Casual Dresses

Show filters
Sort:
Size
Color
Price
All filters
Sort
Loading...

Product Recommendations

STYLE SPOTLIGHT

Cute Sweater Dresses

Floral Print Dresses

Discover New Skater Dress Styles

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!

  • Only View One Shoulder Sweater Dress

    You're the best view around in this one-shoulder dress! It features a sleeveless bodice, a single strap, cutouts along the waist, a bodycon silhouette, and a side slit midi hem. Complete the look in hoop earrings and heels.

    Fit & Features

    • Sleeveless, one-shoulder, single strap
    • Cutouts along the waist
    • Side slit
    • Bodycon silhouette
    • Midi hem 
    • Sweater rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 06005-1489

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Loved Tube Bodycon Midi Dress

    Love at first wear...this tube midi dress elevates your everyday look with curve-accentuating side ruched seams, a bodycon fit, and a side slit for movement.

    Fit & Features

    • Stretchy rib knit fabric, knit lining
    • Strapless tube neckline
    • Side ruched seams
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000309

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L, XL

  • Destination Dinner V-Neck Midi Dress

    Look fabulous in a flash wearing this sleeveless midi dress for dinner and drinks! It features a showstopping bodycon silhouette, a V-neck, tank straps, and side ruched seams that hug every curve like a glove. Complete the look with chic stiletto heels.

    Fit & Features

    • Sleeveless, V-neck, tank straps
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem
    • Slinky knit fabric, knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4834

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Give A Twirl Linen Skater Dress

    Have your twirl-worthy moment in this linen skater dress perfect for casual parties! It features three-quarter-length puff sleeves with ruffled hems, a square neckline, a babydoll-style seam, a flirty open-back with an elasticized lattice strap, and a short-length hem with a flared-out skater silhouette. Complete the look in this skater dress with strappy stiletto heels.

    Fit & Features

    • Three-quarter-length puff sleeves, ruffled elastic cinched hems
    • Square neckline
    • Babydoll style seam
    • Open-back, elasticized lattice strap
    • Short skater silhouette
    • Plaid linen fabric, lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4717

    Category Name: Casual Dresses

    Price: $5.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keep It In Check Plaid Mini Dress

    Keep your stylish look in check with this plaid knit mini dress. It features a collared V-neckline, short sleeves, and a mini-length hem with a form-hugging, bodycon silhouette. Complete the 'fit with a dainty layered necklace and booties.

    Fit & Features

    • Collared V-neckline
    • Short fitted sleeves
    • Mini-length hem, bodycon silhouette
    • Plaid print
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4743

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Alluring Strapless Midi Dress

    This curve-hugging strapless midi dress is simply alluring! It features a strapless straight across neckline, bold cutouts down each side at the waist, a midi-length bodycon silhouette, and a chic high slit. Style with strappy stilettos.

    Fit & Features

    • Strapless straight across neckline, elasticized band
    • Side cutouts at the waist
    • Midi-length bodycon silhouette, form-hugging fit
    • High front slit
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4561

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Deets Knit Mini Dress

    You'll love the trendy deets of this ribbed knit mini dress! It features a crew neckline, short sleeves, a cute side cutout with ruching and an adjustable drawstring, and a short, form-hugging fit. Style with clear mules.

    Fit & Features

    • Crew neckline
    • Short fitted sleeves
    • Side cutout, ruching, adjustable drawstring
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4544

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Days Square Neck Mini Dress

    Give your jeans a break but keep the denim spirit! You'll find yourself reaching for this denim mini dress of those days spent with friends or exploring the city. It features a sleeveless, square neck, adjustable spaghetti straps, princess seam detailing on the bodycon silhouette, and a back zipper closure. Complete the look in simple earrings and sneakers.

    Fit & Features

    • Sleeveless, square neck, adjustable spaghetti straps
    • Back zipper closure
    • Princess seam detailing
    • Bodycon silhouette
    • Mini-length hem
    • Denim fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4571

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Trendsetter Mock Neck Mini Dress

    This adorable mini dress is a must-have for an everyday trendsetter like yourself. It features a sleeveless mock neckline, tank shoulder straps, and a short, form-hugging fit. The soft ribbed knit fabric offers plenty of stretch. Style with a cute shoulder bag and sneakers.

    Fit & Features

    • Sleeveless mock neckline
    • Tank shoulder straps
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4706

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep Knit Chill Color Block Mini Dress

    Keep your look chill for a coffee run or casual hang in this color block mini dress.  Featuring short sleeves, a collared neckline, a button-down front, and a bodycon silhouette on stretchy, rib-knit fabric. Complete the look in sleek hoop earrings.

    Fit & Features

    • Short sleeves
    • Collared neckline
    • Button-down front
    • Bodycon silhouette
    • Mini-length hem
    • Color block pattern
    • Rib-knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4466

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortless Summer Style Knit Midi Dress

    Showcase that effortless summer style this season with this ribbed knit midi dress. It features a sleeveless one-shoulder neckline with a single spaghetti strap, a ruched side cutout with an adjustable drawstring, and a midi-length, curve-hugging silhouette with a chic front slit. Complete the look with strappy sandals.

    Fit & Features

    • Sleeveless one-shoulder neckline, single spaghetti strap
    • Ruched side cutout, adjustable drawstring
    • Form-fitting silhouette, front slit
    • Midi-length hem
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4674

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rare Marble Pattern Midi Dress

    Why blend in when you can stand out! Strut into the party in this marble midi dress featuring a trendy, sleeveless, square neck, bungee spaghetti straps, and a bodycon silhouette. Complete the look in doorknocker earrings.

    Fit & Features

    • Sleeveless, square neck
    • Bungee spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Marble pattern
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4723

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Moments Twist Front Midi Dress

    This midi dress deserves a moment of admiration! It features a sleeveless, v-neck, tank straps, a sultry twisted bust with cutout detail, and a bodycon silhouette on stretchy rib-knit fabric. Complete the look in strappy heels for date night.

    Fit & Features

    • Sleeveless, v-neck, tank straps
    • Sultry twisted bust, cutout detail
    • Bodycon silhouette
    • Midi-length hem
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4610

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Alluring Cutout Midi Dress

    Keep your night out look alluring and chic in this sleek knit midi dress. It features a sleeveless asymmetrical one-shoulder neckline with dual spaghetti straps, a ruched side cutout to add a sultry vibe, and a midi-length, curve-hugging silhouette. Style with hoop earrings and your fave mules.

    Fit & Features

    • Sleeveless asymmetrical one-shoulder neckline
    • Dual spaghetti straps
    • Ruched side cutout
    • Midi-length, form-fitting, bodycon silhouette
    • Smooth knit fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4716

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Throwback Halter Short Dress

    Channel your inner pop princess with this short dress that brings all the glam! The dress features a retro swirl print, a halter neckline with bungee spaghetti straps, dual ruching through hip and hem, and a short length. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete your look with butterfly clips and chrome heels.

    Fit & Features

    • Retro swirl print 
    • Halter neckline, bungee spaghetti straps
    • Dual ruching
    • Short length hem 
    • Bodycon fit 
    • Lined mesh fabric 
    • Moderate stretch, runs true to size

    Style Number/Barcode: 05102-4742

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Muse Maxi Dress

    Show off your casual and trendy style in this sleek knit maxi dress. It features a sleeveless scoop neckline, spaghetti straps that lead to a cross-back design, a ruched wrap-front creating a high slit, and a curve-hugging fit with an asymmetrical hem. Complete the look with clear mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps, cross-back design
    • Ruched wrap-front, high slit
    • Maxi-length asymmetrical hem
    • Form-fitting silhouette
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1740

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Glimpse Floral Tube Midi Dress

    Romantic but make it bodycon. This floral mesh midi dress is the perfect mix of dreamy and daring—made for slow dances, date nights, and second glances. 

    Fit & Features:

    • Sheer floral mesh fabric, stretchy knit lining
    • Strapless tube neckline
    • Curve-hugging bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000206

    Category Name: Casual Dresses

    Price: $32.90

    Availability: In Stock

    Available Color: RUST

    Available Size: XS, S, M, L

  • Out Of Office Ruched Mini Dress

    Log off and get ready for a relaxing getaway in this ruched knit mini dress. It features a sleeveless cowl neckline, spaghetti straps, ruching down one side leading to an adjustable drawstring, and a mini-length, asymmetrical hem. The smooth knit fabric features an all-over tropical palm leaf print. Style with espadrille sandals and your favorite shades.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • High waist seam
    • Ruching down one side seam, adjustable drawstring
    • Short, curve-hugging, bodycon silhouette, asymmetrical hem
    • Stretchy knit fabric, tropical palm leaf print
    • Runs true to size

    Style Number/Barcode: 05102-4691

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Trendy Fave Mesh Mini Dress

    This adorable mini dress will be a new trendy fave! It features a sleeveless square neckline, bungee spaghetti straps, ruching down the side seams, and a short, curve-hugging, bodycon silhouette. The lined mesh fabric features an all-over tie-dye print pattern. Complete the look with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruching down the side seams
    • Mini-length, form-fitting, bodycon silhouette
    • Sheer mesh fabric, full knit lining, plenty of stretch
    • Tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-4679

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple Smooth Knit Mini Dress

    Style up this simple smooth knit mini dress for adorable date looks! It features a sleeveless square neckline, spaghetti straps, ruching down the side seams, a wrap-front design, and a short, curve-hugging, bodycon silhouette. Complete the outfit with strappy mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching down the side seams
    • Wrap-front
    • Mini-length hem, bodycon silhouette
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4594

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Let's Get Brunch Skater Dress

    You'll be ready for weekend brunch with your girls in this adorable swiss dot woven skater dress. It features a sleeveless V-neckline with a twist-front design, spaghetti straps, an open back with a cute tie-back detail, a high waist seam, and a short skater-style silhouette with a ruffled hem. Style with wedges and chic shades.

    Fit & Features

    • Sleeveless V-neckline, twist-front design
    • Spaghetti straps
    • Tie-back closure
    • High waist seam, skater silhouette
    • Ruffled short-length hem
    • Swiss dot woven fabric, lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1582

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Street Riders Graphic Short Dress

    You're not the average Jane...show your edgy side in this graphic short dress for a night of riding! It features a sleeveless, one-shoulder neckline with chain straps, a cutout accent, and a front graphic script that reads, " The Street Riders/Motorcycle Company", a bodycon silhouette, and a short-length hem. Complete the look in combat boots.

    Fit & Features

    • One-shoulder neckline, chain straps, cutout accent
    • A front graphic script that reads, " The Street Riders/Motorcycle Company"
    • Bodycon silhouette
    • Short-length hem
    • Cotton knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1314

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Catch Up Crepe Slip Midi Dress

    This sleek slip midi dress is perfect for bringing chic vibes when catching up with friends! It features a sleeveless V-neck bodice with bungee spaghetti straps, a form-fitting silhouette to show off your figure, and a sultry front slit on the mid-length hem. The crepe fabric offers a moderate stretch. Complete your look with classic block heels.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Form-fitting silhouette
    • Front slit, midi-length hem
    • Crepe knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5400

    Category Name: Casual Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flatter Me Cutout Maxi Dress

    You won't need anyone flattering you in this sexy maxi dress! Featuring a sleeveless, scoop neck, spaghetti straps, a cutout bodice, partial open-back, a form-fitting silhouette, and a sultry slit perfect for showcasing heels.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Cutout bodice
    • Partial open-back
    • Form-fitting silhouette
    • Front slit
    • Maxi-length hem
    • Slinky knit fabric, moderate stretch, fits true to size

    Style Number/Barcode: 05102-4603

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale