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!

  • Mesmerizing Beauty Lace-Up Wrap Dress

    Mesmerize with a wrap dress that showcases your best angles! The dress features a sleeveless scoop neckline, spaghetti straps, a lace-up back, a high slit, and a wrap silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit, Complete look with mules

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Lace-up back 
    • High slit
    • Wrap silhouette
    • Knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05101-0586

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The One Ribbed Knit Midi Dress

    This ribbed midi dress is the one you can't live without, bby! The dress features a sleeveless square neckline, supportive tank shoulder straps, a high side slit accented with metal snap buttons, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless square neckline
    • Tank shoulder straps
    • High side slit 
    • Snap buttons
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0955

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Essential High Slit Ribbed Knit Maxi Dress

    Create a chic moment with a maxi dress that brings the chic details! The dress features a crew neckline, short sleeves, dual side cutouts, and a maxi silhouette accented with a high side slit. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with sneakers for a casual vibe.

    Fit & Features

    • Crew neckline
    • Short sleeves 
    • Dual side cutouts
    • Maxi length silhouette
    • High side slit
    • Ribbed knit fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-1420

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • After Party Ruched Mini Dress

    Hit up those after-parties with a wowing mini dress that creates a head-turning impression! The dress features a sleeveless square neckline, sleek bungee spaghetti straps, a ruched body, and a mini-length silhouette. The dress is composed of a double-lined buttery smooth fabric that offers a form-hugging fit with a moderate stretch. Complete look with a clutch and neon heels

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruched body
    • Mini length silhouette
    • Double-lined fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-2348

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy And True Eyelet Mini Dress

    Keep true to your love of trendy finds in this mini dress! The dress features an off-the-shoulder neckline with a sweetheart bust, short puff sleeves, a ruched center, an eyelet design, and a mini-length silhouette. Complete look with clear mules

    Fit & Features

    • Off the shoulder neckline, sweetheart bust
    • Short puff sleeves
    • Ruched center
    • Eyelet pattern 
    • Mini length silhouette
    • Form hugging fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-0762

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Making Waves Tie Dye Ruched Mini Dress

    Make waves with a stylish mini dress that creates a commotion! The dress features a sleeveless V-neckline, a ruched center drawstring, a tie-dye print, spaghetti straps, and a mini-length silhouette. Complete look with clear mules

    Fit & Features

    • Sleeveless V-neckline
    • Ruched center drawstring
    • Tie-dye print
    • Spaghetti straps
    • Mini length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4056

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vintage Grunge Distressed Graphic Tunic

    Showcase those trendy vintage grunge vibes in this distressed graphic tunic! It features a V-neckline, short sleeves, a center eagle and stars graphic with the script "Born Free, Unknown Destination," slashed detailing, and a short, curve-hugging fit. Style this tunic with sneakers to keep it casual, or combat boots for an edgy look.

    Fit & Features

    • V-neckline, short sleeves
    • Center eagle and stars graphic
    • Script "Born Free, Unknown Destination"
    • Slashed detailing
    • Mini-length, form-hugging fit
    • Cotton fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-0823

    Category Name: Casual Dresses

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Let Style Bloom Ditsy Floral Tube Dress

    Let your style bloom with a tube dress that is perf for those beach days! The dress features a strapless square neckline, a ditsy floral print, and a mini-length silhouette. Complete the look with mules and a crossbody.

    Fit & Features

    • Strapless square neckline 
    • Ditsy floral print
    • Mini-length silhouette
    • Lightweight ribbed knit fabric, knit lining
    • Form-hugging fit, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-2876

    Category Name: Casual Dresses

    Price: $4.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Such A Charmer Ditsy Floral Mini Dress

    You'll charm them all in this adorable ditsy floral mini dress! It features a sleeveless sweetheart neckline with a ruffle trim, a tie-front detail, adjustable spaghetti straps, and a mini-length, curve-hugging silhouette. Style this dress with a pair of strappy sandals.

