How to Dress in Chicago During the Winter Season

Chicago weather can get rather chilly in the wintertime, with a few milder days interspersed with some blistering arctic cold blasts and snow. But when you’re prepared and dressed right for the occasion, you can easily weather the chill and have a pleasurable shopping trip or night out in this extraordinary city. With just a few cold-weather tips to get you ready for Chicago weather, you’ll feel warm and cozy while looking stylish and sophisticated all winter long.

coat – @armani

The coat. In Chicago, the coat is an important investment. When making your choice, consider both style, form, and function to select a piece that will complement your winter wardrobe. Warmth doesn’t always mean bulk, although most quality winter coats are designed to look as fabulous on the runway as they will in Chicago’s exquisite downtown district. Longer styles are both practical and fashionable, so choose a length that falls below the knee. Heavy wool or insulated down are good choices for particularly cold weather – down is lighter but carries more bulk, and heavy wool can be weighty for occasions that call for a long walk outside. Fur or faux fur lining adds warmth, particularly around the neckline. If selecting a parka style to complement your wardrobe, choose a medium-weight style that is rated for -10 to zero degrees Fahrenheit.

hat & scarf -@loropianaofficial

The hat. The hat is an important part of the wardrobe, and for many, each hat is designed as an irreplaceable part of the whole for each outfit. If you plan to spend time outdoors in Chicago during the winter season, plan your outfit and hairstyle to accommodate a warm, woolen piece that covers your entire head and ears, if possible. Soft wool is the best fabric choice for quality winter hats.

The scarf. Every piece of your wardrobe makes a statement, but the scarf stands out as a central item that draws the eye and completes your outfit. The knitted scarf is one of the best selections for Chicago’s winters, keeping you warm with a multitude of colors from which to choose so you’ll always be fashion-forward, no matter what the weather. Today’s fine scarves are worn knotted or draped, and fabrics that are ideal for winter include cashmere and soft wool/silk blends. Colors are your opportunity to express your individualism – choose bright, vivid colors for a look that commands attention or more subtle shades for a conservative, professional style.

boots – @jimmychoo

The shoes. If you’re planning to spend any time outside during the Chicago winter, plan to wear a warm, waterproof pair of boots that stand up to snow, ice, and the cold. Lined boots are ideal. Unless you are selecting fur- or fleece-lined boots, consider choosing a slightly larger size, since winter boots may need to accommodate thick, woolen socks during Chicago’s coldest days. Winter boots need not be knee-high or taller – ankle boots made with high-quality materials and non-slip soles can also be the perfect choice for a sophisticated Chicago winter wardrobe.

Dressing well for winter is easy when you select a few essential pieces that complement your wardrobe, while still emphasizing quality fabrics and styles that keep you warm. At Oak Street District, you’ll find everything you need to outfit your Chicago winter at our exquisite designer boutiques. The world’s most sought-after designers are all represented here, from Christian Dior, Saint Laurent, Vera Wang, Prada, Jimmy Choo, Giorgio Armani, and much more.

Experience the luxury of Chicago’s finest apparel brands, where you’ll find one-of-a-kind, exquisite pieces that transform your winter wardrobe into a unique statement that celebrates your unique personality. You’ll find the Oak Street District right in the heart of downtown Chicago, just steps away from Michigan Avenue. Oak Street District is Chicago’s premier luxury destination, offering luxury accommodations, fine dining, and exquisite boutique shopping at sought-after fashion houses.

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