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!

  • Keep It Classy Shirt Dress

    This classic chic mini shirt dress is everything you need and more. It features a collar, a plunging wrap front V neckline, long sleeves with buttons to cuff, a high waist seam, side ruched detailing, and a short fit. The dress is composed of a woven fabric with no stretch. Complete your chic look with mules and statement hoops

    Fit & Features

    • Collared neckline
    • Plunging v-wrap bust
    • Long sleeves with multi- buttoned cuff
    • Side ruched detailing
    • Mini length silhouette
    • Woven fabric
    • Form hugging fit, minimal stretch 

     

    Model is 5'7" with a 34" bust,  24" waist and 34" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-1015

    Category Name: Casual Dresses

    Price: $22.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classic Chic Scoop Neck Knit Mini Dress

    Fall in love with the classic chic look of this adorable basic knit mini dress! It features bungee spaghetti straps and a short, flattering, curve-hugging fit. This dress can easily be dressed up with heels for date night or kept more casual with a bucket hat and chunky sneakers for a shopping day.

    Fit & Features

    • Bungee spaghetti straps
    • Scoop neckline
    • Mini-length silhouette
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-0897

    Category Name: Casual Dresses

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flowy Floral Woven Midi Dress

    Create an effortlessly pretty look in this floral woven midi dress! It features a trendy tie front detail and a flattering flowy mid-length silhouette. Pair the dress with block heels and gold hoops for the perfect date night outfit.

    Fit & Features

    • V neckline
    • Tie front detail
    • Three-quarter length flowy sleeves
    • Front waist cut out
    • Mid-length flowy fit
    • Floral printed woven fabric

     

    Model is 5'7" with a 32.5" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0962

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Brighter Vibes Lace-Up Chiffon Maxi Dress

    Bring on brighter vibes in this maxi dress that brings a burst of color this season. The maxi dress features a plunging v-neckline, sexy waist cutout to show off a hint of skin, a lace-up back, and a high side slit. Complete your look with fab cork wedges and sunnies for those ultimate summer vibes. 

    Fit & Features

    • Sleeveless v-neckline with spaghetti straps
    • Waist cutouts
    • Lace-up back 
    • High side slit
    • Maxi length silhouette
    • Chiffon fabric 


    Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0505

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lovin' The Basics Cotton Midi Dress

    You'll be lovin' everything about this basic cotton midi dress! Featuring a crew neckline and a mid-length, curve-hugging fit, this dress will flatter your figure. Pair with some gold hoops and chunky sneakers for a laid back, casual vibe you can wear to hang out with your squad.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Mid-length silhouette
    • Cotton fabric

    Style Number/Barcode: 05102-0926

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Girl Faux Wrap Front Ribbed Mini Dress

    You'll look oh so gorgeous in this wrap front ribbed mini dress! Featuring a deep V neckline and a ribbed knit fabric that will hug your curves, this dress is perf for a night out. Pair with some large hoop earrings and heels to complete the vibe.

    Fit & Features

    • Bungee spaghetti straps
    • Deep V neckline
    • Faux wrap front with asymmetric hem
    • Ruched detailing
    • Short, form-hugging fit
    • Ribbed knit fabric


    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0818

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Late Night Fantasy Dress

    Live your wildest dreams in this dress! Bring the wow factor to your date-night outfit in this flirty skater dress. The dress features a flattering v-neckline, spaghetti straps that offer support, sheer lace back detail with a lower back keyhole to show off a hint of skin and a flowy skater silhouette with double-tiered hem. The dress is composed of a form-hugging ponte knit fabric that offers a moderate stretch. Complete your impressive look with rhinestone duster earrings and sleek stiletto heels

    Fits & Features

    • V neckline
    • Spaghetti straps
    • Sheer lace back with zipper
    • Exposed lower back
    • Wide waistband 
    • Flowy skirt with a double-tiered hem 
    • Ponte knit composition, moderate stretch

     

    Black Dress: Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.

    Ivory Dress: Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.

    Burgundy & Red Dress: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small

    Navy Dress: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Mauve Dress: Model is 5'3" with a 32" bust, 22.5" waist and 34" hips. She is wearing a size small.

    *Also available in Plus

    Style Number/Barcode: 05101-7048

    Category Name: Casual Dresses

    Price: $6.97 $47.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Cool And Casual Tunic

    Keep your look cool & casual in a tunic. This tunic looks great worn alone or dressed up with layers for a casually cute date night look. The tunic features a crew neckline, short sleeves, and a short curved hem to flatter curves. The tunic is composed of a cotton-blend fabric that offers a form hugging fit with a moderate stretch. Pair with some white sneakers, a denim jacket, and a baseball cap for that sporty chic vibe.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Short curved hem
    • Form hugging fit
    • Cotton blend fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-0439

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Short And Sweet V-Neck Bodycon Mini Dress

    Keep your style short and sweet in this sassy bodycon mini dress perf for casual weekend plans or dressing up with a cute jacket and heels!

    Fit & Features

    • Stretchy knit fabric
    • Short sleeves
    • V-neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5957

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • That's My Stripe Crepe Triangle Waist Cut Out Mini Dress

    This striped crepe waist cut out mini dress will be just your type! Featuring a sultry cutout, a streamlined silhouette, and trendy stripes, this dress checks all the boxes. Opt for some booties and statement earrings to go with this look for a night out.

    Fits & Features

    • Spaghetti straps
    • V Neckline and vertical dart seams 
    • Square back with no zipper
    • Triangular waist cut out
    • Mini length silhouette 
    • Crepe fabric 
    • Form-hugging fit with moderate stretch

    Style Number/Barcode: 05103-0292

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ribbed Knit Crew Neck Maxi Dress

    This simple yet stunning ribbed knit maxi dress is a must for your fab fall look. Featuring a high crew neckline and a flattering curve-hugging silhouette, this dress can easily be dressed up with some strappy heels or down with a pair of chunky sneakers. Wear on a casual date night with bae.

    Fit & Features

    • High crew neckline
    • Tank-like shoulder straps
    • Form-hugging fit
    • Side slit
    • Maxi length
    • Ribbed knit fabric

     

     

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0870

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feelin' Trendy Tie Dye Midi Dress

    This trendy tie dye knit midi dress is ready for you to style up! Featuring a sleeveless high neckline and a curve-hugging mid-length silhouette, you can easily take this dress from day to night. Layer on a denim jacket and some chunky sneakers for a casual-chic date look.

    Fit & Features

    • High rounded neckline
    • Mid-length silhouette
    • Form-hugging fit
    • Tie dye print
    • Knit fabric

     

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0866

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Floral Polka Dot Mini Dress

    Create a flirty first impression in this pretty floral polka dot mini dress! It features a cowl neckline, a flowy mini length silhouette, and a fun floral print on a polka dot woven fabric. For a cute day date look, layer on a denim jacket and pair with some clear heels.

    Fit & Features

    • Adjustable spaghetti straps
    • Cowl neckline
    • Flowy mini length fit
    • Floral print
    • Polka dot woven fabric

     

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0914

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Flair Woven Midi Dress

    You'll have that total floral flair in this stunning woven midi dress! Featuring a V neckline and a flowy mid-length silhouette, this dress would be perfect for a fall date night. Pair with some clear heels and accessorize with gold hoops to let the dress make the statement.

    Fit & Features

    • Adjustable spaghetti straps
    • V neckline
    • Back zipper closure
    • Flowy mid-length fit
    • Ditsy floral print
    • Woven fabric


    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0915

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirty Silhouette Lace Trim Plaid Mini Dress

    Flirty and adorable, this plaid woven mini dress features a sleeveless sweetheart neckline with a dainty eyelet lace and ribbon trim and front bow detail, spaghetti straps, and a short form-hugging silhouette to highlight your curves. Style with hoop earrings and sleek mules.

    Fit & Features

    • Plaid woven-blend fabric with moderate stretch, knit lining at the bust
    • Sweetheart neckline with lace and ribbon trim, front bow detail
    • Ruched bust, underbust seam
    • Spaghetti straps
    • Mini-length form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5934

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fall For Floral Woven Midi Dress

    Fall head over heels for this adorable ditsy floral midi dress! Featuring a trendy cowl neckline and a flowy mid-length silhouette, this dress would pair perfectly with some simple gold hoops and clear mules. Wear to your next brunch with your girls and you'll receive all the compliments.

    Fit & Features

    • Adjustable spaghetti straps
    • Cowl neckline
    • Flowy mid-length fit
    • Ditsy floral print
    • Woven fabric

     

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0882

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simple And Sleek Tie Shoulder Slip Dress

    Simple and sleek, this slip dress is a gorgeous piece you need to have in your closet. Featuring tie shoulder straps and a flowy mid-length silhouette, it can so easily be dressed up with some clear mules or down with chunky sneaks. Wear to your next date with bae and you'll leave a lasting impression.

    Fit & Features

    • Tie shoulder straps
    • Slight V neckline
    • Square back
    • Flowy mid-length fit
    • Woven fabric

     

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0895

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Walk in the Park Floral Mini Dress

    Take a stroll in style wearing this sweet floral dress! Pair it with sandals and a straw bag.

    Fit & Features

    • Ribbed Fabric
    • Off the Shoulder Puff Sleeves
    • Tie Front Detail
    • Mini Length

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0447

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simply Perfect Knit Mini Dress

    Get a simply perfect 'fit with this basic knit mini dress! With its fitted long sleeves and curve-hugging silhouette, this stretchy knit dress is oh-so-flattering. A definite for your next date night, keep it casual with a pair of chunky sneakers or glam it up with some bold block heels.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Short, form-hugging fit
    • Ribbed knit fabric
    • Plenty of stretch

    Style Number/Barcode: 06002-0519

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Strapless Tube Tie Dye Midi Dress

    Make a splash in a tie-dye dress that brings some serious summer vibes! Step out for that backyard bbq with the squad in this colorful midi dress. The dress features a strapless tube neckline, a tie-dye print, and a curve-hugging midi-length silhouette. Complete your summer outfit with clear heels

    Fit & Features

    • Sleeveless tube neckline
    • Tie-dye pattern
    • Midi length silhouette
    • Form hugging knit fabric
    • Moderate stretch 

     

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0831

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The Every Day Tube Midi Dress

    Step out in this staple dress to wear any day for any occasion! This midi dress is perfect for dressing up with heels to create a night out outfit or dressing down with sneakers for a casual coffee date. The dress features a sleek tube neckline and a midi length silhouette with a mini side slit. 

    Fit & Features

    • Sleeveless straight tube neckline
    • Midi length silhouette
    • Mini side slit
    • Knit fabric
    • Form hugging fit
    • Moderate stretch 

     

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0827

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Everyday Ruched Knit Mini Dress

    Get an effortless everyday 'fit in this adorable ruched knit mini dress! It features trendy ruched detailing with drawstrings and can be worn as a mini or midi. Dress it up with clear mules for a date night or keep it casual with some chunky sneakers for a shopping trip.

    Fit & Features

    • Tank-like shoulder straps
    • High rounded neckline
    • Ruched detailing
    • Drawstrings at hem
    • Form-hugging fit
    • Ribbed knit fabric

    Style Number/Barcode: 05102-1018

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Season of Stripes Cutout Gauze Mini Dress

    Keep it sassy in a striped dress this season to keep on-trend! Make a stunning impression for that upcoming date in a dress that features a plunging V-neckline, sexy bar waist cutouts, and a trendy striped design. Complete look with wedges and fringe earrings to channel bohemian vibes. 

    Fit & Features 

    • Sleeveless V-neckline
    • Smocked waist
    • Bar waist cutouts
    • Striped pattern
    • Mini length silhouette
    • Gauze-linen fabric
    • Form hugging fit, minimal stretch 

     

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0414

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Open Back High Slit Floral Dress

    Show off your affinity for florals in a dress that creates major head-turning appeal! Step out for brunch with your squad in this pretty in pink dress! The dress features a high round neckline, cap sleeves, a lower back keyhole, and a high side slit. Complete look with clear heels and mini purse.

    Fit & Features

    • High round neckline
    • Cap sleeves
    • Lower back keyhole
    • Floral print 
    • High side slit
    • Midi-length silhouette
    • Lightweight woven fabric

     

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0834

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance