Casual Dresses

HomeCasual Dresses
Loading...

Now Trending

STYLE SPOTLIGHT

Cute Sweater Dresses

Floral Print Dresses

Discover New Skater Dress Styles

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!

  • Double Drawstring Floral Mini Dress

    Bring the charm in a floral dress that brings a sweet vibe this season. The mini dress features a sweetheart neckline, adjustable spaghetti straps, and a floral print. Complete your look with cute cork wedges and dainty anklets

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Floral print
    • Drawstring at the side seams
    • Mini length silhouette
    • Form hugging fit

     

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

    Style Number/Barcode: 05101-0878

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stunning In Florals Sleeveless Midi Dress

    Be a stylish stunner in this gorg floral midi dress! Step out for brunch with the squad in this colorful midi dress. It features a sleeveless bodice, adjustable spaghetti straps that cross in the back, a V neckline, side ruched detailing, and an asymmetrical hem. Complete look with wedges.

    Fit & Features

    • Sleeveless v-neckline
    • Adjustable spaghetti straps
    • Crossback straps
    • Floral print
    • Ruched side seam
    • Midi length silhouette with asymmetrical hem 
    • Form hugging fit, plenty of stretch 

     

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

    Style Number/Barcode: 05102-0292

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Romanced in Ruffles A-Line Mini Dress

    Fall for this ruffled dress as you have em' fall for you girl! Step out for a day-date in this mini dress that features a ruffled off the shoulder neckline with a sweetheart bust, a cute tie-front accent, and an A-line mini length silhouette with ruffled hem. Complete your look with sunnies and wedges

    Fit & Features

    • Ruffled off the shoulder neckline
    • Sweetheart bust with tie-front accent
    • Mini length A-line silhouette
    • Ruffled hem 
    • Form hugging fit

     

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

    Style Number/Barcode: 05102-0811

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Denim and Lace Open Back Mini Dress

    Give our denim dress a glam touch with a little lace. The mini dress features a plunging v-neckline with lace trim, adjustable spaghetti straps that offer support, and a bold open back with bar strap ties. Complete your head-turning look with cork heels

    Fit & Features

    • Sleeveless v-neckline with lace trim
    • Adjustable spaghetti straps
    • Open back with bar strap ties
    • Mini length hem with lace trim
    • Denim fabric 
    • Form hugging fit 


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

    Style Number/Barcode: 05102-0774

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Beauty Sleeveless Chiffon Maxi Dress

    Radiate beauty in a floral maxi dress that brings the charm. Perfect for that next bridal shower this maxi dress features a sleeveless plunging v-neckline, a crochet lace detailed lace, and an all-over floral print. Complete your romantic outfit with duster earrings and clear heels

    Fit & Features

    • Sleeveless plunging v-neckline
    • Crochet lace detailed waistband 
    • Floral print
    • Maxi length silhouette
    • Chiffon knit fabric 
    • Relaxed fit 

     

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

    Style Number/Barcode: 05101-0596

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tie-Dye Satin Cowl Neck Mini Dress

    Keep it chic in a tie-dye dress to brighten your cute summer fits girl! The dress features a sleeveless bodice, a cowl neckline, sleek spaghetti straps, and a pretty pastel tie-dye print. Complete your look with a chic scrunchie and a dainty charm necklace.

    Fit & Features

    • Sleeveless bodice
    • Cowl neckline
    • Tie-dye print
    • Mini length silhouette
    • Satin fabric
    • Relaxed fit 

     

    Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0812

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Breeze On By A-Line Mini Dress

    Breeze right through the crowd (and catch some glances doing it!) in this simply chic mini dress! Elevate your look adding some dainty jewels and a pair of strappy mules!

    Fits & Features 

    • Surplice v neckline  
    • Short sleeves 
    • Mini length hem, A-line silhouette
    • Smooth, stretchy knit fabric 
    • Form hugging fit, plenty of stretch 
    • Zipper not included

     

    Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0687

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Too Sweet Sweetheart Ditsy Floral Mini Dress

    You'll look too sweet in a floral dress that brings the charm. This pretty date-night dress features a sweetheart neckline, a tie front accent, and a ditsy floral print. Complete your look with a light wash denim jacket and wedges

    Fit & Features

    • Sleeveless sweetheart neckline
    • Tie front accent at the center of the bodice
    • Spaghetti straps 
    • Ditsy floral print
    • Mini length silhouette

     

    Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0767

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On Your Radar Ruched Maxi Dress

