Casual 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!

  • Picture Perfect Color Block Midi Dress

    For a picture-perfect look you'll be reaching for this color block midi dress for any casual plans! The strapless fitted bodice accentuates your silhouette while the flowy midi-length hem creates an elegant movement as you walk. Plus, keep your hands warm in the convenient hidden side pockets!

    Fit & Features

    • Woven cotton-blend fabric, stretchy knit lining
    • Strapless color block fitted bodice
    • Hidden side pockets
    • Back zipper and hook-eye closure
    • Flowy midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6109

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • 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
  • Bring Knit On Midi Dress

    Bring on the style with this trendy basic knit midi! The dress features a mock neckline, long fitted sleeves, and a mid-length, curve hugging fit. Garment is composed of a brushed knit fabric with a knit lining, offering plenty of stretch.

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

    Style Number/Barcode: 05102-0178

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    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
  • Chic And Spotted Mini Dress

    Get a chic and spotted look in this adorable trendy little mini! The dress features an off the shoulder neckline with short cuffed sleeves with ruffle trim detailing, a front keyhole cut out with a tie closure, a stretchy smocked back, and a short, form hugging fit. The dress is composed of a lightweight woven fabric with a cute all over animal print.

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

    Style Number/Barcode: 05102-0342

    Category Name: Casual Dresses

    Price: $19.97 $48.90

    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
  • 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
  • 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
  • Talk That Talk Tank Dress

    You're a bad gal, bb! Catch some eyes in this simple-yet-sexy tank dress. Including a racerback neckline that flows into a midi length, this spaghetti tank dress features a smooth, stretchy fabric that hugs your body with every move.

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

    Style Number/Barcode: 05102-0183

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Necessary Basic Midi Dress

    Because we all need this necessary basic midi in our closet! The dress features a sleeveless bodice, spaghetti straps, a square neck and back, and a mid-length, curve hugging fit. The smooth knit fabric offers plenty of stretch for comfortable wear.

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

    Style Number/Barcode: 05102-0256

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Girly Gingham Print Ruffled Mini Dress

    You love all things girly, so this adorable gingham print mini dress is perfect for you. The all-over smocked design adds stretch, while the ruffled neck and hem bring the cutesy vibe.

    Fit & Features

    • Smocked cotton fabric, high stretch
    • Gingham print
    • Sleeveless sweetheart neckline, ruffled trim, small bow detail
    • Adjustable spaghetti straps
    • Mini-length ruffled hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-000160

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Plus Crochet In Color Dress

    This cute crochet dress is perfect for a day out! It features a V neckline, adjustable spaghetti straps that create an X back, a sheer crochet waist, and a short flared skirt with a full lining. 

    Style Number/Barcode: 15102-0018

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Into The Florals Dress
    Immerse yourself in all the floral print you can take! This flower bomb features a cowl neck, adjustable narrow straps that create an X back, and a slim fit. Dress is composed of a casual knit fabric with a lightweight feel that offers plenty of stretch. Dress is unlined.

    Style Number/Barcode: 05102-3105

    Category Name: Casual Dresses

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Cut Out Mini Dress

    This cute and casual cut out mini is perf for your next day out. The dress features an off the shoulder elastic banded square neckline, short sleeves, a trendy front cut out at the waist, and a short, form hugging fit. The dress is composed of a stretchy knit fabric with a knit lining.

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

    Style Number/Barcode: 05102-0211

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Don't You Want Me Dress

    They're gonna want you AND your dress! This tank dress features adjustable shoulder straps with a back tie closure and ruched sides. It's structured with a bodycon fit and hits at the mid-thigh. Fully lined and made of a comfy, textured jersey knit fabric for dressing up or down.

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

    Style Number/Barcode: 05102-0258

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simple And Stunning Midi Dress

    Simply stunning is what you are in this trendy knit midi dress.

    Fits & Features

    • Bungee Spaghetti Straps
    • Square Neckline
    • Curve-Hugging Fit
    • Midi Length Silhouette
    • Soft Brushed Knit Composition | Fully Lined
    • Offers Plenty Of Stretch

     

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

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

    Style Number/Barcode: 05102-0175

    Category Name: Casual Dresses

    Price: $10.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Over You Sleeveless Midi Dress

    Show us who is boss in sleek midi! This mid length dress features a crew neckline, and a sleeveless bodice. Hem is tailored to a mid calf length, and dress is composed of a ponte material that offers moderate stretch. Throw on some heels and walk the walk!

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

    Style Number/Barcode: 05102-0189

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pretty And Posh Mini Dress

    Be the it girl of your squad in this pretty and posh mini! The dress features a sleeveless bodice, a rounded neckline, a square back, and a short, form hugging fit. The dress is composed of a stretchy knit fabric with a full knit lining and showcases a trendy all over plaid print.

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

    Style Number/Barcode: 05102-0193

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Charming And Chic Midi Dress

    This charming and chic midi dress will turn your look into a classic. It features a sleeveless bodice, a high round neckline, a back zipper closure, flattering vertical seam detailing along the bust, and a mid-length, curve hugging fit. The dress is composed of a ponte knit 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: 05102-0190

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Rock On Distressed Tunic Top
    Hey, wild child! Show off your spirited side in this distressed tunic top (or be bold and make it a mini!). Top features a crew neck, short sleeves, shredded V detail at chest and hem, and a large "Rock On" contrast graphic. Top is cut for a slim fit and made from an ultra-soft rayon knit with moderate stretch.

    Style Number/Barcode: 06002-0188

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summertime Heat Lace-Up Denim Mini Dress

    Raise the temps, turning heads in this denim mini dress for a day out or night on the town! The strapless neckline with a front lace-up adds a touch of sexy to the bodycon silhouette that hugs your curves in all the right places.

    Fit & Features

    • Denim fabric
    • Strapless neckline with a front lace-up
    • Back zipper closure
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000196

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bad Bee Mini Dress

    You're the baddest B in this simple dress. This piece features a crew neckline, short sleeves, and a bodycon fit throughout. It's made of a rib knit fabric that's perfect for dressing up or down.

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

    Style Number/Barcode: 06002-0164

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance