2016 is finally here and that means new styles popping up and old ones sticking around as we work our way through winter. It can be hard to keep track of everything, especially when your main focus is trying to stay warm. So, we put together a list of a few of our favourite shoe styles you should seek out as you wait for the spring. Stick with our recommendations and your feet will be looking fly all year long.

Chukka Boots

Chukka and desert boots have been a style staple since the 1940s, but they’re now experiencing something of a renaissance in popularity, much like the Chelsea boot. The Chukka has been big in the UK for a while, but now dress boots, in general, are very much on trend, largely due to their versatility. You can do a lot with a boot that goes just as well with a pair of jeans as it does with a suit. The iconic Clark’s desert boot made its debut at the 1949 Chicago Shoe Fair and remains virtually unchanged to this day, which lends credence to the old saying that if it isn’t broke, don’t fix it, buy it.

Chelsea Boots

Chelsea boots were all the rage for 2015, and we fully expect that trend to continue throughout the cold months. There’s something undeniable about the combination of an impeccable style that is always convenient and comfortable. Plus, it’s hard to beat a pair of boots you can just slip on while walking out the door without having to deal with a jumbled mess of laces. The classic leather boot comes in a wide variety of styles from black to tan to oxblood, and the elastic side panel ensures a comfortable fit that still protects your ankles from the cold weather.

Chuck Taylors

We can’t believe we’re saying this but we love the 2015 redesign of the legendary Chuck Taylor sneaker, and we’re not the only ones. The new design marries the best of the old and the new maintaining the classic look of the shoe while upgrading its comfort level with a new Lunarlon insole. Chucks never went out of style, but now that they’re more comfortable than ever there’s really no excuse not to have a pair of these in your closet (or ideally on your feet).


The Timberland is another boot that never really went anywhere but is currently seeing a major spike in popularity. The fashion of Drake’s undeniably catchy hit, “Hotline Bling,” helped to define fashion for fall 2015 and one of the hottest items were the classic Timberland boots sported by Champagne Papi in the music video. The boot has been popping up everywhere in popular music, and we’re personally in full support of this late-’90s throwback style. A pair of Tims are tough, look great and will last forever with the proper care making them a killer pair of boots worth investing in.