    Get on their radar in a sleek maxi dress that shows off curves in all the right places. The maxi dress features a square neckline, sleek spaghetti straps and ruched maxi length silhouette with a high side slit to show off glowing gams. Complete your look with clear heels and statement earrings

    Fit & Features

    • Sleeveless square neckline
    • Sleek spaghetti straps
    • Maxi length silhouette
    • Ruched side seams that streamline design
    • High side slit
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 

     

    Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0332

    Category Name: Casual Dresses

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Adore You Floral High Slit Maxi Dress

    Feel adored in a floral dress that brings some serious butterflies this season. The dress features a gorgeous floral print, a flattering cowl neckline, and a maxi length silhouette that is accented a high side slit. Complete your date-night ready outfit with sleek hoop earrings and strappy heels that mesmerize. 

    Fit & Features

    • Sleeveless bodice
    • Cowl neckline
    • Spaghetti straps that cross at the back
    • Floral print
    • Maxi length silhouette
    • High side slit
    • Smooth knit fabric, form-hugging fit

     

    Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0529

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Covetable Charm Strapless Mini Skater Dress

    From casual outings to chic occasions, this strapless skater dress is one you'll covet for charming looks every time! The non-slip grip lining along the strapless neckline ensures a secure fit while the ruched bodycon bodice flatters your figure. The skater silhouette and pleated short-length hem add a playful touch to this poplin dress! Complete the look in sandals and sunnies.

    Fit & Features

    • Poplin stretchy fabric, sewn-in knit lining
    • Back zipper and hook-eye closure
    • Strapless square neckline
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3079

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Scooped In Style Sleeveless Cutout Ribbed Maxi Dress

    Serve up a stylish look in a maxi dress that slays girl! Step out in this dress that features a sleeveless bodice, a scoop neckline with tank-like straps, a sexy mid-drift cutout to show off a hint of skin, and a maxi length silhouette with twist front accent to reveal a mini length skirt. Complete outfit with wedges and fringe earrings. 

    Fit & Features 

    • Sleeveless scoop neckline
    • Tank-like straps
    • Mid-drift cutout
    • Maxi length silhouette overlay with twist front accent 
    • Mini length skirt 
    • Ribbed knit fabric 
    • Form hugging fit

     

    Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0462

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Daisy Days Smocked Mini Dress

    Keep it fab in florals this season with this charming mini dress! Pair with wedges and a cute tote for the perf lewk honey! 

    Fit & Features 

    • Square Neckline | Smocked Trim
    • Inset | Tie at Bust 
    • Spaghetti Tie Straps 
    • Daisy Floral Print
    • Smocked Knit Fabric 
    • Form Hugging Fit 
    • Moderate Stretch 

     

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

     

    Style Number/Barcode: 05102-0684

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Ditsy Smocked Tie Front Mini Dress

    Spring into a smocked disty mini dress to keep on trend this season. This flirty piece features a sweetheart neckline, a tie front with a small keyhole at the bust, and an all-over floral ditsy print. The relaxed fit bodice leads to a curve-hugging mini-length silhouette. The dress is composed of a smocked knit fabric that offers a moderate stretch. Complete your look with hoop earrings and minimal heels

    Fit & Features

    • Sweetheart neckline
    • Keyhole at bust
    • Floral ditsy print
    • Smoked fabric
    • Form-hugging fit
    • Moderate stretch 

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

    Style Number/Barcode: 05102-0497

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetheart Neck Ruffled Ditsy Print Mini Dress

    Keep on trend in a floral ruffle dress. The ditsy floral dress features a sweetheart neckline, ruffled shoulder straps and an-all over ditsy floral print. The relaxed fit waist leads to a mini length silhouette that offers a curve-hugging fit with slight stretch. Complete your outfit with hoops and dad sneakers for a casual vibe. 

    Fit & Features

    • Sweetheart neckline
    • Ruffled shoulder straps 
    • Ditsy floral print 
    • Mini length silhouette 

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

    Style Number/Barcode: 05102-0538

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Start Fresh Ruffle And Ruched Mini Dress

    It's time to refresh your wardrobe with this adorable mini dress! It features spaghetti straps, a ruffled V neckline, center ruching, and a short, curve-hugging fit. The lined knit fabric offers plenty of stretch for comfortable wear. Accessorize your look with cat-eye sunglasses and heeled mules.

    Fit & Features

    • Spaghetti straps
    • Ruffled V neckline
    • Ruching down the center front
    • Mini-length silhouette
    • Form-hugging fit
    • Fully lined knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-0591

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet like Candy Ruffle Mini Dress

    You’ll be looking sweet for date night in this fab mini dress! It features spaghetti straps, a wrap-front V neckline, front ruching, and a short, form-hugging fit with an asymmetric ruffled front hem. Style the dress with clear heels and a trendy mini bag.

    Fit & Features

    • Spaghetti straps
    • Wrap-front V neckline
    • Ruched detailing
    • Mini-length, asymmetric ruffled hem
    • Curve-hugging silhouette
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4088

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off The Shoulder Ruched Dotted Mini Dress

    Bring the charm in a dotted mini dress to make a flirty impression. The dress features an off the shoulder neckline, sheer long sleeves with a swiss dot pattern and a ruched silhouette throughout. Complete your date night ready look with extra-large hoops and sleek stilettos

    Fit & Features

    • Off the shoulder neckline
    • Sweetheart bust with tie front accent
    • Long sheer sleeves with swiss dot pattern
    • Ruched body
    • Mini length silhouette
    • Form hugging fit

     

    Blue: Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.

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

    Style Number/Barcode: 05101-0801

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tropical Ruffled Chiffon Skater Dress

    Bring the charm in a ruffled dress that gets those tropical island vibes just right! This vacay-approved dress features a tropical palm-leaf print, a plunging V neckline, ruffled shoulder straps, a cinching tie waist belt, and a flirty skater silhouette. Complete the outfit with pretty wedge heels and fringe earrings.

    Fit & Features

    • Tropical palm-leaf print
    • Plunging V neckline
    • Ruffled shoulder straps
    • Tie waist belt 
    • Open back with tie back ties
    • Lower back zipper and hook and eye closure
    • Skater silhouette 
    • Sheer chiffon fabric with a woven lining
    • Runs true to size

    Style Number/Barcode: 05102-0264

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Persuasion Smocked Mini Dress

    Get on this sweet trend this season! Brighten up your closet with pretty florals to make a charming impression! Pair mini dress with your fav wedges to complete the look!

    Fit & Features

    • Square Neckline | Tie Front Accent 
    • Adjustable Spaghetti Straps
    • Smocked Waist and Back 
    • Floral Print 
    • Lined Lightweight Woven Fabric
    • Mini Length Silhouette 
    • Relaxed Fit | Minimal Stretch 

     Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small. 

     


    Style Number/Barcode: 05102-0445

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fresh Blooms Side Slit Maxi Dress

    It's time to refresh and reset for the szn! This spring-ready maxi will be your go-to piece for daytime events! Slip into some mules and add some layered necklaces for a pretty OOTD! 

    Fits & Features

    • Spaghetti Straps
    • Scoop Neckline 
    • Thigh High Side Slit
    • Maxi Length Silhouette 
    • Form Hugging Fit
    • Zipper Not Included 

    Model is 5'9" with a 34" bust, 25" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0289

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Support Smocked Skater Dress

    Grow through what you go through. Look and feel uplifted in this cute AF floral dress! Throw on a crop denim jacket and some sneakers for an OOTD! 

    Fits & Features

    • Self Tie Spaghetti Straps 
    • Square Neckline 
    • Smocked Bodice
    • Mini Length I Skater Silhouette 
    • Woven Fabric I Smooth Knit Lining 
    • Ample Stretch 

    Style Number/Barcode: 05102-0444

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Flirt Skater Dress

    Hey bby! You'll be a total flirt in this pretty floral skater dress! Pair with some strappy sandals and a boho chic panama hat!

    Fit & Features

    • Spaghetti straps | V neck and back
    • Ruched front | Tie closure
    • Small front keyhole cut out
    • High waist
    • Flowy skater skirt
    • Stretchy knit fabric
    • Small all over floral print

    Style Number/Barcode: 05102-0416

    Category Name: Casual Dresses

    Price: $13.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Tropical Surplice Wrap Maxi Dress

    Wrap yourself in a floral maxi dress. Bring the vacation vibes this season in this dress that features an all-over tropical floral print, a sleeveless surplice wrap neckline, and spaghetti straps. The relaxed fit waist leads to a carefree maxi length silhouette. The dress is composed of a lightweight smooth knit fabric that offers a form hugging fit. Complete your outfit with dainty bracelets and face-framing sunglasses.

    Fit & Features

    • Sleeveless
    • Wrap v-neckline
    • Spaghetti straps
    • Tropical floral print
    • Maxi length silhouette
    • Smooth knit fabric
    • Form hugging fit

    Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0194

    Category Name: Casual Dresses

    Price: $21.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free