Men’s Holiday Footwear

Let’s be real, gentlemen, for the style-savvy professional man the holidays have absolutely nothing to do with joy and cheer. Instead, it’s an opportunity to flex one’s sartorial might as you network yourself from Hannukah dinner-party to office Christmas sh*t-show to ringing in the New Year at some decadent boutique hotel. Even if you only pretend to live such a glamourous lifestyle, one item that will help guarantee that you put your best foot forward is a great pair of shoes.

You can truly judge a man from the bottom up. No matter the make, material or price tag of your suit, if you are wearing a salt-battered pair of boats on your feet you’re not going to get very far. Well-polished, well-cared for, stylish shoes indicate an attention to detail, whether you’re drinking Manhattans at the Trump or PBR at a house party. And the best part of being a man (besides being able to pee anywhere, obviously) is that you only really need one solid pair of shoes. No need to lose sleep over having wedges, or pumps, or stilettos, or flats for an occasion. Rather, we men have the luxury of investing in a keystone set of dress shoes that can last an entire season (assuming you take good care of them). With that said, we’ve broken men’s festive footwear into some general stylistic rules to help make sure you look composed and put-together, no matter what you decide to do this holiday.

You Can Never Go Wrong with Black
Black is classic, sleek, sophisticated and versatile. Whether paired with dark blue skinnies or a punk-esque tartan tailored suit, a well-polished pair of black shoes can be the staple of any ensemble. The beauty is always in the details, and Prada has a gorgeous pair of black calf leather lace up derby shoes with brogue detailing that easily can transition from penthouse cocktail to basement cockfight. Also, if you invest in a good pair of black shoes, like said Pradas, and you take care of them (that means no snowball fights after four too many glasses of eggnog) they’ll last forever and only become more comfortable with time. This is because of superior material, craftsmanship and leather soles that will mold perfectly to your feet.

Make Your Point
If you’re dressing up for an occasional, go with a narrow, rounded point-toed shoe. It looks more adult, masculine, and stylish, FYI. We all know James Bond would only ever wear narrow footwear, even if he too was headed to his neighbour’s Kwanzaa kegger. Though on the more audacious side, these Burberry Glossy Calfskin Winklepickers with top stud detailing are a fine example of a fabulous pointed holiday shoe.
Note: Occasional “round” exceptions can be made for loafers but even then, they’re more of a daytime shoe.

Never Be Afraid of Vintage
As mentioned before, men do not need many pairs of shoes and styles (at least in formal footwear) generally do not change drastically from year to year. If you are on a budget (or would like to earn some brownie points with your hipster friends), shop around the vintage stores. Given the high level of taste and curation seen in the plethora surrounding Queen West and Ossington, chances are you’ll find something fabulous. Most just need a quick polish and if you can live with the idea that their previous owner is probably dead, go for it!

Rubber Soles Aren’t the Devil
While formerly a formal footwear faux pas, many high-end producers are now making quality shoes with rubber soles. They last longer in inclement weather (ie Canada) and they are also generally on the more comfortable side.

Polish Between Parties
Given that we live in a slush and salt-filled wasteland around this time of year, if you plan on wearing the same pair of shoes from party to party you should make sure you clean and polish them before each one. Below is a video from Mr. Porter on how to DIY polish, no 1920s shoeshine boy required!

Good Socks
Depending on people’s personalities, they generally either match their socks with the rest of their look or shake things up with a pop of colour. This one is down to personal preference, really.