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!

  • Kiss Me Quick Satin Mini Dress

    Serving flirt first, plans second. This satin mini dress features a plunge V-neckline, lace trim details, and a bust tie front that feels like a vintage-inspired romance.

    Fit & Features

    • Woven satin fabric
    • Sleeveless plunge lace trim V-neckline
    • Lace trim wide shoulder straps
    • Hidden side zipper and hook-eye closure
    • Bust tie-front detail
    • Curve-hugging, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000808

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: PINK

    Available Size: S, M, L

  • Petals & Prosecco V-Neck Midi Dress

    This dress feels like brunch reservations, bridal showers, and having lunch in a European city. The soft floral print, delicate ruffle details, and floaty chiffon fabric make every entrance feel extra pretty.

    Fit & Features

    • Dainty floral print, chiffon-lined fabric
    • V-neckline, spaghetti straps
    • Back zipper and hook-eye closure
    • Curve-hugging fit
    • Ruffled midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001478

    Category Name: Casual Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M

  • Coastal Getaway Printed Mini Dress

    Your vacation itinerary just found its favorite outfit. This printed mini dress brings playful resort vibes with a chic A-line silhouette and postcard-inspired details, perfect for your next trip.

    Fit & Features

    • Linen-like fabric, woven lining
    • Resort/paradise script and graphic pattern
    • Square neckline, adjustable spaghetti straps
    • Side zipper and hook-eye closure
    • Side pockets, button-up front closures
    • A-line mini silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000817

    Category Name: Casual Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: S, M, L

    Product Badge:
    • New Arrival
  • Brunch Booked Gingham Print A-Line Midi Dress

    The kind of dress that gets complimented before you even sit down. This gingham print midi dress brings all the charm with a lace-trimmed sweetheart neckline, dainty tie detail, and an easy A-line fit that’s made for brunch plans.

    Fit & Features

    • Cotton-blend woven fabric
    • Gingham print
    • Sleeveless sweetheart neckline, dainty eyelash lace trim, tie detail
    • Adjustable spaghetti straps
    • Smocked back
    • Midi-length hem, A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000821

    Category Name: Casual Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: PINK

    Available Size: S, M, L

  • Dreamy Vibe Floral Print Woven Midi Dress

    A dress that makes even last-minute plans feel a little more curated. This floral print woven midi dress brings that effortlessly dreamy vibe with a flattering V-neckline, floaty A-line fit, and the kind of silhouette that works for brunch dates and weekend markets.

    Fit & Features

    • Woven fabric
    • Dainty floral print
    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Smocked back, zipper closure
    • Midi-length ruffled hem, A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000820

    Category Name: Casual Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

  • Sweet Talks Embroidered Skater Dress

    This is the dress that turns a casual plan into an outfit moment. Featuring delicate floral embroidery, a flattering fit-and-flare silhouette, and an open tie-back detail, it's made for brunch dates, vacation dinners, and every summer plan.

    Fit & Features

    • Floral embroidered woven fabric
    • Sweetheart neckline
    • Spaghetti straps
    • Open tie-back
    • Fit-and-flare skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000823

    Category Name: Casual Dresses

    Price: $45.90

    Availability: In Stock

    Available Color: CORAL

    Available Size: S, M, L

    Product Badge:
    • Best Seller
  • Good Things Coming Mini Dress

    Featuring a draped cowl neckline, flirty front keyhole detail, and body-hugging fit, this mini dress was made for rooftop hotel bars, vacations, and night-out plans.

    Fit & Features

    • Knit fabric, high stretch
    • Draped cowl neckline
    • Adjustable straps
    • Back strap detail
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000378

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: CHARTREUSE

    Available Size: XS, S, M, L

  • Always On The List Midi Dress

    The dress that handles the RSVP for you. Designed with a textured stretch fabric, a flattering halter neckline, and a leg-baring side slit, this midi dress delivers effortless confidence from dinner reservations to rooftop hotel bars.

    Fit & Features

    • Textured knit stretch fabric
    • Halter neckline
    • Spaghetti straps
    • Open back
    • Side slit
    • Form-hugging midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000396

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Resort State Of Mind Crochet Mini Dress

    Consider this your out-of-office wardrobe in dress form. This crochet halter mini hugs in all the right places with a bodycon fit and lace-up back, making it perfect for sunset dinners, beach city strolls, and spontaneous weekend plans.

    Fit & Features

    • Crochet knit fabric, lined
    • Halter neckline
    • Bodycon mini-length silhouette
    • Lace-up back detail
    • Runs true to size

    Style Number/Barcode: 06005-000370

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

  • Worth The Wait Midi Dress

    Some outfits are good, this dress; was worth holding out for. This textured knit midi dress features a flattering bodycon fit, side slit, and statement open back that delivers from every angle.

    Fit & Features

    • Pointelle knit fabric, smooth knit lining
    • Scoop neckline
    • Adjustable spaghetti straps
    • Dual twist open back detail
    • Side slit
    • Bodycon midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000368

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M, L

  • Midnight Magic Halter Mini Dress

    A little sparkle and magic. Featuring a draped cowl neckline, open back halter design, and celestial-inspired sequin artwork, this sweater mini dress was made for cocktail parties, birthday dinners, and unforgettable entrances.

    Fit & Features

    • Sweater knit fabric
    • Cowl halter neckline
    • Open back with strap detail
    • Sequin-embellished sun
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000360

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Brunch Then Cocktails Midi Dress

    When the invite says casual chic, this is the dress you reach for first. The ribbed knit hugs in all the right places while the hardware detail and thigh-high slit give it that elevated, fashion-girl finish.

    Fit & Features

    • Rib knit stretchy fabric
    • Strapless tube neckline with hardware insert
    • Non-slip grip lining
    • High front slit
    • Form-hugging midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000369

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: SAGE

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Daydreaming Floral Knit Dress

    Equal parts cozy and cute, this floral midi dress is made for brunch, weekend plans, and vacations. The oversized floral design gives it a playful statement feel, while the strapless silhouette keeps the look effortlessly polished.

    Fit & Features

    • Statement floral print, sweater knit fabric
    • Strapless tube neckline
    • Form-hugging fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000417

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BROWN-2

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Polished Halter Bodycon Maxi Dress

    A smooth, shine-kissed finish makes this one feel instantly dressed up. The curve-hugging shape, plunging neckline, and waist cutouts bring the drama for vacation dinners, cocktail parties, and every RSVP that needs a little extra.

    Fit & Features

    • Slinky knit fabric with stretch
    • Halter neckline with plunging V front
    • O-ring hardware at center waist
    • Side and underbust cutout details
    • Body-hugging maxi fit
    • Runs true to size

    Style Number/Barcode: 05102-000825

    Category Name: Casual Dresses

    Price: $46.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sun Chaser Beaded Crochet Mini Dress

    Vacation bag called. This beaded crochet mini dress is first on the list. The bodycon fit, halter neckline, and chic beaded details bring just enough drama for dinner plans, rooftop drinks, and every photo op.

    Fit & Features

    • Crochet knit fabric, moderate stretch
    • Sleeveless V-neckline, beaded trim under the bust
    • Halter strap
    • Open back
    • Mini-length hem, beaded fringe trim
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000375

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • All Eyes Here Crochet Mini Dress

    This is the dress that gets the double-take. With a sculpting crochet-knit texture, side cutouts, and a lace-up back that steals the show, it's made for cocktails, birthday plans, and vacations.

    Fit & Features

    • Crochet fabric
    • Strapless neckline
    • Cutout design
    • Lace-up back detail
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000398

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival