Casual Dresses

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STYLE SPOTLIGHT

Cute Sweater Dresses

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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!

  • Flirty Aura Puff Sleeve Floral Lace Skater Dress

    Captivate them with your flirty aura in the cutest floral lace skater dress! The dainty sheer floral lace fabric will give your look a soft feminine vibe and includes a partial woven lining for coverage. The bodice is shaped with a plunging V-neckline with a tie-front detail and sheer short puff sleeves with elasticized hems. The open back adds to the allure and features a tie-back design. The dual high waist seams lead to a fit-and-flare skater silhouette on a short-length hem that was made to twirl. Style this adorable dress with wedge heels for a spring or summer party!

    Fit & Features

    • Sheer floral lace fabric with partial woven lining, no stretch
    • Plunging V-neckline with tie-front
    • Short puff sleeves with elasticized hems
    • Open back, tie-back, lower back zipper with hook and eye closure
    • Dual high waist seams
    • Fit-and-flare skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-2967

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Floral Ruched Mesh Mini Dress

    Walk into any party looking like a dream in this floral ruched mesh mini dress! The bold multi-colored floral print will capture all the attention, while the airy mesh fabric offers breezy comfortable wear. The mini-length dress features a sleeveless square neckline with adjustable spaghetti straps for a customized fit. The trendy ruched detailing down the side seams will accentuate your curves along the alluring bodycon silhouette. Style this short dress with hoop earrings and clear heels.

    Fit & Features

    • Floral print
    • Sheer mesh, sewn-in knit lining
    • Sleeveless square neckline
    • Spaghetti straps
    • Ruched side seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5534

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Thoughts Sleeveless Cutout Crochet Maxi Dress

    Get summer vibes in an instant wearing this crochet maxi dress perfect for vacation or strolling the boardwalk! Featuring a flattering square neckline, spaghetti straps, and a stunning cutout back with an adjustable drawstring insert and a front slit for movement along the maxi-length silhouette. Complete the look with sunglasses and sandals.

    Fit & Features

    • Crochet knit fabric lined with stretchy knit
    • Spaghetti straps
    • Square neckline
    • Cutout back, adjustable drawstring insert
    • Front slit
    • Maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5742

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Babe Tie-Back Crochet Mini Dress

    Channel a beachy babe vibe in this trendy crochet mini dress! Designed with a sheer crochet fabric with a boho-inspired woven design, the short dress includes a stretchy knit lining for coverage. It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, an adorable tie-back design, a flirty lower back cutout that peaks out on both sides, and a form-hugging fit to flaunt your figure. Style with espadrille sandals.

    Fit & Features

    • Crochet fabric with woven design, stretchy knit lining
    • Square neckline
    • Adjustable spaghetti straps
    • Tie back straps, back cutout
    • Hidden side zipper with hook and eye closure
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5780

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Knit to Stun Open Back Mini Dress

    Keep your look playful and unexpected. This sweater mini dress keeps it sleek in the front, daring in the back. The cable knit keeps it cozy while the open back brings a hint of drama. perfect for fall slays.

    Fit & Features

    • Soft cable knit fabric with stretch
    • Mock neckline
    • Fitted long sleeves
    • Open back cutout design
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000161

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Radiate Romantic Vibes Strapless Floral Chiffon Maxi Dress

    Radiate romantic vibes in this strapless floral chiffon maxi dress at garden parties or showers! The long ruffled silhouette adds flow and movement while the floral chiffon fabric adds a touch of femininity. Perfect for any occasion, this dress will make you stand out with its playful and flirty style! Complete the look with teardrop earrings.

    Fit & Features

    • Floral printed chiffon fabric with stretchy knit lining
    • Strapless neckline
    • Back zipper and hook-eye closure
    • Ruffled flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3044

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charmed And Cute Polka Dot Chiffon Skater Dress

    Envoke a charmed and cute style in this polka dot skater dress perfect for showers or graduates! Show off your curves with the sweetheart neckline and skater silhouette, while adding a touch of cuteness with the short puff sleeves. The tie-back adds a flirty detail and the short-length hem is perfect styling with trendy sneakers for a casual vibe.

    Fit & Features

    • Polka dot, chiffon fabric, woven lining, no stretch
    • Sweetheart neckline
    • Padded bra cups
    • Back zipper hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3289

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Style Short Sleeve Ruched Mini Dress

    Level up your everyday style with this simple yet chic mini dress! The lightweight smooth nylon fabric includes a knit lining and offers plenty of stretch for ultra-comfortable wear. Shaped with a classic scoop neckline and short sleeves, the mini-length dress features ruching down the side seams to flaunt your figure on the bodycon silhouette. Pair with a denim jacket and sneakers.

