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!

  • Pleat The Way Scoop Neck Mini Dress

    Make way for setting the trends in this sleeveless mini dress with trendy spaghetti strap ties and a layered pleated mini-length hem. Pair with sneakers.

    Fit & Features

    • Smooth twill woven fabric, stretchy knit lining
    • Spaghetti strap ties
    • Side zipper and hook-eye closure
    • Scoop neckline
    • Form-hugging fit
    • Layered pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6096

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Set For Vacay Tropical Floral Strapless Midi Dress

    You'll be set for vacay in this strapless knit midi dress featuring a large tropical floral print for a bold allure. The form-hugging silhouette will flaunt your gorgeous curves.

    Fit & Features

    • Sleek knit fabric with full-length knit lining, high stretch
    • Large tropical floral print
    • Strapless straight-across neckline, no-slip strip
    • Midi-length hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6097

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blissful Cutie Eyelet Bodycon Midi Dress

    Enter every room like a blissful cutie in this eyelet bodycon midi dress perfect for brides-to-be or brunch! 

    Fit & Features

    • Eyelet fabric lined with stretchy knit
    • Square neckline, ruffle trim, bust tie
    • Wide shoulder straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6098

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Slay All Day Paisley Mesh Maxi Dress

    Look good from every angle—this paisley mesh dress understood the assignment. The halter square neckline and high side slit bring all the heat for a night out or glam rooftop vibes.

    Fit & Features

    • Paisley print, mesh-lined fabric, moderate stretch
    • Halter square neckline with spaghetti straps
    • Form-hugging silhouette
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6099

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ravishing Florals High-Slit Ruched Maxi Dress

    Usher in romance in a maxi dress that features a sleeveless square neckline with spaghetti straps, an abstract floral pattern, ruching throughout to enhance curves, and a high side slit. Complete the look with block heels that will have you ready for your next brunch date!

    Fit & Features

    • Lined mesh fabrication
    • Sleeveless square neckline
    • Spaghetti straps
    • Abstract floral pattern
    • Ruching
    • High side slit
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3859

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Trend Striped Knit Long Sleeve Mini Dress

    This trendy striped knit mini dress features a scoop neckline, long fitted sleeves, an open lower back accent, and a short bodycon silhouette to hug your curves. Perfect for casual chic styling, pair with knee-high boots.

    Fit & Features

    • Striped ribbed knit fabric
    • Scoop neckline
    • Long fitted sleeves
    • Open lower back
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-2119

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetest Outing Tie Back Ruffled Skater Mini Dress

    Have the sweetest look in this tie back ruffled skater dress at bridal showers or graduations!

    Fit & Features

    • Woven fabric lined with stretch knit
    • Sweetheart neckline with bust tie
    • Adjustable spaghetti straps
    • Tie-back cutout design, zipper and hook-eye closure
    • Skater ruffled silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6101

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feel The Sunshine Sweetheart A-Line Mini Dress

    Step into the sunshine in this adorable sleeveless mini dress! With a captivating sweetheart neckline and hoop insert, this dress flatters your figure in an A-line silhouette and mini-length hem.

    Fit & Features

    • Woven fabric, stretchy knit lining
    • Sweetheart neckline with hoop insert
    • Wide shoulder straps
    • Back zipper closure
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6100

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Turn Heads Abstract Print Strapless High Slit Maxi Dress

    Unveil a chic allure in this lined airy mesh maxi dress designed with an eye-catching abstract print to turn heads. It features a strapless straight-across neckline, a high-cut side slit to reveal some leg, and a fitted silhouette on the maxi-length hem.

    Fit & Features

    • Sheer mesh fabric with soft brushed knit lining, plenty of stretch
    • Abstract print
    • Strapless straight neckline
    • High side slit
    • Maxi-length fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6105

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Cute Tie-Front Pleated Mini Dress

    With just the snap of a finger you'll look simply cute in this tie-front pleated mini dress designed to make a statement! 

    Fit & Features

    • Woven fabric, woven lining
    • Square neckline with dual tie-front
    • Spaghetti strap ties, side zipper and hook-eye closure
    • Drop waist seam
    • Fitted silhouette
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000119

    Category Name: Casual Dresses

    Price: $7.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cosmic Chic Tie-Dye Knit Midi Dress

    The ribbed knit dress features a scoop neckline, fitted long sleeves, a tie-dye pattern, and a midi-length hem accented with a center slit at the hem. Complete the look with ankle booties for a casually chic vibe. 

    Fit & Features

    • Ribbed knit fabrication
    • Scoop neckline
    • Long sleeves
    • Tie-dye pattern
    • Center slit at back of hem
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 06005-2132

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Kiss The Sun Tropical Lace-Up Slit Maxi Dress

    Sipping a mai tai oceanside has never looked cuter in this tropical maxi dress! Made to turn heads, this maxi dress boasts a sexy lace-up back, form-hugging silhouette that shows off your curves, and a high front slit giving major allure.

    Fit & Features

    • Tropical print, mesh-lined fabric
    • V-neckline
    • Spaghetti straps
    • Lace-up back
    • Form-hugging silhouette, high front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6103

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Soft And Chic Ribbed Knit Off-The-Shoulder Mini Dress

    Soft and chic, this mini dress is made with ribbed knit fabric offering plenty of stretch for comfortable wear. It features an off-the-shoulder straight neckline with a long fold-over design for a trendy look and a short bodycon silhouette to highlight your curves.

    Fit & Features

    • Ribbed knit fabric
    • Off-the-shoulder straight neckline
    • Long fold-over design
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2259

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Falling For You Tropical Floral Slit Maxi Dress

    Get the golden hour glow in this tropical floral maxi dress while on vacation! Featuring a chic square halter neckline and a form-hugging fit with a high side slit, this dress beautifully accentuates your silhouette.

    Fit & Features

    • Tropical floral print, mesh-lined fabric
    • Square halter neckline, adjustable spaghetti straps
    • Criss cross back
    • Form-hugging silhouette
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6113

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hidden Treasure Lace-Up Shell Accent Midi Dress

    Discover your new signature look with this irresistible midi dress featuring a unique shell accent neckline,  lace-up back offers undeniable allure, and a sultry side slit creates movement.

    Fit & Features

    • Texture knit fabric, moderate stretch, stretchy knit lining
    • V-neckline with shell accent trim
    • Spaghetti straps
    • Lace-up back
    • Side slit
    • Bodycon silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6119

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Destination Summer Tropical Linen Mini Dress

    This cute mini dress was made for summer vacays featuring a contrast tropical print on lightweight linen fabric. The lace-up strappy back design offers a customized fit and a head-turning vibe.

    Fit & Features

    • Linen-blend woven fabric, woven lining
    • Tropical print
    • Sleeveless square neckline
    • Spaghetti straps
    • Open cross-back lace-up strappy design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6115

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Getaway Girlie Halter Bead Crochet Mini Dress

    Your next getaway calls for this crochet mini dress! This dress has a stunning halter bead neckline that adds a touch of boho, a cutout accent, and a flattering bodycon silhouette.

    Fit & Features

    • Crochet lined fabric
    • Halter beaded neckline, spaghetti strap ties
    • Padded bra cups
    • Back zipper hook-eye closure, lower ruched seam
    • Cutout front accent
    • Bodycon silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6116

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spring Fling V-Neck Paisley Skater Dress

    Swing into spring in this paisley skater dress for an adorable look all season! With a flirty halter V-neck and a flowy mini-length hem, this dress is ready for brunch or day dates.

    Fit & Features

    • Paisley print, chiffon fabric, woven lining
    • Halter V-neck
    • Spaghetti strap ties with tassels
    • Stretchy smocked bodice
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5994

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Maui Nights Strapless Tropical Midi Dress

    Booked a vacation? This tropical midi dress is here to make you look stylish for your getaway! Designed with a flattering bodycon silhouette and side slit for effortless sultriness.

    Fit & Features

    • Tropical print, mesh knit-lined fabric
    • Strapless neckline
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6120

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Hottie Tropical Halter Slit Maxi Dress

    Look hot to trot around the island on vacation in this tropical maxi dress! This stunning maxi features a crisscross halter neckline for a touch of elegance and a front slit to show off those curves.

    Fit & Features

    • Tropical palm print, stretchy knit fabric, bust knit lining
    • Crisscross halter neckline, beaded
    • Front slit
    • Curve-hugging fit
    • Flowy maxi length hem
    • Runs true to size

    Style Number/Barcode: 05102-6117

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Era Woven A-Line Midi Dress

    Enter your effortless era in this woven A-line midi dress featuring a stretchy smocked bodice, hidden side pockets, and a pleated flowy silhouette with a side slit.

    Fit & Features

    • Poplin smooth cotton woven fabric with full-length woven lining
    • Sleeveless square neckline, adjustable spaghetti straps
    • Stretchy smocked bodice
    • V-shaped waist
    • Pleating, hidden side pockets
    • Midi-length flowy A-line silhouette, high side slit
    • Runs true to size

    Style Number/Barcode: 05102-000001

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Into The Sun V-Neck Maxi Dress

    Sun goddess maxi dress boasting a V-neckline with a unique metal accent and a body-skimming silhouette. Style with strappy sandals for a sunset dinner.

    Fit & Features

    • Textured knit fabric, soft knit stretchy lining
    • V-neckline with metal accent
    • Spaghetti straps
    • Body-skimming silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000002

    Category Name: Casual Dresses

    Price: $45.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: L

  • Sunset Girl Abstract Halter Slit Maxi Dress

    Need an unforgettable look? This abstract maxi dress will be the perfect companion for rooftop cocktails and parties, boasting a sultry halter neckline, cutout bodice, and high slit giving major sultry energy.

    Fit & Features

    • Abstract print, stretchy knit fabric, short knit stretch lining
    • Halter neckline with tie straps, hoop insert
    • Cutout bodice
    • High side slit
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000003

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Twist Ribbed Knit Mini Dress

    Add a stylish twist to your look with a mini dress that features a plunging sweetheart neckline with a twisted accent at the center and fitted long sleeves. Complete look with knee-high boots. 

    Fit & Features

    • Ribbed knit fabrication
    • Sweetheart neckline
    • Twist accent at the center of a bust
    • Fitted long sleeves
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 06005-2182

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free