Casual 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!

  • Weekend Vibes High Slit Striped Knit Maxi Dress

    This casual-chic striped knit maxi dress is perfect for your laid-back weekend vibes! Designed with stretchy ribbed knit with a thin striped pattern, it features a sleeveless scoop neckline with spaghetti straps, high-cut side slits on each side for added movement, and a form-hugging slim fit on the maxi-length silhouette. Style this long dress with strappy sandals.

    Fit & Features

    • Striped ribbed knit fabric, short knit lining, moderate stretch
    • Scoop neckline
    • Spaghetti straps
    • High side slits
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5778

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lovely In Lace Ruffled Puff Sleeve Mini Dress

    You'll be looking oh-so-lovely in this adorable ruffled puff sleeve mini dress! The sheer floral lace fabric gives that dainty-chic vibe, while the partial knit lining provides coverage. The mini-length dress features a square neckline and sheer short puff sleeves with the cutest ruffle trim, a small bust cutout with a sleek ribbon tie-front design, and a flattering empire waist seam. The flowy A-line silhouette adds that effortless flair. Style this short dress with heeled mules for date night.

    Fit & Features

    • Sheer floral lace fabric with knit lining, minimal stretch
    • Square neckline, ruffle trim
    • Sheer short puff sleeves, ruffle trim
    • Bust cutout, tie-front design
    • Empire waist seam, hidden side zipper closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3338

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • City Of Love V-Neck Ruffle Babydoll Dress

    Grab your baguette, passport, and this babydoll dress cause the city of love is calling your name! The playful ruffled shoulder straps and convenient side pockets add a touch of whimsy to this flirty dress. The babydoll silhouette and ruffled tiered hem make it perfect to sweep through Paris looking adorable! Complete the look in strappy sandals and a purse.

    Fit & Features

    • Woven fabric
    • Ruffled shoulder straps
    • Side pockets
    • Babydoll silhouette
    • Ruffled tiered short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5423

    Category Name: Casual Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Dream Lace-Up Ruffled Maxi Dress

    A dreamy sleeveless maxi dress perfect for styling for beach city days or coastal vacations! The scoop neckline and bust tie accentuate your figure, while adjustable spaghetti straps provide the perfect fit. The lace-up back adds a touch of charm, while the flowy ruffled silhouette and maxi-length hem exude effortless chicness! Complete the look with strappy sandals and sunglasses.

    Fit & Features

    • Woven fabric, short knit stretchy lining
    • Scoop neckline with bust tie
    • Adjustable spaghetti straps
    • Lace-up back
    • Flowy tiered ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5565

    Category Name: Casual Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Whimsical Cutie Butterfly Polka Dot Satin Maxi Dress

    Soar toward any celebration in this whimsical and cute polka dot satin maxi dress! Featuring cap sleeves and a gorgeous butterfly lace trim sweetheart neckline, this dress adds a touch of elegance. The button-down back with a cutout accent completes the maxi silhouette, making you the center of attention! Complete the look in strappy block heels and a necklace.

    Fit & Features

    • Polka dot print, satin fabric, no stretch
    • Butterfly lace trim sweetheart neckline
    • Button-down back and zipper hook-eye closures
    • Cutout back accent
    • Maxi length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3555

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Dream Strapless Belted Skater Dress

    She’s giving flirty, fun, and just the right amount of edge. The strapless fit and belted waist make this denim skater dress the definition of standout style.

    Fit & Features

    • Denim fabric
    • Strapless fold-over neckline
    • Smocked back
    • Belted drop waist
    • Short pleated skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000232

    Category Name: Casual Dresses

    Price: $54.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: XS, S, M, L

  • Effortlessly Chic Button Front Tunic

    Create an effortlessly chic everyday look with this classic tunic. It features a collared neckline, a complete button-down front, long sleeves, and a cinched waist effect for a figure-flattering silhouette. Style this tunic with sleek hoops and clear mules.

    Fit & Features

    • Collared neckline
    • Button-down front
    • Long sleeves, single-button details
    • Cinched waist effect
    • Pleating detail
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1497

    Category Name: Casual Dresses

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Adoring Cutie Sleeveless Lace-Up A-Line Mini Dress

    An attention-worthy A-line mini dress that'll have everyone adoring your cuteness! This square neck dress accentuates your curves while the lace-up back adds a touch of playfulness. The A-line silhouette and mini-length hem are perfect for any occasion. Complete the look in wedges and a clutch!

    Fit & Features

    • Smooth knit fabric lined with stretchy knit
    • Spagehtti straps
    • Square neckline
    • Lace-up
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5689

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Picture Perfect V-Neck Smocked A-Line Midi Dress

    You'll be the picture of perfection in this adorable A-line midi dress at showers or birthday brunch! With its flattering V-neckline and stretchy smocked bodice, this dress hugs your body in all the right places. The tie spaghetti straps add a touch of delicacy, while the V-cut waist seam and A-line silhouette create a flattering look along the midi-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Woven fabric lined with non-stretch woven
    • Tie spaghetti straps
    • V-neckline
    • Stretchy smocked bodice
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3560

    Category Name: Casual Dresses

    Price: $11.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Match Sleeveless Striped Ribbed Knit Mini Dress

    You and this striped knit mini dress are the perfect match for sunny days! With a playful scoop neckline and cutout back, this mini dress is a cute piece for any fun occasion. Its bodycon fit flatters your figure while the striped pattern adds a touch of quirkiness. The ribbed knit fabric offers a moderate stretch for comfortable wear. Complete the look with flat sandals.

    Fit & Features

    • Striped pattern
    • Ribbed knit fabric with moderate stretch
    • Scoop neckline
    • Tank shoulder straps
    • Cutout back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1940

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Details Basic Ruched Midi Dress

    The true style of this basic midi dress lies in the detail! Features a sleeveless square neckline, sleek bungee spaghetti straps, ruched seams down the sides to accentuate your curves, and a flattering bodycon silhouette. The dress is composed of a brushed soft knit fabric with a full-length lining. Complete the look with a chic handbag for a dinner date.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruched side seams
    • Bodycon silhouette
    • Midi-length hem
    • Brushed soft knit fabric, lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5146

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Artsy Play Abstract Mock Neck Mini Dress

    Play up your artsy side in this mesh mini dress totally giving those Y2K vibes! The mini dress features fitted long sleeves with split cuffs, a mock neckline, and a bodycon silhouette on mesh abstract printed fabric with a sheer mesh stretchy lining. Complete the look in chunky platform heels for a party!

    Fit & Features

    • Fitted long sleeves, split cuffs
    • Mock neckline
    • Bodycon silhouette
    • Mini-length hem
    • Abstract print on mesh fabric, sheer mesh stretchy lining
    • Runs true to size

    Style Number/Barcode: 05102-5398

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Off My Mind Cutout Long Sleeve Ribbed Knit Midi Dress

    Make an unforgettable appearance in this long-sleeved midi dress at brunch or casual parties! The midi dress is designed with an off-the-shoulder neckline, a twisted bust with a sultry cutout, and a bodycon fit on stretchy ribbed knit fabric. Complete the look in strappy heels.

    Fit & Features

    • Ribbed knit fabric with moderate stretch
    • Off-the-shoulder neckline
    • Fitted long sleeves
    • Twisted bust, cutout
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5280

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Smooth Silhouette Mock Neck Mini Dress

    Turn heads in this essential mini dress! Crafted with a double-lined smooth seamless knit fabric, the mini-length dress fits your body like a glove and features a mock neckline, fitted long sleeves, and a flattering bodycon silhouette. Make a statement and get compliments wherever you go styling this mini dress with combat boots and jacket.

    Fit & Features

    • Fitted long sleeves
    • Mock neckline
    • Bodycon silhouette
    • Mini-length hem
    • Double mesh lined smooth seamless knit fabric
    • Buttery soft and stretchy
    • Runs true to size

    Style Number/Barcode: 05102-5384

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sensational City Girl Strapless Cargo Mini Dress

    Hit the streets with a strapless mini dress that'll make you an instant sensational city girl! The strapless straight-across neckline and bodycon silhouette flatter any figure, while the front button closure and belt loop accents add a trendy touch. With a hidden front zipper, cargo flap pockets, and a mini-length hem, this woven dress is both fashionable and functional. Complete the look in lug boots for casual plans!

    Fit & Features

    • Cotton-blend woven fabric, minimal stretch
    • Strapless straight neckline with belt loop detailing
    • Front button closure
    • Hidden front zipper closure
    • Cargo flap pockets
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5503

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Make It Sexy Off-The-Shoulder Mini Dress

    Show off your curves in this sexy mini dress for weekend outings! The short dress features an off-the-shoulder neckline with a flirty bust keyhole tie, long sleeves with flared cuffs, side ruched seams to accentuate your figure, a bodycon silhouette, and a mini-length hem. Complete the look in lace-up stiletto heels and dare to be bold!

