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!

  • Sweetest Style Eyelet Knit Mini Dress

    Show off the sweetest style in this adorable eyelet knit mini dress. It features a sleeveless sweetheart neckline with a knot-front design at the bust, spaghetti straps, a mini-length hem, a form-hugging fit, and a dainty floral eyelet pattern. The lined knit fabric offers plenty of stretch. Complete your look with espadrille sandals for a weekend date.

    Fit & Features

    • Sleeveless sweetheart neckline, knot-front design
    • Spaghetti straps
    • Mini-length hem
    • Form-hugging fit
    • Floral eyelet pattern
    • Lined knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4969

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Cool Crew Neck Mini Dress

    Keep it cool and casual in this effortless knit mini dress for hangs with friends! It features short sleeves, a crew neck, a bodycon silhouette, and a ruched drawstring that lets you customize the style. The dress is composed of a stretchy brushed knit fabric. Complete the look in cute flat sandals.

    Fit & Features

    • Short sleeve, crew neck
    • Bodycon silhouette
    • Ruched, adjustable drawstring
    • Bodycon silhouette
    • Mini-length hem
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4856

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Allure Polka Dot Mesh Mini Dress

    Show off a flirty allure in this adorable polka dot mesh mini dress. It features a square neckline, short puff sleeves with ruffled trims, an open back with a chic bow tie-back design, ruching down the side seams, a mini-length hem, and a curve-hugging silhouette. The sheer mesh polka dot patterned fabric includes a partial knit lining. Style with platform heels for a fresh date look!

    Fit & Features

    • Square neckline
    • Short puff sleeves, ruffled trims, elasticized hems
    • Open back, bow tie-back design
    • Ruched side seams, lower back zipper, hook and eye closure
    • Mini-length hem, bodycon fit
    • Sheer mesh fabric, polka dot pattern, partial knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5133

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Slay Ribbed Knit Midi Dress

    Showcase an everyday slay in this curve-hugging midi dress! It features a sleeveless square neckline, spaghetti straps, an open back with a double strap design, a midi-length hem with a bodycon silhouette, and a thigh-high side slit for a sultry accent. The ribbed knit fabric offers plenty of stretch. Style with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Open back, double strap design, tie closure
    • Midi-length hem, bodycon silhouette
    • High side slit
    • Ribbed knit fabric, lining at the bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4770

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute View Ditsy Floral Chiffon Skater Dress

    You'll be a cute view in this ditsy floral chiffon dress at casual family parties or weekend getaways! It features puff short sleeves, a sweetheart neck, a front bust ruched drawstring, a stretchy smocked back, and a skater silhouette with a short-length hem. The dress is composed of a chiffon fabric with a ditsy floral print and a stretchy knit lining. Complete the look in trendy sandals.

    Fit & Features

    • Puff short sleeves, elastic ruffled hems
    • Sweetheart neckline
    • Front bust ruched drawstring
    • Stretchy smocked back
    • Skater silhouette, short-length hem
    • Ditsy floral print, chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5022

    Category Name: Casual Dresses

    Price: $5.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Endless Sunshine Linen Tie-Back Midi Dress

    For the sun-soaked days ahead, this linen midi dress will make a cute companion! It features a sleeveless square neck, adjustable spaghetti straps, a flirty tie-back closure, and a flowy ruffled hem. Style with trendy sandals and sunglasses.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Tie-back closure
    • Flowy ruffled midi hem
    • Airy linen fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 05102-5012

    Category Name: Casual Dresses

    Price: $5.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Garden Walks Ditsy Floral Chiffon Dress

    For your walks through garden parties or outdoor weddings, this ditsy floral chiffon dress brings the charm! It features a sleeveless sweetheart neck, adjustable spaghetti straps with ruffle trim, a skater silhouette, and a flirty lace-up back with tie closure and a ruffled short-length hem. Complete the look in statement heeled mules.

    Fit & Features

    • Sleeveless sweetheart neck
    • Adjustable spaghetti straps, ruffle trim
    • Skater silhouette
    • Lace-up back, tie closure
    • Ruffled short-length hem
    • Ditsy floral print, chiffon fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2347

    Category Name: Casual Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pleated Princess Bow Back Skater Dress

    Look and feel like a princess in this skater dress for cocktail wedding showers or graduation parties! It features a sleeveless square neck, adjustable spaghetti straps, a pleated bodice with a pretty bow on the back, and a fit-and-flare short silhouette. Complete the look in stiletto mules and a clutch.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Pleated bodice, back bow, zipper closure
    • Skater, fit and flare silhouette
    • Short-length hem
    • Cotton-blend fabric, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2333

    Category Name: Casual Dresses

    Price: $5.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 70s Groove Floral Tie-Back Skater Dress

    Get into the groove of this 70s-inspired printed floral dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty tie-back design, and a flattering skater short-length silhouette. Complete the look in rhinestone mules for a dressy date!

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Tie-back design
    • Skater silhouette
    • Short-length hem
    • 70s-inspired floral print
    • Woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5053

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Soak Up The Sun Tropical Print Maxi Dress

    You'll be ready for those relaxing beachside strolls in this gorgeous tropical print maxi dress. It features a sleeveless V-neckline, spaghetti straps, an alluring backless design, a flowy, floor-length hem, and a thigh-high front slit. The smooth knit fabric showcases a tropical palm leaf print. Style with slip-on sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Backless design, single lattice strap
    • Flowy floor-length hem, high front slit
    • Tropical palm leaf print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4997

    Category Name: Casual Dresses

    Price: $5.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Color Me Cute Linen V-Neck Skater Dress

    Color you cute in this linen skater dress perfect for layering over your swimsuit on a beach day or pool party! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty ruffled underbust trim, and a tiered color block ruffled short-length silhouette. Style with trendy espadrille wedges.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Ruffled underbust trim
    • Tiered ruffle layered skater silhouette
    • Short-length hem
    • Color block pattern
    • Airy woven linen fabric, partial lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4994

    Category Name: Casual Dresses

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Here To Twirl Ruffled Skater Dress

    With this skater dress on, you're just here to twirl at the graduation party or birthday! It features a sleeveless square neck, adjustable spaghetti straps, a flirty tie-back design, and a flattering fit and flare short-length silhouette with a layered ruffled hem. Complete the look in rhinestone fringe earrings.

    Fit & Features

    • Sleeveless square neck, adjustable spaghetti straps
    • Tie-back design
    • Fit and flare, skater silhouette
    • Layered ruffled short-length hem
    • Woven fabric, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2119

    Category Name: Casual Dresses

    Price: $5.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Charm Swiss Dot Chiffon Midi Dress

    Unlock your sweet charm in this chiffon midi dress perfect for bridal showers, graduation parties, and more! It features a sleeveless V-neck with a twisted bust, adjustable spaghetti straps, a flirty tie-back design, and a flowy silhouette and ruffled hem. The dress is composed of an airy chiffon fabric with a swiss dot pattern and a smooth woven lining. Complete the look in faux pearl heels.

    Fit & Features

    • Sleeveless V-neck, twisted bust
    • Adjustable spaghetti straps
    • Tie-back design
    • Flowy silhouette, ruffled midi-length hem
    • Airy chiffon fabric, swiss dot pattern, smooth woven lining
    • No stretch
    • Runs true to size

    Style Number/Barcode: 05102-5047

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Golden Hour Glow Abstract Print Cutout Midi Dress

    Giving goddess vibes only—this midi dress is here to steal the spotlight. With a curve-hugging fit, waist cutout, and ruffled slit, it’s made for rooftop cocktails, date nights, and every content-worthy moment.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch, abstract print
    • Sleeveless plunging cowl neckline
    • Tie-back halter spaghetti straps, partially open back
    • Waist cutout, rectangular metal accent
    • High-cut front slit, ruffled trim
    • Midi-length fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000428

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L, XL

    Product Badge:
    • Best Seller
  • Always Charming Floral Eyelet Lace Dress

    Always charming and cute, this floral eyelet lace dress boasts adorable allure! It features puff short sleeves, a square neck, a tie-back design, and a flattering skater silhouette and short-length hem. Complete the look in strappy sandals for a baby shower or family party.

    Fit & Features

    • Puff short sleeves
    • Square neck
    • Tie-back design
    • Skater silhouette
    • Short-length hem
    • Ditsy floral print, eyelet lace, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5030

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ready To Ruffle V-Neck Mini Dress

    You'll bring the flirty flare with this mini dress for bridal showers or day dates! The dress features a sleeveless ruffle V-neckline, straps with ruffle trim, and a bodycon silhouette on stretchy and smooth knit fabric with lining. Complete the look in trendy flat sandals and a purse!

    Fit & Features

    • Sleeveless ruffle V-neckline
    • Straps with ruffle trim
    • Bodycon silhouette
    • Mini-length hem
    • Stretchy, smooth knit fabric with lining
    • Runs true to size

    Style Number/Barcode: 05102-5049

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Room To Grow Floral Cutout Midi Dress

    You'll flourish this season in this fresh floral midi dress perfect for outdoor parties, family gatherings, and baby showers! The dress features adorable puff short sleeves, a sweetheart neck, a ruched bust seam with a cutout accent, a stretchy smocked back, and a flowy midi-length hem with a flirty side slit. Complete the look in platform wedges.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neck
    • Ruched bust seam, stretchy smocked back
    • Cutout accent
    • Flowy midi-length hem, side slit
    • Floral print, airy woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2358

    Category Name: Casual Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ticket To Flirty Ditsy Floral Mini Dress

    Your ticket to looking fun and flirty is this ditsy floral mini dress perfect for a staycation or weekend getaway! It features a sleeveless sweetheart neckline, spaghetti straps, a front bust tie with a keyhole accent, and a bodycon silhouette. The soft brushed knit fabric offers plenty of stretch. Complete the look in heeled sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Front bust tie, keyhole accent
    • Bodycon silhouette, mini-length hem
    • Ditsy floral print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5115

    Category Name: Casual Dresses

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casually Cute Floral Off-The-Shoulder Dress

    Step out looking casually cute in this floral mesh mini dress for lunch with the girls or a bridal shower! It features an off-the-shoulder neckline, sheer short-sleeve cuffs, a ruched bust, and side, and back ruched seams that accentuate your curves along the bodycon silhouette. Complete the look with a dainty ring set and heels.

    Fit & Features

    • Off-the-shoulder neckline
    • Sheer short-sleeve cuffs
    • Back zipper and hook-eye closure
    • Ruched bust, side and back seams
    • Bodycon silhouette, mini-length hem
    • Ditsy floral print, mesh fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4914

    Category Name: Casual Dresses

    Price: $5.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Sensational Smooth Knit Maxi Dress

    Rise to the occasion looking sensational in this basic smooth knit maxi dress perfect for dressing up or down! It features a sleeveless scoop neck, sleek spaghetti straps, a bodycon silhouette, and a flirty back-slit accent composed of double-lined smooth knit fabric. Complete the look in lucite mules for a bridal shower or casual party!

    Fit & Features

    • Sleeveless scoop neck, spaghetti straps
    • Bodycon silhouette
    • Back slit accent
    • Maxi-length hem
    • Double-lined smooth knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5158

    Category Name: Casual Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pop On Over Bubble Hem Skater Dress

    Pop on over to every party you're invited to in this poplin skater dress featuring adorable puff short sleeves, a wired V-neckline, a high waist seam, and a flattering fit and flare silhouette with a short bubble hem design. The poplin woven fabric includes a sewn-in knit lining. Style this skater dress with rhinestone strappy heels to complete the look!

    Fit & Features

    • Puff short sleeves, cinched hems
    • Wired V-neckline, back zipper, hook and eye closure
    • High waist seam
    • Fit and flare skater silhouette
    • Short bubble hem design
    • Poplin woven fabric, sewn-in knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2299

    Category Name: Casual Dresses

    Price: $6.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Iconic Moment A-Line Mini Dress

    Step out in this iconic little black dress for many chic moments of the night! The dress features a sleeveless V-neckline, spaghetti straps, a flattering A-line silhouette, and a mini-length hem on slinky knit fabric. Complete the look in lace-up heels for a date night!

    Fit & Features

    • Sleeveless V-neckline, spaghetti straps
    • A-line silhouette
    • Mini-length hem
    • Slinky knit fabric, knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5066

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Butterfly Kisses Rhinestone Mini Dress

    Every heart will flutter with your winged beauty! This rib knit mini dress features a sleeveless scoop neck, spaghetti straps, a rhinestone butterfly design, and a bodycon silhouette. Complete the look in cute sandals for a casual party or lunch!

    Fit & Features

    • Sleeveless scoop neck
    • Spaghetti straps
    • Rhinestone butterfly design
    • Bodycon silhouette
    • Mini-length hem
    • Soft rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4944

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Like A Day Dream Eyelet Lace Dress

    Look like a daydream come true in this eyelet lace mini dress for your next date! It features adorable puff sleeves with ruffle trim, a sweetheart neck, a ruched bust seam, and a bodycon silhouette with a flirty tiered ruffle hem. Complete the look in cute stiletto heels.

    Fit & Features

    • Puff short sleeves, ruffle trim
    • Sweetheart neck
    • Ruched bust seam
    • Bodycon silhouette
    • Tiered ruffle mini-length hem
    • Eyelet lace fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2184

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale