Casual Dresses

Perfect for downtime or everyday, Windsor’s fall collection of casual, ready-to-wear dresses come in cute and flirty designs that make dressing up a breeze. Mini, midi, and maxi casual dresses step up your fall style in day to slip dresses. Explore short sleeves, spaghetti straps, off-the-shoulder, and more lovely styles! Keep it chill in casual styles like tank dresses, t-shirt dresses, babydoll rompers, and button-down dresses. Make your off-days your best dressed days with cute and trendy casual wrap dresses. Create a laid-back look with knitted dresses or sweater dresses that effortlessly style up for work or date night. Casual dresses make for fresh autumn looks when paired with boots or booties and bold color cardigans or printed cropped sweaters. With creativity driving our social connections, there are still opportunities to make a statement with fashion so seize the opportunity for fun and trendy dresses too! From long to short sleeves, strapless to off-shoulder, floral prints to animal prints, and chiffon to knit, say yes to these casual dresses that’ll have you looking effortlessly chic. Whether it’s catching up at Sunday brunch with the girls, running errands, or the need for a weekend road trip dress with a special someone, we’ve got the versatile everyday dresses you want - from short to long lengths, sleeveless to high necklines. Although fall means cooler weather, don’t be discouraged from slipping into a comfortable and casual mini dress. A ribbed knit dress adds texture and provides a visually appealing element to your OOTD. Even if you’re just dressing up for a grocery run, a pair of clean, white sneakers and a crossbody purse makes this ensemble all the more on-trend. Casual Fridays at the office? Save the professional attire for your Monday to Thursday grind and opt for a casual work dress in a sweet ditsy print midi dress. Layering on a year-round basic piece, like a cropped jacket will channel that lowkey vibe you’re going for. Once you're off the clock, you’ll be excited to hit the night out in this cute outfit as you’re grabbing drinks with friends! Whether you’re topping off a basic white tee with a satin dress or slipping into some cowboy boots paired with an off-shoulder mini, you truly can’t go wrong with styling up or down your casual dress looks. Shop now to update your fall wardrobe and add your own personal twist on Windsor’s essential and stylish line of casual dresses.