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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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!
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Sleek Silhouette Ribbed Knit Off-The-Shoulder Midi Dress
Showcase a sleek silhouette in this ribbed knit midi dress featuring an off-the-shoulder neckline with a fold-over design and a mermaid silhouette to highlight your curves. Style with knee-high boots for a chic look.
Fit & Features
- Ribbed knit fabric, plenty of stretch
- Off-the-shoulder neckline
- Fold-over design, short sleeves
- Midi-length mermaid silhouette
- Runs true to size
Style Number/Barcode: 05102-5896
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Girl Power Leopard Print Strapless Midi Dress
Show off major girl power in this sexy leopard print midi dress that was made for all eyes on you. It features a strapless straight-across neckline, ruching down the side seams, a midi-length hem, and a bodycon silhouette to put your gorgeous figure on display. The lined sheer mesh fabric features an all-over leopard print pattern to amp up the look. Style this midi dress with strappy stilettos for a nightclub!
Fit & Features
- Strapless straight-across neckline, no-slip strip
- Ruched side seams, hidden side zipper, hook and eye closure
- Midi-length hem
- Bodycon silhouette
- Leopard print
- Sheer mesh fabric, mini-length knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05101-3211
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Chic Long Sleeve Midi Dress
Fit & Features
- Ribbed knit fabrication
- Off-the-shoulder neckline, foldover accent
- Long sleeves
- Snap button accents at the hem
- High side slit
- Midi length hem
- Runs true to size
Style Number/Barcode: 06005-2108
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK, PLUM
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Attract And Allure Marble Print Midi Dress
Attract and allure in this marble print midi dress that puts your curves on display! It features a high crew neckline, long fitted sleeves, a midi-length hem with a form-hugging silhouette, and an all-over trendy marble print pattern. The sheer mesh fabric includes a full-length sleeveless knit lining. Style this mid-length dress with clear heel mules for a cool-girl vibe for a rooftop bar!
Fit & Features
- Crew neckline
- Long fitted sleeves
- Midi-length hem, form-hugging fit
- Marble print, sheer mesh fabric
- Full-length sleeveless knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5403
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
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Sultry Silhouette Abstract Print Mesh Midi Dress
Showcase a sultry silhouette in this sheer mesh midi dress designed with a multi-colored abstract print for a bold vibe. It features a mock neckline with long fitted sleeves, a bodycon silhouette to hug your curves, and a full-length knit lining with a scoop neckline and spaghetti straps.
Fit & Features
- Abstract printed sheer mesh fabric
- Mock neckline
- Long fitted sleeves
- Midi-length bodycon fit
- Full-length knit lining, scoop neckline, spaghetti straps
- Runs true to size
Style Number/Barcode: 05102-5879
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: BLUE
Available Size: L
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Abstract Moment Mesh Mock Neck Midi Dress
Step out in this stylish mesh midi dress and not miss a single moment to have all eyes on you! The knee-length dress features a feminine mock neck with back button closures, fitted sheer long sleeves, and bodycon silhouette with abstract print on mesh fabric. Complete the look with gold hoop earrings for an art gallery opening and dinner downtown!
Fit & Features
- Mock neck, back button closures
- Fitted sheer long sleeves
- Bodycon silhouette
- Midi-length hem
- Abstract print
- Mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5294
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
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Chic Showstopper Abstract Print Mesh Maxi Dress
Serve chic vibes in this airy-lined mesh maxi dress designed with a multi-colored abstract print for a bold allure. It features a strapless straight-across neckline, a high-cut side slit, and a long bodycon silhouette to showcase your stunning curves.
Fit & Features
- Abstract printed sheer mesh fabric with knit lining, plenty of stretch
- Strapless straight neckline
- High side slit
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5982
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: MULTI
Available Size: S, M, L
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Stylish Silhouette Midi Sweater Dress
This curve-hugging sweater dress was made for sunset happy hour! It features a sleeveless V-neckline with a twist-front design, a center cutout under the bust, tank shoulder straps, and a midi-length, form-fitting silhouette with a chic high side slit. Style with classic hoop earrings and clear mules.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless V-neckline, twist-front accent
- Center cutout under the bust
- Tank shoulder straps
- Midi-length hem, form-fitting silhouette, high side slit
- Ribbed sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1462
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
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Modern Stripes Ribbed Knit Long Sleeve Mini Dress
Fit & Features
- Ribbed knit fabrication
- Mock neck
- Fitted long sleeves
- Multi-stripe pattern
- Mini length hem
- Runs true to size
Style Number/Barcode: 06005-2095
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, M, L
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Tropical Fun Chain Strap Midi Dress
Perfect for your next getaway, this tropical midi dress is a must to pack in your carry-on! It features a sleeveless square neck, half chain and adjustable spaghetti straps, a bodycon silhouette, and a flirty side slit. the dress is composed of a tropical print slinky-knit fabric with a sewn-in knit lining. Complete the look in heeled sandals.
Fit & Features
- Sleeveless square neck
- Half chain, adjustable spaghetti straps
- Bodycon silhouette
- Side slit, midi-length hem
- Tropical print
- Slinky knit fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5070
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
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Cute Flirt Drop Waist Ruffled Hem Mini Dress
Show off your stunning figure in this smooth knit mini dress featuring a boat neckline, long fitted sleeves, a cute scoop back, a drop waist design, and a short tiered ruffled hem with an A-line fit for that flirty flair. Style with strappy mules!
Fit & Features
- Smooth nylon knit fabric
- Boat neckline
- Long fitted sleeves
- Scoop back
- Drop waist
- Tiered ruffled mini-length hem, A-line fit
- Runs true to size
Style Number/Barcode: 05102-5938
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Spot Me In Leopard Slit Midi Dress
You can be spotted all season in this leopard print midi dress perfect for a casual lunch or a wine night with friends! It features a sleeveless V-neckline, tank shoulder straps, and a form-hugging, slim silhouette with a flowy slit hem. Complete the look in sleek statement hoop earrings and sandals.
Fit & Features
- Sleeveless V-neckline, tank shoulder straps
- Form-hugging, slim silhouette
- Front slit
- Midi-length flowy hem
- Leopard print
- Woven non-stretch fabric
- Runs true to size
Style Number/Barcode: 05102-4469
Category Name: Casual Dresses
Price: $5.97 $38.90
On Sale: Yes
Availability: Out of Stock
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Stripes In Style Off The Shoulder Mini Dress
Fit & Features
- Ribbed knit fabrication
- Off-the-shoulder neckline
- Long dolman sleeves
- Stripes
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-5885
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, M, L
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Pretty In Paradise Strappy Cutout Maxi Dress
You'll be pretty in paradise in this stunning maxi dress for vacation or a bachelorette weekend! The dress features a sleeveless V-neckline, spaghetti straps that lace up along the open back, flirty waist cutouts, and a high front slit along the flowy hem. Complete the look with earrings and clear block heels for a chic style!
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Lace-up open back
- Waist cutouts, high front slit
- Maxi-length hem
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4752
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
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Toasty Sweetheart V-Neck Bodycon Knit Midi Dress
This sleeveless ribbed knit midi dress features a striking V-neckline and bodycon fit with a front slit detail for movement. Perfect for layering with a jacket and heels.
Fit & Features
- Stretchy ribbed knit fabric
- V-neckline
- Spaghetti straps
- Front slit
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 06005-2065
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: NATURAL, RUST, MAUVE, OLIVE
Available Size: XS, S, M, L
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She's The Main Rib Knit Strapless Midi Dress
Flaunt your look with ease and chicness with this midi dress this season! The knee-length dress features a strapless neckline, a flattering bodycon silhouette, and a fitted maxi-length hem on soft and stretchy rib knit fabric with a short knit lining. Style with the matching bolero and heels for weekend plans!
Shop Matching Bolero: She's The Main Rib Knit Slouchy Bolero
Fit & Features
- Strapless neckline
- Bodycon silhouette
- Fitted midi-length hem
- Soft and stretchy
- Rib knit fabric, short knit lining
- Runs true to size
Style Number/Barcode: 05102-5599
Category Name: Casual Dresses
Price: $33.90
Availability: In Stock
Available Color: IVORY, SAGE, GRAY, BROWN-2
Available Size: XS, S, M, L, XL
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Pretty In Plaid Sleeveless Knit Mini Dress
Fit & Features
- Woven knit fabrication
- Sleeveless v-neckline
- Spaghetti straps
- Plaid print
- Side slit
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-5930
Category Name: Casual Dresses
Price: $26.90
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, M, L
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Sleek Essential Ribbed Knit High Slit Midi Dress
Accessorize a ribbed knit midi dress for the perfect fall outfit. The dress features a plunging V-neckline, long fitted sleeves, and a bold high slit. Complete your outfit with thigh-high boots.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- V-neckline
- Long fitted sleeves
- High side slit
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-2079
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BLACK, DARK, MARSALA
Available Size: XS, S, M, L
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Chic Muse Square Neck Bodycon Mini Dress
Show off your sleek chic style in this bodycon mini dress featuring a sleeveless square neckline, tank-like shoulder straps, and a short form-hugging silhouette. Style with stiletto heels for a rooftop bar!
Fit & Features
- Lined rayon knit fabric, plenty of stretch
- Square neckline
- Tank-like shoulder straps
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5970
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: BLACK, BURGUNDY
Available Size: XS, S, M, L
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Chic Fall Vibe Ditsy Floral Corset Midi Dress
Channel the chic fall vibe in this ditsy floral woven midi dress featuring a sleeveless sweetheart neckline with a ruched bust and tie-front detail, thin tank shoulder straps, and a corset-style bodice. The high waist leads to a flowy A-line silhouette accented with a high-cut front slit.
Fit & Features
- Ditsy floral-printed woven fabric
- Sweetheart neckline, ruched bust, tie-front detail
- Thin tank shoulder straps
- Corset-style bodice with piping, high waist seam
- High front slit
- Midi-length A-line fit
- Runs true to size
Style Number/Barcode: 05101-3706
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
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Chic Night Out Abstract Print Mesh Midi Dress
Create a chic vibe to grab drinks with the girls in this airy mesh midi dress designed with a bold abstract print pattern. The dress features a sleeveless mock neckline, tank shoulder straps, ruching at the waist, and a bodycon silhouette to flaunt your curves.
Fit & Features
- Sheer mesh fabric with brushed knit lining, plenty of stretch
- Abstract print
- Mock neckline
- Tank shoulder straps
- Ruched waist
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5929
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
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Casual Affair Long Sleeve Ruched Midi Dress
Fit & Features
- Smooth knit fabrication, moderate stretch
- Off-the-shoulder neckline, foldover accent
- Fitted long sleeves
- Ruching
- Midi length hem
- Runs true to size
Style Number/Barcode: 05101-3723
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Classic And Sleek Knit Off-Shoulder Long Sleeve Midi Dress
Classic and sleek, this stretchy knit midi dress features an asymmetric off-shoulder neckline with long fitted sleeves, ruching at the waist to accentuate your curves, and a bodycon silhouette. Style with stiletto heels for a chic outing!
Fit & Features
- Jersey knit fabric with plenty of stretch
- Asymmetric off-shoulder neckline
- Long fitted sleeves
- Ruched waist
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5978
Category Name: Casual Dresses
Price: $24.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: S, M, L
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Blooming Beauty Floral Print Mesh Maxi Dress
Let your beauty bloom with a mesh maxi dress that features a sleeveless sweetheart neckline with lace trim, a bodycon-fit silhouette, and a pretty floral print throughout! Complete your date night look with stiletto heels!
Fit & Features
- Mesh fabrication
- Sleeveless sweetheart neckline, lace trim
- Spaghetti straps
- Floral print
- Bodycon-like fit
- Long maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-3785
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: RED
Available Size: L, XL