Casual Dresses

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Cute Sweater Dresses

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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!

  • Knit Mini Dress

    This mini dress is composed of a very soft knit material. It is form fitting, hugs your curves and has a maximum stretch, and the hem meets mid thigh. It features a round neckline and spaghetti straps that lead to a round back. This dress will pair well with sneakers and a jean jacket or a leather jacket and heels! Play dress up with it, it goes with everything!

    Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0232

    Category Name: Casual Dresses

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take The Plunge Floral Maxi Dress
    Add a hint of island-inspired chic to your wardrobe with this gauzy sleeveless maxi dress. Dress features a deep V at front and back, a shirred banded waist, and an all-over floral print. Dress is composed of a rayon fabric and has plenty of stretch in the waist and moderate stretch throughout the rest.

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

    Style Number/Barcode: 05102-4050

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Va Va Venom Knit Dress

    You don't bite, but you're ready to pounce! Channel your wild side in this bold mini. Dress slips on, has a curve-hugging fit, and features spaghetti straps and a scoop neck. Dress is made from a ultra-soft brushed knit fabric with a fair amount of stretch. 

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

    Style Number/Barcode: 05102-0169

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Girl Mini Dress

    Show us your sweet side with this eyelet-detailed mini dress! It features a V neckline, ruffled cap sleeves, single-button closure with keyhole at back, an empire waist, and a short A-line skirt with pockets leading to a wavy hemline. Dress is lined, made from cotton, includes a linen short underlay. 

    Style Number/Barcode: 05102-0310

    Category Name: Casual Dresses

    Price: $16.97 $47.60

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lovely Little Linen Skater Dress

    Leave a flirty impression in this lovely little linen skater dress! It features long fitted sleeves with ruffled elastic cuffs, a deep V neckline with a ruffle trim, a hidden back zipper and hook and eye closure, ruffle detail seams, and a flowy skater skirt. The dress is composed of a lightweight linen fabric with a woven lining and has no stretch.

    Style Number/Barcode: 05102-0300

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortless Beauty Eyelet Mini Dress
    Showcase your effortless beauty in this beyond gorgeous eyelet mini dress! It features a square neck and back, short sleeves with ruffle detailing, a hidden back zipper and hook and eye closure, mini side cut outs at the waist seam, and a short, mid-thigh length. The dress is composed of a woven fabric with a full lining and has no stretch.

    Style Number/Barcode: 05102-0150

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunset Beauty Tropical Print Maxi Dress

    Show off your beauty at sunset happy hour in this tropical print maxi dress designed with sheer mesh fabric and a mini-length lining. The high-cut side slit adds an alluring detail to turn heads.

    Fit & Features

    • Sheer knit fabric with mini-length knit lining, high stretch
    • Tropical print
    • Sleeveless cowl neckline
    • Spaghetti straps, cross-back design
    • High side slit
    • Maxi-length fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6074

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Solid Stunner Ruched Tube Dress
    We'll keep it brief: this mini is made for for your next night out! Tube-style dress features a curve-hugging cut, strapless neckline, and all-over strategic ruching detail. Don't forget to pair it with the matching duster! Dress slips on and is made from a smooth, solid woven material with moderate stretch.

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05103-0165

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Miss Midi Striped Dress

    Hey there miss midi, we see you! and we are on the same page too, filling our closet with midi dresses this season. This piece features a  v-neckline, attached dark neutral marbled buttons, and adjustable spaghetti straps that lead to a square back. This red toned midi dress has a skinny stripe pattern and is composed of a soft knit material that offers maximum stretch. 

    Style Number/Barcode: 05102-3994

    Category Name: Casual Dresses

    Price: $9.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Plus Thrill Of Knit Ribbed Dress

    Toe the perfect line between casually chic and sultry-on-trend in this off-the-shoulder mini. Dress features all-over medium-width ribbing, a scoop neck, decorative wood-like buttons and a full lining. Dress is made from a soft, heavier-weight cotton blend with a fair amount of stretch. 

    Style Number/Barcode: 15102-0035

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ruffle Ride Skater Dress

    Keep it cool in this breezy-beautiful skater dress! It features adjustable spaghetti straps, a seamed V neck bodice, tiers of ruffle trim at the bust, waist, thigh and hem, and an A-line skirt with back zip. Dress is fully lined and made from a lightweight Tencel-blend with natural crinkle-effect and little to no stretch.

    Style Number/Barcode: 05102-0329

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Chic Midi Dress

    Get a total casual chic vibe with this adorable daytime LBD! It features a V neckline, short sleeves, and a mid-length, curve hugging fit. The dress is composed of a ribbed knit fabric that offers plenty of stretch.

    Style Number/Barcode: 05102-0197

    Category Name: Casual Dresses

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Flirt Floral Mini Tube Dress

    Bring the sweet flirty vibes to your weekend plans in this cute mini tube dress with a dainty floral print on lined chiffon fabric. The strapless smocked bodice leads to a V-shaped waist, tiered ruffled design, and flowy skater silhouette.

    Fit & Features

    • Woven chiffon fabric with stretchy knit lining, dainty floral print
    • Strapless straight-across neckline
    • Stretchy smocked bodice
    • V-shaped waist
    • Tiered ruffled design
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4077

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Talk Skater Dress

    This adorable skater dress will definitely sweet talk its way into your closet! It features short flowy sleeves, a plunging V neckline, an open back with a top tie closure with tassel details, a back hidden zipper and hook and eye closure, a high waist seam, a back tie detail, a faux button down front, and a flowy skater skirt. The dress is composed of a woven gauze fabric with a woven lining and has no stretch.

    Style Number/Barcode: 05102-0174

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stun And Snap Mini Dress
    Stun in this snap-worthy LWD (Little White Dress)! The sweater dress features a sleeveless bodice, spaghetti straps, a V neckline, a gold faux snap button front, and a short, curve hugging fit. The black dress is composed of a ribbed knit fabric that offers plenty of stretch.

    Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06005-0175

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ready For My Snap Midi Dress
    Get ready to take all the snaps in this simply stunning midi! The sweater dress features a sleeveless bodice, tank-like shoulder straps, a scoop neckline, double white striped detailing and gold faux snap buttons down each side, and a mid-length fit. The black dress is composed of a ribbed knit fabric with plenty of stretch.

    Style Number/Barcode: 06005-0096

    Category Name: Casual Dresses

    Price: $4.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Smocked Stunner Mini Dress

    Showcase the stylish stunner you are in this adorable smocked mini dress! It features a sleeveless bodice, thick smocked shoulder straps with ruffle detailing, a sweetheart neckline, a stretchy and smocked bust, a high waist seam with a ruffle trim, and a flowy skirt with a tiered ruffle hem. The dress is composed of a lightweight woven fabric with a woven skirt lining.

    Style Number/Barcode: 05102-0230

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay All Day Mini Dress

    Feel like you're on a vacay all day in this fun tropical printed mini! It features a sleeveless bodice, spaghetti straps, a scoop neckline, and a short, form hugging fit. The dress is composed of a scuba knit fabric that offers moderate stretch and showcases a vibrant print.

    Style Number/Barcode: 05102-0008

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Soft And Sweet Dress

    Show off your soft sweet side baby girl! This off shoulder dress is the perfect ensemble for a day in the sun. Featuring a straight off-shoulder neckline and wooden buttons down the middle, this dress has a form fitting bodice and a ribbed knit material that will offer maximum stretch as well as a soft inner lining. Show off those shoulders girl!

    Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-4039

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunshine Dream Open Tie Back Floral Maxi Dress

    A floral print adds to the dreamy charm of this flowy maxi dress boasting an open tie back design and ruffled silhouette perfect for beachside strolls or day parties.

    Fit & Features

    • Floral print, woven fabric, short woven lining
    • Sweetheart neckline with bust tie
    •  Spaghetti straps
    • Open tie back design
    • Ruffled flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3912

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Smocked And Stylin' Mini Dress

    This adorable floral printed mini is smocked and stylin'! The dress features a sleeveless bodice, tie shoulder spaghetti straps, a square neckline with a bust keyhole cut out, a square back, pleated details, and a stretchy and smocked fit. The dress is composed of a lightweight linen fabric that offers a form hugging fit.

    Style Number/Barcode: 05102-0283

    Category Name: Casual Dresses

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Get Sprung On Florals Mini Dress

    Get sprung on this too cute mini dress! It features an off the shoulder neckline with short cuffed sleeves, a trendy tie front with a keyhole cut out, seam detailing, a smocked back, and a short, form hugging fit. The dress is composed of a woven fabric with no stretch.

    Style Number/Barcode: 05102-0099

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Not So Basic Mini Dress

    Sure, you probably have your share of mini dresses. Now it's time for an of-the-moment upgrade! This ultra-chic mini features an off-the-shoulder elasticized neckline, gathered bodice and sleeves, a back zip, banded waist with back smocking, and pencil skirt with gather-drape detail. Dress is made from a mid-weight woven material with little to no stretch.

    Style Number/Barcode: 05101-0165

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral In Love Midi Dress
    Fall in love with this romantic floral midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline created by a knot front detail, a hidden back zipper and hook and eye closure, and an A-line mid-length fit with a front slit. The dress is composed of a lightweight woven fabric.

    Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0209

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance