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!

  • Sweet Intentions Halter Mini Dress

    Turn heads in this curve-loving ruched mini dress that’s all about sleek confidence. The halter neckline and off-shoulder sleeves give it that effortlessly sultry energy, while the front cutout keeps things daring yet refined. Perfect for date night plans or any moment you want to make unforgettable.

    Fit & Features

    • Sleek knit stretchy fabric
    • Off-the-shoulder halter neckline, tie closure
    • Fitted long sleeves
    • Cutout bust
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000343

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Abstract Affair Mesh Mock Neck Dress

    Art meets attitude. This abstract mesh dress brings the heat with its sheer long sleeves, curve-hugging silhouette, and daring open back. It’s bold, lightweight, and made for the nights you want all eyes on you.

    Fit & Features

    • Abstract floral print, mesh-lined stretch fabric
    • Mock neckline, button closures
    • Sheer fitted long sleeves
    • Open back design
    • A-line mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000349

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RUST

    Available Size: XS

    Product Badge:
    • Sale
  • Lace Up and Take Over Mini Dress

    This lace corset mini is equal parts sweet and daring — with a deep V neckline, faux leather lace-up bodice, and tiered lace skirt that moves like you already own the room. It’s that perfect mix of romantic texture and confident structure.

    Fit & Features

    • Lace-lined bodice with plunging V-neckline
    • Sleeveless design, adjustable shoulder straps
    • Faux leather corset waist with grommet lace-up front
    • Back zipper and hook-eye closure
    • Drop-waist seam
    • Tiered lace-lined mini skirt
    • Runs true to size

    Style Number/Barcode: 05102-000352

    Category Name: Casual Dresses

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: M, L

    Product Badge:
    • Sale
  • Wild Plans Animal Print Mesh Halter Mini Dress

    Wild plans call for a dress that knows exactly what it’s doing. This animal print mesh halter mini dress hugs through the waist with ruched shaping and flares out with playful tiers that move with you from dinner reservations to wherever the night decides to go.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Animal print
    • Sleeveless halter neckline with tie-back straps, partially open back
    • Metal hardware accent, keyhole bust cutout
    • Ruched drop waist
    • Tiered ruffled design, mini-length A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-000350

    Category Name: Casual Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: RUST

    Available Size: XS, S, M, L

  • Late Arrival Abstract Maxi Dress

    Moody, sculpted, and impossible to ignore. This maxi dress hugs in all the right places with a plunging neckline and statement ring detail that feels made for vacations, sunset dinners, and GNOs!

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Strapless neckline with cutout and hardware inserts
    • Form-hugging silhouette
    • Maxi-length hemline
    • Runs true to size

    Style Number/Barcode: 05102-000348

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Twist of Fate Mini Dress

    Sleek, sculpted, and a little unexpected. This halter mini dress stuns with its high neckline, open back, and drop waist silhouette that flatters every curve while keeping things effortlessly chic from mimosa brunches to date nights.

    Fit & Features

    • Slinky knit fabric, stretchy knit lining
    • High halter neckline with tie closure
    • Open back
    • Drop waist seam
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000577

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Wild At Heart Lace Leopard A-Line Mini Dress

    Turn up the heat in this sultry leopard mini dress. The fierce leopard print, lace bust, and flared skirt make it the perfect mix of wild and romantic. Whether it’s a night out or a wine bar evening, this dress brings all the allure.

    Fit & Features

    • Leopard print, mesh fabric, stretchy knit lining
    • Lace bust sweetheart neckline, underwire cups
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000353

    Category Name: Casual Dresses

    Price: $18.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fall for Knit Long Sleeve Mini Dress

    Cozy, flattering, and totally fall-coded. This ribbed knit mini dress features a sweetheart neckline and subtle ruching that shapes your silhouette while keeping it soft and effortless. Pair it with knee-high boots for a perfect fall day out.

    Fit & Features

    • Hacci rib knit stretch fabric
    • Sweetheart neckline, ruched bust seam
    • Fitted long sleeves
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000354

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty In Motion Halter Mini Dress

    Caught a vibe and dressed for it. This halter mini dress cinches at the waist with a flowy A-line skirt that moves with you—perfect for weekends that start with plans and end wherever.

    Fit & Features

    • Smooth stretch material
    • Halter neckline with open back, tie straps
    • Ruched waist detail
    • A-line mini silhouette with pleated skirt
    • Runs true to size

    Style Number/Barcode: 05102-000358

    Category Name: Casual Dresses

    Price: $32.90

    Availability: In Stock

    Available Color: ROYAL

    Available Size: XS, S, M, L

  • Coastal Crush Cutout Crochet Maxi Dress

    A dress that does the flirting for you. The cutout crochet shows just enough, while the shell and sequin details add that subtle shimmer that catches light—and attention—without trying. This is your out-all-day, glow-all-night kind of maxi dress.

    Fit & Features

    • Sheer crochet knit fabric, mini-length knit lining, moderate stretch
    • Sleeveless ruched knit top, no-slip strip, wired V-neckline
    • Tie-back halter spaghetti straps, eyelet trim, shell and sequin embellishments
    • Partially open back
    • Maxi-length hem, high-cut side slit
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000360

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Sleek Attitude Cutout Mini Tube Dress

    Sleek with a hint of attitude—this cutout tube dress leans into confidence without overdoing it. The smooth knit hugs effortlessly, while the cutout crisscross beading gives your waist that sculpted, stop-scrolling energy.

    Fit & Features

    • Smooth double-lined knit fabric, high stretch
    • Strapless straight-across neckline
    • Front waist cutout
    • Asymmetric strappy design, beaded stone accents
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000359

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Winter Crush Sherpa Trim Faux Leather Tube Dress

    Think après-ski, but make it going-out glam. The faux leather gives you that sleek, sculpted confidence, while the faux sherpa trim adds that touch of softness that balances the boldness just right. It’s the kind of piece that feels luxe, a little daring, and completely worth showing off.

    Fit & Features

    • Faux leather fabric with sewn-in knit lining, moderate stretch
    • Faux sherpa trims
    • Strapless straight-across neckline, no-slip strip
    • Back zipper with hook-eye closure
    • Dual belted accents at the waist
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000362

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Golden Hour Off-The-Shoulder Mini Dress

    This long sleeve off-the-shoulder mini dress hugs in all the right places for that effortless “oh, this old thing?” vibe. Perfect for brunch, dinner dates, or any casual night out plans.

    Fit & Features

    • Smooth knit-lined stretchy fabric
    • Foldover off-the-shoulder neckline
    • Fitted long sleeves with flare slit cuffs
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000363

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Whispers Ruffle Mini Dress

    Bring the drama (and the movement). This strapless mesh mini features a sweetheart neckline with a sultry O-ring cutout, open tie-back design, and layered ruffle skirt made to turn heads on every dance floor.

    Fit & Features

    • Abstract print mesh-lined stretch fabric
    • Strapless sweetheart neckline
    • Hoop insert, padded bra cups
    • Strappy open tie-back
    • Ruched bodycon fit
    • Tiered ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000367

    Category Name: Casual Dresses

    Price: $18.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Prep School Princess Rhinestone Collar Shirt Dress

    This polished poplin mini dress gets a glam upgrade with a gorge rhinestone-encrusted collar that instantly elevates your whole vibe. The corset-inspired seaming snatches your waist just right, while the flared skirt keeps things flirty. Whether you’re styling it with sheer tights and heels or chunky boots and a shoulder bag, this dress delivers classy-with-a-twist energy every single time.

    Fit & Features

    • Woven cotton-blend poplin fabric with structured hand
    • Pointed collar adorned with rhinestone embellishments
    • Long sleeves with buttoned cuffs
    • Fitted corset-style waist with front pleating
    • Mini-length button-up silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000366

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wildly Fierce Leopard Floral Maxi Dress

    Warning: this dress doesn’t do low profile. The leopard floral mesh print fabric and plunge halter neckline with bead inset sculpt a form-hugging maxi silhouette that’s made for vacations, birthday dinners, and any plan that deserves a little drama.

    Fit & Features

    • Floral, leopard print mesh-lined fabric
    • Plunge halter neckline with tie and bead
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000365

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Barefoot Glam Sequin Mini Dress

    This is the dress that makes every plan feel like a getaway. With its shimmering payette sequin texture and open-back detail, it’s made for sunny getaways, destination dinners, and dancing after sunset.

    Fit & Features

    • Allover payette sequin embellishment, knit lining
    • Spaghetti straps 
    • V-neckline
    • Sleeveless bodice with a fitted silhouette
    • Open back with adjustable lace-up tie detail
    • Mini-length hem with dangling shell trim
    • Runs true to size

    Style Number/Barcode: 05102-000368

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wrapped in Charm Rib Knit Dress

    Soft meets sultry in this rib knit mini dress made for showing a little shoulder. The foldover neckline, waist wrap belt, and ruffled hem bring that flirty-feminine vibe—perfect for when cozy still calls for a look.

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Foldover off-the-shoulder neckline
    • Fitted long sleeves
    • Wrap waist belt accent with hardware insert
    • Bodycon fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000371

    Category Name: Casual Dresses

    Price: $30.00 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, L

    Product Badge:
    • Sale
  • In Your Element Off-Shoulder Mesh Twist Midi Dress

    This midi knows how to move—soft mesh, abstract swirls, and an off-shoulder twist that feels effortlessly seductive. The high side slit adds that perfect hint of drama, making every step a little more intentional.

    Fit & Features

    • Abstract printed mesh fabric, knit lining
    • Off-shoulder neckline with twist detail
    • Bodycon silhouette
    • High side slit for ease of movement
    • Runs true to size

    Style Number/Barcode: 05102-000372

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Untamed Rhythm Halter Mini Dress

    Made for movement and meant to turn heads. This abstract mesh halter mini dress features a soft cowl neckline, open back, and flirty tiered ruffle hem that dances with every step.

    Fit & Features

    • Abstract print, mesh-lined stretch fabric
    • Cowl halter neckline with tie closure
    • Open back
    • Form-hugging fit
    • Tiered ruffle mini hem
    • Runs true to size

    Style Number/Barcode: 05102-000373

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Vibes Geometric Knit Halter Mini Dress

    Meet the mini dress that knows how to make an entrance without trying too hard. The geometric knit hugs just right, giving you that effortless, sculpted look for beach nights, rooftop drinks, and the best vacay vibes.

    Fit & Features

    • Sheer embroidered knit fabric, knit lining, high stretch
    • Abstract geometric pattern, metallic woven threading
    • Sleeveless V-neckline
    • Tie-back halter straps, partially open back
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000377

    Category Name: Casual Dresses

    Price: $45.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Luxe Moments Removable Faux Fur Mini Dress

    Giving retro glam with a cozy twist, this ribbed mini dress brings major soft-lux vibes. The faux fur collar and cuffs add effortless drama, making it the perfect piece for chilly nights when you still want to look very put together.

    Fit & Features

    • Rib knit fabric
    • Deep V neckline with a removable faux fur collar
    • Long sleeves with removable faux fur cuffs
    • Front button-down design for adjustable coverage
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000378

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Brunch Crush Eyelet Skater Dress

    Caught feelings for this one instantly. This eyelet knit skater dress hugs through the bodice, then flares into the prettiest mini, made for brunch dates, grad pics, and those “just stepped out” kind of days.

    Fit & Features

    • Eyelet knit fabric with knit lining, moderate stretch
    • Sleeveless square neckline
    • Princess seams
    • Adjustable spaghetti straps
    • Mini-length hem
    • Skater silhouette, godet detailing
    • Runs true to size

    Style Number/Barcode: 05102-000381

    Category Name: Casual Dresses

    Price: $38.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wander Off Tie Back Skater Dress

    This paisley skater dress flows effortlessly with a halter V-neckline and an open tie back that feels easy, breezy, and effortlessly styles with sandals for sun-soaked days.

    Fit & Features

    • Paisley print, airy woven fabric
    • Halter V-neckline with tie straps
    • Open tie-back design
    • Flowy skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000380

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS, S, M, L