A new year means the anticipation of the unknown. This year you could be promoted or you could be fired. You could meet the love of your life or you could shack up with the craziest piece to ever burn all your clothes in a pile. Who knows? I don’t. So stop asking.

However, with the right styling you can steer 2016 in a better-looking direction. And there’s no better place to start shaping your look this year than footwear. Picking a few pairs of Italian leather shoes gives you a foundation on which you can build your wardrobe around this year. Here are my picks…

The Dean Chelsea Boot - Nero

During the short days of winter I have one objective: to stay warm while looking cool. The Dean Chelsea Boot in black accomplishes both aspects of said objective. This cold-weather staple can be worn with a suit or jeans so no matter what drags me out of the warmth of my apartment I’ll be prepared.

The Cagney Cap-Toe Oxford – Oxblood

These are my official power shoes of 2016. Nothing like the boldness of oxblood full-grain leather helps you stand out amongst the hoards of pavement pounders in the city. The classic design of the cap-toe oxford balances the color and is as versatile as it is comfortable. I’ll be pairing it with this matching Italian leather belt to round out the outfit and show the world I mean business.

The Legend High-Top Sneaker - Blue

This year, I resolve to not leave the house in ugly shoes. That means even for a quick trip down to the bodega I will not—I repeat, WILL NOT—put on my grungy gym shoes. No sir, this year I will have these stylish and super comfortable high-tops by the door for snap decision dressing. You know how running errands in the city can lead to a day of networking and partying… be ready for whatever life throws at you this year.

The McQueen Driving Shoe – Cognac

This year I want to travel my ass off. Seriously, have you ever been in the car for so many hours you can’t feel your ass anymore? That’s how much I want to travel. No matter where I go, The McQueen Driving Shoe will be my traveling companion. Their grips provide support and keep these slip-ons from getting slippery when you’re shifting gears. Their easy-on/easy-off styling makes them perfect for getting through airport security (just wear with a pair of invisible socks because those floors are GROSS). As far as mandatory travel accessories go, the McQueen ranks up there with my passport.

The Olivier Single Monk Strap – Marrone

You have to try something new every year. I’ve never had a pair of monk strap shoes before, so this is the year I finally commit to some. These are going to be my “challenge” shoes. I’ll find a way to work them into my summer casual wardrobe and pair them with wool socks when fall comes around. I predict by New Year’s Eve 2017 I’ll be sick of telling people where I got them.

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