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!

  • 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
  • Sweet Day Sleeveless Mermaid Denim Midi Dress

    Look cute and casual wherever you go in this denim midi dress! Featuring spaghetti straps, a sweetheart neckline, a flattering mermaid silhouette, and a flared midi-length hem, this dress will have you looking and feeling amazing. Complete the look in strappy espadrille wedges.

    Fit & Features

    • Denim fabric, minimal stretch
    • Spaghetti straps
    • Sweetheart neckline
    • Back zipper and hook-eye closure
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5567

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: S

    Product Badge:
    • Sale
  • Sweet Style Bow Detail Polka Dot Mesh Mini Dress

    Show off the sweetest style on summer dates in this bow detail polka dot mini dress! Designed with an airy sheer mesh fabric with a knit lining for coverage, this mini-length dress is accented with an adorable polka dot pattern for the cutest vibe. It features a sleeveless V-neck and back design with a dainty eyelet trim, tank shoulder straps, a mini bow detail at the bust for a sweet touch, tie-back spaghetti straps, and a flirty flowy A-line silhouette. Pair with strappy mules.

    Fit & Features

    • Polka dot printed sheer mesh fabric with knit lining
    • Plenty of stretch
    • V-neck and back, tank shoulder straps
    • Mini bow detail, eyelet trim
    • Tie-back straps
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5828

    Category Name: Casual Dresses

    Price: $14.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Perfect Always Strapless Cutout Ruffle Maxi Dress

    Have all eyes on you in this strapless maxi dress boasting a sweetheart twist neckline and a cutout bodice. The smooth knit fabric hugs your curves along the form-hugging silhouette and creates a front center ruffle design. 

    Fit & Features

    • Smooth knit lined fabric, moderate stretch
    • Strapless sweetheart twist neckline
    • Cutout bodice
    • Center front ruffle design
    • Form-hugging, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3601

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M

    Product Badge:
    • Sale
  • Beyond Precious V-Neck Ruffle Babydoll Dress

    You'll be looking beyond precious in this babydoll dress - the perfect summer staple!  The ruffle trim shoulder straps and v-neckline create a delicate and alluring look, while the ruffled babydoll silhouette and side pockets add a touch of playful charm to the short-length hem. Complete the look in trendy sandals.

    Fit & Features

    • Woven fabric, bust lining, no stretch
    • Ruffle trim shoulder straps
    • V-neckline
    • Ruffle babydoll silhouette
    • Side pockets
    • Runs true to size

    Style Number/Barcode: 05102-5422

    Category Name: Casual Dresses

    Price: $35.00 $48.90

    On Sale: Yes

    Availability: In Stock

    Available Color: OLIVE

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Made To Amaze Strapless Marble Bodycon Midi Dress

    Everyone will admire your style in this strapless marble bodycon midi dress at the art show downtown! Made from a mesh fabric boasting a gorgeous marble print, you'll be sure to amaze. With a strapless neckline and side ruched seams, this dress hugs your curves in all the right places for a bodycon fit along the midi-length hem. Complete the look with stiletto heels.

    Fit & Features

    • Marble print, stretchy mesh fabric, sewn-in knit lining
    • Strapless neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5576

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

  • Weekend Plans Ribbed Knit Maxi Dress

    This casual-chic maxi dress is perfect for your upcoming weekend plans. It features a sleeveless one-shoulder neckline for an effortless and trendy vibe, a single tank shoulder strap, an open back with a dual strap design, a fitted, maxi-length silhouette, and a high side slit. Style this dress with hoop earrings.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Single tank shoulder strap
    • Open back, dual strap design
    • Maxi-length hem, form-hugging fit, side slit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4737

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Breezy Chic Floral Embroidered Chiffon Skater Dress

    This breezy chic floral chiffon skater dress is perfect for your summer parties! The airy sheer embroidered chiffon fabric is detailed with a dainty floral print and includes a stretchy full-length knit lining. The short dress features a sleeveless sweetheart neckline, a bustier-style bodice with a padded bust and structured underwire, and ruched cups. The adjustable spaghetti straps lead to a partially smocked back design for added stretch with a secure back zipper closure. The front faux buttons lead to a high waist seam flowing out to a short skater skirt with a flirty fit and flare A-line silhouette. Complete your look with strappy sandals.

    Fit & Features

    • Sheer embroidered chiffon fabric, floral print, stretchy knit lining
    • Sweetheart neckline, bustier bodice, padded bust with underwire, ruching
    • Adjustable spaghetti straps
    • Partial stretchy smocked back, zipper with hook and eye closure
    • Front faux buttons, high waist seam
    • Fit and flare A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3067

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY-3

    Available Size: M, L

    Product Badge:
    • Sale
  • Cute And Fab Sweater Dress

    You'll look so cute and fab in this trendy sleeveless sweater dress. It features a mock neckline, a short, curve-hugging fit, and is composed of a fuzzy eyelash knit fabric. Style this dress with combat booties.

    Fit & Features

    • Sleeveless
    • Ribbed mock neckline
    • Mini-length, form-fitting silhouette
    • Eyelash knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1112

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendsetting Effect Ruffled Denim Skater Dress

    You'll always make a trendsetting impression in this denim skater dress perfect for country concerts or the fair. Featuring a square neckline, wide shoulder straps, and faux button closures, this dress flatters your figure with its underbust seam and skater silhouette. The ruffled hem adds a fun touch to the stylish denim twill fabric. Complete the look in cute cowboy boots.

    Fit & Features

    • Denim twill fabric with minimal stretch
    • Square neckline
    • Wide shoulder straps
    • Back zipper and hook-eye closure
    • Ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5472

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M

    Product Badge:
    • Sale
  • Simple And Stunning Ruched Mini Dress

    Simple and stunning, this classic mini dress is a closet staple. It features a sleeveless cowl neckline with a draped design, tank shoulder straps, a scoop back design, ruching down the side seams, a mini-length hem, and a bodycon silhouette that will hug your curves. Style with strappy mules for a dinner date or party.

    Fit & Features

    • Sleeveless cowl neckline
    • Tank shoulder straps
    • Scoop back design
    • Ruched side seams
    • Mini-length hem, bodycon silhouette
    • Double-lined smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5028

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Laid Back Fave Crew Neck Tank Maxi Dress

    Your new laid-back fave tank maxi dress for styling up or down for any occasion! Crafted from rib knit fabric, this crew neck dress offers a form-hugging fit and a maxi-length hem for a flattering silhouette. Complete the look in cute sandals and sunnies!

    Fit & Features

    • Rib-knit stretchy fabric
    • Crew neck
    • Form-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5572

    Category Name: Casual Dresses

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: TAUPE

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Most Noteworthy Ponte Pleated Mini Dress

    A classic little black dress for your most noteworthy look for date night! The short dress features a sleeveless square neckline, spaghetti straps, and a side pleated seam that leads to the form-hugging mini-length hem on lined ponte fabric. Style the mini dress with a rhinestone necklace for a glam touch!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Side pleated seam
    • Form-hugging silhouette
    • MIni-length hem
    • Lined ponte knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05103-5077

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Passion V-Neck Color Block Maxi Dress

    Dress to impress in this V-neck maxi dress to make a chic impression at parties or rehearsal dinners! The flowy silhouette and color block panels give you a stunning look, while the spaghetti straps and neck tie add a trendy touch. Complete the look with a clutch and heels.

    Fit & Features

    • Woven fabric, no stretch
    • V-neck
    • Spaghetti straps, spaghetti strap neck tie
    • Color block panels, flowy silhouette
    • Maxi length
    • Runs true to size

    Style Number/Barcode: 05102-5803

    Category Name: Casual Dresses

    Price: $59.90

    Availability: Out of Stock

  • Autumn Attitude Strapless Pleated Plaid Mini Dress

    Embrace the new season in this plaid mini dress featuring a strapless neckline, form-hugging silhouette, and a flirty pleated mini-length hem. Perfect for back-to-school and styling with flats.

    Fit & Features

    • Plaid pattern, knit fabric, moderate stretch
    • Strapless folded neckline
    • Form-hugging silhouette
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5863

    Category Name: Casual Dresses

    Price: $25.00 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: GRAY

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Chic And Seamless Midi Sweater Dress

    Chic and seamless, this sweater dress is perf for creating a simple yet elevated look. It features a sleeveless scoop neckline, adjustable spaghetti straps, a mid-length, curve-hugging silhouette, and a sultry thigh-high side slit. Style this dress with clear mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps
    • Mid-length, form-fitting silhouette
    • High side slit
    • Sweater knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1085

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Class Act Cowl Neck Polka Dot Midi Dress

    A sleeveless polka dot midi dress features a flattering cowl neckline, spaghetti straps, and a flowy silhouette with a front slit. Perfect for styling with stiletto heels for any occasion.

    Fit & Features

    • Polka dot print, mesh fabric lined with stretchy knit
    • Spaghetti straps
    • Cowl neckline
    • Front slit
    • Flowy midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5849

    Category Name: Casual Dresses

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Give Me Butterflies Square Neck Skater Dress

    Show up to the party in this short skater dress and give everyone a fluttery heart for you! It features three-quarter-length puff sleeves, a square neck, a smocked back, and a fit and flare silhouette. The dress is designed with delicate butterfly embroidery on twill woven fabric with a woven lining. Complete the look with lace-up sandals.

    Fit & Features

    • Three-quarter-length puff sleeves
    • Square neck
    • Smocked back
    • Fit and flare, skater silhouette
    • Short-length hem
    • Butterfly embroidery, twill woven fabric and lining
    • Runs true to size

    Style Number/Barcode: 05102-5009

    Category Name: Casual Dresses

    Price: $5.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Out Of Office One Shoulder Tropical Maxi Dress

    This tropical maxi dress says it's time for vacation! Switch your email to out of office and enjoy a sunny destination in this sleeveless dress featuring a one-shoulder neckline adorned with a knotted shoulder strap, a flattering mermaid silhouette, and a maxi-length hem. Complete the look with sunglasses and a cocktail in hand!

    Fit & Features

    • Tropical palm leaf print, stretchy knit fabric
    • One-shoulder neckline
    • Knotted shoulder strap
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5695

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS

    Product Badge:
    • Sale
  • Such A Flirt Floral Mini Dress

    Bring the flirtatious vibes in this adorable floral mini dress! It features a sleeveless square neckline, adjustable spaghetti straps, ruched detailing with drawstrings at the hem, and a mini-length, curve-hugging silhouette. Style this dress with sneakers for a cute and casual look.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Ruched detailing, drawstrings at the hem
    • Short, form-hugging fit
    • Ribbed knit fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05102-1404

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

  • Vacay Vibes High Slit Tropical Knit Maxi Dress

    Give off effortless vacay vibes in this high slit tropical knit maxi dress. The tropical palm leaf print on the lightweight knit fabric will have you looking like you're ready for a getaway, even if you're just grabbing drinks at a local happy hour! The dress is shaped with a sleeveless V-neckline and spaghetti straps, and features a high-cut side slit to showcase some leg on the form-hugging mid-length silhouette. Style with gold hoops and strappy wedges!

    Fit & Features

    • Stretchy knit fabric with a bust lining
    • Tropical print
    • Sleeveless V-neckline
    • Spaghetti straps
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5537

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Express Your Style V-Neck Ruffle Bodycon Mini Dress

    Express your devotion to style in this charming sleeveless mini dress perfect for casual showers or brunch! This dress features adjustable spaghetti straps for the perfect fit, a flirty V-neckline with a bust tie for added charm, and a bodycon fit to accentuate your curves. The mini-length hem and ruffle trim throughout add a touch of romance to this head-turning dress. Complete the look with earrings.

    Fit & Features

    • Ruffle trim throughout, knit fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • V-neckline with bust tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5789

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLUE, WHITE

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Catch A Cutie Short Sleeve Cutout Eyelet Skater Dress

    Catch yourself a cutie wearing this eyelet skater dress to day parties this season! With playful puff sleeves and a flirty cutout. The sweetheart neckline and bust drawstring add a touch of romance, while the skater silhouette and tiered ruffled hem keep it fun and flirty. Complete the look in wedge sandals.

    Fit & Features

    • Eyelet fabric lined with stretchy knit
    • Sweetheart neckline
    • Adjustable bust drawstring, cutout
    • Skater silhouette
    • Tiered ruffles
    • Runs true to size

    Style Number/Barcode: 05102-5430

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S

    Product Badge:
    • Sale
  • Sweet Dreams Hanky Hem Floral Mini Dress

    Sweet and dreamy will be your vibe in this adorable floral mini dress! Designed with a stretchy sheer mesh fabric with a knit lining for coverage, the short dress showcases a blooming floral print for the prettiest look. It features a sleeveless V-neckline with dainty lace trim for a feminine touch, spaghetti straps, a trendy drop waist silhouette, and a mini-length asymmetric hanky hem with a flowy A-line fit. Style with bow hair pins and strappy mules.

    Fit & Features

    • Floral print
    • Stretchy sheer mesh fabric with knit lining
    • V-neckline with lace trim
    • Spaghetti straps
    • Drop waist silhouette
    • Asymmetric hanky hem, A-line fit
    • Runs true to size

    Style Number/Barcode: 05101-3462

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock