2016 Fall Boot Guide

Autumn has given us quite the reprieve this year from bad weather, at least around here. But make no mistake, winter is coming. And with winter comes the need to protect your ankles, socks, and pants from cold rain, slush, snow, and ice. There is no better way to do that than with some quality boots. I like to lump boots into the shoe category as one of the places I feel comfortable splurging on my style. I understand the need to question spending a good chunk of cash on boots that will be run through the ringer and subjected to repeated abuse at the hands of Mother Nature. Fortunately, with a little extra care in the form of shining and conditioning, the leather will actually improve over time. But you must take care of the leather, even more so than you do with your dress shoes. Water and salt form a corrosive mixture which can irreversibly damage the leather, flushing good money away. Shoe care is essential during the foul weather months.

I think a common misconception is that boots are only worn or at least best worn when working outdoors. That is a practical idea and one that makes a lot of sense. But, in reality, boots have incredibly versatile applications in the world of men’s style. From the workplace board room meeting to snow-packed driveway shoveling, I’d like to run through a some of my favorite pant and boot combinations. Why only pants? Well, I think the pairing of a pair of pants and boots or shoes provides a solid foundation on which to build the rest of an outfit. With this post, I really wanted to focus on starting with a solid base when expanding outside the common uses for boots.

Chelsea boots are some of the easiest boots to pair with an outfit. I love them with dark denim like I have here. But they also work with suits, they work with flannel trousers, they work with corduroy pants, they work with chinos. I you want to buy a pair of boots outside your typical outdoor boots, chelsea boots should be your first purchase.

Boots: Cheaney  //  Jeans: AG

If any look is going to give a guy trouble when it comes to boots, it’s going to be wearing boots with a suit. I think there are two key components to remember. First, think of it like a high dress shoe. If you’re investing in quality leather and quality construction, a boot is absolutely as appropriate as a pair of oxfords. Second, this is primarily a cold weather look. Keep reminding yourself that the boots are as functional as they are stylish. That should ease any insecurities.

Boots: To Boot New York  //  Suit: Hugo Boss

Yes, snow is coming. But one of my favorite things is hunkering down inside during a nor’easter with a good book or movie and a few glasses of something to keep me warm. Cords are a perfect way to stay warm, and you can throw your boots on whenever you need to run out for a quick shovel or dog walk.

Boots: L. L. Bean  //  Pants: Vineyard Vines

Think chopping wood, think flannel shirts, think campfires. Two brands that scream hard work are Levi’s and Red Wing. This combination will carry you through any yard project standing up to the toughest you can throw its way.

Boots: Red Wing  //  Jeans: Levi’s

What are some of your favorite boot pairings? Leave a comment below.