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Casual Winter Dresses That Style Effortlessly

Looking to add casual dresses that style effortlessly for winter? Check out Windsor’s assortment of mini, midi, and maxi dress styles! Slay everyday events and occasions in the prettiest prints and hues that look so cute peaking out from under knit cardigans, denim jackets, and trench coats with your favorite boots or booties. These casual dresses from Windsor feature a variety of silhouettes like a fitted bodycon, stylish short hem, or a must-have mid-length. Try pairing any of these casual dresses for winter with lace-up heels or sweater midi dresses that style effortlessly with sleek hoop earrings, a moto jacket, and ankle boots for a holiday concert.

A ribbed knit midi is also a closet essential! Shop long sleeve to sleeveless styles with tie-fronts and chain-belted waists to layer with cropped jackets or sweaters, pointed-toe booties, and your favorite block heels from Windsor. Collared button-down midi dresses are a stylish option with trendy details like slits and cutouts perfect for showing peaks of skin! Complete your look with layered chokers and ring sets, and then top it off with a cute beret.

With the holiday season coming up, your outfit will be one less thing to worry about! Shop casual polo or henley dresses with short- and long-sleeve styles or collared necklines perfect for styling with trendy jewelry sets, edgy lug boots, or low-heel mules to look stylish for gift exchanges or Christmas shopping!

Elevate your look for weekend plans with a casual dress boasting eye-catching details like ruching, slits, and cutout accents that pair effortlessly with plaid shackets, layered necklace sets, and peep toe or lattice cutout booties to take your outfit to the next level! Layer a slouchy chenille crop sweater over a basic casual dress to keep cozy and cute for a dinner and movie date. Winter florals on bodycon dresses with short sleeves and sleek straps are perfect for holiday dinners and family gatherings! Floral dresses also style flawlessly to create a women's winter vacation look with a classic boyfriend blazer with a dainty tennis bracelet, pumps, or boots.

Whatever the occasion, shop Windsor for new casual dresses that style effortlessly for winter!

Why Casual Dreses From Windsor Make Stylish Brunch Outfits

No matter the season, brunch is always in session! Windsor has you covered with chic mock necks, off-the-shoulder, and square neck dresses to accessorize with a sleek choker and crossbody bags. Discover the most stylish casual dresses in neutral prints, plaid, and marble patterns so you'll always stand out from the crowd! Getting ready for brunch is effortless with a fitted casual dress from Windsor that features trendy details and endless styling possibilities! For example, casual dresses pair perfectly with heels, mules, boots, and booties to elevate your look. Layer on a denim jacket or crop shacket with a ring set and layered necklace to complete your outfit for brunch.

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 complementing 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!