Five Shoes Every Man Should Have for Winter


When it comes to what to wear this winter, it looks as though what was old is new again. The trend for this season seems to be the comeback of the old school boots that once dominated the footwear fashion of the 1990s and early 2000s in addition to a newfound popularity of the casual dress boot. We’ve pointed out before that designer shoes can often be prohibitively expensive. However, with a good pair of boots, a man can feel more comfortable spending a little more money on his investment. Unlike a lot of footwear, a pair of boots will last for years with proper care and continue to look and feel great. That can make it much easier to part with that extra cash. But before you go dropping more than a hundred quid on a new pair of boots, you might want to read on to make sure you’re making the right choice.

L.L. Bean Boots

We never expected the comeback of of L.L. Bean’s classic “duck boot,” but… it’s back! If you haven’t already grabbed yourself a pair, you might be out of luck because there’s a major shortage of the popular boot. With the resurgence in the popularity of earth-tones and plaids this season, the L.L. Bean boot is a classic, rustic item that is simultaneously fashionable and functional. It will keep you feeling warm and looking good whether you’re camping in the woods or hitting the office holiday party (where someone will probably offer to buy them off you).

Dress Boots

Boots are back in a big way for winter and there’s no shortage of styles to choose from when it comes to finding the perfect fit for your feet. The classic high-top Chelsea boot is very much in vogue and can be found in a variety of styles to suit your specific needs. We pulled a lot of personal inspiration from this collection of styles for the upcoming season and learned that there’s a sneaker-style Chelsea boot. This one’s for those fashion mavens who want to have their cake and eat it too when it comes to their choice of footwear. We personally this style for its convenient lack of laces and the comfortable stretch you get with the elastic side panel. A pair of these is pretty much the easiest and simplest pair of dress shoes you’ll ever own.

Timberland Classic 8″ Boot

If you’ve been watching music videos or paying attention to the latest rap trends, you might have noticed a sharp increase in the visibility of the classic Timberland boot that once dominated the industry. The shoe has been prominently featured in music videos for both Drake and Justin Bieber. They’re also remarkably well made and will last you forever as long as you take care of them. This list of 20 fashion hacks has some terrific advice on how to keep your boots in their best shape, including how to get rid of unsightly water spots on leather that can ruin a pair of pristine Timberlands.

Chukka or Desert Boots

It’s hard to beat a good pair of desert boots when it comes to wardrobe versatility. They’re comfortable, look great, and can easily pair with either a suit or a clean pair of jeans. The desert boot has long been the shoe of choice for the fashionable British male and the popularity of the minimalist boot only continues to grow. Like the traditional Chelsea boot, the Chukka pairs well with both casual and semi-formal ensembles. It can be matched nicely with a suit, pair of slacks, or just some fresh jeans.

Military Combat Boots

There’s something timelessly tough and effortlessly edgy about the traditional combat boot. The sleek, black leather and rugged soles make these a shoe that stomps the competition and harkens back to the glory days of the British punk scene. Combine your combat boots with some plaid for an iconic punk look that even Johnny Rotten would be proud of.