Casual Dresses

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Cute Sweater 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!

  • Island Attention Floral Tube Mini Dress

    Booked the trip just to wear this dress. The bold tropical floral print and bodycon silhouette will make heads turn at the beach clubs, island resort, or a weekend pool party!

    Fit & Features

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

    Style Number/Barcode: 05102-000751

    Category Name: Casual Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Sultry Edge Faux Suede Halter Mini Dress

    Low-cut confidence, no apologies. This sultry faux suede halter mini dress hugs just right with a plunging cowl neck and open back that are both daring and effortless.

    Fit & Features

    • Faux suede fabric, moderate stretch
    • Rhinestone and studded trim
    • Sleeveless plunging cowl neckline
    • Halter tie-back straps
    • Open back, lower cross-back design
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000862

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS

    Product Badge:
    • Sale
  • Meet Me In Maui Mesh Maxi Dress

    Covered in oversized tropical blooms and saturated sunset shades, this mesh midi dress brings vacation energy, whether you're headed to dinner by the water or a relaxing cruise.

    Fit & Features

    • Tropical print, lined mesh fabric with stretch
    • Strapless neckline
    • Bodycon silhouette
    • Fitted maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000763

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: PINK

    Available Size: S, M, L

    Product Badge:
    • New Arrival
  • Game Day Crush LA Bodycon Mini Dress

    Serving varsity vibes with zero effort required. This bodycon mini dress hugs in all the right places with a sporty crewneck design that’s made for stadium games and casual hangs.

    Fit & Features

    • Knit cotton fabric, high stretch, knit lining
    • Striped crew neckline
    • Striped short sleeves
    • "Los Angeles" front embroidered script
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000771

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • West Coast Icon LA Bodycon Mini Dress

    West coast icon, LA attitude. This bodycon mini dress hugs your shape with a soft, stretchy feel that moves with you from game day to spontaneous plans.

    Fit & Features

    • Ribbed cotton-blend knit fabric, high stretch, knit lining
    • Sleeveless crew neckline, contrast trim
    • Tank shoulder straps
    • "Los Angeles" front embroidered script
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000772

    Category Name: Casual Dresses

    Price: $32.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Retro Crush Floral Chiffon Mini Dress

    Serving vintage flirt energy in this floral mini dress. It brings the vibe with a breezy A-line fit, playful cutouts, and a tie-front bust made for sunny days.

    Fit & Features

    • Vintage-inspired floral print
    • Chiffon fabric, smooth woven lining
    • V-neckline, tie-front bust, adjustable spaghetti straps
    • Stretchy smocked back panel
    • Side cutouts along the bodice
    • A-line fit, ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000775

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: LAVENDER

    Available Size: S, M, L

  • Polished But Fun Skater Mini Dress

    Clean, classic… and cuing all the compliments. This striped skater mini dress brings that tailored, put-together vibe with a cinched bodice and flared skirt perfect for sunny days.

    Fit & Features

    • Striped pattern, linen-like woven fabric
    • Square neckline, spaghetti straps
    • Hidden side pockets
    • Skater mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000776

    Category Name: Casual Dresses

    Price: $56.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

  • Flirty Confidence Lace One-Shoulder Mini Dress

    A little bold, a little soft—exactly the balance you were going for. This lace one-shoulder A-line mini dress hugs up top and flares at the hem, giving you that confident, caught-in-the-moment kind of vibe.

    Fit & Features

    • Lace fabric with knit lining, high stretch
    • Sleeveless one-shoulder neckline, tank straps
    • Fitted bodice, ruched detailing
    • Drop waist design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000778

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: S, M, L

  • Polka Dot Plans Ruffle Mini Tube Dress

    The dress code? Looking effortlessly put together. This polka dot mini tube dress combines a curve-hugging fit with a playful, ruffled, A-line hem, making it an easy pick for brunch dates, party invites, and any excuse to wear something cute.

    Fit & Features

    • Mesh fabric with knit lining, high stretch
    • Polka dot print
    • Strapless straight-across neckline
    • Drop waist
    • Tiered ruffled design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000780

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Pretty Little Tie-Back Skater Dress

    The kind of dress that makes plans for you. This chiffon skater dress with a sweetheart neckline, lace trim, and tie-back detail feels light, flirty, and ready for any plans.

    Fit & Features

    • Swiss dot chiffon fabric, smooth woven lining
    • Sweetheart lace trim neckline
    • Adjustable spaghetti straps
    • Open tie-back design, stretchy smocked panel
    • Sheer lace trim waist insert
    • Skater silhouette, lace trim ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000777

    Category Name: Casual Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: WHITE, BLACK

    Available Size: S, M, L

  • Chic Agenda Plunge Maxi Dress

    From meetings to martinis without missing a beat. This cap sleeve maxi dress with a center drape accent and front slit keeps it polished for work hours and chic for after-hours plans.

    Fit & Features

    • Smooth knit stretch fabric
    • Cao sleeves with shoulder pads for structure
    • Plunge V-neckline
    • Center front drape and slit designs
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000784

    Category Name: Casual Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: S, M, L

  • Weekend Romance Floral Cotton Midi Dress

    Feels like a soft yes to every plan on your calendar. This flowy ruffle midi dress brings an easy, romantic fit with a smocked waist and tie back, perfect for brunch, showers, or vacations.

    Fit & Features

    • Dainty floral pattern, cotton woven fabric and lining
    • Sleeveless ruffle trim V-neckline
    • Button front bust accents, stretchy smocked panel
    • Tie-back design
    • A-line silhouette, ruffled midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001392

    Category Name: Casual Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

  • RSVP To Sunshine Striped Mini Dress

    This striped halter mini dress hugs in all the right places with a flattering curve-hugging fit that’s made for brunch, beach city strolls, and vacations.

    Fit & Features

    • Striped pattern, ribbed knit fabric, knit lining, high stretch
    • Halter V-neckline with tie straps
    • Partially open back
    • Curve-hugging fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000785

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: GREEN

    Available Size: XS, S, M, L

  • Flown Away Butterfly Print Dress

    Somewhere between flirty and fully unforgettable. This butterfly print dress features a plunge halter neckline and a fluttery ruffled hem, perfect for pairing with strappy heels.

    Fit & Features

    • Butterfly print, mesh fabric, knit lining
    • Plunge halter neckline, tie straps
    • Butterfly hardware inserts
    • Open back
    • Ruched fitted bodice
    • Ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000791

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

  • Effortlessly Booked Midi Dress

    The kind of dress that makes last-minute reservations feel completely intentional. This open back midi dress combines a sleek body-skimming fit with a draped sash detail for an elevated look that works everywhere from cocktail parties to weddings.

    Fit & Features

    • Slinky knit double-lined fabric
    • Sleeveless boat neckline
    • Open back, center back slit
    • Form-hugging midi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000816

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS, S, M, L

  • Late Dinner Plans Tube Maxi Dress

    This is what you wear when the evening calls for something a little elevated. This tube maxi dress hugs through the bodice with a ruched finish, then falls into a soft shark hem that moves with every step.

    Fit & Features

    • Soft jersey knit fabric, stretchy lining
    • Strapless tube neckline, non-slip grip lining
    • Ruched fitted bodice
    • Flowy curve-hugging silhouette
    • Shark-cut maxi hem
    • Runs true to size

    Style Number/Barcode: 05102-000787

    Category Name: Casual Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M

  • In Your Good Graces Halter Mini Dress

    Sweet, but make it a little unexpected. This halter mini skims your shape with a soft, textured feel and a lace trim hem that adds just enough detail for showers, graduations, or dressy brunch plans.

    Fit & Features

    • Textured chiffon fabric, sewn in knit stretchy lining
    • High halter neckline with tie straps
    • Open back
    • Bodycon mini silhouette
    • Lace trim hem
    • Runs true to size

    Style Number/Barcode: 05102-000794

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L

  • Worth The Stare Striped Knit Midi Dress

    This striped sweater dress does all the hard work the second it’s on. The body-hugging fit and trending striped pattern were made for dinners out, cocktail parties, and walking in fashionably late.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Vertical striped pattern
    • Strapless sweetheart neckline
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000420

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: M, L

  • Back For More Halter Mini Dress

    All eyes on you always. This knit mini dress hugs your shape with side ruching and an open-back moment that keeps the focus on you.

    Fit & Features

    • Sweater knit fabric, moderate stretch
    • High halter neckline with tie straps
    • Open back, adjustable strap
    • Side ruched seams
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000419

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LAVENDER

    Available Size: M, L

    Product Badge:
    • Sale
  • Wild Card Printed A-Line Mini Dress

    Vacation mood: activated. This printed A-line mini dress combines a flattering ruched fit with playful ruffles, making it an easy pick for rooftop drinks, weekend getaways, and every photo op in between.

    Fit & Features

    • Mesh fabric, knit lining, high stretch
    • Tropical floral and animal multi-print pattern
    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Ruched bodice, V-shaped drop waist
    • Tiered ruffled design with mini-length hem, A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000796

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: GREEN

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Fresh Cut Florals Strapless Midi Dress

    This strapless midi dress features a soft floral print, smocked bodice, and flowy midi length that's polished, pretty, and just a little romantic. Pair it with strappy heels or keep it casual with flats.

    Fit & Features

    • Floral print, linen-blend woven fabric, woven lining
    • Strapless neckline, non-slip grip lining
    • Stretchy smocked bodice detail
    • Ruffled A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000799

    Category Name: Casual Dresses

    Price: $72.90

    Availability: In Stock

    Available Color: BLUE, ROSE

    Available Size: S, M, L

  • Sunday In Bloom Strapless Midi Dress

    This midi dress feels like a soft yes to every pretty plan on your calendar. The delicate floral print, smocked bodice, and flowy silhouette make it perfect for vacations, brunch, or any sunny day plans.

    Fit & Features

    • Floral borderprint, cotton woven fabric, smooth woven lining
    • Strapless smocked bodice with stretch
    • Back zipper and hook-eye closure
    • Flowy A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000798

    Category Name: Casual Dresses

    Price: $72.90

    Availability: In Stock

    Available Color: BLUE, PINK

    Available Size: S, M, L

  • Rare Find Animal Print Maxi Dress

    A little wild, a little glamorous, and impossible to scroll past. This animal print mesh maxi dress pairs a sweetheart neckline, cutout details, hardware accents, and a dramatic front sash for the kind of entrance people remember.

    Fit & Features

    • Multi-animal print, lined mesh fabric
    • Strapless sweetheart neckline
    • Hardware bust insert with cascading sash
    • Cutout bodice
    • Curve-hugging, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000803

    Category Name: Casual Dresses

    Price: $54.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Picnic Flirt Eyelet Mini Dress

    Sweet, but with a little attitude—just how we like it. This eyelet skater dress shapes you with a corset bodice and flexible boning, while the flutter sleeves and lace-up back keep it playful for every dressy event.

    Fit & Features

    • Eyelet woven fabric, woven lining
    • Sweetheart neck, ruffle trim, bust tie
    • Flutter short sleeves
    • Lace-up back, zipper and hook-eye closure
    • Corset bodice, flexible boning
    • Skater mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001431

    Category Name: Casual Dresses

    Price: $56.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L