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!

  • Loving Is Easy Eyelet Lace Tie Mini Dress

    Loving this eyelet lace mini dress is easy! Perfect for lunch with friends or bridal showers. The dress features a sleeveless square neck, spaghetti straps, a ruched bust tie, and a bodycon silhouette. Complete the look in trendy sandals.

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Ruched bust tie
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet lace fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4873

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Queen Tropical Floral Midi Dress

    Slay in all of your vacation pics like the stylish queen you are in this tropical floral midi dress! It features a sleeveless square neckline, spaghetti straps, a midi-length hem, a bodycon silhouette that will hug your curves, and a bold tropical floral print pattern. The sheer mesh fabric includes a stretch knit lining. Complete the look with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Midi-length hem
    • Bodycon silhouette
    • Tropical floral print
    • Sheer mesh fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4980

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt And Twirl Chiffon Open Back Skater Dress

    Flirt and twirl in this sassy little chiffon dress perfect for date nights or parties! It features adorable sheer puff short sleeves, a ruched square neck with a bust tie and keyhole, an open back with tie closure, and a flowy short skater silhouette. Complete the look in platform block heels.

    Fit & Features

    • Sheer puff short sleeves
    • Ruched square neck, bust tie, keyhole
    • Open back, tie closure
    • Flowy skater silhouette
    • Short-length hem
    • Airy chiffon fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5040

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Escape With Me Tropical Mini Dress

    Escape to an island getaway with this tropical mini dress perfect for a sunset dinner by the shore! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a knotted bust accent, and a bodycon silhouette. The smooth lined knit fabric offers a moderate stretch. Complete the look in trendy sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Knotted bust accent
    • Bodycon silhouette, mini-length hem
    • Tropical print
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5004

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Marvel Lace-Up Mini Dress

    Everyone will marvel at you in this marble print mini dress featuring a sleeveless square neck, spaghetti straps that lace up along the back, and a bodycon silhouette. The mini-length dress is composed of a marble-printed mesh fabric with a stretch knit lining. Complete the look in platform wedges for dinner by the beach!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Lace-up back
    • Bodycon silhouette
    • Mini-length hem
    • Marble print, mesh fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4990

    Category Name: Casual Dresses

    Price: $5.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Strolls Floral Tie-Back Skater Dress

    Your stroll through the garden party will be so sweet in this floral chiffon dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty tie-back design, and a fit-and-flare skater silhouette with a short hem. Complete the look in cute sandals.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Tie-back design
    • Fit and flare, skater silhouette
    • Short-length hem
    • Watercolor floral print
    • Airy chiffon, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4903

    Category Name: Casual Dresses

    Price: $9.97 $41.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Weekend Vibes Floral Mini Dress

    Give off those effortless weekend vibes in this adorable floral mini dress! It features a V-neckline with a twist-front design, a front keyhole cutout under the bust, adjustable spaghetti straps, a smocked design down the back and body of the dress, a mini-length hem with a form-hugging silhouette, and a ditsy floral print pattern. The woven fabric offers a moderate stretch. Style with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline, twist-front design
    • Keyhole cutout under the bust, adjustable spaghetti straps
    • Smocked design down the back and body of the dress
    • Mini-length hem, form-hugging fit
    • Ditsy floral print
    • Woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4920

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everlasting Bliss Ditsy Floral Mini Dress

    You'll be blissful all season with this ditsy floral mini dress in your closet! Blossom into florals for spring bridal showers, graduations, and casual parties. Featuring a sleeveless square neck, adjustable spaghetti straps, and side ruched seams to accentuate your natural curves along the bodycon silhouette. Complete the look in strappy sandals.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti traps
    • Side ruched seam
    • Bodycon silhouette, mini-length hem
    • Ditsy floral print
    • Lined knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5046

    Category Name: Casual Dresses

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Moves Eyelet Lace Mini Dress

    The perfect sundress for bridal showers or outdoor parties! It features adorable puff short sleeves, a square neck, side ruched seams along the bodice, and a bodycon silhouette with a mini-length hem. Complete the look in trendy espadrille wedges.

    Fit & Features

    • Puff short sleeves
    • Square neck
    • Side ruched seams on bodice
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet lace, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4874

    Category Name: Casual Dresses

    Price: $5.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Romance Floral Lace Skater Dress

    Sweet? Always. Innocent? Rarely. This lace mini gives flirty vintage feels with a neckline made to be noticed and a hem made to be twirled.

    Fit & Features

    • Floral print, lace fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • Ruched square neckline
    • Skater silhouette, drop waist seam
    • Flared mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000240

    Category Name: Casual Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Vineyard Gal Floral Linen Skater Dress

    Perfect for vineyard weddings, wine tasting, and daytime soirees! This vintage-inspired floral linen dress features adorable puff short sleeves, a sweetheart neck with a bust tie, a lace-up back design, and a tiered fit and flare skater silhouette with a short hem. Complete the look in on-trend espadrille wedges.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neck, bust tie
    • Lace-up back design
    • Tiered fit and flare skater silhouette
    • Short-length hem
    • Vintage floral print, linen fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4919

    Category Name: Casual Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romantic Roots Floral Chiffon Short Dress

    Get back to your romantic roots this season in this breezy ditsy floral chiffon dress perfect for baby showers to Sunday brunch! It features a sleeveless V-neck with a flirty bust tie, adjustable spaghetti straps, a stretchy smocked back, and a flattering skater short-length silhouette. Complete the look in strappy espadrille wedges.

    Fit & Features

    • Sleeveless V-neck, bust tie, adjustable spaghetti straps
    • Stretchy smocked back, padded bust
    • Skater silhouette
    • Short-length hem
    • Ditsy floral print
    • Chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4939

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Getaway Midi Sweater Dress

    This adorable retro print sweater dress is giving major weekend getaway vibes! It features a sleeveless scoop neckline, a front O-ring accent with a small keyhole cutout, tank shoulder straps, a scoop-back design, a midi-length hem, and a form-hugging silhouette. The sweater knit fabric features a trendy retro-inspired multi-print pattern. Style with espadrille sandals.

    Fit & Features

    • Sleeveless scoop neckline
    • Front O-ring accent, small keyhole cutout
    • Tank shoulder straps, scoop-back design
    • Midi-length hem, form-hugging fit
    • Retro-inspired multi-print pattern
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1642

    Category Name: Casual Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Always Picked First Floral Lace-Up Dress

    You'll always be picked first in this floral mini dress perfect for afternoon soirees! It features a sleeveless square neck, spaghetti straps that shape the lace-up open back, a bodycon silhouette, and a mini-length hem. The dress is designed with a watercolor floral print on knit fabric with a stretch lining. Complete the look in adorable wedge sandals.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Lace-up, open-back
    • Bodycon silhouette
    • Mini-length hem
    • Watercolor floral print, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5020

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Cutie Denim Tube Dress

    Keep it chic with a tube dress that is perf to dress up for your next brunch date! The dress features a sleeveless square neckline, belt loops, side pockets, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form hugging fit with a moderate stretch. Complete look with a faux leather belt and mules. 

    Fit & Features

    • Sleeveless square neckline
    • Belt loops
    • Side pockets
    • Mini length silhouette
    • Denim fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4128

    Category Name: Casual Dresses

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Legend Lace-Up Graphic Short Dress

    Everyone will make way for you, a major legend walking through! This graphic short dress flaunts your edgy-cool girl style featuring a sleeveless scoop neckline, spaghetti straps, dual side lace-up plackets that reveal some skin, a short bodycon fit, and a front script that reads, "Legend" with graphic detailing. Complete the look with a chain choker necklace and earrings.

    Fit & Features

    • Sleeveless scoop neckline, spaghetti straps
    • Dual side lace-up plackets, cutouts
    • Short bodycon fit
    • Front script reads, "Legend", graphic details
    • Mini-length hem
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1525

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pretty Cute Eyelet Lace Mini Dress

    Achieve an effortless pretty and cute style in this eyelet lace mini dress for your casual dates or strolling downtown with the girls! The dress features adorable puff short sleeves, a ruffle trim sweetheart neckline with a front bust tie, a bodycon fit, and side ruching with an adjustable tie. Complete the look in trendy flat sandals.

    Fit & Features

    • Puff short sleeves
    • Ruffle trim sweetheart neckline
    • Front bust tie
    • Bodycon silhouette
    • Side ruching with adjustable tie
    • Mini-length hem
    • Eyelet lace fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4912

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendsetting Style Chain Strap Mini Dress

    Show off your trendsetting style in this sleeveless bodycon mini dress! It features a scoop neckline, adjustable spaghetti straps with chunky chain-link accents, a mini-length hem, and a curve-hugging fit. The ribbed knit fabric offers plenty of stretch. Complete the look in this short dress with a mini handbag and clear mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps, chain-link accents
    • Mini-length hem
    • Form-hugging fit
    • Stretchy ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4917

    Category Name: Casual Dresses

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Slay Tropical Print Midi Dress

    Slay your vacay look with this curve-hugging tropical print midi dress! It features a sleeveless V-neckline, spaghetti straps, a ruched side seam, a midi-length asymmetric hem creating a chic side slit, and a bodycon silhouette. The all-over tropical palm leaf print will really bring those vacay vibes. Complete the look with clear mules.

    Fit & Features

    • Sleeveless V-neckline, spaghetti straps, bust lining
    • Ruched side seam
    • Midi-length asymmetric hem, side slit
    • Bodycon silhouette
    • Tropical palm leaf print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4948

    Category Name: Casual Dresses

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dream Escape Tropical Midi Dress

    Pack right for your dream escape with this tropical print midi dress perfect for a dinner with a beachside view! It features a sleeveless V-neckline, adjustable spaghetti straps that crisscross in the back, a bodycon fit, and a ruched side seam to accentuate your curves atop a sultry slit. The smooth knit fabric features a gorgeous tropical floral print that will give off major vacay vibes. Complete the look with sleek earrings and a choker necklace.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, crisscross back
    • Bodycon silhouette
    • Side ruched seam, slit accent
    • Asymmetric midi-length hem
    • Tropical floral print, knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4957

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In Paradise Tropical Print Midi Dress

    You'll be ready for your paradise getaway with this tropical print midi dress! It features a sleeveless V-neck, spaghetti straps, a sultry cutout back, a bodycon silhouette, and an asymmetrical side slit cutout. Complete the look in wedges.

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Cutout back
    • Bodycon silhouette
    • Asymmetrical side slit cutout
    • Midi-length hem
    • Tropical print, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4987

    Category Name: Casual Dresses

    Price: $19.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy In Floral Satin Midi Dress

    Create a dreamy look in this floral satin midi dress for brunch or bridal showers! It features a sleeveless cowl neckline, adjustable spaghetti straps, a curve-hugging slim silhouette, and a flirty side slit accent. Complete the look in heeled mules.

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Curve-hugging, slim silhouette
    • Side slit accent
    • Midi-length hem
    • Floral print, silky satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4985

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Favorite Pick Ruched Slit Midi Dress

    Your new favorite midi dress for looking stylish and cute! It features a sleeveless square neck, sleek bungee spaghetti straps, a bodycon silhouette, and a side slit with a ruched drawstring that lets you customize the fit. The midi dress is composed of a rib-knit fabric with lining and plenty of stretch. Complete the look in trendy flat sandals for a bridal shower or brunch! 

    Fit & Features

    • Sleeveless square neck
    • Bungee spaghetti straps
    • Bodycon silhouette
    • Side slit, ruched adjustable drawstring
    • Midi-length hem
    • Rib knit-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5034

    Category Name: Casual Dresses

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Just Peachy Keen Off-The-Shoulder Midi Dress

    Look and feel peachy keen in this cute swiss dot midi dress perfect for strolls downtown or grabbing brunch! It features an off-the-shoulder neckline with adorable flutter short-sleeve cuffs, a stretchy smocked bodice, and a flowy hem with a front-slit accent. Complete the look in sleek hoop earrings and sandals.

    Fit & Features

    • Off-the-shoulder neckline
    • Flutter short-sleeve cuffs
    • Stretchy smocked bodice
    • Flowy midi-length hem, front slit accent
    • Swiss dot woven fabric, mini-length woven lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4953

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale