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!

  • Pretty Plans Chiffon And Lace Skater Dress

    Booked, busy, and dressed like it. This chiffon and lace skater dress gives you that soft, floaty fit that moves with you from daytime plans to whatever the night turns into.

    Fit & Features

    • Lightweight chiffon fabrication, lace trim woven lining
    • Sleeveless V-neckline with delicate lace insert
    • Spaghetti straps
    • Flared skater silhouette
    • Adjustable waist tie
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05102-000463

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Flirt With The Breeze Skater Mini Dress

    This flowy skater dress was made for sunny days. It features a flattering V-neckline and a breezy silhouette that moves with you from brunch to beachside strolls.

    Fit & Features

    • Cotton fabric, woven cotton lining, delicate embroidery
    • V-neckline
    • Adjustable spaghetti straps
    • Tiered ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000465

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Getaway Mood Tropical Floral Halter Maxi Dress

    Lightweight, curve-loving, and made to move with you. The airy sheer mesh fabric and tropical floral print bring a bold edge that feels right for nights out and getaway moods.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Tropical floral print
    • Sleeveless V-neckline
    • Metal flower hardware accent, keyhole cutout
    • Tie-back halter spaghetti straps, partially open back
    • Maxi-length hem, form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000464

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S

  • Bare It All Open Back Bodycon Midi Dress

    Clean lines, confident fit, no extra effort required. This ribbed midi dress keeps things sleek and minimal with a body-hugging silhouette that feels just as good as it looks. Perfect for dressing up or down.

    Fit & Features

    • Soft ribbed knit fabric with comfortable stretch
    • Square neckline with slim spaghetti straps
    • Sleeveless bodycon silhouette
    • Low open back design
    • Midi length that hits below the knee
    • Runs true to size

    Style Number/Barcode: 05102-000467

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XL

    Product Badge:
    • Sale
  • Wrapped In Charm Off-Shoulder Mini Dress

    This mini dress is that perfect mix of soft and sculpted—the one you reach for when you want to look undone in a chic way. The foldover off-shoulder neckline adds a flirty twist, while the rib knit hugs you with just the right amount of confidence.

    Fit & Features

    • Soft rib knit fabric with stretch
    • Foldover off-shoulder neckline with subtle twist detail
    • Fitted long sleeves
    • Bodycon silhouette
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05102-000469

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Picture Perfect Lace Trim Floral Woven Skater Dress

    You booked the brunch. Now match the vibe. This lace trim floral lace-up skater dress snatches at the corset bodice and flares into a twirl-ready mini made for parties, day dates, and every camera roll moment in between.

    Fit & Features

    • Floral printed woven fabric with lining, dainty lace trims
    • Strapless straight-across neckline, ruched bust, tie detail
    • Corset-style bodice, V-shaped drop waist
    • Lace-up back design, tie closure
    • Mini-length skater silhouette, pleated detailing
    • Runs true to size

    Style Number/Barcode: 05101-000973

    Category Name: Casual Dresses

    Price: $13.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty Plans Eyelet Mini Dress

    Caught feelings for this one instantly. This eyelet dress feels light and playful, perfect for brunch dates, daytime plans, or wherever the mood takes you.

    Fit & Features

    • Eyelet knit fabric, smooth knit lining
    • V-neckline
    • Adjustable spaghetti straps
    • Fitted bodice
    • Tiered ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000471

    Category Name: Casual Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: WHITE

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

  • Backstage Flirt Denim Skater Dress

    Caught feelings for a denim moment this good. This plunge halter mini dress brings the drama with an open tie back and skate silhouette that’s made for weekend plans and concerts.

    Fit & Features

    • Denim fabric, slight stretch, built-in panty lining
    • Plunge halter neckline, tie straps
    • Button front closures
    • Open back with tie
    • Drop waist seam
    • Skater silhouette, mini-length raw hem
    • Runs true to size

    Style Number/Barcode: 05102-000474

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

  • Sunny Day Invites Eyelet Knit Skater Dress

    This adorable eyelet knit skater dress will have you instantly weekend-ready. The short dress hugs up top, flares just right, and is basically made for last-minute brunches and sunny day invites.

    Fit & Features

    • Eyelet knit fabric with knit lining, high stretch
    • Sleeveless V-neckline
    • Halter tie-back straps, partially open back
    • Drop waist design, V-shaped seam
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000694

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, L

  • Serving Sweetness Denim Mini Dress

    This lace-up denim skater dress features a plunge V-neckline, structured bodice, and a playful drop waist skirt that’s made for concerts, festivals, and every plan in between.

    Fit & Features

    • Denim fabric, built-in pant knit lining, some stretch
    • Plunge halter V-neckline
    • Structured bodice with lace-up design
    • Drop waist seam
    • Back zipper with hook-eye closure
    • Pleated skater mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000478

    Category Name: Casual Dresses

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Fab Polka Dot Halter Mini Dress

    This polka dot halter mini dress is ready for your weekend plans. It features a draped cowl neckline and curve-hugging bodycon fit that keeps you looking flirty, fab, and right on time for every outing.

    Fit & Features

    • Sleek knit fabric with high stretch
    • Polka dot print
    • Sleeveless V-neckline, draped cowl design
    • Tie-back halter straps, partially open back
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000475

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Sunshine State Of Mind Eyelet Mini Dress

    This eyelet skater mini dress offers a breezy fit and ruffled details—perfect for graduations, showers, or brunch.

    Fit & Features

    • Eyelet woven fabric
    • Sweetheart neckline
    • Smocked shoulder straps and bust
    • Flowy skater silhouette
    • Ruffle trim mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000988

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Impact Mock Neck Midi Dress

    This midi is your secret weapon—clean, sculpting, and quietly commanding. The ribbed knit dress smooths and contours while the mock neck adds that cool, editorial structure that never tries too hard.

    Fit & Features

    • Rib knit fabric
    • Mock neckline
    • Smooth bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000479

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Second Look Open Back Midi Dress

    Simple from the front, unforgettable from the back. This ribbed halter midi dress features a plunging neckline and open back with subtle ruching that hugs your shape and keeps the look smooth, polished, and confidently put together.

    Fit & Features

    • Soft rib knit stretch fabric
    • Plunge halter neckline
    • Open back design with subtle ruching
    • Bodycon midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000482

    Category Name: Casual Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS, S, M, L

  • Daydream Bloom Floral Print Midi Dress

    This is the kind of dress that makes every plan feel a little prettier. The fitted bodice and flowy skirt create that effortless shape, while the soft floral print keeps things light and romantic.

    Fit & Features

    • Woven fabric, soft floral print, woven lining
    • Square neckline, tie bust keyhole accent
    • Adjustable spagehtti straps
    • Stretchy smocked back panel, side zipper and hook-eye closure
    • Fitted bodice with button accents
    • Drop waist seam, a-line midi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000481

    Category Name: Casual Dresses

    Price: $9.97 $62.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • After Hours Bloom Floral Burnout Mesh Mini Dress

    Flirty with a side of intention—this one moves differently. The floral burnout mesh mini dress hugs up top, flows below, and shows up perfectly for plans that turn into after-hours moments.

    Fit & Features

    • Lined mesh fabric with floral burnout texture
    • Strapless neckline, tube silhouette with a fitted bodice
    • Drop waist with tiered ruffle mini skirt for movement
    • Runs true to size

    Style Number/Barcode: 05101-000999

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Flirt Babydoll Mini Dress

    Floaty, flirty, and effortless in the best way. This babydoll mini dress brings that easy, throw-on-and-go feel with a breezy fit that moves with you from daytime plans to last-minute outings.

    Fit & Features

    • Cotton-blend fabric with lining
    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Partially smocked back
    • Mini-length asymmetric hem, subtle distressed detailing
    • Flowy babydoll silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000485

    Category Name: Casual Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: L

    Product Badge:
    • Best Seller
  • Denim Days Button Front Mini Dress

    Denim, but make it plans. This button-up mini dress cinches you in with a flattering fit and an unexpected back buckle moment that turns heads anywhere you go.

    Fit & Features

    • Dark wash denim
    • Strapless tube neckline
    • Button-up front
    • Adjustable back buckle 
    • Curve-hugging fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000490

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: DARK, DENIM

    Available Size: XS, S, M

  • Ready In Five Tie-Back Mini Dress

    This A-line mini dress is your “I have nothing to wear” fix—handled. A flirty ruffled dress with a tie-back detail that cinches just right and a flowy skirt made for last-minute plans and weekend brunches.

    Fit & Features

    • Woven fabric
    • V-neckline
    • Spaghetti straps
    • Tie-back detail
    • A-line fit
    • Layered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000486

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE, YELLOW, SAGE

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

    Product Badge:
    • Sale
  • Picnic Date Lace Cotton Skater Dress

    Straight out of your Euro summer mood board. This cotton skater dress with a lace ruffled bodice and tie shoulder straps gives you that floaty, twirl-worthy fit made for brunch, bridal celebrations, and cute getaways.

    Fit & Features

    • Cotton fabric, tulle and woven linings
    • Square neckline, tie shoulder straps
    • Hidden side zipper and hook-eye closure
    • Mini lace tiered ruffled fitted bodice
    • Tie-waist design
    • Voluminous skater silhouette, lace trim mini hem
    • Runs true to size

    Style Number/Barcode: 05101-001009

    Category Name: Casual Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: WHITE

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

  • Flirty Flowy Chiffon Strapless Babydoll Dress

    Made for spontaneous plans and extra mirror checks. This strapless chiffon babydoll dress brings the flirty vibes with flowy layers, a mini hem, and that effortlessly dressed-up look.

    Fit & Features

    • Sheer chiffon fabric with lining
    • Strapless sweetheart neckline
    • Hidden side zipper and hook-eye closure
    • Flowy, tiered, ruffle design
    • Mini-length hem
    • Babydoll silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000489

    Category Name: Casual Dresses

    Price: $45.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Cutie Vibe Lace Strapless A-Line Mini Dress

    Cute plans only—this one’s already booked. This lace strapless A-line mini dress hugs up top and flares out with an easy, flirty fit that’s made for last-minute invites.

    Fit & Features

    • Sheer lace fabric with knit lining, high stretch
    • Strapless straight-across neckline
    • Mini-length asymmetric hem
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000492

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Dreamy Eyelet Ruffle Mini Dress

    This sweet eyelet dress brings soft romance with a playful twist. The square neckline, puff sleeves, and tiered ruffle skirt create a flattering A-line silhouette that feels effortlessly feminine. Perfect for brunch dates, garden parties, or sunny day plans.

    Fit & Features

    • Eyelet fabric, knit lining
    • Square neckline
    • Short puff sleeves
    • Fitted bodice
    • Drop waist A-line silhouette
    • Tiered ruffle mini hem
    • Runs true to size

    Style Number/Barcode: 05102-000493

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, M, L

  • Sweet Breeze Eyelet Mini Dress

    This one feels like sunshine in dress form. The smocked bodice keeps it easy and flattering, while the tiered eyelet skirt adds flirty movement, perfect for showers, graduations, brunches, and any dressy plans.

    Fit & Features

    • Eyelet embroidered woven fabric, stretchy knit lining
    • Strapless neckline
    • Stretchy smocked bodice
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001022

    Category Name: Casual Dresses

    Price: $44.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free