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!

  • Definitely Darling Tie Back Babydoll Mini Dress

    Fall in love with this darling eyelet mini dress!. Featuring an open tie-back design and a charming babydoll silhouette, this dress is perfect for brunch, shower celebrations, or graduations.

    Fit & Features

    • Eyelet fabric, stretchy knit lining
    • Short puff sleeves
    • Square neckline
    • Open tie-back design
    • Babydoll silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000061

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Steal The Show Strapless Lace Maxi Dress

    Steal the show in this strapless lace maxi dress designed in a semi-sheer style and a flattering form-hugging fit with a flared hem. Pair with earrings and heels.

    Fit & Features

    • Semi-sheer lace fabric with knit lining
    • Strapless neckline
    • Form-hugging fit
    • Flared maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3965

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Spring Has Sprung Floral Bubble Hem Skater Dress

    Let your beauty bloom in this adorable floral skater dress with the sweetest allure. The corset bodice will highlight your waist while the short skater skirt offers the cutest fit-and-flare silhouette.

    Fit & Features

    • Floral-printed woven fabric with knit lining, minimal stretch
    • Sleeveless sweetheart neckline, padded bust with underwire
    • Thin tank shoulder straps
    • Corset bodice, tie-front detail, high waist seam
    • Smocked back design, zipper with hook and eye closure
    • Short skater skirt with bubble hem, fit and flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3826

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • Sophisticated Vibe Double-Breasted Longline Vest

    Redefine business casual in this longline vest, perfect for polishing your everyday look! This vest has a lapel collar neckline, double-breasted buttons, and a belted waist, It's a chic layer to have in your closet.

    Fit & Features

    • Woven fabric, sewn-in knit lining
    • Lapel collar neckline
    • Double-breasted button closures
    • Belted waist
    • Longline hem
    • Runs true to size

    Style Number/Barcode: 06204-000004

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

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  • Most Lovely Tie Back Ruffled Skater Floral Romper

    A sleeveless floral romper features a flirty surplice V-neckline, a strappy back with a lower tie closure for head-turning detail, and a flattering ruffled skater silhouette. Perfect for the school dance or a dressy brunch.

    Fit & Features

    • Floral pattern, woven fabric, sewn-in knit lining
    • Surplice V-neckline
    • Adjustable spaghetti straps
    • Strappy back, tie-back closure, zipper and hook-eye closure
    • Ruffled skater short-length silhouette
    • Runs true to size

    Style Number/Barcode: 06403-0572

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cutest Picnic Gingham A-Line Eyelet Mini Dress

    From BBQs, picnics, to summer parties, this gingham mini dress will make the cutest impression! The faux button accents add a touch of vintage charm, while the A-line silhouette and eyelet ruffled trim create a flattering and playful look.

    Fit & Features

    • Gingham print, cotton-blend woven fabric, woven lining
    • Sweetheart neckline, eyelet trim
    • Adjustable spaghetti straps
    • Stretchy smocked back panel
    • Faux button accents
    • A-Line fit, eyelet ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000067

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Best For Last Halter A-Line Denim Mini Dress

    Be the talk of the town in this flirty denim mini dress perfect for festivals, concerts, or country bars! The plunging halter neckline shows some skin while the flattering A-line silhouette cinches your waist and flows into a flirty flared mini hem.

    Fit & Features

    • Denim fabric, moderate stretch
    • Plunge halter V-neckline, tie straps
    • A-line silhouette
    • Flared mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000070

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Twirling Beauty Halter Floral Skater Dress

    Twirl through the day in this floral skater dress boasting a lace trim halter neckline for added romance and a flirty mini-length hem to show off your shoes.

    Fit & Features

    • Floral print, woven fabric lined with tulle and woven linings
    • Lace trim halter neckline, tie straps, tie bust
    • Pleated detailed bodice, back zipper and hook-eye closure
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3817

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Flirty Instinct Flocked Floral Velvet Ruffle Romper

    Everyone will bask in your flirtatious allure in this flocked velvet floral romper designed to wow with a ruffled mini-length and a form-hugging fit. Pair with statement flats.

    Fit & Features

    • Flocked velvet floral pattern
    • Mesh fabric, stretchy knit shorts
    • Wide shoulder straps, sweetheart neckline
    • Back zipper and hook-eye closure
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 06503-1252

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Uptown Doll Off-The-Shoulder Abstract Maxi Dress

    Dress to impress in this abstract print maxi dress flaunting a folded off-the-shoulder neckline, sheer fitted long sleeves, and a flattering ruched bodycon silhouette. Pair with heels.

    Fit & Features

    • Abstract print, mesh partially lined fabric
    • Folded off-the-shoulder neckline
    • Sheer fitted long sleeves
    • Ruched bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6021

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • East Coast Girlie Button Linen Skater Dress

    Pack for the perfect East Coast summer with this chic linen skater dress! Adorned with faux button accents and a ruffled mini-length hem, this dress will make you stand out in style.

    Fit & Features

    • Linen-blend woven fabric, woven lining, shorts lining
    • Boat neckline
    • Back zipper and hook-eye closure
    • Faux button accents
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000073

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Charming Look Puff Sleeve Ruffled Skater Dress

    Create a charming look for weekend brunch in this eyelet knit skater dress with the cutest puff sleeves and ruffled mini-length silhouette!

    Fit & Features

    • Eyelet knit fabric, stretchy knit lining
    • Square neckline
    • Short puff sleeves, ruffled hems
    • Drop waist
    • Tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000075

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Floral Fantasy Strapless Cutout Maxi Dress

    Easy to wear, impossible to forget! Make your entrance in this floral maxi dress designed with a flirty cutout and form-hugging fit that accentuates your figure.

    Fit & Features

    • Floral print, mesh-lined fabric
    • Strapless neckline
    • Cutout bodice
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000079

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Meet Your Match Striped Lace-Up Midi Dress

    Your new stylish striped midi dress for casual soirees! Featuring a cutout bodice accented with sleek hardware trim, this dress offers a bold, modern edge. The lace-up open back adds a touch of allure, while the side slit offers effortless movement.

    Fit & Features

    • Striped pattern, texture knit fabric, stretchy knit lining
    • High halter neckline, spaghetti strap tie
    • Lace-up open back, lower zipper and hook-eye closure
    • Cutout bodice with hardware trim
    • Side slit
    • Form-hugging silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000081

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Abstract Effect Strapless Bodycon Mini Dress

    Every head will turn towards you in this abstract mini dress designed in a flattering bodycon silhouette that hugs your curves just right!

    Fit & Features

    • Abstract print, mesh-lined stretchy fabric
    • Strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000078

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sweet On You Denim Halter Skater Dress

    Too cute to handle, too flirty to forget. This denim skater dress brings all the charm with a trendy halter neckline, heart detail at the bust, and a twirl-worthy pleated silhouette. Perfect for rooftop brunches, weekend vibes, or a little crush-worthy moment.

    Fit & Features

    • Denim fabric, minimal stretch
    • Sleeveless V-neckline, metal heart accent
    • Tie-back halter straps, partially open back
    • Hidden back zipper with hook-eye closure
    • Drop waist
    • Short pleated skater silhouette, built-in knit panty lining
    • Runs true to size

    Style Number/Barcode: 05102-000085

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Forever Fave Strapless Bodycon Mini Dress

    This curve-flaunting mini dress will be a forever fave for rooftop bars or dressy date nights. The textured knit fabric adds a chic allure to the strapless bodycon silhouette.

    Fit & Features

    • Textured knit fabric, full-length knit lining, high stretch
    • Strapless sweetheart neckline, no-slip strip
    • Padded bust, bust seam outline
    • Back zipper with hook-eye closure
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000190

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Head-Turning Flirt Bodycon Mini Dress

    A bodycon mini dress that makes the perfect foundation to create flirty looks!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000086

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cheerful Cutie Gingham Skater Dress

    From casual plans to picnics, this cheery gingham dress will have you feeling cute all day long! This delightful dress is designed with a smocked waist for a flattering fit, a cute mini-length hem, and a flared skater silhouette.

    Fit & Features

    • Gingham print, woven fabric, stretchy knit lining
    • Sweetheart neckline with bust tie
    • Adjustable spaghetti straps
    • Stretchy smocked waist
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000093

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Too Cute to Care Babydoll Mini Dress

    Low effort, high reward kind of vibe. This babydoll mini dress features a strappy cutout back and hidden pockets—aka your new throw-on-and-slay essential.

    Fit & Features

    • Poplin woven fabric
    • Square neckline
    • Spaghetti straps
    • Spaghetti strap tie-back and cutout accent
    • Hidden side pockets
    • Babydoll silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000092

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Love Language Floral Print Mesh Maxi Dress

    This airy mesh maxi dress speaks your love language designed with a bold floral print and long fitted silhouette. Style with mules for date night.

    Fit & Features

    • Sheer mesh fabric with full-length knit lining, high stretch
    • Large floral print
    • V-neckline
    • Adjustable spaghetti straps
    • Maxi-length hem, fitted silhouette
    • Floral print placement may vary
    • Runs true to size

    Style Number/Barcode: 05101-3978

    Category Name: Casual Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Cutie Denim Lace Trim Mini Dress

    This figure-flattering denim mini dress features delicate lace trim and a flirty ruffled hem that adds movement to your silhouette. The bodycon fit hugs your curves in all the right places, creating a stunning look.

    Fit & Features

    • Denim fabric, lace trim, minimal stretch
    • Sweetheart neckline, added bra cups
    • Wide shoulder straps
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000104

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachy Breeze Strapless Slit Maxi Dress

    Enjoy a sunset dinner by the beach in this chic strapless maxi dress showcasing a high slit for effortless movement and a flattering bodycon silhouette.

    Fit & Features

    • Texture knit fabric, stretchy knit lining
    • Strapless sweetheart neckline, twist accent
    • Bodycon silhouette
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000052

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Head Turner Floral Bodycon Mini Dress

    With a sultry strut and this floral mini dress, you'll be a major head turner on vacation or at parties! 

    Fit & Features

    • Floral print, knit-lined stretchy fabric
    • Strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000103

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free