    Fit & Features

    • Smooth nylon fabric with knit lining, plenty of stretch
    • Scoop neckline
    • Short sleeves
    • Ruched side seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5669

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Thing Strappy Back Halter Babydoll Dress

    Experience the ultimate blend of sweet and sultry in this babydoll mini dress at shower celebrations or backyard parties! The delicate lace trim on the halter V-neckline adds a touch of femininity, while the strappy open back turns heads along the ruffled, flowy silhouette.

    Fit & Features

    • Woven fabric, woven lining
    • Halter V-neckline, lace trim, bust tie
    • Strappy open back, adjustable spaghetti straps
    • Ruffled babydoll silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6036

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Well Played Denim Bodycon Wrap Midi Dress

    Well played! This denim midi dress is the perfect pick for having all eyes on you. It features a square neckline, adjustable straps, and a side pleated seam that creates the bodycon silhouette with an asymmetrical wrap slit hem. Complete the look in cute stiletto mules for a day or night out!

    Fit & Features

    • Sleeveless square neckline, adjustable straps
    • Back zipper and hook-eye closures
    • Side pleated seam
    • Bodycon silhouette, asymmetrical wrap slit
    • Midi-length hem
    • Denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5251

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Modern Masterpiece Short Sleeve Marble Midi Dress

    Your look will be a modern masterpiece in this marble print mesh midi dress - a stunning piece for art gallery openings or cocktail parties! The airy sheer mesh fabric is lined with a stretchy knit for comfortable wear. The short sleeves and crew neckline create a classic look, while the bodycon silhouette accentuates your curves down to the midi-length hem with a back slit for movement. Complete the look with a purse and strappy stiletto heels.

    Fit & Features

    • Marble print
    • Sheer mesh fabric lined with stretchy knit
    • Crew neckline
    • Short sleeves
    • Bodycon silhouette
    • Back slit
    • Runs true to size

    Style Number/Barcode: 05102-5535

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute And Sunny Floral Skater Dress

    Made for cute sunny day dressing, this floral mini dress flaunts adorable puff sleeves and a skater silhouette that flatters any figure!

    Fit & Features

    • Floral print, eyelet knit fabric, stretchy knit lining
    • Puff short sleeves
    • Square neckline, ruched bust
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6041

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Sunny Scoop Neck Skater Eyelet Mini Dress

    Sunshine days are ahead and this skater mini dress is perfect for enjoying the weekend and weather! Crafted from an adorable eyelet knit fabric, this mini dress is designed with a flattering scoop neckline, adjustable spaghetti straps for a perfect fit, and a flirty tie-back detail to show off your style. The skater silhouette and tiered ruffled hem allow for movement and a fashionable sway with every step! Complete the look in heeled sandals.

    Fit & Features

    • Eyelet knit fabric, sewn-in knit lining
    • Adjustable spaghetti straps
    • Tie-back detail
    • Skater silhouette
    • Tiered ruffles
    • Runs true to size

    Style Number/Barcode: 05102-5426

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine And Good Time V-Neck Mermaid Maxi Dress

    This mermaid maxi dress is here for sunshine and good times! Made from textured mesh fabric, this dress will have you feeling so cute. Features a flattering V-neckline, dual spaghetti straps, a crisscross back, and a bust cutout. The mermaid silhouette and high front slit accentuate your curves, while the maxi-length hem adds a touch of chicness. Complete the look with sandals and sunglasses!

    Fit & Features

    • Textured mesh fabric, stretchy knit lining
    • Dual spaghetti straps
    • V-neckline
    • High front slit
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5690

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tea Time Ruffled Short Skater Dress

    It's time for afternoon tea and this skater dress will make an adorable entrance! Get ready to sashay in this dress featuring a ruffle trim square neckline and tiered ruffled short-length hem to add a playful touch to the skater silhouette. And with adjustable spaghetti straps and a stretchy smocked bodice, you'll be comfortable all day. Complete the look in chic wedges and a flouncy hat.

    Fit & Features

    • Woven fabric lined with woven fabric
    • Ruffle trim neckline
    • Adjustable spaghetti straps
    • Stretchy smocked bodice
    • Tiered ruffled short-length hem
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3059

    Category Name: Casual Dresses

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Evening Ember Floral Midi Dress

    With its warm floral print and sleek silhouette, this midi dress is a fall-ready stunner. The mock neck detail adds sophistication, while the ruched fit keeps it fresh for date nights, parties, or a night out at the wine bar with the girls.

    Fit & Features

    • Abstract floral print, mesh-lined fabric
    • Sleeveless mock neck
    • Ruched bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000257

    Category Name: Casual Dresses

    Price: $35.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Island Oasis Tropical Cutout Skater Dress

    Enter a sweet oasis looking cute in this tropical woven skater dress ready for some serious island time! Featuring adorable puff short sleeves, a V-neckline, a back cutout with trim detail, a stretchy smocked back, and a tiered fit-and-flare short-length silhouette. The airy sheer woven fabric features a tropical floral print pattern and includes a knit lining. Complete the look in strappy wedges.

    Fit & Features

    • Tropical floral print
    • Sheer woven fabric, knit lining, minimal stretch
    • Puff short sleeves, elastic cinched hems, tie-back straps
    • V-neckline, cutout back with trim detail
    • Stretchy smocked back
    • Tiered fit-and-flare skater silhouette, short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-4890

    Category Name: Casual Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daydream Tie-Dye Bodycon Mini Dress

    You'll be lookin' like a daydream in this trendy tie-dye bodycon mini dress! Designed with an asymmetric tie-dye pattern on the airy mesh fabric, it features a sleeveless square neckline, bungee spaghetti straps, ruching down the side seams, a mini-length hem, and a bodycon silhouette to accentuate your curves. The sheer mesh fabric includes a full-length knit lining. Style this short dress with platform heels.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruched side seams
    • Mini-length hem, bodycon fit
    • Asymmetric tie-dye pattern
    • Sheer mesh fabric, full-length sewn-in knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5481

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Radiant Vacay V-Neck Floral Chiffon Skater Dress

    Twirl your problems away on vacay in this radiant floral chiffon skater dress! The sheer peasant long sleeves, V-neckline, and corset-inspired bodice add a touch of romance, while the skater silhouette and ruffled hem bring a playful charm. Perfect for any occasion, from vacation to brunch! Complete the look in cute wedge sandals and sunnies.

    Fit & Features

    • Floral print, chiffon fabric lined with woven fabric
    • Keyhole back with button closure
    • Skater silhouette
    • Ruffled short-length hem
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05101-3186

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Inspired Charm Strapless Watercolor Print Mini Dress

    Envoke an inspired charm in this watercolor print mini dress and capture attention at parties or casual dinners!  With its strapless straight-across neckline and bodycon silhouette, this mini dress will accentuate your curves and flatter your figure. Made from airy lined mesh fabric with an eye-catching watercolor print, this dress is a must-have for any fashion-forward girlie! Complete the look in stiletto heels and a purse!

    Fit & Features

    • Watercolor print
    • Mesh fabric lined with stretchy knit
    • Strapless straight neckline
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5605

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Contemporary Sleek Bodycon Midi Dress

    Made in a soft rib knit fabric that snatches your figure, this sleeveless midi dress offers a contemporary and sleek style with a sleeveless square neckline and a bodycon silhouette. Pair with hoop earrings and a blazer.

    Fit & Features

    • Soft rib knit fabric, moderate stretch
    • Square neckline
    • Wide angled shoulder straps
    • Bodycon silhouette
    • Center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5951

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Love Eyelet Knit Mini Dress

    You'll fall in love with the effortless summer vibes of this eyelet knit mini dress! It features a sleeveless square neckline, spaghetti straps, a mini-length hem, a form-hugging fit, and a pretty floral eyelet pattern. The lined knit fabric offers plenty of stretch for comfortable wear. Style with strappy sandals.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Mini-length hem
    • Form-hugging fit
    • Floral eyelet pattern, knit fabric, knit lining
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5113

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Day Gal Strapless Ruffled Skater Dress

    Let your shoulders out in this strapless skater dress suited best for sunny days! This dress features a stretchy smocked bodice for a comfortable fit and a skater silhouette that will flatter your figure. The layered ruffled short-length hem adds a playful touch, and the cotton woven fabric ensures all-day comfort. Complete the look with a choker necklace.

    Fit & Features

    • Cotton woven fabric
    • Strapless straight neckline, no-slip strip
    • Stretchy smocked bodice
    • Layered ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5476

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Sweet Eyelet Knit Tiered Skater Dress

    You'll look extra sweet for your next weekend brunch in this adorable eyelet knit skater dress. The strapless neckline, ruched side seams, drop waist, and short tiered design are all flirty details you'll adore.

    Fit & Features

    • Sheer eyelet knit fabric with full-length knit lining, moderate stretch
    • Strapless straight neckline
    • Ruched side seams
    • Drop waist
    • Short tiered design, skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6012

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free