Casual Dresses

Best Sellers
Now Trending

Winter Casual Dresses for Everyday

Looking to switch up your sweaters and jeans this winter? A casual dress is a fab go-to for achieving those effortless vibes. Discover From hitting the books, workwear, or a casual date outfit—there’s a casual dress for you. Discover casual dresses with fun seasonal plaids, warm brown tie-dyes, and neutral color blocks. You'll find styling effortless for day or night with this year's hottest casual dress trends like corset hoodie dresses, dresses with cutouts, and casual dresses with ruching that flatters the figure! Lock in your dress game with classic neutral hues like ivory, tan, black, and brown or go bold with fiery reds and rich greens. Casual midi dresses are a fashionista pick for a style that is truly versatile and begs for our favorite winter layering hacks! Keep it chic and stylish with basic dresses that come in comfortable ribbed knit, cable knit, and soft chiffon fabrications. Style your favorite casual dress with a trendy plaid shacket or faux leather moto, ankle booties, and finish off with a cute cabby hat! By simply layering your casual styles like turtleneck dresses, collard dresses, or buttoned-down dresses you can go from day to night with ease! Stepping out for a coffee date? Slip into a wrap sweater dress that cinches with a cute tie waist and then finish your casual outfit with thigh-high boots! A sexy cutout mini dress or spaghetti strap dress is perfect for those dates where you want to make a bold first impression. A casual dress is versatile enough to be worn at your holiday parties, NYE events, birthday gatherings, and bachelorette parties. For holiday events, choose dressier fabrications like sequin, glitter, and velvet. You can dress up a casual dress with a flashy statement necklace, embellished heels, or other rhinestone jewelry. Countdown in style with a comfortable, ruched mini dress that can be layered with a sequin blazer or an edgy moto jacket. A casual dress isn’t limited to the office or school—you can totally rock them for dressier events or your best winter outfits when styled just right.

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 for fall and winter, are stylish casual 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 dresses is an easy way to instantly dress down a dress. Casual dresses with drawstrings and tie or button fronts are details that 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 chunky dad sneakers 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.