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!

  • Flowy Feels Paisley Maxi Dress

    You'll love the flowy fit of this paisley maxi dress, perfect for the warmer months! It features a sleeveless cowl neckline, spaghetti straps, a maxi-length hem, and a thigh-high front slit. The smooth and stretchy knit fabric features a trendy paisley print pattern. Complete the look with strappy sandals.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Maxi-length hem, high front slit
    • Flowy silhouette
    • Paisley print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4967

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So In Love Floral A-Line Midi Dress

    You'll fall so in love with this floral midi dress to wear for day dates! It features a sleeveless square neckline, elastic ruched straps with lettuce-edge trim, an A-line silhouette, and a flirty front slit. The dress has a dainty rose floral print on stretchy knit-lined fabric. Complete the look in heeled sandals.

    Fit & Features

    • Sleeveless square neckline
    • Elastic ruched straps
    • Lettuce-edge trim
    • A-line silhouette
    • Front slit, midi-length hem
    • Dainty rose floral print, stretchy knit-lined fabric
    • Runs true to size

    Style Number/Barcode: 05102-4921

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trip To The Tropics Printed Midi Dress

    You'll look like you're ready to whisk away on a tropical vacay in this printed midi dress! It features a sleeveless V-neckline, spaghetti straps, a midi-length hem, a hip-hugging fit and an A-line silhouette, a thigh-high front slit, and an eye-catching tropical palm leaf print. Style with trendy wedges.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Midi-length hem, hip-hugging fit, A-line silhouette
    • High front slit
    • Tropical palm leaf print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4979

    Category Name: Casual Dresses

    Price: $19.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Let's Go Party Marble Mesh Mini Dress

    You'll be ready to live it up this festival season in this trendy marble mesh mini dress! It features a sleeveless square neckline, spaghetti straps, an alluring open back with a lace-up strappy design, a mini-length hem with a curve-hugging bodycon silhouette, and a fab marble swirl printed design. The lined mesh fabric offers plenty of stretch. Complete your party look with a faux leather jacket.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Open back, lace-up strappy design, tie closure
    • Mini-length hem, bodycon silhouette
    • Marble swirl print
    • Sheer mesh fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4960

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fiercely Stylish Leopard Print Maxi Dress

    Keep it fiercely stylish with a maxi dress that brings a chic flair! The lightweight knit dress features a sleeveless V-neckline, spaghetti straps, a maxi-length, flowy, A-line silhouette, a sultry thigh-high front slit, and a trendy leopard print pattern. Complete the look with clear mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Maxi-length A-line silhouette
    • High front slit
    • Leopard print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4968

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spice It Up Cutout Midi Dress

    Serving sultry vibes with zero effort required. This knit midi hugs in all the right places with a bold cutout back and leg slit that was made for double takes.

    Fit & Features

    • Textured knit fabric with stretch
    • V-neckline, tank shoulder straps
    • Open back cutout with racer strap detail
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000109

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: RUST

    Available Size: XS, S, M, L

  • On The Go Crew Neck Slit Midi Dress

    The perfect casual midi dress to look stylish while on the go! It features cap short sleeves, a crew neck, a bodycon silhouette, a side ruched drawstring, and a flirty slit along the hem. The dress is composed of a super soft brushed knit fabric with plenty of stretch. Style with cute slide sandals and a tote bag! 

    Fit & Features

    • Cap short sleeves
    • Crew neck
    • Bodycon silhouette
    • Side ruched drawstring, slit accent
    • Midi-length hem
    • Soft brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4872

    Category Name: Casual Dresses

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Charm Tie-Front Midi Dress

    Make them all fall for your stylish charm in this adorable midi dress! It features a sleeveless V-neckline with a cute tie-front detail, spaghetti straps, a midi-length hem with a high front slit for a subtle sultry vibe, and a slim-fit silhouette. The lightweight knit fabric has plenty of stretch. Pair with hoop earrings and block heels for a date night.

    Fit & Features

    • Sleeveless V-neckline, tie-front detail
    • Spaghetti straps
    • Midi-length hem, high front slit
    • Slim-fit silhouette
    • Lightweight knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4864

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Irresistible Mesh Midi Dress

    You'll be a vision in this simply irresistible mesh midi dress perfect for an engagement party or cocktail soiree! It features a sleeveless plunge v-neck, adjustable straps, a back slit accent, and ruched seams that accentuate your curves along the bodycon silhouette. Complete the look in stiletto heels.

    Fit & Features

    • Sleeveless plunge v-neck
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Ruched seams, back slit accent
    • Bodycon, midi-length hem
    • Mesh fabric, sewn-in knit lining, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05101-1857

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blooming Beauty Floral Midi Dress

    Bloom with beauty in this gorgeous floral midi dress perfect for the season! It features a sleeveless square neckline, spaghetti straps, a knot-front design at the waist with ruching, a midi-length hem with a chic high front slit, and a curve-hugging fit. The stretchy knit fabric showcases a stunning bold floral print. Style with platform heels for a bridal shower.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps, square back
    • High waist seam, knot-front design, ruching
    • Midi-length hem, high front slit
    • Form-hugging fit
    • Bold floral print, knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1678

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Staple Wrap-Front Mini Dress

    Update your wardrobe with this cute and casual mini dress that is a stylish staple! It features a crew neckline, short sleeves, a trendy wrap-front design at the waist with a tie closure, a form-hugging fit, and a mini-length hem. The soft brushed knit fabric offers plenty of stretch for comfort. Complete the look with ankle booties.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Wrap-front design at the waist, tie closure
    • Form-fitting silhouette
    • Mini-length hem
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5007

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Prowlin' Cutie Leopard Crepe A-Line Dress

    Look cute for your daytime prowls in this leopard print crepe dress! It features long bell sleeves, a scoop neck with a ruched tie-front bust, halter straps with self-tie closure, and a flattering A-line silhouette and dual side slit accents. Complete the look in sassy sandals!

    Fit & Features

    • Long bell sleeves
    • Scoop neck, ruched tie-front bust
    • Halter straps, self-tie closure
    • A-line silhouette
    • Short-length hem with dual side slit accents
    • Leopard print, crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4959

    Category Name: Casual Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple Chic Style Satin Mini Dress

    The simple chic style of this satin mini dress is perf for the babe who loves a classic look. It features a sleeveless V-neckline, bungee spaghetti straps, a fitted A-line silhouette, and a mini-length hem with an alluring front slit. The lightweight satin-knit fabric offers a moderate stretch. Complete the outfit with strappy heels.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Fitted A-line silhouette
    • Mini-length hem
    • Front slit
    • Satin-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1965

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfectly Striped Shirt Skater Dress

    Step out in this perfectly striped shirt dress to look cute for picnics in the park, family gatherings, or graduations! It features long sleeves with buttoned cuffs, a collar v-neckline, a corset-seam illusion waist, a cutout lace-up back design, and a short skater silhouette. Complete the look with teardrop earrings.

    Fit & Features

    • Long sleeves, buttoned cuffs
    • Collar v-neckline
    • Corset-seam illusion waist
    • Cutout lace-up back design
    • Skater silhouette, short-length hem
    • Striped print, poplin non-stretch woven fabric
    • Runs true to size

    Style Number/Barcode: 05102-5048

    Category Name: Casual Dresses

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Moves Long Sleeve Bodycon Mini Dress

    Showcase your silhouette in this chic bodycon mini dress! It features a V-neckline, long fitted sleeves, ruched detailing at the shoulders, a mini-length hem, and a curve-hugging fit. The smooth knit fabric offers plenty of stretch. Style with clear lucite heels.

    Fit & Features

    • V-neckline
    • Long fitted sleeves
    • Ruching at the shoulders
    • Mini-length hem
    • Fitted bodycon silhouette
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05103-4835

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance For One Rose Tie-Front Dress

    Romance yourself! Look sweet in this rose print casual dress on a day date or brunch. It features a sleeveless sweetheart neck, spaghetti straps, bust tie-front, and keyhole, side ruched seams to accentuate your figure along the mini, bodycon silhouette. Style with a denim jacket to complete the look!

    Fit & Features

    • Sleeveless sweetheart neck, spaghetti straps
    • Bust tie-front and keyhole
    • Side ruched seams
    • Bodycon silhouette, mini-length hem
    • Ditsy rose print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4929

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Beauty Floral Mini Dress

    Radiate effortless beauty in this gorg floral mini dress! It features a square neckline, sheer long peasant sleeves to add a chic flair, all-over ruching, a mini-length hem with a form-hugging fit, and an all-over blooming floral print. The sheer chiffon fabric includes a partial knit lining down the body of the dress. Style with dainty duster earrings and a pair of neutral heels.

    Fit & Features

    • Square neckline
    • Sheer long peasant sleeves, elastic cinched hems
    • All-over ruching, back zipper, hook and eye closure
    • Mini-length hem, form-hugging fit
    • Floral print
    • Sheer chiffon fabric, partial knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1860

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tie Dye Over Bodycon Mini Dress

    You'll tie-dye over this casual mini dress to add some color to your closet for warmer seasons ahead! It features a square neck, bungee spaghetti straps, and side ruched seams that accentuate your curves along the bodycon silhouette. The dress is composed of stretchy mesh fabric with a sewn-in knit lining. Complete the look in a cropped denim jacket and sneakers.

    Fit & Features

    • Sleeveless, square neck
    • Bungee spaghetti straps
    • Side ruched seams, bodycon silhouette
    • Mini-length hem
    • Tie-dye pattern, mesh fabric, sewn-in knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4931

    Category Name: Casual Dresses

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Staple Long Sleeve Midi Dress

    This long sleeve midi dress is such a stylish staple! Featuring a square neckline with a chic center cutout at the bust, long fitted sleeves, a midi-length hem with a front slit, and a form-hugging fit, this crepe dress can be styled up or down. Pair with strappy mules for a date night.

    Fit & Features

    • Square neckline
    • Small bust cutout
    • Long fitted sleeves
    • Midi-length hem, front slit
    • Form-hugging fit
    • Crepe fabric, short knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5529

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Paradise Halter Open Back Slit Midi Dress

    Own the spotlight on vacation in this midi dress! Featuring a bold halter neckline and an sexy open back, this dress exudes allure, while the bodycon silhouette and slit add a flattering look.

    Fit & Features

    • Slinky knit fabric, smooth stretchy knit lining
    • Halter cowl neckline, beaded spaghetti strap tie
    • Open back with spaghetti strap tie
    • Bodycon silhouette
    • Slit accent, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000283

    Category Name: Casual Dresses

    Price: $45.90

    Availability: In Stock

    Available Color: RED, BROWN

    Available Size: XS, S, M, L

  • True Colors Marble Print Mini Dress

    Show your true colors of style in this marble print dress perfect for casual plans! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, and a mini-length hem. Style with trendy heels and a denim jacket to complete the look!

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Marble print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5000

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Extra Flair Floral Skater Dress

    You'll be a darling delight in this short skater dress perfect for parties and ceremonies! It features three-quarter-length puff sleeves, a square neck, a smocked back, and a fit and flare silhouette. The dress is composed of a floral burnout woven fabric with a chiffon lining and no stretch. Style with earrings and a choker to complete the look!

    Fit & Features

    • Three-quarter-length puff sleeves
    • Square neck
    • Smocked back
    • Fit and flare skater silhouette
    • Short-length hem
    • Floral burnout woven fabric, chiffon lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2211

    Category Name: Casual Dresses

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Into Floral Chiffon Skater Dress

    Transition your winter blues into fresh spring florals! This breezy chiffon skater dress is perfect for dressy brunches or engagement parties. It features a surplice V-neckline, sheer peasant sleeves, a tie-back belted waist, and a tiered ruffle short-length hem with an adorable ditsy floral print. Complete the look in lace-up heels.

    Fit & Features

    • Surplice V-neckline
    • Sheer peasant sleeves 
    • Tie-back belted waist, back zipper and hook-eye closure
    • Skater, fit and flare silhouette
    • Tiered ruffle short-length hem
    • Ditsy floral print, chiffon fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1711

    Category Name: Casual Dresses

    Price: $5.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Babe Cutout Sweater Dress

    You'll be such a trendy babe in this adorable cutout sweater dress! Featuring a sleeveless high neckline with a racerback design, a front keyhole cutout at the bust, alluring side cutouts at the waist, a midi-length hem, and a curve-hugging silhouette, this dress is a perfect pick for a night out with the girls. Style with platform heels and a chic handbag.

    Fit & Features

    • Sleeveless high neckline, racerback design
    • Front keyhole cutout at the bust
    • Dual side cutouts at the waist
    • Midi-length hem, curve-hugging fit
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1633

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance