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!

  • Flowy Floral Woven Halter Dress

    Perfect for the warmer months, this flowy floral woven dress is a must-have for weekend brunches and picnic dates! It features a sleeveless square neckline, halter tie straps, a back bar strap design, a fitted stretchy smocked bodice, and a flowy skirt with an A-line silhouette. Pair this ditsy floral printed dress with cute wedges and a trendy straw tote.

    Fit & Features

    • Square neckline
    • Halter tie straps
    • Back bar strap design
    • Fitted stretchy smocked bodice
    • Flowy skirt, A-line silhouette
    • Ditsy floral print
    • Woven fabric, knit lining
    • Runs true to size

    Style Number/Barcode: 05101-1001

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pep It Up Plaid Mini Dress

    Pep it up in a cute plaid mini dress! The dress features a sleeveless square neckline, spaghetti straps, a plaid print, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Plaid print 
    • Mini-length silhouette
    • Knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1866

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Enchanting Floral Maxi Dress

    You will look effortlessly enchanting in this stunning floral maxi dress! It features adjustable spaghetti straps, a square neckline with a ruffled trim, a stretchy smocked bodice, and a lace-up back. The elastic-banded high waist flows out to a floor-length skirt with an A-line silhouette and a thigh-high slit. Complete the look with dainty earrings and cute wedges.

    Fit & Features

    • Adjustable spaghetti straps
    • Square neckline, ruffled trim
    • Stretchy smocked bodice, lace-up back
    • Elastic-banded high waist
    • Floor-length skirt, A-line silhouette, high slit
    • Floral printed sheer chiffon fabric, knit lining
    • Runs true to size

    Style Number/Barcode: 05101-0998

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Heart Of Bloom Ditsy Floral Mini Dress

    Go full bloom with a pretty mini dress! The dress features a sleeveless square neckline, a tie-front accent, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules.

    Fit & Features

    • Sleeveless sweetheart neckline 
    • Tie-front 
    • Spaghetti straps
    • Ditsy floral print
    • Mini-length silhouette, form-hugging fit
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-2041

    Category Name: Casual Dresses

    Price: $18.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Preppy And Trendy Plaid Mini Dress

    Keep it on a trend with a preppy plaid dress to channel those cool-girl vibes. The mini dress features a sleeveless square neckline, spaghetti straps, plaid print, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Plaid print
    • Mini-length silhouette 
    • Knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1508

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Chic Ribbed Knit Dress

    Style up your everyday outfit with this elevated basic dress. It features a crew neckline, short sleeves, side ruching that leads to a slit, and a curve-hugging silhouette. The ribbed knit fabric includes a lining and offers plenty of stretch. Complete your look with sneakers and cool shades for the day or a faux leather crossbody purse and mules for the night.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Side ruching
    • Side slit
    • Form-hugging fit
    • Lined ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-1466

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Sleek Asymmetric Maxi Dress

    Keep your look sleek and on-trend with this chic sweater maxi dress. It features a one-shoulder neckline with a tank shoulder strap and a curve-hugging maxi silhouette with a dramatic asymmetric hem creating a sultry side slit. Pair this sweater knit dress with clear heels and a new purse

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • One-shoulder neckline
    • Tank shoulder strap
    • Form-hugging maxi silhouette
    • Asymmetric hem creating a side slit
    • Sweater knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1295

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirty Vibes Butterfly Printed Mini Dress

    Showcase those sweet and flirty vibes in this trendy knit mini dress. It features spaghetti straps, a square neckline, ruching down the sides, ties at the hem, and a short, form-hugging silhouette. The lightweight ribbed knit fabric has an adorable colorful butterfly print, making it a perf dress for the spring season. Complete your look with a denim jacket and strappy sandals.

    Fit & Features

    • Spaghetti straps
    • Square neckline
    • Ruched detailing and ties at the hem
    • Mini-length, curve-hugging fit
    • Unlined ribbed knit fabric
    • Plenty of stretch
    • Colorful butterfly print

    Style Number/Barcode: 05102-1705

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Trendsetter Status Mini Dress

    Showcase your major trendsetter status in this knit mini dress! It features short sleeves, a deep V neckline, a front waist cutout design, and a mini-length, curve-hugging silhouette. Wear the dress with the cutout in the back for a versatile look. Complete the outfit with cute sneakers.

    Fit & Features

    • Short sleeves
    • V neckline
    • Waist cutout design
    • Short, form-hugging fit
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-2122

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Preppy And Trendy Plaid Ruched Mini Dress

    Keep it preppy in a plaid mini dress that is perf for your next brunch with the squad! The dress features a plaid print, a sleeveless square neckline, spaghetti straps, dual ruched drawstrings, and a mini-length silhouette. Complete look with mules and a jelly purse.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Plaid print
    • Dual ruched drawstrings
    • Mini length silhouette
    • Knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-1679

    Category Name: Casual Dresses

    Price: $19.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Match Ponte Knit Skater Mini Dress

    This mini dress and you are a perfect match, babe! The dress features a sleeveless square neckline, spaghetti straps, tie-back straps, a lower back keyhole, and a pleated tennis-style styled skater skirt. The dress is composed of a lined Ponte knit that offers a form-hugging fit with a moderate stretch. Complete look with wedges

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Tie-back straps, lower back keyhole
    • Pleated tennis skirt, skater silhouette
    • Lined Ponte knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1863

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Ruched Knit Mini Dress

    Create an effortless everyday outfit with this on-trend knit mini dress. It features a mock neckline, short sleeves, a front ruched detail with a drawstring, and a mini-length, curve-hugging silhouette. Complete the look with classic sneakers and a cute crossbody purse.

    Fit & Features

    • Mock neckline
    • Short sleeves
    • Front ruched detail with a drawstring
    • Short, form-hugging fit
    • Double-lined brushed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1478

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring And Chic Brushed Knit Mini Dress

    Create an alluring and chic everyday look with this must-have mini dress! It features a sleeveless bodice, a scoop neck and back, tie shoulder straps, and a mini-length, curve-hugging silhouette. Complete your outfit with heeled mules and a trendy shoulder bag.

    Fit & Features

    • Scoop neck and back
    • Tie shoulder straps
    • Short, form-hugging fit
    • Brushed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1088

    Category Name: Casual Dresses

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sprung On You Floral Lace-Up Mini Dress

    Get sprung on this cute floral mini dress! The dress features a sleeveless scoop neckline, spaghetti straps that lead to a cross-back lace-up back design, cute floral print, ruched side seams, and a mini-length silhouette. Complete the look with wedges and butterfly earrings for that brunch-ready look.

    Fit & Features

    • Sleeveless scoop neckline 
    • Spaghetti straps, cross at back 
    • Lace-up straps 
    • Floral print
    • Ruched side seams
    • Mini-length silhouette 
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-1243

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Showstopper Cutout Ruffle Slit Maxi Dress

    Serve major allure in this sleeveless maxi dress while on vacay or weekend getaway! The maxi dress delivers a sultry design with a twist plunge V-neckline, cutout bodice, and a high front slit with a ruffled trim.

    Fit & Features

    • Slinky knit fabric, short knit lining
    • Plunge twist V-neckline
    • Shoulder straps, one metal accent piece
    • Cutout bodice
    • High front slit with ruffle trim
    • Bodycon maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4070

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • What A Look Ruched Mini Dress

    Create a head-turning look with a mini dress that stuns! The dress features a sleeveless square neckline, tank shoulder straps, a ruched body, and a mini-length silhouette. The dress is composed of smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with sunnies and a moto jacket

    Fit & Features

    • Sleeveless square neckline
    • Tank shoulder straps
    • Ruched body 
    • Mini length silhouette 
    • Smooth knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1121

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Free Spirit Knit Skater Dress

    Live your best in this season ready skater dress! 

    Fit & Features

    • Plunging V-Neckline
    • Halter Neck Tie Straps 
    • Skater Silhouette 
    • Fully Lined Gauze-Like Fabric 
    • Relaxed Fit
    • Minimal Stretch 

    Style Number/Barcode: 05102-0485

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Romance Corset Lace-Up Floral A-Line Mini Dress

    The flirty romantic allure of this floral mini dress will take you from brunch and garden party soirees! This mini dress boasts a cinched waist with a corset bodice and head-turning lace-up back design while the a-line silhouette flatters your figure. Pair with ballet flats.

    Fit & Features

    • Dainty floral print, poplin woven fabrication
    • Sweetheart neckline with bust tie, underwire bust
    • Adjustable spaghetti straps
    • Corset bodice, lace-up back, flexible boning
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3768

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fabulously Retro Ruched Tie Dye Dress

    Keep it fab and retro with a mini dress that is perf for your next night out! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, dual ruched drawstrings, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and butterfly earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross straps
    • Dual ruched drawstrings 
    • Mini-length silhouette 
    • Smooth knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1079

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Drawn To Tie Dye Ruched Mini Dress

    Get drawn to this cute dress that gives off those totally retro feels. The dress features a sleeveless crew neckline with a racer front, a tie-dye print, and ruched drawstrings that allow you to customize the length of the dress. The dress is composed of a mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with sleek hoops and mules

    Fit & Features

    • Sleeveless crew neckline
    • Racer bust
    • Tie-dye print
    • Ruched drawstrings 
    • Mini/midi length silhouette 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1080

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Babe Sleeveless Midi Dress

    Hey babe, show off your adorable style in this floral midi dress that is perf for spring. It features a sleeveless square neckline, thin ruffle shoulder straps, a fitted bodice, and a flowy mid-length silhouette with a thigh-high slit. Complete the look with hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless square neckline
    • Thin ruffle shoulder straps
    • Fitted bodice
    • Flowy mid-length silhouette
    • High front slit
    • Ditsy floral print
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-0741

    Category Name: Casual Dresses

    Price: $20.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Cutie Cutout Ruched Mini Dress

    Keep it cute and casual with a mini dress that is perfect to dress up! The dress features a crew neckline, short sleeves, a twist knot accent at the center of the bodice, a cutout at the midriff, ruched side seams, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with sneakers.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Twist knot accent 
    • Cutout at midriff
    • Ruched side seams
    • Mini-length silhouette, form-hugging fit
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-1108

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Stunning Crochet Waist Maxi Dress

    You'll look effortlessly stunning in this flowy maxi dress that is perfect for the warmer months. It features spaghetti straps that lead to a cross-back design, a lace top with a V neckline, a sheer crochet high waist, and a flowy floor-length gauze skirt with a side slit. Complete the look with on-trend wedges.

    Fit & Features

    • Spaghetti straps
    • Cross back design
    • Lace top, V neckline
    • Sheer crochet high waist
    • Floor-length gauze skirt, side slit
    • Flowy silhouette
    • Runs true to size

    Style Number/Barcode: 05102-0754

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feeling Sweet And Stylish Eyelet Mini Dress

    Channel a sweet look with a floral dress that makes a flirty impression. The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print with eyelets, and a mini-length silhouette. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ditsy floral print 
    • Eyelets
    • Mini length silhouette
    • Lightweight woven fabric, relaxed fit, runs true to size

    Style Number/Barcode: 05102-1130

    Category Name: Casual Dresses

    Price: $6.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale