Casual Dresses

STYLE SPOTLIGHT

Cute Work Dresses

Women's Boots & Booties

Floral Print Dresses

Everyday Fall Casual Dresses

Fall is the perfect time to blend a cozy and stylish look with casual dresses from Windsor. Whether you're heading to a pumpkin patch for photos, getting together with your besties for an autumn brunch, or just want to refresh your fall wardrobe, our collection of trendy casual dresses has got you covered.

When it comes to fall fashion, opt for casual dresses in rich and warm colors like burgundy, mustard, or olive green. These hues are perfect for capturing the cozy vibes of the season. Choose dresses made from comfortable and cozy fabrics like sweater knit, jersey, or flannel to keep you warm as the temperatures drop. If you prefer a more casual and relaxed vibe, go for a T-shirt dress. This easy-to-wear style is perfect for running errands or hanging out with friends. Dress it up with a wide-brimmed hat, tall boots, and a flannel shacket for an on-trend fall look.

Looking for a versatile dress that can take you from day to night? Consider casually chic sweater dresses. These versatile and polished styles are effortlessly chic and can be dressed up or down depending on the occasion. Pair your casual dress ensemble with ankle booties and a faux leather jacket for a cool and edgy look.

Long casual dresses are also a great option for fall. Opt for casual maxi dresses in smooth contouring styles in a jersey knit. Choose from neutral colors like taupe and brown or go for a classic black color for the most versatile ensemble. Style your long casual dress with an oversized denim jacket, chunky sneakers, and a shoulder purse for the perfect #OOTD look.

Whether you're heading to back-to-school or just want to update your fall wardrobe, casual dresses are a must-have. They're comfortable, versatile, and perfect for any occasion. Refresh your wardrobe with chic casual dresses from Windsor and stay on-trend this fall.

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 style 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 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!