Casual Dresses

Explore the array of casual dresses perfect for brunch with your besties to stroll around the farmers market on the weekends. Discover a variety of casual fabrics like ribbed knit, denim, mesh, linen, or cotton gauze. Browse the variety of skater dresses, sundresses, t-shirt dresses, and boho-inspired maxis. Look out for off-the-shoulder mini dresses, tropical print shift dresses, and tie-dye ribbed dresses perfect for a laid-back vibe but always with a chic aesthetic.

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CASUAL DRESSES
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STYLE SPOTLIGHT

Cute Work Dresses

Women's Boots & Booties

Floral Print Dresses

Everyday Casual Dresses That Are Essential For Fall

It's time to elevate your look with cozy and stylish casual dresses from Windsor. Whether you're planning a leaf-peeping trip, catching up with friends over a warm latte, or simply looking to refresh your fall closet, our selection of trendy casual dresses for women has you covered.

For fall 2024, embrace rich autumnal colors like deep burgundy, burnt orange, or olive green. These shades perfectly capture the cozy essence of the season. Opt for casual dresses made from comfortable fabrics like rib knit, jersey, or faux suede to keep you warm as the weather cools. If you prefer an effortlessly chic look, try a sweater dress. This versatile style is ideal for transitioning from a casual day out to a cozy evening gathering. Pair it with ankle boots, a wide-brim hat, and a faux leather jacket for an on-trend fall look.

Looking for a dress that effortlessly takes you from day to night? Consider our selection of casually chic sweater dresses. These styles are polished yet cozy, perfect for any occasion. Elevate your casual dress ensemble with a pair of knee-high boots and a statement scarf for a sophisticated fall outfit.

Long casual dresses are also a must-have for fall 2024. Opt for casual maxi dresses in smooth, contouring designs made from lightweight fabrics. Choose from earthy tones like taupe and chocolate brown or go for classic black for the most versatile look. Wear your long casual dress with a chunky cardigan, leather sneakers, and a crossbody bag for a flawless #OOTD.

Whether you're planning a holiday getaway or simply updating your wardrobe, a smart casual dress code is an essential addition. They're comfortable, versatile, and perfect for any occasion. Refresh your closet with elevated casual dresses from Windsor and stay on-trend this fall. Shop now online or in-store!

What Makes A Dress Casual?

Aside from special occasion dresses and gowns, dresses can be casual depending on how you style them. Fabrication and design can also innately make a dress casual so choose knits and cotton blends or ditsy florals or neutral tone prints, like a snake print dress, as everyday basics. Knit and sweater dresses, updated regularly here, are stylish choices for work or date night. Avoiding heels and heeled mules, and pairing sneakers and lug boots instead come in handy to make any dress look more laid back. Layering knits like cardigans, sweaters, or even classic jean jackets that are naturally casual over any dress is an easy way to instantly dress down the look. Casual dresses with drawstrings and tie or button fronts are details that can give those laid-back vibes too. Like with shoes, often it’s what you wear with the dress that “dresses down” your look so choose hair accessories, makeup, and jewelry accordingly.

How Do I Style A Dress Casually?

Style a dress casually by choosing to complement apparel and accessories that are naturally casual like jean jackets, t-shirts, scrunchies, dainty or basic jewelry, simple crossbody bags, and casual shoes like strappy sandals or combat boots. Take a ruched form-hugging mini dress and add on a simple lariat necklace and chunky sneakers for a cool and casual look. Layer on a denim jacket over a basic knit midi dress and pair it with slides for a casual-chic feel. For road trips or weekend getaways, maxi and midi dresses can be layered any time of year with graphic tees and sandals or cropped sweaters and combat boots to create that laid-back vibe. Windsor has the best-selling selection of women's casual dresses and accessories to pair them with for that must-have chill look. Need some help? Our in-store stylists are always ready to help you find your perfect outfit. Come shop with us!

  • Darling Details Floral Eyelet Mini Dress

    This floral eyelet mini dress has darling details that make it perfect for spring and summer looks! Made from a beautiful floral printed woven eyelet fabric, this dress will make you feel like a blooming flower. With a flirtatious square neckline and bust keyhole tie, this dress is perfect for any occasion. The adjustable spaghetti straps ensure a perfect fit while the curve-hugging silhouette and mini-length hem show off your figure. Complete the look with a ring set.

    Fit & Features

    • Floral printed woven eyelet fabric with knit lining
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Square neckline, keyhole tie
    • Curve-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3013

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Blooms Floral Ruffle Chiffon Skater Dress

    Let this tropical floral skater dress bloom into your summer lineup! With a sweetheart neckline featuring delicate ruffle trim, adjustable spaghetti straps and padded bra cups, this skater silhouette will flatter your figure. The mini-length hem adds a flirty touch to this tropical floral printed chiffon dress. Complete the look with a crossbody purse and sandals!

    Fit & Features

    • Tropical floral print
    • Chiffon fabric with woven lining, no stretch
    • Sweetheart ruffle trim neckline
    • Padded bra cups
    • Adjustable spaghetti straps
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3204

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PINK

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Covetable Charm V-Neck Ruffled Maxi Dress

    You'll covet the charm of this sleeveless maxi dress all season!  With a flattering V-neckline and adjustable spaghetti straps, this dress will hug you in all the right places. The crisscross and smocked back add a trendy touch, while the flowy silhouette and ruffled long-length hem offer a breezy style. Complete the look in sandals.

    Fit & Features

    • Woven fabric, bust lining, no stretch
    • Adjustable spaghetti straps
    • Crisscross and smocked back
    • Flowy silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5546

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Silhouette Rosette Ruffled Knit Mini Dress

    The knit mini dress features a sleeveless scoop neckline accented with a dainty rosette detail for an adorable touch. The tiered ruffled mini-length hem and bodycon fit add a flirty feel while highlighting your curves.

    Fit & Features

    • Ribbed knit fabric with knit lining, plenty of stretch
    • Scoop neckline with rosette detail
    • Spaghetti straps
    • Tiered ruffled mini-length hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5846

    Category Name: Casual Dresses

    Price: $14.97 $25.90

    On Sale: Yes

    Availability: In Stock

    Available Color: HEATHER, GRAY, NAVY

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Vacay Mode Tropical Floral Mesh Maxi Dress

    Activate vacay mode and radiate dreamy vibes in this alluring tropical maxi dress! Designed with an airy sheer mesh fabric with a mini-length knit lining, this maxi-length dress is accented with a blooming tropical floral print for a stunning look. It features a sleeveless square neckline, spaghetti straps, ruched detailing at the waist to accentuate your curves, and a bodycon silhouette with a thigh-high side slit to showcase some leg. Style with stiletto heels for a sunset dinner!

    Fit & Features

    • Tropical floral print
    • Sheer mesh fabric with mini-length knit lining, plenty of stretch
    • Square neckline
    • Spaghetti straps
    • Ruched waist, side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5543

    Category Name: Casual Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M

    Product Badge:
    • Sale
  • Graceful Presence Sweetheart Floral Skater Dress

    Have a graceful presence in this floral skater dress at showers or graduations! A charming dress with a sweetheart neckline and tie spaghetti straps, the skater silhouette flatters your figure, while the short-length hem adds a playful touch. Complete the look in wedge sandals.

    Fit & Features

    • Floral print, woven fabric lined with stretchy knit
    • Tie spaghetti straps
    • Sweetheart neckline
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3194

    Category Name: Casual Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

  • Show Off Your Glow Tropical Lace-Up Midi Dress

    Show off your vacation glow in this tropical midi dress all over the island or resort! With a square neckline, spaghetti straps, and a lace-up back, this side slit dress hugs your body in all the right places with side ruched seams and a bodycon fit. Complete the look in sandals.

    Fit & Features

    • Tropical print, mesh fabric, sewn-in knit lining, moderate stretch
    • Spaghetti straps
    • Square neckline
    • Lace-up back
    • Ruched side seams, bodycon fit
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5866

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fiji Feeling Sleeveless Lace-Up Tropical Maxi Dress

    Escape to the island or look like you did in this tropical maxi dress for an effortless summer style! With a flattering V-neckline and delicate spaghetti straps, this dress will keep you stylish all day long. The lace-up back adds a touch of playful detail, while the A-line silhouette and maxi-length hem create a flowy and romantic look.

    Fit & Features

    • Palm leaf tropical and border print, woven fabric with lining, no stretch
    • V-neckline
    • Spaghetti straps
    • Lace-up back
    • A-line maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5864

    Category Name: Casual Dresses

    Price: $11.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Darling Babe Floral Woven Puff Sleeve Skater Dress

    Create a darling day date look with this floral puff sleeve skater dress! Made with a lightweight woven fabric, it is detailed with a charming dainty floral print for those sweet feminine vibes. The short dress features a V-neckline with a cute tie-front detail, short puff sleeves with a ruffled trim, a high waist seam, and a skater hem with a flirty fit-and-flare silhouette. Style with a dainty charm necklace and heels.

    Fit & Features

    • Dainty floral print
    • Woven fabric
    • V-neckline, tie-front detail
    • Short puff sleeves, ruffled trims
    • Back zipper closure, high waist seam
    • Short skater skirt, fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3466

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Effortlessly Trendy Striped Slit Maxi Dress

    A trendy maxi dress features a flattering square neckline, form-hugging fit, and a high front slit to show off your shoes. Perfect for styling with a denim jacket and sandals.

    Fit & Features

    • Striped pattern, stretchy knit fabric
    • Square neckline, spaghetti straps
    • High front slit
    • Form-hugging maxi-length fit
    • Runs true to size

    Style Number/Barcode: 05102-5867

    Category Name: Casual Dresses

    Price: $14.97 $32.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Chic Design Cutout Bodycon Knit Midi Dress

    This bodycon midi dress features a sultry lower back cutout and back slit accent for a chic allure. The curve-hugging dress is made with a lined, soft, brushed knit fabric offering plenty of stretch for comfortable wear.

    Fit & Features

    • Lined brushed knit fabric, plenty of stretch
    • Square neckline
    • Tank shoulder straps
    • Lower back cutout
    • Back slit
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5595

    Category Name: Casual Dresses

    Price: $22.00 $30.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Think Sunshine Long Sleeve Cutout Crochet Mini Dress

    Get in the summer vibe with this crochet mini dress perfect for pool parties or vacation! Featuring sheer flared long sleeves for a trendy touch, a sexy V-neckline, and a cutout waist and back for a daring look. The hoop insert adds a unique twist and the tie-back design creates a flattering look along the bodycon silhouette. Complete the look with sunglasses and sandals!

    Fit & Features

    • Crochet fabric, sewn-in knit lining, slight stretch
    • Sheer flared long sleeves
    • V-neckline
    • Hoop insert, cutout waist and back
    • Tie-back design
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5732

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Of Romance Tie Back Rose Floral A-Line Dress

    Let your love bloom for this rose floral chiffon midi dress perfect for garden parties and weddings! Featuring a square neckline, adjustable spaghetti straps, and a tie-back for the perfect fit, this flowy A-line silhouette dress will have you feeling flirty and feminine. With a front slit and midi-length hem, it's perfect for styling with chic stiletto heels.

    Fit & Features

    • Rose floral print, chiffon fabric lined with stretchy knit
    • Square neckline
    • Adjustable spaghetti straps
    • A-Line silhouette
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05101-3257

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Perfectly Poised Sweetheart Polka Dot A-Line Dress

    Always put your best sweet self forward in this sleeveless polka dot dress at parties or on day dates! The sweetheart neckline with bust tie and spaghetti strap shoulder ties elevate your look, while padded bra cups provide support and comfort. The A-line silhouette and mini-length hem create a flattering style. Complete the look with hoop earrings.

    Fit & Features

    • Polka dot print, lined woven fabric, no stretch
    • Spaghetti strap shoulder ties
    • Sweetheart neckline with bust tie
    • Padded bra cups
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5822

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PEACH

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Cute Charmer Ribbon Bow Bodycon Mini Dress

    Show off your cute charm in this bodycon mini dress on day dates or weekend brunch! Designed with a double-lined brushed knit fabric, this mini-length dress offers plenty of stretch for comfortable wear. It features a sleeveless square neckline with a dainty sheer eyelet lace trim and ribbon bow detail, spaghetti straps, and ruching down the side seams to accentuate your curves along the bodycon silhouette. Complete your coquette-inspired look with pearl earrings and strappy mules!

    Fit & Features

    • Stretchy double-lined brushed knit fabric
    • Square neckline
    • Sheer eyelet lace trim, ribbon bow detail
    • Spaghetti straps
    • Ruched side seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5735

    Category Name: Casual Dresses

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PINK

    Available Size: M, L

    Product Badge:
    • Sale
  • Natural Sweetheart Halter Marble Print Midi Dress

    Look naturally cute for any occasion in this marble print midi dress! The cowl halter neckline and flowy silhouette add a relaxed style, while the side slit and midi-length hem add flirty touches. Complete the look in strappy sandals and a clutch!

    Fit & Features

    • Marble print, mesh fabric lined with stretchy knit
    • Cowl halter neckline with tie closure
    • Flowy silhouette
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5593

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Be My Forever Ribbon Bow Bodycon Mini Dress

    Flattery will get you everywhere in this sleeveless mini dress perfect for boasting an adorable look! The scoop neckline is adorned with delicate lace and charming bow detail, while the tank shoulder straps give a flirty touch. The bodycon silhouette and mini-length hem finish this flawless dress. Complete the look in platform high heels for a party.