    Fit & Features

    • Off-the-shoulder neckline, bust keyhole tie
    • Long sleeves with flared cuffs
    • Side ruched seams, bodycon silhouette
    • Mini-length hem
    • Slinky knit fabric, sewn-in knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5212

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute And Casual Everyday Ribbed Knit Midi Dress

    This ribbed knit midi dress is cute, casual, and perf for everyday styling! It features a sleeveless V-neckline, spaghetti straps, a midi-length hem with a side slit accent, and a form-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a cropped denim jacket and strappy mules.

    Fit & Features

    • Stretchy ribbed knit fabric
    • V-neckline
    • Spaghetti straps
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-4934

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Showstoppin' Staple Long Sleeve Maxi Dress

    Put your curves on display in this basic maxi dress perfect for dressing up or down! The long dress features fitted long sleeves, a classic crew neck, and a flattering bodycon silhouette on hacci rib knit fabric. Complete the look with strappy heels and a purse!

    Fit & Features

    • Hacci rib knit fabric, plenty of stretch
    • Fitted long sleeves
    • Crew neckline
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5331

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Charm Ruffled Chiffon Tube Skater Dress

    Your go-to summer floral dress has arrived! With charming ruffles and skater silhouette, this short dress is perfect for shower celebrations, brunch, or day dates.

    Fit & Features

    • Floral print, chiffon fabric, stretchy knit lining
    • Strapless tube neckline
    • Stretchy, smocked fitted bodice
    • Skater silhouette
    • Ruffled short hem
    • Runs true to size

    Style Number/Barcode: 05101-4125

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L

  • Truly Chic High Slit Bodycon Midi Dress

    Create a truly chic look for dinner and drinks in this high slit bodycon midi dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, ruching down the side seams, an asymmetric midi-length hem creating a thigh-high side slit, and a bodycon fit to showcase your stunning silhouette. The lined smooth knit fabric offers plenty of stretch. Style with rhinestone fringe earrings to add a touch of glam!

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Ruched side seams
    • Asymmetric midi-length hem, thigh-high side slit
    • Bodycon silhouette
    • Smooth knit fabric, mini-length knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5521

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Fab Marble Print Mesh Mini Dress

    Oh so fab, you'll turn heads in this alluring marble print mesh mini dress. It features a sleeveless cowl neckline, adjustable spaghetti straps to customize the fit, a mini-length hem with a cute lettuce-edge trim, and a bodycon silhouette that will hug your natural curves. The airy sheer mesh fabric includes a full knit lining and features an all-over marble print pattern. Style with lace-up heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Mini-length hem, lettuce-edge trim
    • Bodycon silhouette
    • Marble print
    • Sheer mesh fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5509

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Right Impression V-Neck Floral Ruffle Skater Dress

    A cutie like you will always make the right impression in this floral skater dress on dates or at brunch!  Featuring sheer peasant long sleeves and a flattering V-neckline, this skater silhouette is completed with a ruffled short-length hem. The V-cut back with a spaghetti strap tie adds a touch of allure. Style this floral skater dress with block heels.

    Fit & Features

    • Floral print, chiffon fabric with woven lining, no stretch
    • V-neckline, V-cut back with spaghetti strap tie
    • Skater silhouette
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-2894

    Category Name: Casual Dresses

    Price: $6.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Look Ditsy Floral Chiffon Babydoll Dress

    Create the sweetest look for your summer plans with this adorable babydoll dress! The airy sheer chiffon fabric is detailed with a ditsy floral print and includes a full-length lining for coverage. The short dress features a sleeveless scoop neckline with ruching at the bust, adjustable spaghetti straps for a customized fit, a smocked back for added stretch, and a ruffled tiered A-line silhouette with an effortless flowy fit. Style with sneakers for a cute and casual summer outfit.

    Fit & Features

    • Ditsy floral print
    • Sheer chiffon fabric with stretchy knit lining
    • Ruched scoop neckline
    • Adjustable spaghetti straps
    • Smocked back
    • Ruffled tiered A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5451

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Strut And Snap Ribbed Knit Midi Dress

    Strut it out in a knit midi dress that is perf for every day! Designed with a ribbed knit fabric, this dress offers a form-hugging fit with a moderate stretch. It features a sleeveless square neckline, tank shoulder straps, a high side slit accented with glossy metal buttons, and a midi-length hem. Complete the look with mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Ribbed knit fabric with moderate stretch
    • Square neckline
    • Tank shoulder straps
    • Metal button accents
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-1167

    Category Name: Casual Dresses

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free