    Fit & Features

    • Sleeveless sweetheart neckline, ruffle trim
    • Tie-front detail
    • Adjustable spaghetti straps
    • Partial smocked back
    • Short, form-hugging fit
    • Chiffon fabric, ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-0757

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casually Chic Ribbed Knit Mini Dress

    Elevate your everyday look with this casually chic mini dress. It features a sleeveless scoop neckline, tank shoulder straps, and a mini-length, curve-hugging silhouette. Style this ribbed knit dress with the matching jacket and sleek hoop earrings.

    Shop Matching Jacket: Casually Chic Ribbed Knit Cropped Jacket

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Short, form-hugging fit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1492

    Category Name: Casual Dresses

    Price: $19.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Vibes Linen Mini Dress

    Channel those flirty vibes with a mini dress that brings those girly details! The dress features an off-the-shoulder neckline, a tiered ruffle popover, a smocked waist, and an A-Line silhouette. The dress is composed of a linen knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges and hoops.

    Fit & Features

    • Off the shoulder neckline
    • Tiered ruffle popover
    • Smocked waist
    • Mini length silhouette
    • A-Line
    • Linen knit fabric
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05101-1058

    Category Name: Casual Dresses

    Price: $22.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Fit Strapless High Slit Maxi Dress

    Show off a sleek fit in this chic smooth knit maxi dress featuring a strapless neckline and high-cut side slit. The form-hugging silhouette will flaunt your gorgeous figure.

    Fit & Features

    • Smooth knit fabric, high stretch
    • Strapless straight neckline
    • Ruched high front slit
    • Maxi-length hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000684

    Category Name: Casual Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: GREEN-2, PINK

    Available Size: XS, S, M, L

  • Alluring Tropical Floral Maxi Dress

    Create a stylish and alluring look for your next vacay in this gorgeous maxi dress! It features a sleeveless V-neckline, spaghetti straps that lead to a lace-up back design, a high waist, a floor-length hem with a chic side slit, and a flowy, relaxed fit. The knit fabric has an all-over tropical floral print, making this dress a perf pick for summer. Complete the outfit with strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Lace-up back design
    • High waist
    • Floor-length hem, side slit, relaxed fit
    • Knit fabric, tropical floral print
    • Runs true to size

    Style Number/Barcode: 05102-0195

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Carefree Style Tie-Dye Mini Dress

    Showcase an effortless and carefree style this summer with this tie-dye mini dress! It features a sleeveless square neckline, spaghetti straps, side ruching with drawstrings at the hem, and a mini-length, curve-hugging silhouette. The soft brushed knit fabric offers a moderate stretch. Complete the look with casual sneakers.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Side ruching, drawstrings at the hem
    • Short, form-hugging fit
    • Brushed knit fabric, moderate stretch
    • Tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-4057

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classically Chic Button Up Mini Dress

    Button up in a chic mini dress that is oh so chic! The dress features a collared neckline, a button-down front, long sleeves, a ruched body, 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 heels

    Fit & Features

    • Collared neckline
    • Button-down front
    • Long sleeves
    • Ruched body
    • Mini length silhouette
    • Smooth knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4190

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Swept Away Off-The-Shoulder Ruched Mini Dress

    Get swept away with this glam mini dress that brings chic details! The dress features an off-the-shoulder neckline with short flutter sleeves, a sweetheart bust with a drawstring, a ruched body, and a mini-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.

    Fit & Features

    • Off-the-shoulder neckline, short flutter sleeves
    • Sweetheart bust with a drawstring
    • Ruched body
    • Mini-length silhouette
    • Lined smooth knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1167

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Drawn To You One-Shoulder Mini Dress

    Everyone will be drawn to you in this chic one-shoulder mini dress! It features stylish ruched detailing, a drawstring at the hem, and a short, curve-hugging silhouette. Pair this dress with clear heels and a sleek clutch for your next night out.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Ruched detailing
    • Drawstring at the hem
    • Mini-length, form-hugging fit
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-3784

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Staple Open Back Ruched Mini Dress

    Make this mini dress a casual staple to rotate into your wardrobe. The dress features a crew neckline, short sleeves, a lower back keyhole, a ruched body, and a mini-length silhouette. Complete look with sneakers and hoops. 

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Lower back keyhole
    • Ruched body 
    • Mini length silhouette 
    • Cotton knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-1097

    Category Name: Casual Dresses

    Price: $18.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortlessly Pretty Floral Mini Dress

    Get an effortlessly pretty look in this adorable mini dress. It features short puff sleeves, a sweetheart neckline with a tie-front detail, a stylish waist cutout, and a mini-length, curve-hugging silhouette with a flirty ruffled hem. The dress is composed of a lightweight woven fabric with an all-over disty floral print and features a stretchy smocked body. Complete the look with a charm necklace.

    Fit & Features

    • Short puff sleeves, cinched hems
    • Sweetheart neckline, tie-front detail
    • Front waist cutout
    • Short, form-hugging fit
    • Tiered, ruffled hem
    • Lightweight woven fabric, ditsy floral print
    • Stretchy smocked body
    • Runs true to size

    Style Number/Barcode: 05102-3061

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Glam Tie Dye Ruched Mini Dress

    Keep it dreamy in a tie-dye dress that channels a retro feel! The dress features a sleeveless square neckline, spaghetti straps, a ruched body, tie-dye print, and a mini-length silhouette. Complete look with wedges and a denim jacket for a cute date outfit. 

    Fit & Features

    • Sleeveless square neckline 
    • Spaghetti straps 
    • Ruched body
    • Tie-dye print 
    • Mini length silhouette
    • Brushed knit fabric 
    • Form hugging, moderate stretch, runs true to size

    Style Number/Barcode: 05102-1520

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Just Like That Mini Dress

    Show them you've got your style locked down just like that! This mini dress features a sleeveless scoop neckline, spaghetti straps, and a short, curve-hugging silhouette. The lined stretchy knit fabric has contrasting exposed seams on the front for a trendy vibe. Complete the outfit with sneakers to keep it casual, or style with clear heels for an elevated look.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Mini-length, form-hugging fit
    • Lined stretchy knit fabric
    • Contrasting exposed seams
    • Runs true to size

    Style Number/Barcode: 05102-2180

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mesmerizing Beauty Floral Mini Dress

    Showcase your mesmerizing beauty in this chic floral mini dress. It features a sleeveless wrap-front V-neckline, spaghetti straps, a wrap skirt with an asymmetric hem, and a curve-hugging silhouette. Style this dress with clear heels and a sleek clutch for a summer date night.

    Fit & Features

    • Sleeveless wrap-front V-neckline
    • Spaghetti straps
    • Wrap skirt, asymmetric hem
    • Form-hugging fit
    • Floral printed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-0567

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Style Babydoll Dress

    Showcase a sweet style this season in this adorable babydoll dress. It features a square neckline, three-quarter length puff sleeves with ruffled cinched hems, a high waist seam under the bust, and a flowy short A-line silhouette. Pair this dress with dainty earrings and cute wedges for an effortless look.

    Fit & Features

    • Square neckline
    • Three-quarter length puff sleeves, ruffled cinched hems
    • Back zipper closure
    • High waist seam under the bust
    • Flowy short A-line silhouette
    • Cotton fabric, pleated detailing
    • Runs true to size

    Style Number/Barcode: 05102-2412

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Can't Live Without Glam Ruched Mini Dress

    Channel a glam look with a mini dress that showcases your fab taste! The dress features a sleeveless V-neckline, spaghetti straps, a backless design, a ruched body, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules

    Fit & Features

    • Sleeveless V-neckline
    • Backless
    • Spaghetti straps 
    • Ruched body
    • Mini-length silhouette
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05103-2928

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale