Casual Dresses

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Perfect for downtime, our summer 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 warm-weather style in day to slip dresses from Windsor. 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 that effortlessly style up for work or date night. Casual white dresses make for fresh summer looks when paired with wedges or sandals. From long to short sleeves, strapless to off-shoulder, floral 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 a weekend getaway trip with a special someone, we’ve got versatile designs you want - from short to long. Although summertime means more sunshine, don’t be discouraged from slipping into a comfortable and casual sweater 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 trendy. 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 denim 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 and add your own personal twist on Windsor’s essential and stylish line of casual dresses.