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 On Plans Polka Dot Mini Dress

    Caught mid-stroll and looking sweet in this polka dot dress. This dress hugs just right with a form-hugging fit and a flirty ruffle hem made for daytime plans.

    Fit & Features

    • Polka dot print, knit, stretchy fabric
    • One-shoulder neckline
    • Form-hugging ruched fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000710

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

  • Kissed In Polka Dot Mesh Mini Dress

    A little playful, a little risky, and fully worth the attention. This polka dot mesh mini dress hugs in all the right places with a plunge halter neckline, open back, and layered ruffle hem that was made for stealing the scene.

    Fit & Features

    • Polka dot print, mesh fabric, knit lining
    • Plunge halter neckline, tie straps
    • Open back
    • Side ruched seams, fitted bodice
    • Layered ruffle mini hem
    • Runs true to size

    Style Number/Barcode: 05102-000709

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Ocean Air Mood Halter Maxi Dress

    This is the kind of dress that makes every plan feel a little more exciting. The soft hue, textured fabric, and waist cutouts bring just the right amount of drama for beachside dinners, cocktails, and those nights that somehow turn into your favorite memories.

    Fit & Features

    • Texture knit fabric, knit lining
    • Sweetheart halter neckline, tie strap, non-slip grip lining
    • Hoop insert and cutout bodice and back
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000714

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XS, S, M, L

  • Caught Daydreaming Polka Dot Mini Dress

    Serving flirty little getaway vibes in this polka dot dress! It features a breezy blouson fit and a tiered ruffle skirt that moves perfectly from brunch to spontaneous plans.

    Fit & Features

    • Polka dot print, mesh fabric, smooth lining
    • Strapless tube neckline
    • Blouson relaxed bodice
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000716

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Make Plans Eyelet Ruffle Mini Dress

    Last-minute plans just got a major upgrade. This eyelet ruffle mini dress hugs through the bodice with a flirty drop waist and tiered skirt that’s made for showing up and standing out.

    Fit & Features

    • Eyelet knit fabric with knit lining, high stretch
    • Strapless straight-across neckline
    • Fitted bodice, ruched detailing
    • Drop waist seam
    • Tiered ruffled design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000715

    Category Name: Casual Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Stripe Right Tube Midi Dress

    This rib knit striped tube bodycon midi dress hugs in all the right places with a side slit that keeps every step looking effortlessly put together, from vacations, weekend plans, and spontaneous brunch dates. 

    Fit & Features

    • Striped pattern, rib knit fabric, smooth knit lining
    • Tube strapless neckline
    • Side slit
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000717

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: XS, S, M, L

  • Brunch Plans Floral Chiffon Skater Dress

    Brunch turned into all-day plans? You’re covered. This floral chiffon skater dress keeps it light and flirty with a tie-back detail and a layered ruffle skirt that moves with you.

    Fit & Features

    • Sheer chiffon fabric with lining, floral print
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Open back, tie-back design, hidden zipper and hook-eye closure
    • Tiered ruffled design
    • Short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000719

    Category Name: Casual Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: M, L

  • Hot Weather Plans Strapless Maxi Dress

    Serving sunshine with zero effort. This strapless bodycon dress hugs in all the right places with a bold floral moment that makes getting dressed for vacations or weekend plans easy.

    Fit & Features

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

    Style Number/Barcode: 05102-000721

    Category Name: Casual Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: ORANGE

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

  • Charming Sweet Polka Dot Mini Dress

    This polka dot mini dress was for the kind of getaway where your camera roll fills up before noon. With a draped halter neckline, and flirty sash details, this dress is ready for hotel brunches and strolling downtown.

    Fit & Features

    • Polka dot print, mesh fabric, smooth lining
    • V-neckline
    • Form-hugging fit
    • Sash detailing
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000723

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Effortlessly Sculpted Bodycon Midi Dress

    Serving sculpted silhouettes with effortless vibes. This bodycon midi dress hugs your curves with a ruched waist, V-neckline, and leg slit that knows how to make an entrance without doing too much.

    Fit & Features

    • Smooth nylon-lined fabric, high stretch
    • Sleeveless V-neck and back design
    • Tank straps
    • Ruched waist
    • High-cut side slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000728

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L, XL

    Product Badge:
    • Best Seller
  • Weekend Glow A-Line Midi Tube Dress

    Sunshine, but make it wearable. This A-Line midi tube dress hugs through the ruched bodice, then flows into an effortless, breezy silhouette that’s made for everything from brunch plans to last-minute invites.

    Fit & Features

    • Sleek knit fabric, high stretch
    • Strapless straight-across neckline
    • Fitted ruched bodice
    • Maxi-length flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000722

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Effortlessly Done One Shoulder Dress

    Easy and elevated, this one-shoulder dress is the perfect plus-one for everything on your calendar. The one-shoulder moment and cinched waist keep it flattering, while the flowy skirt gives a trendy flare.

    Fit & Features

    • Woven fabric
    • One-shoulder neckline with ruched tails
    • Stretchy smocked fitted waist
    • A-line mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000730

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

  • Spotted And Booked Polka Dot A-Line Mini Dress

    Already RSVP’d and now you have the dress. This polka dot A-line mini dress hugs just right up top, then flares for that easy, flirty fit you’ll wear from dinner plans to after.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Polka dot print
    • Sleeveless V-neckline, eyelet trim, bow detail
    • Adjustable thin eyelet shoulder straps
    • Mini-length hem, ruffled trim
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000729

    Category Name: Casual Dresses

    Price: $49.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Café Cutie Floral A-Line Midi Dress

    The dress equivalent of getting flowers just because. This floral midi dress brings a dreamy strapless fit, twirl-worthy volume, and hidden pockets that make brunch dates, bridal showers, and every occasion feel prettier.

    Fit & Features

    • Floral print, poplin woven fabric
    • Strapless neckline
    • A-line silhouette
    • Hidden side pockets
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000733

    Category Name: Casual Dresses

    Price: $69.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

  • Love This For Me Halter Mini Dress

    Soft, flirty, and already on your weekend lineup. This chiffon mini dress hugs your shape with a bodycon fit while the open back and ruffled trim keep things playful.

    Fit & Features

    • Chiffon fabric, smooth woven lining
    • Sweetheart halter neckline, padded bra cups, tie straps
    • Open back, stretchy smocked band
    • Ruffled trim
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000732

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: YELLOW, PINK, WHITE

    Available Size: M, L, S, XS

  • Weekend Repeat Striped Midi Dress

    The kind of dress that makes outfit decisions feel way too easy. This striped halter midi dress hugs comfortably with a bodycon feel, making it the one you'll reach for on coffee dates, weekend plans, and vacations.

    Fit & Features

    • Striped knit fabric
    • Halter neckline
    • Bodycon fit
    • Center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000389

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Vacation Flirt Striped Mini Dress

    A little flirty on vacay without even trying. This striped bodycon dress hugs close with a strapless tube fit, front cutout neckline, and beaded strap accents that give you a stylish look.

    Fit & Features

    • Striped pattern, crinkle cotton-blend knit fabric
    • Strapless tube neckline
    • Front cutout with beaded strap accents
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000740

    Category Name: Casual Dresses

    Price: $32.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Tropic Temptation Mesh Mini Dress

    This floral and animal print mesh mini dress brings all the playful drama with a sweetheart neckline, flirty ruffle tiers, and cascading side sash details made for beach clubs, birthday trips, and late-night dancing.

    Fit & Features

    • Floral and animal print, mesh-lined fabric
    • Strapless cutout neckline
    • Ruched bodycon silhouette
    • Side ruffled drapes
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000745

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Easy Days Off-Shoulder Mini Dress

    Thrown on in two seconds, styled like you meant it all along. This off-shoulder mini dress brings a relaxed blouson bodice, fitted skirt, and smooth stretch feel for brunch plans, casual weekends, and last-minute plans.

    Fit & Features

    • Soft knit stretchy fabric, short knit lining
    • Striped pattern
    • Off-shoulder neckline, short sleeves
    • Blouson bodice
    • Fitted mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000743

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: GRAY

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Off Duty Darling Striped Mini Dress

    Vacation mode looks good on you. This striped mini dress hugs close with a strapless tube neckline, ruched sides, and a fitted drop waist that pairs perfectly with sandals and sunnies!

    Fit & Features

    • Striped print, terry knit fabric, knit lining
    • Strapless tube neckline
    • Side ruched seams, fitted bodice
    • Drop waist seam
    • Layered ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000744

    Category Name: Casual Dresses

    Price: $32.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Flirty Serve Square Neck Skater Dress

    Serving clean lines and flirty movement. This square neck skater dress hugs up top, flares in all the right places, and keeps up with everything from dinner reservations to spontaneous group chat plans.

    Fit & Features

    • Smooth nylon fabric, high stretch, lining
    • Sleeveless square neckline
    • Thin tank shoulder straps
    • Side pockets
    • Short skater silhouette
    • Pleated detailing
    • Runs true to size

    Style Number/Barcode: 05102-000741

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS, S, M, L

  • Weekend Wandering Embroidered A-Line Midi Dress

    Just add plans and let this do the rest. This embroidered A-line midi dress brings that easy, put-together feel with a breezy fit that works from brunch to wherever the day drifts next.

    Fit & Features

    • Woven fabric with lining, no stretch
    • Embroidered pattern
    • Sleeveless V-neckline
    • Adjustable spaghetti straps, partially stretchy smocked back, zipper closure
    • V-shaped waist seam, dual side pockets
    • Midi-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000749

    Category Name: Casual Dresses

    Price: $56.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

  • Major Fling Flutter Sleeve Maxi Dress

    Fling into the spring season in this maxi dress that has an effortlessly breezy feel, while the V-neck and cutout back give it that easy, getaway-ready charm.

    Fit & Features

    • Airy cotton fabric, woven lining
    • Flutter short sleeves
    • V-neckline
    • Cutout back
    • Ruffled tiered flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000748

    Category Name: Casual Dresses

    Price: $54.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Playful Romance Floral Ruffle Mini Dress

    Romantic, but still a little playful. This floral mesh halter mini dress features a plunging neckline and tiered ruffle hem with a sash detail that moves effortlessly from brunch plans to sunset drinks.

    Fit & Features

    • Floral print, mesh-lined stretchy fabric
    • Plunge halter neckline with tie strap
    • Open back design with tie strap
    • A-line silhouette, ruffled trim detail
    • Side ruffled drape
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001337

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: YELLOW

    Available Size: S, M, L

    Product Badge:
    • Sale