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!

  • Effortless Vibes Babydoll Dress

    Effortless and chic, this babydoll dress is perf for casual days where you still want to dress up. It features a V-neckline, three-quarter length sleeves, and a short, flowy silhouette with a tiered design. Style this dress with cute mules.

    Fit & Features

    • V-neckline
    • Three-quarter length sleeves, cinched hems
    • Mini-length, flowy babydoll fit
    • Tiered design
    • Woven crepe fabric, textured pattern
    • Runs true to size

    Style Number/Barcode: 05102-4294

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Wild Sleeveless Slip Dress

    Showcase a chic wild style in this sleeveless slip dress! It features a lined V-neckline, spaghetti straps, a cute tie-back detail, and a flirty short silhouette with a subtle flared-out hem. The lightweight woven fabric has a trendy all-over animal print. Complete the look with strappy mules.

    Fit & Features

    • Sleeveless lined V-neckline
    • Spaghetti straps
    • Tie-back detail
    • Mini-length silhouette
    • Woven fabric, no stretch, animal print
    • Runs true to size

    Style Number/Barcode: 05102-4245

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendsetting Stunner Slinky Knit Midi Dress

    Show off your trendy stunner status in this of-the-moment slinky knit midi dress. It features a collared neckline, long sleeves, a complete button-down front, ruching at the waist, and a mid-length, curve-hugging silhouette. Complete the look with sleek hoop earrings.

    Fit & Features

    • Collared neckline
    • Long fitted sleeves
    • Complete button-down front
    • Ruching at the waist
    • Mid-length, form-hugging fit
    • Slinky knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4222

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cool Girl Vibes Tie-Dye Mini Dress

    Bring those effortless cool girl vibes in this fab tie-dye mini dress. It features a square neckline, short sleeves, and a short, curve-hugging silhouette. Style this knit dress with sneakers to keep it casual or clear heels for an elevated glam look.

    Fit & Features

    • Square neckline
    • Short sleeves
    • Mini-length, form-hugging fit
    • Tie-dye print
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4249

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Perfectly Plaid Knit Mini Dress

    You'll look perfectly stylish in this plaid mini dress that you can take from day to night! It features a sleeveless square neckline, spaghetti straps, and a short, form-fitting silhouette that will hug your curves. Style with sneakers for a casual daytime look, and layer on a faux leather jacket and style with ankle booties for night.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Mini-length, form-hugging fit
    • Lined knit fabric, moderate stretch
    • Plaid print
    • Runs true to size

    Style Number/Barcode: 05102-1687

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Baddie Chic Tie Front Mini Dress

    Rock on like the baddie you are with a tie-front mini dress that is part edgy, part chic! The dress features a plunging V-neckline, short sleeves, a sexy tie-front, cutout at the midriff, and a mini-length silhouette. The dress features an image of eagle wings, roses, and a script that reads: "American Motorcycles. The dress is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with chunky sneakers.

    Fit & Features 

    • Plunging V-neckline, short sleeves
    • Tie-front, cutout at the midriff 
    • Mini length silhouette
    • Image of eagle wings, roses
    • Script: "American Motorcycles"
    • Cotton knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 06002-0943

    Category Name: Casual Dresses

    Price: $10.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Born To Ride Lace Up Mini Dress

    Let this mini dress let everyone know that you were born to be wild! The dress features a crew neckline, a plunging keyhole at the bodice, a chain-link lace-up front, short sleeves, and a mini-length silhouette. The dress features a graphic that reads: "Riders, Motorcycle" with an image of eagle wings. The dress is composed of a cotton knit fabric. Complete look with sneakers.

    Fit & Features

    • Crew neckline
    • Keyhole at bodice
    • Chain link lace-up front
    • Short sleeves
    • Mini length silhouette
    • Graphic: "Riders, Motorcycle", image of eagle wings
    • Form hugging fit, moderate stretch

    Style Number/Barcode: 06002-0944

    Category Name: Casual Dresses

    Price: $10.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Start A Spark Ruched Mini Dress

    Start a spark with a mini dress that showcases your luxe style! The dress features a sleeveless square neckline, bungee spaghetti straps, a ruched body, and a mini-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with lucite heels and gold jewelry. 

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruched body
    • Mini length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4191

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Set It Off Ruffled Bodycon Dress

    Set off your night with a head-turning bodycon that raises the heat! The dress features a sleeveless wrap V-neckline, spaghetti straps, a ruched body, and a mini-length silhouette with a ruffled hem. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with rhinestone heels and a clutch. 

    Fit & Features

    • Sleeveless wrap V-neckline
    • Spaghetti straps
    • Ruched body
    • Mini length silhouette, ruffled hem 
    • Smooth knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4464

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Uniquely Darling Strapless Pleat Skater Denim Mini Dress

    Darling and adorable, this denim mini dress brings flirtiness to any scene with a skater silhouette and pleated mini-length hem perfect for pairing with cowboy boots!

    Fit & Features

    • Denim fabric
    • Strapless sweetheart neckline
    • Back zipper closure
    • Skater silhouette
    • Pleated mini-length hem
    • Runs small

    Style Number/Barcode: 05102-000099

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: S, M, L, XS

  • Making My Mark Ribbed Mini Dress

    Make your style mark with a mini dress that is part casual, part glam! The dress features a sleeveless crew neckline, tank shoulder straps, and an open back with criss-cross straps. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Open back, criss-cross straps
    • Lined ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4270

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island It Girl One-Shoulder Cutout Maxi Dress

    Giving tropical baddie with a side of luxury, this one-shoulder maxi brings the heat with a bold leaf print, cutout waist, and gold hardware that says, "I didn’t come to play." It's made for vacation slays, beach weddings, or poolside parties!

    Fit & Features

    • Tropical leaf print, smooth stretchy knit fabric, short lining
    • One-shoulder neckline with hardware trim
    • Side cutout bodice
    • High side slit
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000082

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Baroque Bohemian Glam Mini Dress

    Stand out like the glam trendsetter you are with a mini dress that is a true one of a kind! The dress features a sleeveless cowl neckline, spaghetti straps, a bohemian paisley print with baroque-inspired accents, 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 mules

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Bohemian paisley print
    • Baroque print
    • Mini length silhouette
    • Smooth knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4148

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Trendsetter Ruched Knit Mini Dress

    Showcase casual trendsetting looks in this stylish knit mini dress. It features a square neckline, short sleeves, ruched side detailing with drawstrings, and a short, form-hugging silhouette. Pair this dress with a denim jacket and cute mules for an effortless everyday outfit.

    Fit & Features

    • Square neckline
    • Short sleeves
    • Ruched side detailing
    • Adjustable drawstrings
    • Mini-length, form-hugging fit
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4333

    Category Name: Casual Dresses

    Price: $4.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruched Ribbed Knit Cutout Mini Dress

    Keep it casually chic with a mini dress that stuns with stylish details! The dress features a crew neckline, long sleeves, a cutout at the midriff with criss-cross straps, ruched drawstrings, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and statement earrings. 

    Fit & Features 

    • Crew neckline
    • Long sleeves
    • Cutout at the midriff
    • Criss-cross straps, ruched drawstrings
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4242

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off The Shoulder Ribbed Knit Mini Dress

    Button up in a chic mini dress that is perf to dress up or dress down in for your next outing! The dress features an off-the-shoulder neckline, short sleeves, a faux button-down front, and a mini-length silhouette. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and denim jacket

    Fit & Features

    • Off the shoulder neckline
    • Short sleeves
    • Faux button down front
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1911

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Endless Summer Halter Cutout Dress

    Embrace the summer vibes in this chic curve-hugging dress! It features a sleeveless halter neckline, an open back, a center knot detail with dual waist cutouts, and an ankle-length, form-fitting silhouette. Style this dress with sleek hoop earrings.

    Fit & Features

    • Sleeveless halter neckline
    • Open back
    • Center knot detail
    • Dual waist cutouts
    • Long, form-hugging fit
    • Ribbed sweater knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1216

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutie In Floral Puff Sleeve Mini Dress

    You'll look like such a cutie in this adorable floral mini dress! It features a subtle sweetheart neckline with a mini tie-front at the bust, short puff sleeves, and a mini-length, curve-hugging silhouette. Style this dress with your fave pair of sandals.

    Fit & Features

    • Sweetheart neckline
    • Mini tie-front at the bust
    • Short puff sleeves
    • Back zipper and hook and eye closure
    • Short, form-hugging fit
    • Floral print, knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4153

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Daring Diva Open Back Midi Dress

    Dare to go bold with a midi dress that wows! The dress features a sleeveless scoop neckline, adjustable spaghetti straps that cross at the back, and a midi-length silhouette. Complete look with stilettos and door knocker earrings

    Fit & Features

    • Sleeveless scoop neckline 
    • Adjustable spaghetti straps, cross at back
    • Open back 
    • Midi length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-1210

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Staple Ribbed Knit Mini Dress

    This comfy ribbed knit mini dress will be a new casual staple in your closet. It features a sleeveless scoop neckline, adjustable spaghetti straps, and a short, curve-hugging silhouette with a rounded hem. Style this dress with a denim jacket and sneakers for the perf everyday look.

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps
    • Mini-length, form-hugging fit
    • Rounded hem
    • Ribbed sweater knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-0968

    Category Name: Casual Dresses

    Price: $4.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Crew Ribbed Knit Mini Dress

    Show em' all that you roll with the chic crew in this fab mini dress! The dress features a crew neckline with a racer bust, a ruched body, and a mini side slit. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a denim jacket

    Fit & Features

    • Sleeveless crew neckline
    • Racer bust
    • Ruching
    • Mini side slit
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 05102-4240

    Category Name: Casual Dresses

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Chic Ditsy Floral Mini Dress

    Bring the charm with a floral mini dress that is perf for date night! The dress features a sleeveless sweetheart neckline with a lace trim, spaghetti straps, a ditsy floral print, 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 wedges.

    Fit & Features

    • Sleeveless sweetheart neckline, lace trim
    • Spaghetti straps
    • Ditsy floral print
    • Mini-length silhouette, lace trim at the hem
    • Smooth knit fabric, knit lining
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4196

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Stunner Cutout Midi Dress

    Stand out like the major stunner you are with a midi dress that brings the style! The dress features a plunging halter neck with a V-neck bust, a cutout at the midriff with sleek straps, and a midi-length silhouette with a high side slit. The dress is composed of a lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Halter neck, V-neck bust
    • Cutout at the midriff with straps
    • Midi length silhouette
    • High side slit
    • Lurex knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4157

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blooming Beauty Ditsy Floral Cutout Mini Dress

    Let your beauty bloom with a gorge mini dress that reveals your sweet side! The dress features a ditsy floral print, a sleeveless V-neckline, a ruched drawstring at the center, spaghetti straps, a cutout at the midriff, 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 mules and a denim jacket

    Fit & Features

    • Ditsy floral print
    • Sleeveless V-neckline
    • Ruched drawstring at the bodice
    • Spaghetti straps
    • Cutout at midriff
    • Mini length silhouette
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4126

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free