How to upgrade your winter wardrobe this season

Winter Guide

Jan 16, 2019 at 1:00 am
Carhartt's Detroit flagship store.
Carhartt's Detroit flagship store. Courtesy of Carhartt

Michigan winters have a penchant for drama. You've likely experienced one day (or several) where the weather went from a blissful 50 degrees Fahrenheit to a cataclysmic blizzard all in a matter of hours. With that sort of tumultuous behavior, it can be difficult to dress appropriately — let alone dress cute. Beyond just outward appearances, the season forces us to play a constant game of "would you rather?" — the terrible winter activity where you have to choose whether you'll be cozy but not serving looks, or fashionable and terribly uncomfortable.

To help you avoid the crippling anxiety of not knowing what to wear, here are a few tips that will help you upgrade your wardrobe this season.

Buy boots that you can easily get on and off

You've likely experienced the scenario where you're running late to work and you try to save time by slipping on your sneakers rather than take the extra two minutes to lace up your winter boots. "It will be fine," you tell yourself, "there's not that much snow," only to step out the door and immediately plunge ankle-deep in powder. It's cold. It's miserable. And it can ruin your whole day. Instead, invest in a pair of boots that you can easily slip into and that are suitable for your work and lifestyle. Locally owned Chester Boot Shop (28037 Gratiot Ave., Roseville; 586-779-8460; has been serving metro Detroit since 1948 and offers a wide selection of biker boots, soft moccasins, and weatherproof hiking boots that are essential for Michigan winters.

Invest in a coat for formal occasions

In the winter, most of us know to bundle up so we don't turn into a block of ice. And though that's a great strategy for staying warm, it doesn't always equate to a clean look when you have a formal event to attend. Luckily, you can solve that problem with a formal outercoat that will keep you warm without making you look like a country bumpkin when you head to the opera. In particular, coats that are 3/4 or 7/8 in length will protect your legs from the winter chill and will instantly elevate your look with a classic profile.

For those looking for a statement piece that will last for decades, Dittrich Furs (7373 Third Ave., Detroit; 313-873-8300; is one of Detroit's longest running local retailers and offers thousands of outerwear options that include fine furs, leather, and shearling jackets.

Don't skimp out on good socks

Picture this: You've got your new pair of winter boots that you've calmly spent the extra two minutes to put on. You're laced up and ready to go, but get just a few feet out the door when the worst thing that could possibly happen occurs — your dinky sock slips underneath your heel, causing you to raise your fists to the sky cursing the malevolent god that would allow something like this to happen.

Let's get one thing clear — not all socks are created equal. The regular cotton socks that you wear every day can easily lose elasticity, resulting in deep emotional trauma when they slip under your heel. Instead, look for compression socks that fit higher on your ankle or calf so that you never suffer a treacherous sock slip-up. Additionally, take care to purchase socks that are made with high-quality fibers that will keep you warm while wicking away moisture from your feet, so that you don't end up in a stinky situation.

Outdoor retailers like Moosejaw (1275 Woodward Ave., Detroit; 313-338-3661; will have a stock of high-performance socks that will help keep your feet at peace all winter long.

Cover your dome in cold weather

Knit beanies are the unsung hero of winter. They're warm, they're fashionable indoors and out, and they hide the fact that you may have not washed your hair in three days. Better than that, they tend to run cheap, meaning that you can stock up on different textures, colors, and styles.

Whether you're a rugged worker or just a hipster appropriating the style, Detroit's Carhartt retailer (5800 Cass Ave., Detroit; 313-831-1274; is a go-to for the simple-yet-hard-working beanie.

Stay on top of Detroit news and views. Sign up for our weekly issue newsletter delivered each Wednesday.