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!

  • Flourish In Floral Print Mini Dress

    Flourish for spring in this dainty floral mini dress you'll love styling for casual plans! It features a sleeveless scoop neck with a tie-front bust, spaghetti straps, and a bodycon fit on stretchy rib knit fabric. Complete the look with new trendy sandals.

    Fit & Features

    • Sleeveless scoop neck, spaghetti straps
    • Tie-front bust
    • Bodycon fit
    • Mini-length hem
    • Dainty floral print, stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4930

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smooth Essential Square Neck Mini Dress

    A sleek and smooth mini dress a fashionista such as yourself will adore styling up or down! It features a sleeveless square neckline, spaghetti straps, and a bodycon silhouette. The dress is composed of a smooth, double-lined knit fabric with a moderate stretch. Complete the look in statement heels and jewelry.

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Smooth, double-lined knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5071

    Category Name: Casual Dresses

    Price: $5.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bae Breeze Cotton A-Line Short Dress

    Enter looking like bae just breezed in! Capture cuteness in this cotton short dress featuring short puff sleeves, a square neck, an open lace-up back, and an A-line silhouette. Style with a trendy crossbody bag and heels.

    Fit & Features

    • Short puff sleeves
    • Square neck
    • Open lace-up back, zipper and hook-eye closure
    • A-line silhouette
    • Short-length hem
    • Cotton fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4876

    Category Name: Casual Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dream Look Floral Ruched Mini Dress

    Create your dream look for a spring date in this adorable floral mini dress! It features a sleeveless sweetheart neckline with ruching at the bust, spaghetti straps, an open back with a lace-up strappy design, ruching down the side seams, a mini-length hem, and a curve-hugging silhouette. The lined mesh fabric features a dainty rose print pattern for the prettiest look. Style with clear heels.

    Fit & Features

    • Sleeveless sweetheart neckline, ruching at the bust, spaghetti straps
    • Open back, lace-up strappy design, tie closure
    • Ruching down the side seams
    • Mini-length hem, form-hugging fit
    • Dainty rose print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4888

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picnic Time Gingham Mini Dress

    You'll be the cutest girl in this gingham casual dress at the picnic! It features ruffle trim puff short sleeves, a sweetheart neck with a lace-up bust, a bodycon silhouette, and a mini-length hem on stretchy rib knit fabric. Complete the look in sandals.

    Fit & Features

    • Ruffle trim puff short sleeves
    • Sweetheart neck, lace-up bust
    • Bodycon silhouette
    • Mini-length hem
    • Gingham print
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4995

    Category Name: Casual Dresses

    Price: $27.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Everyday Style Midi Dress

    This form-fitting midi dress is perfect for creating that chic everyday style! It features a sleeveless V-neckline with a matching V-back design, tank shoulder straps, a fitted silhouette that will hug your curves, and a midi-length hem. The ribbed knit fabric offers plenty of stretch. Complete the look with strappy mules.

    Fit & Features

    • Sleeveless V-neckline, V-back design
    • Tank shoulder straps
    • Form-hugging fit
    • Midi-length hem
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4844

    Category Name: Casual Dresses

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Bae Crew Neck Slit Maxi Dress

    A cute basic maxi dress for looking trendy on your off-duty days! It features short sleeves, a crew neck, a bodycon silhouette, and a high side slit to show off some leg! The dress is composed of a brushed knit stretchy fabric. Complete the look in flat sandals and a handbag.

    Fit & Features

    • Short sleeves
    • Crew neck
    • High side slit
    • Bodycon silhouette
    • Maxi-length hem
    • Brushed knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 05102-4786

    Category Name: Casual Dresses

    Price: $18.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Brunch Eyelet Skater Dress

    This adorable skater dress is a perfect pick for weekend brunch! It features a sweetheart neckline, short puff sleeves with tie accents, a high waist seam, a short skater skirt with a ruffled hem, and a fit and flare silhouette. The lightweight knit fabric features a dainty eyelet pattern for the prettiest look. Style with espadrille wedges.

    Fit & Features

    • Sweetheart neckline, shirring at the bust
    • Short puff sleeves, cinched hems, tie accents
    • High waist seam
    • Short skater skirt, ruffled hem
    • Fit and flare silhouette
    • Eyelet knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4915

    Category Name: Casual Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everlasting Pretty Floral Chiffon Skater Dress

    Freshen up your closet in this pretty floral chiffon dress for a blissful day date to jaunt through a garden party! It features sheer peasant long sleeves, a smocked and stretchy V-neck bodice, a fit and flare silhouette, and a flowy short-length hem. The dress is designed with a gorgeous floral pattern on airy chiffon with a stretchy knit lining. Complete the look with strappy platform heels.

    Fit & Features

    • Sheer peasant long sleeves
    • Smocked and stretchy V-neck bodice
    • Back zipper closure
    • Skater silhouette
    • Flowy short-length hem
    • Floral pattern, chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4977

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twirl All Day Linen Skater Dress

    You'll be twirling all day in this linen skater dress perfect for a day date or Sunday brunch! It features a sleeveless, square neck, adjustable spaghetti straps, fitted bust, open-back with an elasticized band, and a flowy short hem. Complete the look in PVC strap heels.

    Fit & Features

    • Sleeveless, square neck, adjustable spaghetti straps
    • Fitted bust
    • Open-back, elasticized band
    • Flowy skater silhouette
    • Short length hem
    • Linen woven fabric, knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1667

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Deets Crepe Lace-Up Midi Dress

    This crepe midi dress has the pretty deets you're looking for! The dress features a sleeveless square neck, spaghetti straps, an open lace-up back with tie closure, a ruched bust, and a bodycon silhouette. Complete the look in chic flat sandals.

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Open lace-up back, tie closure
    • Ruched bust
    • Bodycon silhouette
    • Midi-length hem
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4891

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sent You A Text Square Neck Mini Dress

    You might want to reply back to your new favorite casual mini dress for weekend outings or day dates! It features a sleeveless square neck, tank-style straps, and a bodycon silhouette, and is composed of a textured fabric with a stretch knit lining. Style with a denim jacket and sandals.

    Fit & Features

    • Sleeveless square neck
    • Tank-style straps
    • Bodycon silhouette
    • Mini-length hem
    • Textured fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4860

    Category Name: Casual Dresses

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Like Honey Linen Skater Dress

    You'll be sweet like honey in this breezy linen skater dress for afternoon tea or a weekend brunch! The dress features adorable puff short sleeves, a ruffle trim sweetheart neck, a ruched bust, and a fit and flare silhouette with a ruffled hem. Style with heeled sandals to complete the look.

    Fit & Features

    • Puff short sleeves
    • Ruffle trim sweetheart neck, ruched bust
    • Back zipper and hook-eye closure
    • Fit and flare skater silhouette
    • Ruffle short-length hem
    • Linen fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4991

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Encore Crepe Slit Maxi Dress

    Prepare for a standing ovation whenever you're seen in this crepe maxi dress perfect for casual wine nights by the fire pit or a spring getaway! Featuring a sleeveless square neck, spaghetti straps, a curve-hugging silhouette, and a sultry high slit along the flowy long hem. Complete the look in cute flat sandals.

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Curve-hugging silhouette
    • Front high slit
    • Flowy maxi-length hem
    • Crepe knit fabric, mini-length knit lining
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5058

    Category Name: Casual Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boldly Chic Abstract Cowl Neck Maxi Dress

    Bold, body-hugging, and ready to break hearts—this halter maxi dress brings the drama with an abstract print and deep cowl neckline, perfect for sunset dinners and cocktails!

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Cowl halter neckline, tie closure
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000315

    Category Name: Casual Dresses

    Price: $45.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M, L

  • Effortlessly Pretty Chiffon Midi Dress

    Showcase your effortless beauty in this airy, lightweight chiffon midi dress. It features a sweetheart neckline with a ruched bodice, long sheer peasant sleeves, a stretchy smocked back design, a fitted high waist seam, a midi-length hem with a high front slit, and a flowy, A-line silhouette. Style with clear mules for a weekend brunch date.

    Fit & Features

    • Sweetheart neckline, ruched bodice
    • Long sheer peasant sleeves, elastic cinched hems
    • Stretchy smocked back design
    • Fitted high waist seam
    • Midi-length hem, high front slit, A-line silhouette
    • Sheer chiffon fabric, partial knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4954

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Freshly Picked Floral Skater Dress

    Freshly picked from the garden. This floral skater dress is ready for your springtime festivities! It features short puff sleeves, a sweetheart neck with a tie-front closure, an open lace-up back design, and a tiered ruffled short-length hem. Complete the look in trendy new mules.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neck, tie-front closure
    • Open lace-up back design
    • Skater silhouette
    • Tiered ruffle short-length hem
    • Watercolor floral print, non-stretch fabric, woven lining
    • Runs true to size

    Style Number/Barcode: 05102-4993

    Category Name: Casual Dresses

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Mart Chiffon Skater Dress

    Always look like you've just come from somewhere with flowers! This breezy ditsy floral skater dress embodies every girl's favorite thing about spring. It features sheer 3/4 length sleeves with elastic cuffs, a sweetheart neck with a bust tie and keyhole, a smocked back, and a flowy fit and flare short-length hem. Complete the look in platform wedges.

    Fit & Features

    • Sheer 3/4 length sleeves, elastic cuffs
    • Sweetheart neck, bust tie, and keyhole
    • Smocked back
    • Skater silhouette, short-length hem
    • Ditsy floral print
    • Chiffon fabric with lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2161

    Category Name: Casual Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet As Can Be Lace Midi Dress

    Look and feel sweet as can be in this lace midi dress for a chance at romance! Features adorable short puff sleeves, a sweetheart neckline, a form-hugging silhouette, a flirty front slit, and a slight flare hem. Style with heeled sandals for a cute look for day dates and brunch!

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline
    • Back zipper and hook-eye closure
    • Form-hugging silhouette
    • Front slit, slight flare midi-length hem
    • Lace fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2020

    Category Name: Casual Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Stroll Ditsy Floral Midi Dress

    Take a springtime stroll in this adorable ditsy floral midi dress! Featuring a square neckline, short puff sleeves, a midi-length hem with a front slit, and a flowy A-line silhouette, this dress is perfect for weekend plans. The ditsy floral printed woven fabric includes a short knit lining. Style with sandals for a date with your special someone.

    Fit & Features

    • Square neckline
    • Short puff sleeves, elastic cinched hems
    • Smocked back panel, hidden side zipper
    • Midi-length hem, front slit, A-line silhouette
    • Ditsy floral print
    • Woven fabric, short knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1985

    Category Name: Casual Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Daze Eyelet Tie Mini Dress

    If you've got sunshine on your mind, this eyelet mini dress is the one you want for those warmer days ahead. Featuring an off-the-shoulder ruffle neckline, short sleeve cuffs and spaghetti straps, a bust tie front design, and a bodycon silhouette. Complete the look in cute sandals for a family picnic!

    Fit & Features

    • Off-the-shoulder ruffle neckline
    • Short sleeve cuffs, spaghetti straps
    • Bust tie front design
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4908

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Like A Dream Chiffon Skater Dress

    Look and feel like a dream in this chiffon skater dress perfect for baby showers or birthdays! It features an off-the-shoulder, ruffle trim sweetheart neckline, sheer peasant long sleeves with elastic cuffs, a lightly padded bust, and a flowy tiered ruffled short-length hem. Complete the look in cute mules.

    Fit & Features

    • Off-the-shoulder, smocked back
    • Ruffle trim sweetheart neck, lightly padded bust
    • Sheer peasant long sleeves, elastic cuffs
    • Fit and flare skater silhouette
    • Flowy tiered ruffled short-length hem
    • Chiffon fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2113

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flower Power Lace-Up Mini Dress

    Keep your spring look on point with this cute and casual floral mini dress! It features a sleeveless scoop neckline, spaghetti straps, a lace-up back with tie closure, a bodycon silhouette, and a charming flower print on stretchy knit fabric. Complete the look with sandals for a day date!

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Lace-up back with tie closure
    • Bodycon silhouette, mini-length hem
    • Flower print
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4955

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Text Me Later Strappy Back Mini Dress

    Their text can wait. You'll be too busy catching all the attention in this casual mini dress featuring a sleeveless square neck, bungee spaghetti straps, a strappy open-back, and a bodycon silhouette. The dress is composed of a texture knit fabric with a stretchy lining. Complete the look in a crop denim jacket.

    Fit & Features

    • Sleeveless square neck
    • Bungee spaghetti straps
    • Strappy open back
    • Bodycon silhouette
    • Mini-length hem
    • Texture knit fabric, stretchy lining
    • Runs true to size

    Style Number/Barcode: 05102-4981

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale