Casual Dresses

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STYLE SPOTLIGHT

Cute Sweater Dresses

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Everyday Ease: Casual Dresses for Cool-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.

Laid-Back & Versatile

Knit, ribbed, and sweater dresses bring comfort and style to crisp fall 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 burgundy 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!

  • Flirt With Confidence Strappy Back Midi Dress

    Blow kisses to all of your admirors as you pass by in this chic one-shoulder midi dress! It features a wide shoulder strap and an asymmetrical strappy back design, a bodycon silhouette, and a center back slit accent on stretchy ribbed knit fabric. Complete the look with a sleek bracelet and clutch. 

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Wide shoulder strap, asymmetrical strappy back design
    • Bodycon silhouette
    • Center back slit accent
    • Midi-length hem
    • Stretchy ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5054

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flaunt Your Figure Bodycon Mini Dress

    Flaunt your gorgeous figure in this curve-hugging mini dress! Featuring a sleeveless square neckline, bungee spaghetti straps, an alluring open back with a cross-back strap design, a mini-length hem, and a bodycon fit, you'll look amazing from any angle. The textured knit fabric offers plenty of stretch. Style with hoop earrings and clear heels.

    Fit & Features

    • Sleeveless square neckline, dart seam detailing
    • Bungee spaghetti straps
    • Open back, cross-back bungee strap design
    • Mini-length hem
    • Bodycon silhouette
    • Textured knit fabric, smooth knit lining at the bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5205

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Show Up And Stun Geometric Print Midi Dress

    Show up and stun for casual drinks with the girls in this trendy midi dress! It features a sleeveless square neckline, spaghetti straps, a midi-length hem, a form-hugging silhouette, and a color block geometric printed pattern to catch everyone's eye. The buttery-smooth lined knit fabric offers plenty of stretch for comfortable wear. Style with clear mules!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Midi-length hem
    • Form-hugging silhouette
    • Color block geometric print
    • Smooth and stretchy knit fabric, full knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5260

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Totally Iconic Bubble Mesh Bodycon Mini Dress

    Create a fabulous club look that is totally iconic with this bodycon mini dress! It features a sleeveless square neckline, bungee spaghetti straps, a mini-length hem, a bodycon silhouette that will flaunt your figure, and is composed of a textured bubble mesh fabric. The lined mesh fabric offers plenty of stretch. Style with platform heels.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Mini-length hem
    • Bodycon fit
    • Textured bubble mesh fabric, sewn-in knit lining
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5202

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Love Tropical Print Maxi Dress

    Fall in love with the island you're vacationing on in this breezy tropical maxi dress perfect for sunset cocktails and dinners! It features a sleeveless V-neckline, adjustable spaghetti straps, a stretchy smocked bust, and a flowy maxi-length silhouette with a flirty front slit. Complete the look in wedge sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Stretchy smocked bust
    • Flowy maxi-length hem
    • Front slit
    • Tropical palm leaf print, airy woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5111

    Category Name: Casual Dresses

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Daydreamer Tie-Dye Ruffled Chiffon Mini Dress

    Your daydreams will come true in this stunning tie-dye chiffon mini dress. It features a sleeveless V-neckline with a ruffled overlay, adjustable spaghetti straps, an elasticized high waist seam with a cute tie-front belt to highlight your waist, a ruffled and tiered short silhouette, and a flowy A-line fit. The sheer airy chiffon fabric features a pretty watercolor-like tie-dye pattern and includes a woven lining. Pair with clear heels for weekend brunches or day dates!

    Fit & Features

    • Sleeveless V-neckline, ruffled overlay
    • Adjustable spaghetti straps
    • Elasticized high waist seam, tie-front belt
    • Ruffled and tiered short silhouette, A-line fit
    • Watercolor-like tie-dye pattern
    • Sheer chiffon fabric, full woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5329

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Walk The Line Crepe Geo Mini Dress

    Walk the line into this artsy geometric print crepe dress to give your closet must needed prints! It features a sleeveless V-neckline, sleek bungee spaghetti straps, a bodycon silhouette, and a flirty slit along the mini-length hem. Complete the look in heeled sandals for a casual brunch downtown!

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Bodycon silhouette
    • Front slit, mini-length hem
    • Geometric print
    • Stretchy crepe fabric
    • Runs true to size

    Style Number/Barcode: 05102-4849

    Category Name: Casual Dresses

    Price: $6.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Of-The-Moment Chic Swirl Print Midi Dress

    This of-the-moment chic swirl print midi dress is perf for happy hour! It features a sleeveless V-neckline, bungee spaghetti straps, a hip-hugging fit that flows out to a midi-length A-line silhouette, and a sultry front slit. The smooth jersey knit fabric showcases an alluring all-over swirl print pattern. Style with a faux leather blazer and strappy stilettos.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Hip-hugging fit, midi-length A-line silhouette
    • Thigh-high front slit
    • Swirl print pattern
    • Jersey knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4817

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Staple Ribbed Knit Skater Dress

    A chic staple skater dress featuring a flirty off-the-shoulder folded neckline and a short-length perfect for styling with boots or heels.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch
    • Off-the-shoulder neckline, fold-over accent
    • Long fitted sleeves
    • Short-length hem
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2291

    Category Name: Casual Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK, RUST, WINE, DARK, DENIM

    Available Size: S, M, XS, L

    Product Badge:
    • Back In Stock
  • Sunshine Beauty Floral Ruffled Short Dress

    This adorable floral ruffled short dress was made for sunny summer days! It features a sleeveless square neckline, adjustable spaghetti straps that lead to a cross-back design, a flowy relaxed A-line silhouette, and a drop waist seam with a ruffled short-length hem. The dress showcases a dainty floral embroidered pattern on the lightweight cotton fabric. Style with espadrille sandals for a day party!

    Fit & Features

    • Sleeveless square neckline, elasticized back hem
    • Adjustable spaghetti straps, cross-back design
    • Flowy A-line silhouette
    • Drop waist seam, ruffled short-length hem
    • Dainty floral embroidered pattern
    • Cotton fabric, full woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5322

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Summer Days Ruffled Cotton Skater Dress

    Capture the perfect casual-chic summer vibe with this lightweight ruffled cotton skater dress. It features a pleated V-neckline with a ruffled collar and a tie-front design, short puff sleeves with ruffled hems, sheer crochet inserts down the bodice and along the skirt, a stretchy smocked high waist, a short ruffled and tiered skater skirt with a layered design, and a flattering fit and flare silhouette. The cotton fabric includes a woven skirt lining. Style with strappy mules.

    Fit & Features

    • Pleated V-neckline, ruffled collar, tie-front design, tassel accents
    • Short puff sleeves, elastic cinched ruffled hems
    • Sheer crochet inserts down the bodice and along the skirt
    • Stretchy smocked high waist
    • Short ruffled and tiered skater skirt, layered design, fit and flare silhouette
    • Cotton fabric, woven skirt lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5324

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless And Breezy Short T-Shirt Dress

    Style up this effortless and breezy short T-shirt dress for your casual weekend plans! It features a crew neckline, short sleeves, dual side pockets, a loose T-shirt fit, a short-length hem, and an A-line silhouette. The cotton-blend fabric has a moderate stretch. Pair with hoop earrings and strappy sandals.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Dual side pockets
    • Loose T-shirt fit
    • Short-length hem, A-line silhouette
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5044

    Category Name: Casual Dresses

    Price: $8.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Style Icon Cutout Bodycon Midi Dress

    This sultry-chic midi dress will level up your look and make you a casual style icon! It features a sleeveless asymmetric one-shoulder neckline with a tank strap, a bold asymmetric waist cutout for a hint of skin, a midi-length hem, and a bodycon silhouette that will hug your curves. The ribbed knit fabric offers plenty of stretch. Pair with clear mules.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Tank strap
    • Asymmetric waist cutout
    • Midi-length hem
    • Bodycon silhouette
    • Stretchy ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5201

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Set The Curve Square Neck Maxi Dress

    Set the tone for flaunting your curves in this essential maxi dress perfect for day or night styling! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, and a sexy center-back high slit on double-lined knit fabric with a buttery soft feel. Complete the look with a crop denim jacket and sandals for a sunset dinner date!

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Bodycon silhouette
    • Center back high slit
    • Maxi-length hem
    • Double-lined knit fabric
    • Buttery soft and stretchy
    • Runs true to size

    Style Number/Barcode: 05102-5200

    Category Name: Casual Dresses

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Blissfully Beautiful Ditsy Floral Mini Dress

    Embrace the summer season looking blissfully beautiful in this adorable ditsy floral mini dress! It features a sleeveless round neckline with an adjustable tie-front design, a ruched bust with a small front cutout, spaghetti straps, a mini-length hem with a short front slit, and a slim-fit A-line silhouette. The ditsy floral printed knit fabric has a lightweight feel and offers plenty of stretch. Style with espadrille sandals for a weekend outing.

    Fit & Features

    • Sleeveless round neckline, adjustable tie-front design
    • Ruched bust, small front cutout, spaghetti straps
    • Mini-length hem, short front slit
    • Slim-fit A-line silhouette
    • Ditsy floral print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5313

    Category Name: Casual Dresses

    Price: $5.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Breeze Ruffled Cotton Skater Dress

    Capture an iconic summer look perfect for day parties in this breezy ruffled cotton skater dress! It features a crew neckline, adorable short puff sleeves, a small back keyhole cutout, a stretchy smocked high waist, a short ruffled and tiered skater skirt with pleated detailing, and a flattering fit and flare silhouette. The lightweight cotton fabric includes a woven skirt lining. Style with strappy sandals.

    Fit & Features

    • Crew neckline, short puff sleeves, elastic cinched hems
    • Small back keyhole cutout, button closure
    • Stretchy smocked high waist
    • Short ruffled and tiered skater skirt, pleating
    • Fit and flare silhouette
    • Cotton fabric, woven skirt lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5323

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Sway Ruffled Tiered Short Dress

    Keep your daytime look sweet in this lightweight woven short dress perfect for stylishly swaying to your summer playlist! It features a V-neck and back, a wrap-front design with a dainty crochet trim, tie-back spaghetti straps, short sleeves with ruffled trims, a sheer crochet trim waist, a short-length hem with an adorable ruffled and tiered silhouette, and a flowy A-line fit. The gauze fabric includes a partial woven lining. Pair with strappy sandals.

    Fit & Features

    • V-neck and back, wrap-front design, tie-back straps, metal beaded accents
    • Short sleeves, ruffled trims
    • Sheer crochet waist and trim
    • Hidden back zipper, hook and eye closure
    • Short-length hem, ruffled and tiered silhouette, A-line fit
    • Gauze fabric, partial woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5321

    Category Name: Casual Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Staple Tie-Front Midi Dress

    This trendy tie-front midi dress is a stylish summer staple! It features a sleeveless V-neckline, a tie-front design at the bust with a small keyhole cutout, spaghetti straps, a midi-length hem, and a bodycon silhouette that will hug your natural curves. The ribbed knit fabric offers plenty of stretch. Pair with espadrille sandals for happy hour.

    Fit & Features

    • Sleeveless V-neckline
    • Tie-front design, small keyhole cutout
    • Spaghetti straps
    • Midi-length hem
    • Bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5250

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Beauty Abstract Cutout Maxi Dress

    Embrace your vacation looking like beauty in this abstract print maxi dress destined for sunset dinners and cocktails by the pool! It features a sleeveless square neck, sleek bungee spaghetti straps, a sassy cutout waist with a hoop insert, a slim form-hugging silhouette, and a high front slit on lined smooth knit and stretchy fabric. Complete the look in cute sandals and earrings.

    Fit & Features

    • Sleeveless square neck
    • Bungee spaghetti straps
    • Cutout waist, hoop insert
    • Slim form-hugging silhouette
    • High front slit, maxi-length hem
    • Abstract print, smooth knit fabric, short knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5101

    Category Name: Casual Dresses

    Price: $5.97 $43.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Basic Crew Neck Tank Mini Dress

    A sweet basic mini dress for all your styling needs this season! It features a sleeveless crew neckline, a bodycon silhouette, and a mini-length fitted hem on smooth and stretchy knit fabric. Complete the look with trendy sunglasses and sandals for a trip to the farmer's market!

    Fit & Features

    • Sleeveless crew neckline
    • Bodycon silhouette
    • Mini-length fitted hem
    • Smooth and stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5079

    Category Name: Casual Dresses

    Price: $5.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elite Summer Style Marble Print Maxi Dress

    Show off an elite summer style in this eye-catching marble print maxi dress! It features a sleeveless scoop neckline, spaghetti straps, an alluring lower back cutout, a maxi-length hem with a thigh-high side slit to showcase some leg, and a bodycon silhouette that will hug your curves. The stretchy knit fabric features a trendy multi-colored marble print pattern. Complete the look with strappy heels for sunset happy hour. 

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps, lower back cutout
    • Maxi-length hem, high side slit
    • Bodycon silhouette
    • Multi-colored marble print
    • Slinky knit fabric, short knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5261

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sergeant Of Style Cargo Pocket Mini Dress

    Elevate your status to sergeant of style in this edgy mini dress perfect for casual plans! Featuring a sleeveless square neckline, adjustable spaghetti straps, a lightly padded bust, an underbust seam, cargo-style flap side pockets, and a short bodycon silhouette. Style with strappy clear strap heels.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Lightly padded bust, underbust seam
    • Back zipper and hook-eye closure
    • Bodycon silhouette, mini-length hem
    • Twill woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5104

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Perfection Striped Tank Mini Dress

    This adorable striped tank mini dress is the perfect casual style for a subtly elevated look! It features a sleeveless crew neckline, tank shoulder straps, a mini-length subtle curved hem, and a bodycon silhouette that offers a form-hugging fit. The striped ribbed knit fabric has plenty of stretch. Pair with strappy sandals.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Mini-length subtle curved hem
    • Bodycon silhouette
    • Striped print
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5102

    Category Name: Casual Dresses

    Price: $19.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dangerously Divine Long Sleeve Bodycon Dress

    Bring the heat—this long sleeve bodycon dress is bold, fitted, and ready to steal the night. The sleek ruching and daring neckline make it perfect for dressy events and date nights.

    Fit & Features

    • Smooth knit stretch fabric
    • V-neckline
    • Fitted long sleeves
    • Ruched detail
    • Bodycon fit, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000308

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S