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!

  • Getaway Bound Tropical Cowl Neck Maxi Dress

    You'll be ready for your getaway with this tropical maxi dress in your carry-on! It features a sleeveless cowl neckline, spaghetti straps that crisscross in the back, a curve-hugging slim silhouette, and a flirty front slit. Complete the look in espadrille wedges and sunnies!

    Fit & Features

    • Sleeveless cowl neckline, bust lining
    • Spaghetti straps, crisscross back
    • Curve-hugging, slim silhouette
    • Front slit
    • Maxi-length hem
    • Tropical print, smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4999

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Chic Cutout Midi Sweater Dress

    Create the perfect casual chic look with this of-the-moment sweater dress. It features a sleeveless scoop neckline with contrast piping, thin tank shoulder straps, a front waist cutout with matching contrast piping, a midi-length hem with a front slit, and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Style with clear mules.

    Fit & Features

    • Sleeveless scoop neckline, contrast piping
    • Thin tank shoulder straps
    • Front waist cutout, contrast piping
    • Midi-length hem, front slit
    • Curve-hugging fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1700

    Category Name: Casual Dresses

    Price: $44.90

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Whirlwind Romance Floral Abstract Maxi Dress

    This maxi dress is giving goddess in the wild. The sheer mesh and abstract floral print bring soft drama to any scene, whether it's brunch or rooftop party soirees! 

    Fit & Features

    • Abstract floral print, mesh lined fabric
    • Sweetheart neckline, padded bra cups, ruched bust seam
    • Spaghetti straps
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000242

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: MAUVE

    Available Size: XS, S, M, L

  • Sassy Speed Racer Graphic Mini Dress

    Amp up your bar hopping 'fits with this edgy graphic mini dress! It features a sleeveless crew neckline, a notched V-neck design with safety pin accents, a racecar graphic with various scripts like, "Champions Racing," a mini-length hem, and a bodycon silhouette that will hug your curves. Style with a layered necklace set and sneakers.

    Fit & Features

    • Sleeveless crew neckline
    • Notched V-neck design, safety pin accents
    • Racecar graphic, various scripts like "Champions Racing"
    • Mini-length hem
    • Bodycon silhouette
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1607

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunset Chaser Cowl Neck Mini Dress

    The perfect mesh mini dress for a sunset dinner by the beach! It features a sleeveless cowl neckline, sleek bungee spaghetti straps, and side-ruched seams to accentuate your curves along the bodycon silhouette. Complete the look with a sleek choker and earrings.

    Fit & Features

    • Sleeveless cowl neckline
    • Bungee spaghetti straps
    • Side ruched seams, bodycon silhouette
    • Mini-length hem
    • Sunset beach graphic design
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5197

    Category Name: Casual Dresses

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Fave Ribbed Knit Mini Dress

    This basic casual ribbed knit mini dress will be a new fave for the season! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, a mini-length hem, and a form-hugging silhouette. The lightweight ribbed knit fabric offers plenty of stretch. Style with a denim jacket and sandals for a cute everyday vibe.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Mini-length hem
    • Form-hugging bodycon fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5086

    Category Name: Casual Dresses

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Sweetheart Midi Dress

    Sweet but sexy, this denim midi dress was made for you! It features a sleeveless, sweetheart neck, adjustable spaghetti straps, corset-style bodice, and a high-waist seam leading to the bodycon silhouette with a back slit accent. Complete the look in statement earrings.

    Fit & Features

    • Sleeveless, sweetheart neck, adjustable spaghetti straps
    • Corset-style bodice, back zipper closure
    • High-waist seam, back slit accent
    • Bodycon silhouette
    • Midi-length hem
    • Denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4477

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heat Things Up Cutout Mini Dress

    Heat things up in this showstopping bodycon mini dress on vacation or at a summer party! It features a sweetheart neckline, spaghetti straps that crisscross in the back, dual front center O-ring inserts and cutout accents, side ruched seams, and a fitted hem. Complete the look with geo-shaped earrings and a layered necklace.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps, crisscross back
    • Dual front center O-ring inserts, cutout accents
    • Bodycon silhouette, side ruched seams
    • Mini-length fitted hem
    • Double-lined brushed knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 05102-5137

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dinner With A View Tropical Slit Maxi Dress

    You may be on vacay with incredible views but you'll be the main attraction in this tropical maxi dress perfect for dining on the island! It features a sleeveless square neck, adjustable spaghetti straps, a front adjustable ruched drawstring that lets you customize the style, a sultry front slit, and a flattering slim curve-hugging silhouette. The maxi dress is composed of a slinky knit fabric with a tropical print and a short stretchy knit lining. Complete the look in strappy heels.

