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!

  • Compliment Me High Slit Knit Midi Dress

    You'll spark up all the compliments in this simply chic high slit midi dress! Designed with a stretchy structured knit fabric, this dress is shaped with a sleeveless square neck and back with thin tank shoulder straps. The mid-length hem is accented with a high-cut side slit to show off some leg, and the bodycon silhouette will flaunt your stunning curves. Style with a faux leather jacket and heels to go bar-hopping!

    Fit & Features

    • Stretchy structured knit fabric
    • Sleeveless square neck and back
    • Tank shoulder straps
    • High side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5526

    Category Name: Casual Dresses

    Price: $5.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Striped Delight Surplice Collared Mini Dress

    You're sure to have a day full of sweetness in this delightful striped mini dress perfect for upcoming weekend plans! This dress is designed with chic long sleeves with button cuffs, along with a flattering collar V-neckline and wrap tie waist belt for that cinched look. The surplice mini-length hem adds a touch of sass while the pleated form-hugging fit accentuates your curves. Complete the look in clear sandals and earrings.

    Fit & Features

    • Striped non-stretch woven lightweight fabric
    • Collared V-neckline
    • Long sleeves with buttoned cuffs
    • Wrap tie waist belt with pleating
    • Surplice mini-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5610

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunny Afternoons Collar Open Back Skater Dress

    Enjoy a sunny afternoon looking like a cutie in this skater dress perfect for a girl's day! With a sleek halter collar neckline and flattering button-down front, this dress will accentuate your figure with its fitted high waist seam. The playful open back with tie closure adds a touch of allure, while the skater silhouette and short-length hem create a fun and flirty look. Complete the look in strappy sandals and earrings.

    Fit & Features

    • Lightweight woven fabric with lining
    • Open back with tie closure
    • Button down front
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5616

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Late Night Whispers Lace-Up A-Line Mini Dress

    Slip into your spotlight moment—this flocked velvet pattern mesh mini dress is sleek, strappy, and just the right amount of flirty. With its open tie-back and barely-there vibe, it’s basically made for GNOs!

    Fit & Features

    • Flocked velvet pattern, mesh-lined fabric
    • V-neckline
    • Spagehtti straps
    • Lace-up open back
    • A-line fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000387

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: GRAY

    Available Size: L

  • Trendy Topic Strapless Denim Midi Dress

    You'll be the topic of conversation in this denim midi dress for the trendiest look at casual hangs or brunch! This stunning denim dress features a strapless neckline and a form-hugging silhouette that will accentuate your curves. The belt loop accents and four-pocket styling add cute functional details, while the front center slit and midi-length hem provide a modern touch. Complete the look in sleek hoop earrings and pumps!

    Fit & Features

    • Denim fabric with minimal stretch
    • Belt loops, four-pocket styling
    • Front center slit
    • Side zipper closure
    • Form-hugging silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5455

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ready For Romance Floral Velvet Lace Mini Dress

    Unleash your inner daring in this floral velvet mini dress on an evening out! With a lace-trim V-neckline, sleek adjustable bungee spaghetti straps, and a low-cut back, this bodycon dress will turn heads. The front bow adds a touch of romance, while the floral velvet pattern on mesh fabric adds an alluring texture. Complete the look with a clutch, heels, and a bolero for a stylish head-to-toe outfit!

    Fit & Features

    • Floral velvet pattern, mesh fabric lined with knit
    • Bungee adjustable spaghetti straps
    • Lace trim and bow inset
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-5315

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Loved In Lace V-Neck Long Sleeve Short Dress

    A divine lace short dress for modern brides, birthday babes, or any dressy occasion! The mini dress features sheer lace long sleeves with flared cuffs, a V-neckline, a bodycon silhouette that hugs your curves and is composed of a lace knit fabric with stretchy knit lining. Complete the look with fringe earrings and heels.

    Fit & Features

    • Sheer long sleeves, flared cuffs
    • V-neckline
    • Bodycon silhouette
    • Short-length hem
    • Lace knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-3171

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

  • Pretty Bloom Floral Ruffled Mesh Mini Dress

    This blooming floral ruffled mesh mini dress will give off the prettiest vibes at spring parties! The stretchy lined mesh fabric showcases a bold floral print to capture all the compliments. The sleeveless sweetheart neckline and adjustable spaghetti straps shape the bodice, while the ruching at the bust and down the seams accentuate your curves on the bodycon silhouette. The mini-length dress features a ruffled sash accent at the side that cascades down for that effortless flair. Style with nude heels.

    Fit & Features

    • Floral printed stretchy sheer mesh fabric, knit lining
    • Sleeveless sweetheart neckline, padded bust
    • Adjustable spaghetti straps
    • Ruching
    • Ruffled sash
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3272

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Favorite Tune Sleeveless Tank Midi Dress

    Get ready to sing about this sleeveless midi dress and how much you love it! With a stylish sleeveless square neckline and flattering shoulder straps, this midi dress will hug your curves in the form-hugging silhouette and show some skin with the front slit. Perfect for any occasion, style this midi dress with a denim jacket and long necklace for an effortlessly chic look!

    Fit & Features

    • Sleeveless square neckline, shoulder straps
    • Form-hugging silhouette
    • Front slit
    • Midi-length hem
    • Rib knit fabric, bust knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5397

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Destination Cutout Tropical Print Maxi Dress

    Get ready to jet set to your dreamy destination with this sexy tropical maxi dress! The lightweight woven fabric showcases an abstract tropical print to bring that bold allure to your next getaway. The maxi-length dress features a sleeveless halter neckline with tie-back straps that can be styled as a criss-cross high neck or a sultry plunging design according to your fashion mood! The long dress has a chic center O-ring accent and eye-catching waist cutouts with thin straps that lead to an open back with a tie-back design. The flowy A-line fit will bring those breezy vibes, while the dual thigh-high side slits add a sexy silhouette. Complete your look with heeled sandals!

    Fit & Features

    • Tropical printed woven fabric
    • Sleeveless halter neckline, tie-back straps
    • Waist cutouts, O-ring accent
    • Open back, lower tie-back straps
    • Dual high-cut side slits
    • Flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5356

    Category Name: Casual Dresses

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sheer Desire Square Neck Bodycon Mesh Midi Dress

    Unveil a desirably chic look in this mesh midi dress at daytime parties and brunch! The adjustable spaghetti straps provide a customizable fit while the side ruching and bodycon silhouette accentuate your figure for a confident and alluring look. Elevate any occasion with this must-have dress by styling it with block heels and earrings!

    Fit & Features

    • Sheer mesh fabric lined with sewn-in knit
    • Adjustable spaghetti straps
    • Side ruching
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5506

    Category Name: Casual Dresses

    Price: $5.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Creative Side Abstract Print Mesh Mini Dress

    A mesh mini dress that showcases your creative side in a stunning abstract print that'll have all eyes on you at parties! With a flattering mock neckline, fitted long sleeves with flared slit cuffs, and a bodycon silhouette, this mini dress elevates your every day with stylish detail. Complete the look in sleek mules and earrings.

    Fit & Features

    • Abstract print, mesh fabric lined with mesh
    • Long sleeves with flared slit cuffs
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5516

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Flair High Slit Ditsy Floral Knit Midi Dress

    Bring the sweet flair to date night in this high slit ditsy floral midi dress! The all-over ditsy floral print on the stretchy knit fabric is the perfect amount of sweetness with the sultry details of the mid-length dress. The sleeveless scoop neckline features a tie-front at the bust for a cute touch, spaghetti straps, an alluring thigh-high side slit to showcase some leg, and a slim-fit silhouette to showcase your figure. Style this midi dress with a faux leather jacket and heels!

    Fit & Features

    • Ditsy floral print, stretchy knit fabric
    • Sleeveless scoop neckline with bust tie
    • Spaghetti straps
    • Thigh-high side slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5485

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet And Chic Lace-Trim Knit Midi Dress

    So sweet and chic, this lace-trim knit midi dress is perfect for elevating your date night look! Designed with a stretchy ribbed knit fabric, this mid-length dress includes an airy mesh lining. The sleeveless V-neckline has spaghetti straps and is accented with a dainty sheer lace trim for a stylish touch, and includes an angled underbust seam to accentuate your figure. The bodycon silhouette will show off your gorgeous curves. Pair this adorable midi dress with hoop earrings and strappy mules!

    Fit & Features

    • Stretchy ribbed knit fabric, full-length mesh lining
    • Sheer lace trim
    • Sleeveless V-neckline, underbust seam
    • Spaghetti straps
    • Mid-length hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5497

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smooth Silhouette Crew Neck Cutout Midi Dress

    Dress this smooth midi dress up or down for any occasion! With a sleek crew neckline and sultry front cutout with bar trim, this bodycon dress accentuates your curves for a flattering fit. Made with buttery soft fabric that has a stretchy knit lining, you'll feel both sexy and comfortable. Complete the look in a moto jacket and boots for weekend plans!

    Fit & Features

    • Sleeveless crew neckline
    • Front cutout with bar trim
    • Bodycon silhouette
    • Midi-length hem
    • Smooth buttery soft knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5482

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jet Set For Sun Strapless Tropical Midi Dress

    Jet set for fun under the sun in this tropical midi dress for endless compliments while on vacation! The midi-length dress features a strapless neckline, a form-hugging silhouette, a flirty side slit and asymmetrical hem, and an adjustable side drawstring so you customize the style. Complete the look in sandals for a sunset dinner!

    Fit & Features

    • Strapless neckline
    • Form-hugging silhouette
    • Adjustable side drawstring, side slit
    • Asymmetrical midi-length hem
    • Tropical print, mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5486

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • My Main Chic V-Neck Ruched Midi Dress

    Ultra-flattering and soft, this sleeveless midi dress will be your main chic style! The knee-length dress is designed with a classic V-neckline, spaghetti straps, side ruched seams, and a bodycon silhouette that shows off your curves on smooth-lined knit fabric. Complete the look with stiletto heels for a birthday brunch or bridal shower!

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Side ruched seams, bodycon silhouette
    • Midi-length hem
    • Lined smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5479

    Category Name: Casual Dresses

    Price: $6.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Style On Point Bodycon Mini Dress

    Keep your style on point with this simply chic bodycon mini dress. It features a sleeveless mock neckline, tank shoulder straps, ruching down the side seams to accentuate your curves, a mini-length hem, and a bodycon silhouette. The double-lined smooth knit fabric offers plenty of stretch for comfortable wear. Pair this short dress with strappy heels to grab drinks!

    Fit & Features

    • Sleeveless mock neckline
    • Tank shoulder straps
    • Ruched side seams
    • Mini-length hem
    • Bodycon silhouette
    • Double-lined smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5520

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • It Girl High Neck Lace Up Maxi Dress

    That “did she just walk in?” kind of dress. The bodycon knit dress hugs in all the right places with a lace-up back that does the flirting for you.

    Fit & Features

    • Texture knit fabric, knit lining
    • High neckline
    • Spaghetti straps
    • Lace-up back
    • Bodycon fit, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000108

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK, BROWN

    Available Size: XS, S, M, L

  • Stunning Vision Abstract Mesh Midi Dress

    You'll be a stunning vision in this mesh midi dress out for a day date or brunch! It features a sleeveless square neckline, adjustable spaghetti straps, side ruching that accentuates your natural curves, and a flattering bodycon silhouette. The dress is designed with an artsy abstract print on mesh fabric and has a sewn-in knit lining. Complete the look with a trendy denim crop jacket.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Side ruching, bodycon silhouette
    • Midi-length hem
    • Abstract print, mesh fabric, sewn-in knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5496

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fashion Lovers Of Basic Mock Neck Mini Dress

    Calling all fashion girlies! Check out this basic mini dress perfect for daring bold girls. The mini-length dress is designed with fitted long sleeves, a mock neckline, a front half-zip-up closure, and a flattering bodycon silhouette on smooth rib knit fabric that fits like a glove. Style with a baseball cap, jacket, and your favorite kicks!

    Fit & Features

    • Fitted long sleeves
    • Mock neckline
    • Half zip-up closure
    • Bodycon silhouette, mini-length hem
    • Smooth rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5357

    Category Name: Casual Dresses

    Price: $5.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Demeanor Mock Neck Ribbed Knit Midi Dress

    Stay sweet and comfy in this ribbed knit midi dress perfect for any occasion! Designed with cap sleeves, a mock neckline, and a flattering bodycon silhouette, this mid-length dress is trend-worthy with a flirty front slit along the hem. Complete the look with a cute crop jacket and booties!

    Fit & Features

    • Stretchy ribbed knit fabric
    • Mock neckline
    • Cap sleeves
    • Bodycon fit
    • Front slit, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5304

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Stylish Linen Dress

    You'll look effortlessly stylish this season in this lightweight and flowy linen dress! Designed with a breezy woven fabric, this short dress is perfect for your summer parties. The bodice is shaped with a square neckline with ruching at the bust and long balloon sleeves. The fitted waistband creates a cinched silhouette, flowing out to a short ruffled hem with an A-line fit for a pretty flair. Complete the look with clear heels.

    Fit & Features

    • Linen woven fabric, no stretch
    • Square neckline, ruched bust
    • Long balloon sleeves, elastic cinched hems
    • Front waistband, back zipper closure
    • Ruffled hem
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-4246

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Classic In Plaid Pleated Mini Dress

    Stay classic and chic in this plaid mini dress! Featuring a flattering square neckline and spaghetti straps, this bodycon dress also has a chic side pleated seam and a faux wrap mini-length hem. Complete the look in a sleek moto jacket and boots.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps, back zipper and hook-eye closure
    • Pleated side seam
    • Bodycon silhouette
    • Wrap mini-length hem
    • Plaid print, woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5507

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale