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!

  • Casual Stroll Rib Knit Midi Dress

    Take a casual stroll looking cute in this rib knit midi dress essential for afternoon pick-me-ups with the girls! Featuring a sleeveless square neck, spaghetti straps, a form-hugging silhouette, and a sultry front slit along the hem. Complete the look with a layered choker necklace.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Form-hugging silhouette
    • Front slit
    • Midi-length hem
    • Rib knit fabric, bust lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5183

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute And Casual Moment High Slit Maxi Dress

    Have a cute and casual moment in this high slit maxi dress that will give you a streamlined bodycon silhouette. It features a sleeveless square neckline, bungee spaghetti straps, an asymmetric maxi-length hem creating a trendy thigh-high side slit, and a curve-hugging fit. The smooth knit fabric includes a full lining and offers plenty of stretch. Style with a crossbody bag and clear mules for dinner with the girls.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Asymmetric maxi-length hem
    • High side slit
    • Bodycon fit
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5105

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Mode Tropical V-Neck Midi Dress

    Enter vacay mode with the perfect tropical midi dress that'll have you looking fabulous! It features a sleeveless V-neckline, adjustable spaghetti straps, a form-hugging silhouette, and a sultry side slit cutout. Complete the look in chic mules for a dinner by the beach!

    Fit & Features

    • Sleeveless V-neckline 
    • Adjustable spaghetti straps
    • Form-hugging silhouette
    • Side slit cutout, slit
    • Midi-length hem
    • Tropical palm leaf print, stretchy knit fabric, bust lining
    • Runs true to size

    Style Number/Barcode: 05102-5056

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Miami Mood Tropical Print Cutout Maxi Dress

    This alluring tropical print maxi dress is an iconic pick for a summer vacay to Miami! It features a sleeveless halter neckline with cross-front straps, a sultry center bust cutout followed by a chic O-ring accent, dual waist cutouts on each side, a backless design with dual tie-back straps, a floor-length hem with dual thigh-high front slits, and a flowy A-line silhouette. The lightweight woven fabric showcases an all-over tropical palm leaf pattern. Style with hoop earrings and clear mules.

    Fit & Features

    • Sleeveless halter neckline, cross-front straps, tie-back design
    • Center bust cutout, O-ring accent, dual waist cutouts
    • Backless design, dual tie-back straps, elasticized back waistband
    • Floor-length hem, dual high front slits, A-line silhouette
    • Tropical palm leaf print
    • Woven fabric, lined bust, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5087

    Category Name: Casual Dresses

    Price: $5.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Noteworthy Flirt Ruffled Lace-Up Mini Dress

    Everyone will take note of your flirtiness in this mesh mini dress perfect for daytime parties! It features a sleeveless square neck, spaghetti straps that lace up along the open back, a bodycon silhouette, and all-over ruffled trim detail. Complete the look with statement earrings.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Lace-up, open back
    • Bodycon silhouette
    • Mini-length hem
    • All-over ruffled trim, mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5168

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Refresh One-Shoulder Bodycon Mini Dress

    This chic bodycon mini dress is the summer style refresh you need! It features an asymmetric one-shoulder neckline with an O-ring accent, a thin braided shoulder strap, a mini-length hem, and a curve-hugging silhouette. The double-lined brushed knit fabric offers plenty of stretch. Complete the look with strappy sandals.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • O-ring accent, thin braided shoulder strap
    • Mini-length hem
    • Bodycon fit
    • Double-lined brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5151

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Babe Tropical Print Maxi Dress

    Create an iconic vacay babe look with this alluring tropical print maxi dress! It features a sleeveless square neckline, spaghetti straps, a flattering high waist seam, ruching down one side leading to a thigh-high slit, and a long-length hem with a curve-hugging silhouette. The lightweight knit fabric features an all-over tropical palm leaf print. Complete the 'fit with strappy sandals and sleek shades.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • High waist seam, ruched side seam, thigh-high slit
    • Long-length hem, curve-hugging fit
    • Tropical palm leaf print
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5178

    Category Name: Casual Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual-Chic Style Muse High Slit Maxi Dress

    Show off your elevated casual-chic style in this high slit maxi dress. Featuring a sleeveless crew neckline with tank shoulder straps, trendy side cutouts at the waist, a maxi-length hem, and a thigh-high side slit, this dress will get you major compliments. The ribbed knit fabric offers plenty of stretch. Complete the look with sleek hoops and strappy heels.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Dual side cutouts at the waist
    • Maxi-length hem
    • High side slit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4866

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunkissed Beauty Tropical Print Cutout Maxi Dress

    You'll be a stunning sunkissed beauty in this tropical print maxi dress that will give off alluring energy. It features a sleeveless asymmetric one-shoulder neckline with a single bungee spaghetti strap, a bold asymmetric side cutout at the waist with a chic O-ring accent, a hip-hugging fit, a sultry thigh-high side slit, and a floor-length hem. The smooth and stretchy knit fabric features an all-over tropical palm leaf print. Style with strappy sandals.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Single bungee spaghetti strap
    • Asymmetric side cutout at the waist, O-ring accent
    • Hip-hugging fit, high side slit, floor-length hem
    • Tropical palm leaf print
    • Knit fabric, mini-length lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5091

    Category Name: Casual Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Instant Fave Disty Floral Short Sleeve Midi Dress

    This adorable disty floral midi dress will be an instant fave of yours for the summer season. It features a crew neckline, short fitted sleeves, a small top keyhole cutout at the back with a button closure, a larger lower back cutout, a high waist seam, a midi-length hem with a high front slit, and a form-hugging silhouette. The floral printed brushed knit fabric offers plenty of stretch. Style with espadrille sandals.

    Fit & Features

    • Crew neckline, short sleeves
    • Small back keyhole cutout, button closure
    • Larger lower back cutout, high waist seam
    • Midi-length hem, front slit, form-hugging fit
    • Ditsy floral print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5184

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Passport To Paradise Tropical Print Ruched Midi Dress

    Whether you're headed on a weekend getaway or a plane ride to paradise, pack this tropical print midi dress for a gorgeous glow! It features a sleeveless cowl neckline, spaghetti straps, ruching down one side seam, an asymmetric midi-length hem creating a thigh-high side slit, and a curve-hugging silhouette. The smooth and stretchy knit fabric features an all-over tropical palm leaf print. Style with espadrille sandals.

    Fit & Features

    • Sleeveless cowl neckline, spaghetti straps
    • Ruched side seam
    • Asymmetric midi-length hem, high side slit
    • Bodycon fit
    • Tropical palm leaf print
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5136

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Fall Vibe Ditsy Floral Corset Midi Dress

    Channel the chic fall vibe in this ditsy floral woven midi dress featuring a sleeveless sweetheart neckline with a ruched bust and tie-front detail, thin tank shoulder straps, and a corset-style bodice. The high waist leads to a flowy A-line silhouette accented with a high-cut front slit.

    Fit & Features

    • Ditsy floral-printed woven fabric
    • Sweetheart neckline, ruched bust, tie-front detail, underwire bust
    • Thin tank shoulder straps
    • Corset-style bodice with piping, high waist seam
    • Hidden side zipper and hook-eye closure
    • High front slit
    • Midi-length A-line fit
    • Runs true to size

    Style Number/Barcode: 05101-3706

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M

    Product Badge:
    • Best Seller
  • Flirtatious Charm Cutout Midi Dress

    Say hello to this adorable cutout midi dress that will bring those cute and fun vibes! This midi dress features an off-the-shoulder sweetheart neckline and short fitted sleeves. The center knot detail at the bust with a tie-front adds a charming touch, while the dual waist cutouts add a hint of playfulness. The midi-length hem with a high side slit showcases your legs for a sassy look. With its form-hugging silhouette and ribbed knit fabric offering plenty of stretch, this dress ensures both comfort and style. Complete your outfit with a pair of sandals to bring that flirtatious charm!

    Fit & Features

    • Off-the-shoulder sweetheart neckline
    • Center knot detail at the bust, tie-front design
    • Dual waist cutouts
    • Midi-length hem, high side slit
    • Form-hugging fit
    • Ribbed knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4992

    Category Name: Casual Dresses

    Price: $6.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Happy Hour Tropical Print Maxi Dress

    This tropical print maxi dress was made for sippin' margaritas and enjoying the ocean breeze! It features a sleeveless V-neckline with the cutest tie-front design, adjustable spaghetti straps, a stretchy smocked back panel, a high waist seam, and a flowy floor-length hem with a thigh-high front slit. The lightweight gauze fabric features an all-over palm leaf print to capture those vacay vibes. Style with slip-on sandals.

    Fit & Features

    • Sleeveless V-neckline, tie-front
    • Adjustable spaghetti straps, stretchy smocked back
    • High waist seam
    • Flowy floor-length hem, high front slit
    • Tropical palm leaf print
    • Gauze fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5117

    Category Name: Casual Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pick Me Floral Lace-Up Maxi Dress

    This floral maxi dress will be the first pick in your closet! It features a sleeveless V-neckline with a knotted bust, spaghetti straps that creates the open lace-up back design, and a flowy slim silhouette. Complete the look in cute new sandals for a baby shower or casual lunch out!

    Fit & Features

    • Sleeveless V-neckline, knotted bust
    • Spaghetti straps
    • Lace-up open back
    • Flowy slim silhouette
    • Maxi-length hem
    • Floral print, breezy woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4947

    Category Name: Casual Dresses

    Price: $5.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fresh In Paisley Floral A-Line Dress

    Serve your closet a fresh style by adding this paisley floral short dress to it! Featuring a sleeveless V-neckline, sleek bungee spaghetti straps, a flattering A-line silhouette, and a flirty slit hem. Complete the look in trendy sandals for an afternoon in the city!

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • A-line silhouette
    • Short-length hem, slit accent
    • Paisley floral print
    • Smooth stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4943

    Category Name: Casual Dresses

    Price: $5.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casually Stylish Ribbed Knit Midi Dress

    This simple yet chic ribbed knit midi dress is the casually stylish staple you need. It features a sleeveless scoop neckline, thin tank shoulder straps, a midi-length hem, and a curve-hugging silhouette. The lined knit fabric offers plenty of stretch. Complete the look with a denim jacket and clear mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Thin tank shoulder straps
    • Midi-length hem
    • Form-hugging fit
    • Lined ribbed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5077

    Category Name: Casual Dresses

    Price: $5.97 $23.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Marvelous Style Marble Print Maxi Dress

    Showcase a marvelous style in this trendy marble print maxi dress! It features a sleeveless square neckline, spaghetti straps, an asymmetric side cutout at the waist to add a sultry vibe, ruching down one side seam with an adjustable drawstring, an asymmetric maxi-length hem creating a thigh-high side slit, and a curve-hugging silhouette. The all-over eye-catching marble print pattern on the smooth and stretchy knit fabric will draw all the attention to you! Complete your summer party look with clear heels.

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Asymmetric side cutout at the waist
    • Ruching down one side seam, adjustable drawstring
    • Asymmetric maxi-length hem, high side slit, curve-hugging fit
    • Marble print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5119

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Love Letters Floral Chiffon Skater Dress

    Don't be surprised if your mailbox is full of love letters after wearing this floral chiffon skater dress to the party! It features a sleeveless V-neckline, adjustable spaghetti straps, and a flattering fit and flare short silhouette. Complete the look in faux leather block heels for a graduation or dressy birthday party!

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Short-length hem
    • Floral embroidered chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2035

    Category Name: Casual Dresses

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunset Moments A-Line Mini Dress

    This gorgeous mini dress was made for sunset dates! It features a sleeveless cowl neckline, spaghetti straps, an open back with a cross-back strap design and a low back draped accent, and a mini-length hem with an A-line silhouette. Style this short dress with a dainty necklace and espadrille wedges.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Open back, cross-back strap design
    • Low back draped accent
    • Mini-length hem, A-line silhouette
    • Lightweight woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5325

    Category Name: Casual Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Match Plaid Lace-Up Mini Dress

    Find your perfect match in this casual-chic plaid mini dress! Featuring a sleeveless square neckline, spaghetti straps, an open back with a cross-back lace-up strappy design, a mini-length hem, a form-hugging fit, and a classic plaid windowpane print, this dress is a stylish must-have. Pair with hoop earrings and clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Open back, cross-back lace-up straps, tie closure
    • Mini-length hem, form-hugging fit
    • Plaid windowpane print
    • Lined soft knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5159

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Sultry Vibes Cutout Maxi Dress

    Bring the casual sultry vibes to your weekend plans with this curve-hugging maxi dress. It features a sleeveless sweetheart neckline with a twist-front design, spaghetti straps, a bold waist cutout at the front, a maxi-length hem with a chic back slit accent, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch. Style with clear mules for drinks with the girls.

    Fit & Features

    • Sleeveless sweetheart neckline, twist-front design
    • Spaghetti straps
    • Waist cutout
    • Maxi-length hem, back slit
    • Bodycon fit
    • Ribbed knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5186

    Category Name: Casual Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Revamp Zip-Front Mini Dress

    This trendy zip-front mini dress will revamp your basic looks! It features a sleeveless mock neckline with a front zipper to style into a V-neckline, tank shoulder straps, a mini-length hem, and a bodycon silhouette that will hug your curves. The soft brushed knit fabric offers plenty of stretch. Style this mini dress with sneakers to keep it casual or mules for an elevated vibe!

    Fit & Features

    • Sleeveless mock neckline
    • Zip-front design
    • Tank shoulder straps
    • Mini-length hem
    • Bodycon fit
    • Brushed knit fabric, full lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5092

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Striking Style Marble Print Midi Dress

    Showcase a striking style and a stunning look in this curve-hugging marble print midi dress! It features a sleeveless cowl neckline, spaghetti straps, an asymmetric midi-length hem creating a sultry thigh-high side slit, a bodycon silhouette, and an all-over alluring marble print pattern. The smooth knit fabric offers plenty of stretch. Complete the look with clear mules.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Asymmetric midi-length hem, high side slit
    • Bodycon fit
    • Marble print
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5001

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale