Casual Dresses

Show filters
Sort:
Size
Color
Price
All filters
Sort
Loading...

Product Recommendations

STYLE SPOTLIGHT

Cute Sweater Dresses

Floral Print Dresses

Discover New Skater Dress Styles

Everyday Ease: Casual Dresses for Cool-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.

Laid-Back & Versatile

Knit, ribbed, and sweater dresses bring comfort and style to crisp fall 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 burgundy 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!

  • Sharp Lines Asymmetrical Long Sleeve Midi Dress

    Strike a fierce impression in a ribbed knit dress with an asymmetrical off-the-shoulder neckline, a pleated popover accent, fitted long sleeves, and a midi-length hem. Complete the look with strappy heels for the perfect work-to-happy hour look! 

    Fit & Features

    • Ribbed knit fabrication
    • Asymmetrical off-the-shoulder neckline
    • Pleated popover accent at the neckline
    • Long sleeves
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5947

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Luxe Charm Cashmere Knit Hanky Hem Mini Dress

    Channel a luxe aura in a ribbed cashmere-like knit dress that features a boat neckline, long fitted sleeves, a partially open back design, and a short hanky hem with an A-line silhouette. Complete the look with knee-high boots and leg warmers for a chic moment!

    Fit & Features

    • Ribbed cashmere-like knit fabrication, moderate stretch
    • Boat neckline
    • Long fitted sleeves
    • Partial open back, tie-back spaghetti straps
    • Mini-length hanky hem
    • A-line silhouette
    • Runs true to size 

    Style Number/Barcode: 05102-6053

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Vibes Long Sleeve Ruched Midi Dress

    Channel sleek vibes in a midi dress that features a boat neckline, fitted long sleeves with thumb holes, and ruching that enhances curves. Complete look with strappy heels to take you from the office to happy hour! 

    Fit & Features

    • Smooth knit fabrication, double-lined
    • Boat neckline
    • Long sleeves with thumb holes
    • Ruching
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3954

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Glam Ribbed Knit Long Sleeve Mini Dress

    The ribbed knit dress features a mock neck, long sleeves accented with thumb holes, and a mini-length hem. For a casually glam vibe, complete the look with ankle booties.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch
    • Mock neckline
    • Long fitted sleeves with thumb hole accents
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6014

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Button-Down Drop Waist Mini Dress

    So elevated, this adorable mini dress is designed with a textured knit fabric and a sleek button-down front. It features a sleeveless square neckline with tank straps, a drop waist, and a short pleated A-line silhouette for that cute flair.

    Fit & Features

    • Textured knit fabric, sewn-in knit lining
    • Square neckline
    • Tank shoulder straps
    • Button-down front
    • Drop waist
    • Mini-length pleated A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3842

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Vibes Off The Shoulder Knit Midi Dress

    Keep it sleek and stylish in a ribbed knit dress that features a v-neckline that can be worn off-the-shoulder, fitted long sleeves, and a midi-length hem. Complete the look with sneakers to add a casual touch! 

    Fit & Features

    • Lined ribbed knit fabrication
    • V-neckline and off-the-shoulder 
    • Long sleeves
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5942

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Adorable Stunner Strapless A-Line Mini Dress

    You'll be an adorable stunner in this mini dress designed with crepe fabric with a contrast color block outline for a chic look. It features a strapless straight-across neckline, a high waist seam, and a short A-line silhouette to add that flirty flair.

    Fit & Features

    • Crepe fabric, stretchy knit lining
    • Contrast color block outline
    • Strapless straight neckline
    • High waist seam
    • Back zipper closure
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3801

    Category Name: Casual Dresses

    Price: $14.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Things Cozy High Slit Knit Midi Dress

    Oh-so-cute and cozy, this knit midi dress is a seasonal staple. It features a mock neckline, long fitted sleeves, an asymmetric mid-length hem creating a thigh-high side slit, and a form-hugging silhouette. The ribbed hacci knit fabric has an ultra-soft feel with plenty of stretch. Style this midi dress with knee-high boots for a latte date.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Asymmetric mid-length hem
    • Thigh-high side slit
    • Form-hugging fit
    • Ribbed hacci knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5333

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Curves Ribbed Knit Off-The-Shoulder Midi Dress

    Showcase your perfect curves in this midi dress designed with soft ribbed knit fabric. It features an off-the-shoulder neckline with a chic fold-over design, long fitted sleeves, and a midi-length bodycon silhouette.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch
    • Off-the-shoulder neckline, fold-over design
    • Long fitted sleeves
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5894

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Perfection Long Sleeve Knit Mini Dress

    This ribbed knit mini dress will create perfect casual 'fits! It features a square neckline, long fitted bell sleeves with cute flared-out hems, and a mini-length, form-hugging silhouette. The lined knit fabric offers plenty of stretch for comfortable wear. Style with knee-high boots.

    Fit & Features

    • Ribbed knit fabric, knit lining, plenty of stretch
    • Square neckline
    • Long fitted bell sleeves, flared hems
    • Form-hugging fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5889

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Seasonal Staple Ribbed Knit Bell Sleeve Mini Dress

    This adorable ribbed knit mini dress will be your fave staple of the season featuring a square neckline, long bell sleeves, and a short form-hugging silhouette. Style with knee-high boots for a casual party.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch
    • Square neckline
    • Long bell sleeves
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-2086

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Like Me Scoop Neck Skater Mini Dress

    Showcase your sweet side in this ribbed knit mini dress made to please the crowd! It features a sleek scoop neckline and a skater silhouette that flatters every figure. Style with a handbag.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Scoop neckline
    • Tank shoulder straps
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000006

    Category Name: Casual Dresses

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Embrace Cable Knit Midi Dress

    Embrace a cozy vibe in a cable knit dress that features a trendy v-neckline, fitted long sleeves, and a midi-length hem. Complete look with ankle booties!

    Fit & Features

    • Unlined cable knit fabrication
    • V-neckline
    • Fitted long sleeves
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 06005-2097

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Layered In Glam Ribbed Knit Long Sleeve Maxi Dress

    Nail that layered look in a ribbed knit dress featuring a plunging square neckline, a bralette inset with lace trim, fitted long sleeves, and a maxi-length hem with a back slit accent. Complete the look with trendy ankle booties for the ultimate vibe.

    Fit & Features

    • Ribbed knit fabrication, plenty of stretch
    • Square neckline
    • Bralette inset with lace trim
    • Fitted long sleeves
    • Long hem length
    • Back slit
    • Runs true to size

    Style Number/Barcode: 05102-5848

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mesmerizing Glam Abstract Ruched Midi Dress

    Step out and mesmerize in a midi dress that features a sleeveless square neckline, ruching throughout to enhance curves, and an abstract marble print. Complete look with strappy heels for a look that's ready for date night!

    Fit & Features

    • Lined mesh fabrication
    • Sleeveless square neckline
    • Ruching
    • Abstract marble print
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5937

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Love Game Plunge V-Neck Bubble Skater Dress

    Win hearts in this adoring bubble skater dress perfect for dressy occasions! Boasting a flattering skater silhouette, this poplin woven dress is designed with a plunge V-neckline and back to show some skin, short ruffled bubble sleeves, and a bubble short-length hem. Complete the look in strappy sandals.

    Fit & Features

    • Poplin woven fabric, sewn-in knit lining
    • Plunge V-Neckline
    • Short ruffled bubble sleeves
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-2935

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Social Butterfly Square Neck Floral Mini Dress

    A dreamy butterfly floral mini dress perfect for social girlies! The mini-length dress features a square neckline that showcases a ribbon trim for romance, adjustable spaghetti straps to get a perfect fit, front metal closures, and a form-hugging silhouette that will flatter your figure. Complete the look in lace-up stiletto heels and a purse for a date!

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Butterfly floral print
    • Adjustable spaghetti straps
    • Ribbon trim, front metal closures
    • Back zipper and hook-eye closure
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5623

    Category Name: Casual Dresses

    Price: $5.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Leopard Print Woven A-Line Midi Dress

    Trendy and elevated, this leopard-printed woven midi dress features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, and a partially smocked back for added stretch. The high front slit adds a bold vibe to the mid-length A-line silhouette.

    Fit & Features

    • Leopard-printed woven fabric, no stretch
    • Square neckline, underbust seam
    • Adjustable spaghetti straps
    • Partially smocked back design
    • High front slit
    • Midi-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5923

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Polished Perfection Vest Pleated Short Dress

    Capture polished perfection in this chic vest pleated short dress! Designed with a structured twill woven fabric, this dress features a fitted vest top with an A-line skirt. The top is shaped with a sleeveless V-neckline and tank shoulder straps, followed by a button-front design and an angled cropped hem for a snatched look. The chic waist cutout adds a touch of allure, leading to a fitted high waist and a flowy, pleated short-length hem. The dress includes a back zipper closure for effortless styling. Complete your look with gold hoops and strappy mules!

    Fit & Features

    • Non-stretch twill woven fabric
    • Sleeveless V-neckline with tank shoulder straps
    • Button-front design, angled cropped hem
    • Back zipper with hook and eye closure
    • Waist cutout, high-rise skirt with pleating
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5536

    Category Name: Casual Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twist Of Chic High-Slit Knit Midi Dress

    Bring a twist of chic to the every day with a midi dress that features an asymmetrical one-shoulder neckline with a trendy twist shoulder accent and a daringly high side slit. Complete look with slingback shoes to take you from the office to happy hour! 

    Fit & Features

    • Stretchy knit fabrication
    • Asymmetrical one-shoulder neckline
    • Twist shoulder strap accent
    • High side slit
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5983

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On The Down Low Denim Strapless Midi Dress

    Take your look on the down low in this denim midi dress! The knee-length dress features a strapless neckline, stretchy smocked back, and button-down front closures, this bodycon dress will have you breaking the fashion barriers. With belt loop accents, three-pocket styling, and a midi-length hem, this denim stunner gives you the power to take risks and turn heads! Style this midi dress with a purse and block heels for a birthday brunch!

    Fit & Features

    • Strapless neckline
    • Stretchy smocked back
    • Button-down front closures
    • Bodycon silhouette, midi-length hem
    • Belt loop accents, three-pocket styling
    • Denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5283

    Category Name: Casual Dresses

    Price: $5.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Choice Knit Off-The-Shoulder Maxi Dress

    This trendy ribbed knit maxi dress is a chic choice for the season offering plenty of stretch for comfortable wear. It features an off-the-shoulder fold-over neckline, long fitted sleeves, and a maxi-length bodycon silhouette accented with a back slit.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch
    • Off-the-shoulder neckline, fold-over design
    • Long fitted sleeves
    • Back slit
    • Maxi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2104

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girl Power Leopard Print Strapless Midi Dress

    Show off major girl power in this sexy leopard print midi dress that was made for all eyes on you. It features a strapless straight-across neckline, ruching down the side seams, a midi-length hem, and a bodycon silhouette to put your gorgeous figure on display. The lined sheer mesh fabric features an all-over leopard print pattern to amp up the look. Style this midi dress with strappy stilettos for a nightclub!

    Fit & Features

    • Strapless straight-across neckline, no-slip strip
    • Ruched side seams, hidden side zipper, hook and eye closure
    • Midi-length hem
    • Bodycon silhouette
    • Leopard print
    • Sheer mesh fabric, mini-length knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-3211

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serving Sleek Square Neck Bodycon Midi Dress

    Serve a gorgeous sleek silhouette in this brushed knit midi dress featuring a sleeveless square neckline, thin tank straps, and a midi-length bodycon fit to hug your curves. Style with hoop earrings and stiletto heels.

    Fit & Features

    • Brushed knit fabric with knit lining, plenty of stretch
    • Square neckline
    • Thin tank shoulder straps
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5975

    Category Name: Casual Dresses

    Price: $39.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free