Casual Dresses

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Everyday Ease: Casual Dresses for Transitional-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. Layer your favorite long sleeve to keep the chill out, or pick your Windsor shoes and accessories, and you're ready for the day.

Laid-Back & Versatile

Knit, ribbed, crochet, and sweater dresses bring comfort and style to cooler 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 nuetral 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!

  • Tropic Heat Floral Mini Dress

    Serving vacation energy even if you’re not booked yet. This floral mesh dress contours your shape with a plunging neckline and open back that does all the talking.

    Fit & Features

    • Tropical floral print, mesh-lined fabric
    • Plunge halter neckline, tie straps
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000625

    Category Name: Casual Dresses

    Price: $39.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Heat Tube Maxi Dress

    This strapless rib knit bodycon maxi dress hugs you just right and features a side floral crochet accent that feels equal parts flirty and elevated for dinners, birthdays, and any weekend plans.

    Fit & Features

    • Rib knit fabric with stretch
    • Strapless neckline
    • Side floral crochet accent
    • Bdoycon fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000345

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: L, XL

  • Passport Ready Sequin Sheer Knit Maxi Dress

    Vacation photos called—they want this dress in every frame. This sequin embroidered sheer knit maxi dress pairs a sculpting bodycon fit with a striking hardware cutout and leg-baring slit that was made for rooftop dinners, destination weddings, and every RSVP in between.

    Fit & Features

    • Sheer textured knit fabric, mini-length knit lining, moderate stretch
    • Sequin embroidery
    • Strapless sweetheart neckline, bust cutout with asymmetric metal hardware accent
    • Open tie-back design
    • Maxi-length hem with high-cut side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000632

    Category Name: Casual Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Bare It Back Knot Detail Mini Dress

    Business in the front, drama in the back. This mini dress keeps it sleek with a high neckline and bodycon fit, then flips the script with an open back moment perfect for turning heads.

    Fit & Features

    • Soft stretch knit fabric
    • Mock neckline with cap sleeves
    • Twist front knot detail at waist
    • Open back cutout design
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000635

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Effortless Plans Striped A-Line Midi Dress

    Plans made themselves. This striped flowy A-line midi dress keeps it breezy with a smocked high waist, adjustable straps, and an effortless silhouette that works for brunch, day dates, and last-minute invites.

    Fit & Features

    • Striped texture woven fabric
    • Sleeveless scoop neckline
    • Adjustable spaghetti straps
    • Smocked high waist, hidden side seam pockets
    • Midi-length hem
    • Flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000812

    Category Name: Casual Dresses

    Price: $48.90

    Availability: In Stock

    Available Color: SAGE

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

    Product Badge:
    • New Arrival
  • Bold Bloom Floral Knit Midi Tube Dress

    Big blooms, bold plans. This floral knit midi tube dress hugs in all the right places with a sleek bodycon fit and effortless strapless neckline—perfect for brunch dates, rooftop drinks, or any moment that deserves a standout look.

    Fit & Features

    • Ribbed knit fabric, moderate stretch
    • Large floral print
    • Strapless neckline
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000344

    Category Name: Casual Dresses

    Price: $39.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • City After Sunset Paisley Midi Dress

    A midi dress for any occasion! This strapless mesh midi dress hugs in all the right places with a moody paisley print and a flirty front slit for effortless movement and allure.

    Fit & Features

    • Paisley print, mesh fabric, smooth lining
    • Tube strapless neckline
    • Front slit
    • Form-hugging fit
    • Flowy midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000637

    Category Name: Casual Dresses

    Price: $35.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS, S, M, L

  • Flirting With Florals Mini Dress

    Cute enough to cause a few double takes. This floral tube mini dress hugs in all the right places with a sleek bodycon fit that’s made for brunch dates, weekend plans, and wineries.

    Fit & Features

    • Dainty floral print, eyelet knit-lined fabric
    • Strapless tube neckline
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000638

    Category Name: Casual Dresses

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Sunlit RSVP Lace Ruffle Romper

    Soft lace, flirty ruffles, and that open-back tie moment make this halter romper perfect for showers, brunch, and vacations. Light, pretty, and impossible to ignore—in the best way.

    Fit & Features

    • Lace-lined fabric
    • Plunge halter neckline, tie straps
    • Strappy open back with tie
    • Form-hugging fit
    • Ruffled tiered mini-length hem
    • Stretchy knit shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000263

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Sunkissed Stunner Halter Maxi Dress

    Vacation mode called, and this maxi dress already answered. With a plunging halter neckline, bold cutout details, and a flowy front slit silhouette, this maxi dress was made for beachside brunches, sunny getaways, and weekend plans.

    Fit & Features

    • Artsy print, woven fabric
    • Halter neckline
    • Strappy cutout bodice, back zipper and hook-eye closure
    • High front slit
    • Flowy maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000645

    Category Name: Casual Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: XS, S, M, L

  • Blue Skies And Late Nights Mini Dress

    This is the dress that makes every summer plan feel a little more exciting. Featuring a breezy bandana-inspired print, open-back halter neckline, and flirty skater silhouette, it's made for vacation dinners, sunset strolls, and saying yes to plans that weren't on the calendar.

    Fit & Features

    • Paisley print, chiffon fabric, woven lining
    • Halter neckline, spaghetti straps
    • Open back
    • Stretchy smocked waist panel
    • Skater mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000646

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • City Crush Polka Dot Lace Maxi Dress

    Caught feelings… for this dress. This polka dot slip maxi dress hugs just right with a sleek silhouette that’s made for dinners, drinks, and a little lingering eye contact.

    Fit & Features

    • Lightweight woven knit fabrication
    • Sleeveless v-neckline
    • Contrast lace trim bodice
    • Polka dot pattern
    • Slip silhouette styled fit
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05101-001218

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: S, M, L, XL

    Product Badge:
    • Best Seller
  • Simply Sweet Ruffle Skater Dress

    Consider this your excuse to romanticize even the simplest plans. The ruffle skater dress hugs up top with a soft stretch fit, then flows into that twirl-ready skirt made for brunch dates, parties, and everything in between.

    Fit & Features

    • Smooth knit fabric, high stretch
    • Sleeveless V-neckline, ruched bust
    • Adjustable spaghetti straps
    • V-shaped drop waist seam
    • Asymmetric tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001227

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XXS, XS, S, M

  • Second Look Polka Dot Mesh Midi Dress

    Absolutely dressed with somewhere to be. This polka dot mesh midi dress serves a sleek bodycon fit with a draped cowl neckline and open tie-back for plans that deserve a second look.

    Fit & Features

    • Mesh fabric with full-length knit lining, high stretch
    • Polka dot print
    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Open back, tie-back spaghetti straps
    • Side zipper and hook-eye closure
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000815

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Getaway Glam Tropical Floral Maxi Tube Dress

    One dress, endless compliments. This tropical floral maxi tube dress combines a sleek bodycon fit with oversized blooms for a look that feels both getaway and glam.

    Fit & Features

    • Knit fabric with lining, high stretch
    • Large tropical floral print
    • Strapless straight-across neckline
    • Maxi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000644

    Category Name: Casual Dresses

    Price: $54.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

  • Take Me Somewhere Maxi Dress

    Currently accepting compliments and vacation invitations. This halter maxi dress hugs in all the right places with a plunging neckline and open back that feels made for dinners, destination weddings, and packed itineraries.

    Fit & Features

    • Stitched striped pattern, knit fabric, knit lining
    • Plunge halter neckline
    • Open back
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000643

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

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

  • Double Take Paisley Print Mesh Maxi Dress

    Low back, high impact. This paisley print mesh maxi dress brings the drama with a curve-skimming fit, barely-there straps, and a draped back that keeps every exit memorable.

    Fit & Features

    • Paisley printed mesh fabric with knit lining, high stretch
    • Sleeveless deep V-neckline, bar strap detail
    • Spaghetti straps
    • Open cross-back strappy design with tie closure
    • Lower draped back
    • Maxi-length hem, bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000647

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: RED, BROWN

    Available Size: XS, S, M, L

  • Downtown Dinner Column Midi Dress

    This midi dress keeps things polished from the front with a high boat neckline, then flips the script with a low back, sleek column fit, and just enough movement from the back slit. Perfect for pairing with heels.

    Fit & Features

    • Linen-like woven fabric, stretch knit lining
    • High baot neckline
    • Sleek spaghetti straps
    • Low back, lower zipper and hook-eye closure
    • Column midi-length silhouette
    • Center back slit
    • Runs true to size

    Style Number/Barcode: 05102-000814

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: BLACK-2

    Available Size: XS, S, M, L

  • Soft Curve Alert Rib Knit Midi Dress

    Warning: compliments incoming. This rib knit midi dress features a sweetheart neckline, wide shoulder straps, and a cutout back that keeps things chic, while the form-hugging fit and side slit do all the subtle showing off for you.

    Fit & Features

    • Soft, stretch rib knit fabric
    • Sweetheart neckline
    • Wide shoulder straps
    • Cutout back
    • Side slit
    • Form-hugging, midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000660

    Category Name: Casual Dresses

    Price: $24.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gallery After Hours Cowl Neck Midi Dress

    It’s giving art opening energy, but make it wearable. This artsy abstract print midi dress features a draped cowl neckline, delicate spaghetti straps, and a front slit on a form-hugging silhouette that feels equal parts effortless and elevated.

    Fit & Features

    • Abstract print, knit-lined stretch fabric
    • Cowl neckline, Adjustable spaghetti straps
    • Front slit
    • Form-hugging fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000661

    Category Name: Casual Dresses

    Price: $42.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Serving Chic Halter Cutout Bodycon Midi Dress

    Serving subtle drama with zero effort. This halter bodycon midi dress sculpts your shape with ribbed stretch and bold cutouts—made for nights when you want to feel chic and a little daring.

    Fit & Features

    • Hacci ribbed knit-lined fabric, high stretch
    • Sleeveless crew neckline
    • Halter tie-back straps, open back
    • Waist cutouts leading to an open lower back
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000666

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Soft Curve High Slit Midi Tube Dress

    Serving soft curves with a little edge—this one knows exactly what it’s doing. The midi tube dress hugs in all the right places with a high slit that makes every step feel intentional.

    Fit & Features

    • Ribbed cotton-blend knit fabric, high stretch
    • Strapless sweetheart neckline, knot-front design
    • High-cut side slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000665

    Category Name: Casual Dresses

    Price: $22.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Vibe Paisley Print Bodycon Maxi Dress

    The kind of dress that does all the talking the second you walk in. This paisley print bodycon maxi dress skims your shape with a soft, sculpting stretch—perfect for sultry nights out.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Paisley print
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • High-cut side slit
    • Maxi-length hem, bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000687

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: RUST

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

  • Vacay Ready Halter Mesh Romper

    Booked the trip just to wear this. This tropical floral halter mesh romper drapes effortlessly, with a strappy open back and a cascading ruffle sash that moves with you.

    Fit & Features

    • Tropical floral print, mesh fabric, built-in shorts lining
    • Halter cowl neck, tie straps
    • Open strappy tie-back
    • Tiered ruffled hem with flower inset, cascading ruffle sash
    • Runs true to size

    Style Number/Barcode: 06503-000269

    Category Name: Casual Dresses

    Price: $44.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free