    Fit & Features

    • Sleeveless square neck, adjustable spaghetti straps
    • Front adjustable ruched drawstring
    • Slim curve-hugging silhouette
    • Front high slit
    • Maxi-length hem
    • Tropical print, slinky knit fabric, short stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5031

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Mood Cutout Bodycon Midi Dress

    Keep your summer style sultry and on-trend with this curve-hugging bodycon midi dress. It features a sleeveless square neckline, thin tank shoulder straps, an asymmetric cutout that continues all around the waist with a sleek O-ring accent at the front, and a midi-length hem. The ribbed knit fabric offers plenty of stretch. Pair with strappy heels.

    Fit & Features

    • Sleeveless square neckline
    • Thin tank shoulder straps
    • Asymmetric cutout, all around the waist, metal O-ring accent
    • Midi-length hem
    • Bodycon fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5189

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Silhouette One-Shoulder Midi Dress

    Showcase a sultry silhouette in this chic sleeveless midi dress that will hug your curves! The midi dress features an asymmetric one-shoulder neckline with a thin tank strap and a trendy O-ring accent, a bold cutout at the bust for an alluring vibe, an asymmetric midi-length hem creating a thigh-high side slit, and a bodycon fit. Style with lace-up heels for a date night.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Thin tank shoulder strap, O-ring accent
    • Bust cutout, high waist seam, side ruching
    • Asymmetric midi-length hem, high side slit
    • Bodycon fit
    • Ribbed knit fabric. moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4927

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacation Awaits Tropical Print Cutout Maxi Dress

    Be sure to pack this bold tropical print maxi dress in your carry-on for your next warm-weather vacay! It features a sleeveless V-neckline with a twist-front design at the bust, a sultry waist cutout at the front, adjustable spaghetti straps, a floor-length hem with a thigh-high front slit, and a flowy A-line silhouette. The smooth and stretchy knit fabric features an all-over tropical palm leaf print for an island vibe. Style with strappy sandals.

    Fit & Features

    • Sleeveless V-neckline, twist-front design
    • Front waist cutout
    • Adjustable spaghetti straps
    • Floor-length hem, high front slit
    • Flowy A-line silhouette
    • Tropical palm leaf print
    • Knit fabric, mini-length lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4928

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Romance Tropical Print Maxi Dress

    Give off a romantic allure at your sunset dinner date in this form-hugging maxi dress! It features a sleeveless cowl neckline, spaghetti straps, an open back with a cross-back lace-up strappy design, a floor-length hem with a sultry asymmetric high side slit to showcase some leg, ruched detailing, and an all-over tropical palm leaf print. Style with hoop earrings and espadrille wedges.

    Fit & Features

    • Sleeveless cowl neckline, spaghetti straps
    • Open back, cross-back lace-up strappy design, tie closure
    • High waist seam, floor-length hem, asymmetric high side slit
    • Form-hugging fit, ruched detailing
    • Tropical palm leaf print
    • Knit fabric. lined bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4996

    Category Name: Casual Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Nautical Vibes Striped Mini Dress

    Elevate your summer style and give off chic nautical vibes in this striped mini dress! It features a sleeveless scoop neckline, spaghetti straps, a faux wrap waist design with a tie-front detail, a mini-length hem, and a form-hugging fit. The stretchy brushed knit fabric features an all-over horizontal striped pattern. Complete the look with espadrille sandals for a beachside brunch!

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Faux wrap waist design, tie-front detail
    • Mini-length hem, form-hugging fit
    • Horizontal striped print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5067

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine Girlie Crochet Chevron Sweater Dress

    Calling all the sunshine girlies! Slip on this playful crochet chevron sweater dress for backyard pool parties or vacations. It features a sleeveless halter V-neckline, tie-back spaghetti straps, an open back, a bodycon silhouette, and a mini-length hem with ribbed trim. Style with chunky platform heels for a complete look!

    Fit & Features

    • Sleeveless halter V-neckline
    • Tie-back spaghetti straps
    • Open back
    • Bodycon silhouette
    • Mini-length hem with ribbed trim
    • Chevron pattern, crochet sweater fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06005-1658

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Mood Ditsy Floral Mini Dress

    This adorable ditsy floral mini dress will have you in the mood for easy summer days! It features a sleeveless scoop neckline, a small bust cutout with a tie-front detail, spaghetti straps, a mini-length hem, and a form-hugging silhouette. The ditsy floral printed ribbed knit fabric offers plenty of stretch. Style with hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless scoop neckline
    • Small bust cutout, tie-front detail
    • Spaghetti straps
    • Mini-length hem, form-hugging fit
    • Ditsy floral print
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5114

    Category Name: Casual Dresses

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Untamed Aura Animal Print Halter Maxi Dress

    Giving wild energy in the sleekest way possible—this maxi dress is pure confidence wrapped in an abstract animal print. The halter neckline and curve-hugging fit make it perfect for nights when subtle just isn’t on the agenda.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Abstract animal print
    • Sleeveless plunging V-neckline, cutout below the bust
    • Halter tie-back spaghetti straps, open back, lower back bar strap
    • Maxi-length hem
    • Curve-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000253

    Category Name: Casual Dresses

    Price: $45.90

    Availability: In Stock

    Available Color: PURPLE

    Available Size: XS, S, M, L

  • Flirty Floral Vibes Ruched Mini Dress

    Capture a sweet romantic look in this flirty floral mini dress! It features a sleeveless V-neckline with ruching at the bust, spaghetti straps, a mini-length hem, and a form-hugging fit. The stretchy ribbed knit fabric features an all-over ditsy floral print for an adorable summer style. Pair with espadrille sandals for a day date.

    Fit & Features

    • Sleeveless V-neckline
    • Ruching at the bust
    • Spaghetti straps
    • Mini-length hem, form-hugging fit
    • Ditsy floral print
    • Ribbed knit fabric, smooth knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4760

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dial B For Basics Square Neck Mini Dress

    Dial B for this basic mini dress that'll inspire all your fashion-forward looks! It features a sleeveless square neckline, sleek bungee spaghetti straps, a form-hugging silhouette, and a mini-length hem. The double-line buttery knit fabric offers a seamless design and plenty of stretch. Style with a minimalistic necklace and earrings to inspire your day or night outfit! 

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Form-hugging silhouette
    • Mini-length hem
    • Double-lined buttery knit fabric, moderate stretch
    • Seamless design
    • Runs true to size

    Style Number/Barcode: 05102-5134

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Getaway Tropical Print Midi Dress

    Get a gorgeous look for your next vacay getaway with this alluring tropical print midi dress. It features a sleeveless square neckline, spaghetti straps, an open back with a cross-back lace-up strappy design, ruching at the waist, a midi-length hem with an asymmetric high side slit, and a curve-hugging silhouette. The all-over palm leaf pattern on the stretchy knit fabric will bring those tropical vacation vibes. Style with cute wedges.

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Open back, cross-back lace-up strappy design, tie closure
    • Ruched detailing at the waist
    • Midi-length hem, asymmetric high side slit
    • Curve-hugging silhouette
    • Tropical palm leaf print, knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5008

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Time To Escape Tropical Print Maxi Dress

    Get ready to escape on a gorgeous getaway in this sultry tropical print maxi dress! It features a sleeveless asymmetric one-shoulder neckline with a spaghetti strap, a bold and alluring asymmetric waist cutout with a trendy O-ring accent, a hip-hugging fit that will hug your natural curves, and a floor-length hem with a thigh-high side slit to showcase some leg. The all-over palm leaf print on the stretchy knit fabric captures those tropical oasis vibes. Style with strappy sandals.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Single adjustable spaghetti strap
    • Asymmetric waist cutout, O-ring accent
    • Hip-hugging fit, floor-length hem, high side slit
    • Tropical palm leaf print
    • Knit fabric, mini-length lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5016

    Category Name: Casual Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • A Way With Lace V-Neck Mini Dress

    Let this lace mini dress speak your favorite language, romance! The short dress features a sleeveless V-neckline, spaghetti straps, a bodycon silhouette, and a sheer lace overlay with a sewn-knit lining. Complete the look in rhinestone mules for a wedding shower or birthday brunch!

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Sheer lace overlay, sewn-in knit lining
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5088

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Refresh Ruched Bodycon Mini Dress

    Update your dress collection with this ruched bodycon mini dress that will be a chic refresh! It features a sleeveless crew neckline, tank shoulder straps, a partially open back with a cross-back strap design for a trendy detail, ruching down the side seams, and a mini-length hem with a bodycon silhouette that will hug your natural curves. The lined ribbed knit fabric offers plenty of stretch. Style with clear lucite heels for happy hour.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Open back, cross-back strap design
    • Ruched side seams
    • Mini-length hem, bodycon fit
    • Ribbed knit fabric, smooth sewn-in knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5143

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Stunner Chain Strap Midi Dress

    Embrace the warmer months and showcase a stunning summertime style in this ribbed knit midi dress. It features a sleeveless square neckline, adjustable spaghetti straps with multi-colored front beaded and chain accents, a hip-hugging fit that will show off your natural curves, and a midi-length hem with a thigh-high front slit for a sassy detail. The ribbed knit fabric offers plenty of stretch. Complete the look with espadrille wedges for a playful summer vibe.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps, multi-colored front beaded and chain accents
    • Hip-hugging fit
    • Midi-length hem, high front slit
    • Ribbed knit fabric, lined bust
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4871

    Category Name: Casual Dresses

    Price: $5.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale