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish In Spots Tunic
    Spotted! A stylish tunic perfect for transitioning to the fall season. It features a sleeveless bodice, spaghetti straps that tie at the neck and lead to a square back, a wrap front creating a V neckline, a hidden side zipper and hook and eye closure, a trendy twist front detail, and a short hem. The tunic is composed of a lightweight woven fabric with no stretch and includes a woven lining.

    Style Number/Barcode: 06003-0397

    Category Name: Casual Dresses

    Price: $4.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Classic Basic Mini

    We are loving a mini dress with a square neckline! This basic mini is composed of a fully lined ribbed knit material that offers moderate stretch and a form fitting silhouette. The spaghetti straps are bungee style. The skinny straps are flattering and offer stretch as well. This look says it all! Throw on some heels and throw your hair up for a sexy effortless look!

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

    Style Number/Barcode: 06002-0152

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    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