    Fit & Features

    • Woven fabric with minimal stretch
    • Scoop neckline, lace and ribbon trim, bow
    • Back zipper and hook-eye closure
    • Tank shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5817

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M

    Product Badge:
    • Sale
  • A Little Wild One-Shoulder Zebra Print Maxi Dress

    Your next night out just got a little wild in this sassy zebra print maxi dress perfect for vacation or the weekend! This form-hugging dress features a one-shoulder neckline and spaghetti strap, with a side drawstring cutout to show some skin. The high side slit and maxi-length hem add a flirty touch to this fierce and flattering piece. Complete the look with heeled sandals and earrings.

    Fit & Features

    • Zebra printed knit fabric, plenty of stretch
    • One-shoulder neckline, spaghetti strap
    • Side drawstring cutout
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5821

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: TAUPE

    Available Size: S, M

    Product Badge:
    • Sale
  • Sure To Love Floral Woven Puff-Sleeve Skater Dress

    You'll love wearing this sweet floral puff-sleeve skater dress all summer long! The lightweight woven fabric is detailed with a soft floral print for a pretty feminine look. The short dress features a scoop neckline with ruching and a tie-front accent, short puff sleeves with elastic cinched hems, a stretchy smocked high waist, and an adorable fit-and-flare silhouette with a ruffled hem for a flirty vibe. Style with sneakers for a cute and casual outfit.

    Fit & Features

    • Floral print
    • Woven fabric with smooth woven lining
    • Ruched scoop neckline with tie-front detail
    • Short puff sleeves with elastic cinched hems
    • Stretchy smocked high waist
    • Fit-and-flare silhouette, ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5716

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M

    Product Badge:
    • Sale
  • Floral Day Dream Lace Up Eyelet Skater Dress

    Make your garden party daydream come true in this floral eyelet skater dress! This playful skater dress features a sweetheart neckline, spaghetti straps, and a lace-up back for a flirty touch. Its skater silhouette and short-length hem make it perfect for twirling! Complete the look with teardrop earrings and a bracelet.

    Fit & Features

    • Floral print, eyelet woven lined fabric, no stretch
    • Sweetheart neckline
    • Spaghetti straps
    • Lace-up back
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3197

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine On My Mind Strapless Tropical Skater Dress

    This tropical skater dress will inspire sunshine on your mind! Perfect for vacations or a beach day, this strapless dress features a stretchy waist leading to the skater silhouette and a flirty ruffled mini-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Tropical palm print, gauze woven fabric, bust lining
    • Strapless neckline
    • Skater silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5744

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RUST, GREEN

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Bohemain Charm Halter Open Back Tie Dye Maxi Dress

    Meet the bohemian charm of this tie dye maxi dress for summer soirees and parties! Featuring a halter cowl neckline and an alluring open back with tie closure, this dress exudes sensuality. The side ruched seams and form-hugging fit accentuate your curves, while the front slit and sheer maxi-length hem add a chic touch! Complete the look with earrings and a clutch.

    Fit & Features

    • Tie dye print, stretchy mesh fabric, sewn-in knit lining
    • Halter cowl neckline
    • Open back with tie closure
    • Form-hugging fit
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05101-3445

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lovely Look Cold Shoulder Bodycon Lace Mini Dress

    Nothing can compare to your lovely look in this lace mini dress as a stunning bride-to-be or birthday girlie! Featuring a trendy cold shoulder V-neckline, feminine flutter short sleeve cuffs, and delicate spaghetti straps, this dress hugs your curves for a bodycon fit that will turn heads. Complete the look with earrings and clutch.

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Cold shoulder V-neckline
    • Flutter short sleeve cuffs, spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3423

    Category Name: Casual Dresses

    Price: $14.97 $38.90

    On Sale: Yes

    Availability: In Stock

    Available Color: OATMEAL

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Blissful Afternoons Corset A-Line Midi Dress

    Enjoy an afternoon of bliss looking so sweet in this A-line midi dress at showers or semi-formal weddings! The sweetheart neckline and adjustable spaghetti straps accentuate your figure while the corset bodice with built-in padded underwire bust provides support. The flowy A-line silhouette and midi-length hem add elegance to your look. Complete the look in strappy heeled sandals.

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Sweetheart neckline
    • Corset bodice, built-in padded underwire bust
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3309

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: S

    Product Badge:
    • Sale