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!

  • Trendy Basic Bodycon Mini Dress

    Simple and sleek, this bodycon mini dress is a trendy basic! It features a sleeveless scoop neckline, tank shoulder straps, and a short, curve-hugging silhouette. Style with strappy mules and a faux leather clutch.

    Fit & Features

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

    Style Number/Barcode: 05102-4551

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Have We Met Lace-Up Mini Dress

    Say hello to your new fave mini dress for day-to-night soirees! Featuring a sleeveless, square neck, spaghetti straps, high waist seam, side ruched seams, and an open-back with lace-up closure. Composed of brushed soft and stretchy knit fabric that hugs your curves like an hourglass. Finish the look in a sleek cropped jacket.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • High waist seam
    • Side ruched seams
    • Open-back, lace-up closure
    • Bodycon silhouette, mini-length hem
    • Brushed soft and stretchy knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4593

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mesmerizing Swirl Mesh Midi Dress

    Captivate the room with your unique style! Unveil this swirl print midi dress featuring a sleeveless V-neckline with sleek spaghetti straps, a bodycon silhouette, and an asymmetrical hem with a side slit cutout. Complete the look in strappy heels for a birthday party.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Asymmetrical midi hem, side slit cutout
    • Swirl print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4823

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Links Chain Strap Midi Dress

    This stylish midi dress entered the chat! It features a sleeveless V-neckline with trendy chain link shoulder straps, a bodycon silhouette, and a front slit on stretchy, double-lined ribbed knit fabric. Complete the look in clear strap heels.

    Fit & Features

    • Sleeveless V-neckline
    • Chain link shoulder straps
    • Bodycon silhouette
    • Front slit
    • Midi-length hem
    • Double-lined, rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4773

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All Eyes On You Strapless Maxi Dress

    Effortlessly sleek, this strapless maxi is giving luxe with zero effort. The body-hugging fit and flowy hem make it your go-to for dinner dates or rooftop hotel bars.

    Fit & Features

    • Rib knit stretchy fabric
    • Strapless neckline
    • Bodycon fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000088

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: M, L

  • Keep It Cute Cable Knit Mini Dress

    Keep it cute and light in this cable knit mini dress perfect for a casual day date! It features a sleeveless scoop neckline, spaghetti straps, a lower back cutout, underbust trim, and a bodycon silhouette. The cable knit fabric offers a moderate stretch. Complete the look in a dainty necklace and heels.

    Fit & Features

    • Sleeveless scoop neckline, spaghetti straps
    • Lower back cutout
    • Underbust trim
    • Bodycon silhouette
    • Mini-length hem
    • Cable knit design, knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1412

    Category Name: Casual Dresses

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Set The Tone Rib Sweater Dress

    Set the tone for the new season in this fresh two-tone sweater dress for all the autumn vibes! It features long sleeves, a mock neck, a bodycon silhouette, and a mini-length hem on stretchy ribbed knit fabric. Complete the look in dainty linear earrings.

    Fit & Features 

    • Long fitted sleeves
    • Mock neck
    • Bodycon silhouette
    • Two-tone pattern
    • Mini-length hem
    • Stretchy ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1432

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chain My Mind Side Slit Midi Dress

    This knit midi dress will change your mind about going out for the night! Catch all the attention in this sultry dress featuring a sleeveless square neck, chain link adjustable spaghetti straps, a bodycon silhouette, and a side slit. Complete the look with a bold clutch purse.

    Fit & Features

    • Sleeveless square neck
    • Chain link adjustable spaghetti straps
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Slinky knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4800

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take A Trip Sweater Halter Dress

    Taking a trip somewhere fab? You're gonna need this sweater halter dress perfect for looking chic on the go! It features a sleeveless bodice, cross straps with neck-tie closure, a bodycon silhouette, and a mini-length hem. Complete the look in linear earrings.

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Sleeveless halter neck
    • Cross straps, neck-tie closure
    • Bodycon silhouette
    • Mini-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1605

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Major Flirt Polka Dot Two Tone Mini Dress

    Showcase your flirty side with a mini dress that brings some seriously sultry appeal! The dress features a sleeveless sweetheart neckline with mesh trim, a plunging lace-up front, bungee spaghetti straps, ruching throughout, and a stylish swiss dot design. The dress is composed of a lined mesh fabric that reveals a two-tone effect. Complete date night outfit with heels and rhinestone duster earrings

    Fit & Features

    • Sleeveless sweetheart neckline, mesh trim 
    • Adhesive bra recommended, bungee spaghetti straps
    • Lace-up front 
    • Ruching
    • Swiss dot design 
    • Lined mesh fabric, two-tone color 
    • Form hugging fit, minimal stretch, runs true to size 

    Style Number/Barcode: 05102-4746

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Must-Have Ribbed Knit Mini Dress

    This ribbed knit mini dress is a basic must-have that needs to be in your wardrobe! It features a classic crew neckline, long fitted sleeves, and a short, form-hugging fit. The ribbed knit fabric offers a moderate stretch. Style with hoop earrings and knee-high boots.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Mini-length hem, form-fitting silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1407

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Minimalistic Sultry Midi Dress

    Chanel a sultry minimalistic wardrobe for fall in this staple crepe midi dress featuring a sleek sleeveless V-neckline, bungee spaghetti straps, a curve-hugging silhouette, and a front slit accent. Complete the look in low-heeled mules and a chic hat.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Curve-hugging silhouette
    • Front slit accent
    • Midi-length hem
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4782

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Work Of Art Marble Midi Dress

    Girl, your taste is a work of art! Step out in a midi dress that features a gorge marble print, a sleeveless scoop neckline with bungee spaghetti straps, and a midi length hem with ruching throughout. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and a quilted crossbody. 

    Fit & Features

    • Sleeveless scoop neckline
    • Bungee spaghetti straps
    • Marble print
    • Ruching
    • Midi-length hem
    • Lined mesh fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4732

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Muse Bodycon Mini Dress

    Show off an alluring style in this sultry-chic mini dress. It features a sleeveless mock neckline, an asymmetrical cutout above the bust, a keyhole cutout at the back, and a short, curve-hugging, bodycon silhouette. Complete the look with clear mules.

    Fit & Features

    • Sleeveless mock neckline
    • Asymmetrical cutout above the bust
    • Back button closure, keyhole cutout
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4556

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • In Knots Faux Wrap Mini Dress

    You'll get tied up in knots for this elevated basic mini! It features a sleeveless, scoop neck, spaghetti straps, a bodycon silhouette, and an asymmetrical faux-wrap skirt with a knot accent. Complete the look in trendy sandals for a coffee date.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Bodycon silhouette
    • Asymmetrical faux-wrap skirt
    • Knot accent
    • Mini-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4661

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • It-Girl Status Midi Dress

    Showcase major it-girl status in this chic lace-up midi dress. It features a sleeveless scoop neckline, tank shoulder straps, an open back with a cross-back lace-up strappy design, a midi-length hem, and a curve-hugging silhouette. Style with clear mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Open back, cross-back lace-up strappy design, tie closure
    • Midi-length hem
    • Form-fitting, bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4489

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • She's Got Bold Style Midi Dress

    Showcase your fearless bold style in this alluring and chic midi dress! It features a sleeveless one-shoulder neckline with an asymmetrical shoulder strap, a center O-ring cutout, dual waist cutouts, and a midi-length, curve-hugging silhouette with a thigh-high side slit. Complete the look with hoop earrings.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Asymmetrical single shoulder strap
    • Center O-ring cutout
    • Dual waist cutouts
    • Midi-length hem, bodycon silhouette, high side slit
    • Smooth knit fabric, partial knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4774

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Choice Bodycon Mini Dress

    This simple and stylish mini dress is an effortless choice for every day! It features a sleeveless one-shoulder neckline, a thin tank strap, and a short, curve-hugging, bodycon silhouette. The lightweight ribbed knit fabric offers plenty of stretch. Complete the look with heeled mules and a crossbody purse.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Single thin tank strap
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4550

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Add Some Spice Mini Dress

    This fiery bodycon mini dress will add some spice to your night-out look! It features a sleeveless square neckline, trendy chain-link shoulder straps, and a short, curve-hugging silhouette. The smooth knit fabric offers plenty of stretch. Style this sexy mini dress with platform heels.

    Fit & Features

    • Sleeveless square neckline
    • Chain-link shoulder straps
    • Mini-length hem, bodycon silhouette
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4755

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Petals and Plans Floral Lace-Up Maxi Dress

    For date nights, rooftop drinks, or weddings, this floral maxi dress is perfect for every event! The curve-hugging fit, flirty slit, and open lace-up back effortlessly flatters your figure and makes heads turn.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Square neckline
    • Spaghetti straps
    • Lace-up open back
    • High front slit
    • Curve-hugging fit, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4160

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: TAUPE

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

    Product Badge:
    • Sale
  • So Sleek Zebra Print Midi Dress

    Keep your look so sleek with a midi dress that levels up your casual outfits! It features a sleeveless V-neckline with a knot-front design, a small keyhole cutout under the bust, spaghetti straps, a midi-length, fitted, A-line sihouette, and a chic front slit. The smooth knit fabric features an all-over zebra print pattern. Stye with strappy mules.

    Fit & Features

    • Sleeveless V-neckline, knot-front design
    • Keyhole cutout under the bust
    • Spaghetti straps
    • Midi-length hem, fitted A-line silhouette
    • High front slit
    • Knit fabric, plenty of stretch
    • Zebra print
    • Runs true to size

    Style Number/Barcode: 05102-4703

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Refresh Striped Sweater Dress

    Refresh your closet in this striped sweater dress featuring a sleeveless, crew neckline, bodycon silhouette, and a mini-length hem on stretchy, rib-knit fabric. Complete your trendy look in statement heels.

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Sleeveless, crew neckline
    • Bodycon silhouette
    • Mini-length hem
    • Striped pattern
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 06005-1485

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Varisty Babe Graphic Tunic

    Level up your look to varsity status with this adorable tunic! It features a crew neckline, short fitted sleeves, a center football helmet graphic with a script that reads "New Season," dual waist cutouts with a center O-ring cutout accent, and a short, form-hugging fit. Style with a cute shacket and sneakers.

    Fit & Features

    • Crew neckline, short sleeves
    • Football helmet graphic
    • Script that reads "New Season"
    • Dual waist cutouts, center O-ring cutout
    • Short, form-fitting silhouette
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1350

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendsetting Icon Mesh Mini Dress

    Show off your trendsetter status in this of-the-moment mini dress. It features a sleeveless square neckline, bungee spaghetti straps that lead to cross-back design, ruching down the side seams, and a short, curve-hugging, bodycon silhouette. The lined mesh fabric features an all-over marble print pattern. Style with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps, cross-back design
    • Ruching down the side seams
    • Mini-length hem, fitted bodycon silhouette
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Marble print
    • Runs true to size

    Style Number/Barcode: 05102-4702

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale