Casual Dresses

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STYLE SPOTLIGHT

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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!

  • Sultry Spice Cutout Maxi Dress

    Sultry and spicy! Make jaws drop in this sleeveless maxi dress featuring a one-shoulder neckline, waist cutout details and a form-fitting silhouette with a high-cut side slit for a show of skin. Composed of stretchy slinky knit fabric. Finish the look in lucite mules.

    Fit & Features

    • Sleeveless, one-shoulder neckline
    • Waist cutout details
    • Form-fitting silhouette
    • High-cut side slit
    • Maxi-length hem
    • Slinky knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4528

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take Me On A Getaway Midi Dress

    Pack this alluring and chic midi dress for your next weekend getaway. It features a sleeveless halter neckline with thin straps, front ruched detailing with an adjustable drawstring, a bold front waist cutout, and a midi-length, curve-hugging fit with a high side slit. Style this dress with sleek hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless halter neckline, thin straps that tie at the back of the neck
    • Front ruching, adjustable drawstring
    • Front waist cutout
    • Midi-length, form-fitting silhouette, side slit
    • Ribbed sweater knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1414

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Beachy Vibes Maxi Sweater Dress

    Bring the beachy vibes to your summer look with this effortlessly chic maxi sweater dress. It features a sleeveless scoop neckline, spaghetti straps, an open back with a cross-back strap design, and a fitted, maxi-length silhouette with a high side slit. The sweater knit fabric features pretty crochet detailing. Style this dress with sandals.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Open back, cross-back strap design
    • Fitted, maxi-length silhouette, side slit
    • Sweater knit fabric, crochet detailing, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1421

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Neutral Tie-Dye Mini Dress

    This trendy neutral tie-dye mini dress will step up your casual summer looks. It features a sleeveless scoop neckline, dual spaghetti straps that lead to a cross-back, strappy design, and a short, curve-hugging, bodycon silhouette. The brushed knit fabric offers plenty of stretch. Style with chic mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Dual spaghetti straps
    • Cross-back strap design, lower back bar straps
    • Mini-length, form-fitting, bodycon silhouette
    • Tie-dye print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4690

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Can’t Stop Staring Bodycon Midi Dress

    This sleek knit midi dress is giving heartbreaker energy! The ruched bodycon fit hugs in all the right places—perfect for date nights, girls’ nights, and spotlight-stealing entrances.

    Fit & Features

    • Smooth, stretchy knit fabric, knit lining
    • Sleeveless V-neckline, padded bra cups
    • Adjustable spaghetti straps
    • Ruching
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000153

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

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

  • Beachy-Chic Bodycon Mini Dress

    Showcase a beachy-chic vibe in this curve-hugging bodycon mini dress. It features a sleeveless square neckline, spaghetti straps, ruched detailing down the side seams, and a short, form-fitting silhouette. The stretchy brushed knit fabric features an all-over tropical palm leaf print. Style this dress with espadrille sandals.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching down the side seams
    • Mini-length, form-fitting, bodycon silhouette
    • Tropical palm leaf print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4696

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Flower Lattice Back Dress

    Look as pretty as the island flowers in this tropical maxi dress perfect for a luau dinner! It features a sleeveless, square neck, sleek spaghetti straps, an open back with lattice detailing, a sultry side slit, and a curve-hugging silhouette. Complete your vacay look in large hoop earrings.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Open-back, lattice straps
    • Side slit, curve-hugging silhouette
    • Maxi-length hem
    • Tropical floral print, knit fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4506

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mesmerizing Marble Print Mini Dress

    You'll look mesmerizing in this trendy-chic marble print mini dress! It features a sleeveless square neckline, spaghetti straps, a short, curve-hugging, bodycon silhouette, and an all-over marble print pattern. Style this dress with clear heels.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Mini-length, form-fitting, bodycon silhouette
    • Marble print
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4514

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Mood Geo Print Mini Dress

    In the mood for some newness? Add this retro mini dress to your lineup this new season! It features a sleek, sleeveless, square neck, bungee spaghetti straps, and a geo print design on soft knit-lined fabric that offers a form-hugging fit. Complete the look in statement earrings for a yacht party.

    Fit & Features

    • Sleeveless, square neck, bungee spaghetti straps
    • Geo print design
    • Form-hugging fit
    • Mini-length hem
    • Soft knit lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4569

    Category Name: Casual Dresses

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Allure Ruffle Eyelet Knit Mini Dress

    Bring the cutest allure to summer dates in this flirty eyelet knit mini dress that will get you all the compliments. The adorable dress features a plunging V-neck with a ruffled trim under the bust, ruffled spaghetti straps, and a short A-line silhouette.

    Fit & Features

    • Eyelet knit fabric, stretchy knit lining
    • Sleeveless plunging V-neckline, bar strap detail, keyhole cutout
    • Ruffled trim under the bust
    • Ruffle trim spaghetti straps, adjustable
    • Open back, tie-back strap design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6091

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Paradise Ready One-Shoulder Maxi Dress

    This gorgeous tropical printed maxi dress will have you looking ready for a vacay off to paradise! It features a sleeveless one-shoulder neckline, a single bungee spaghetti strap, an asymmetrical waist cutout with a chic O-ring accent, and a curve-hugging, floor-length silhouette with a front slit. The stretchy knit fabric features an all-over palm leaf print. Complete your look with slip-on sandals and your fave shades.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Single bungee spaghetti strap
    • Asymmetrical waist cutout, O-ring accent
    • Maxi-length hem, form-fitting silhouette, front slit
    • Tropical palm leaf print
    • Knit fabric, short knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4484

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Hopping Tropical Maxi Dress

    Feel the island breeze in this tropical maxi dress for your next holiday in the sun! It features a sleeveless, halter neck, a sultry cutout bodice that leads to the open tie-back closure, and a flowy maxi hem with a slit. Complete your vacay look with lace-up heels.

    Fit & Features

    • Sleeveless, halter neck with tie
    • Cutout bodice
    • Open-back, tie closure
    • Side slit
    • Flowy maxi silhouette
    • Tropical print, woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4500

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Away On Vacay Tropical Mini Dress

    Going away on vacation? This tropical mini dress will definitely get you in the vacay mood! It features a sleeveless, scoop neck, spaghetti straps, a form-hugging silhouette, and a side ruched seam that leads to the asymmetrical slit hem. Complete the look in chic oversized sunnies.

    Fit & Features

    • Sleeveless, scoop neck
    • Spaghetti straps
    • Form-hugging silhouette
    • Side ruched seam, asymmetrical slit hem
    • Mini-length 
    • Tropical print, sleek knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4682

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Desert Vacay Sleeveless Maxi Dress

    Make sure to pack this effortlessly-chic maxi dress in your weekend bag for your desert vacay! It features a sleeveless plunging V-neck and back design, tank shoulder straps, a high-rise banded waist with side cutouts, and a flowy, floor-length silhouette with a front slit to show some leg. Style this dress with espadrille sandals.

    Fit & Features

    • Sleeveless plunging V-neck and back design
    • Tank shoulder straps
    • High-rise banded waist, side cutouts
    • Maxi-length hem, flowy silhouette
    • Front slit
    • Woven gauze fabric, pleated detailing, knit skirt lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4504

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Summer Halter Maxi Dress

    Sultry for summer. Raise the chicness in this halter maxi dress featuring a sleeveless bodice with tie-closure, o-ring inset, and a cutout accent leading to the bodycon silhouette with an asymmetrical slit hem. Complete your sultry look in espadrille wedges.

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • O-ring inset, cutout accent
    • Bodycon silhouette
    • Asymmetrical slit
    • Maxi-length hem
    • Rib-knit fabric, moderate stretch, fits true to size

    Style Number/Barcode: 05102-4467

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Not Your Angel Mesh Mini Dress

    You're no one's angel. Make their jaw drop in this mesh mini dress featuring a sleeveless, square neck, spaghetti straps, bodycon silhouette, front ruched seams, and an angel multi-print design. Complete the look in large hoops for a party.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Front ruched seams
    • Bodycon silhouette
    • Angel multi-print 
    • Mesh-lined fabric
    • Fits true to size

    Style Number/Barcode: 05102-4617

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Brush With Fate Halter Mini Dress

    Fate must've brought you and this halter mini dress together! It features a sleeveless, plunge V-neckline, tie-back neck closure, and a center front hoop insert atop the form-fitting silhouette. Complete the look in simple block heels for a sultry vibe.

    Fit & Features

    • Sleeveless, plunge halter V-neck, tie-back neck closure
    • Center front hoop insert
    • Form-fitting silhouette
    • Mini-length hem
    • Rib-knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4669

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Soft Serve Marble Print Mini Dress

    Look sweet enough to eat in this marble print mini dress featuring a sleeveless, square neck, bungee spaghetti straps, a form-fitting silhouette, and a fitted hem. Complete the look in lace-up heels for a date night.

    Fit & Features

    • Sleeveless, square neck, bungee spaghetti straps
    • Form-fitting silhouette
    • Mini fitted hem
    • Marble print 
    • Fits true to size

    Style Number/Barcode: 05102-4662

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daydream Graphic Cutout Tunic Top

    You gotta hustle girl! Work for your dreams while showcasing your edgy style in this tunic top featuring short sleeves, a V-notch neckline, and graphic front detail with side drawstring cutouts and a fitted hem. Complete the look in retro boots.

    Fit & Features

    • Short sleeves, V-notch neckline
    • Graphic front detail
    • Script reads, "Hustle Daydream"
    • Side drawstring cutouts
    • Fitted hem
    • Jersey knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1257

    Category Name: Casual Dresses

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Striped Sensation Ruche Mini Dress

    You'll be such a sensation in this striped mini dress featuring a sleeveless square neck, spaghetti straps, and ruched side ties on ribbed knit fabric offering a form-hugging fit and a moderate stretch. Complete your casual look in a denim jacket and tennis shoes.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Ruched side ties
    • Form-hugging fit
    • Mini-length hem
    • Striped print, ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4614

    Category Name: Casual Dresses

    Price: $9.97 $23.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blooming Beauty Floral Print Mesh Maxi Dress

    Let your beauty bloom with a mesh maxi dress that features a sleeveless sweetheart neckline with lace trim, a bodycon-fit silhouette, and a pretty floral print throughout! Complete your date night look with stiletto heels! 

    Fit & Features

    • Sheer mesh fabric with knit lining, plenty of stretch
    • Floral print
    • Sleeveless sweetheart neckline, lace trim
    • Spaghetti straps
    • Bodycon-like fit
    • Long maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3785

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: RED

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

  • Gorgeous Getaway Sleeveless Maxi Dress

    Get ready for a gorgeous getaway in this alluring sleeveless maxi dress! It features a V-neckline, spaghetti straps, a cross-back strap design, a fitted high waist seam, and a floor-length silhouette with a chic high front slit. The knit fabric features an all-over tropical palm leaf print. Style this dress with strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back strap design
    • Fitted high waist seam
    • Floor-length silhouette, high front slit
    • Palm leaf print
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4362

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beach Beauty Halter O-Ring Dress

    You'll be a beautiful view on the beach in this halter midi dress featuring a sleeveless, sweetheart neck, a front O-ring atop the cutout bodice that leads to the form-fitting silhouette. Complete the look with a straw purse.

    Fit & Features

    • Sleeveless, sweetheart halter neck
    • Front O-ring
    • Cutout bodice
    • Form-fitting silhouette
    • Midi-length hem
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4443

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Beach Babe Mini Dress

    This adorable retro floral mini dress will have you looking like a total beach babe! It features a sleeveless V-neckline, spaghetti straps, a short, curve-hugging silhouette, and an all-over bold floral print pattern. The lightweight ribbed knit fabric offers a moderate stretch. Complete the outfit with braided mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Mini-length, form-fitting, bodycon silhouette
    • Floral print
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4700

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale