The Boot Guide

With Winter fast approaching, your feet are going to need some coverage. Boots not only have huge versatility, there are a ton of different types to accommodate to your every need. Once broken in, boots can be some of the most comfortable shoes in your rotation. This article serves to help you navigate the massive world of men’s bootwear, and the staggering confusion that it may bring. Edit: To learn how to better take care of the boots/shoes you already have, check out this article.

chukka bootsChukkas:

Usually distinguished by their relatively low-rise, and few eyelets. This style was made popular by Clark’s Desert Boots. I know you’ve seen them, everyone has a damn pair. They are great for casual wear, either with chinos or jeans and can be fairly protective from the elements. They last a long time, they are ridiculously comfortable, and extremely versatile. Another great option are the Red Wing Heritage Work boots.

Clarks Desert Boots

Red Wing Heritage Work Boots

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Work Boots:

Work Boots are accurately named, and can withstand a lot of heavy use. A thick rubber sole means they are usually waterproof, and good for colder weather. Another benefit is the deeper grooves that often make for better traction. Work boots are usually made of a thicker leather, and are to be worn un-polished. Make sure you don’t buy pre-stressed boots, you’ll wear them enough to make them look well loved. Great brands include Chippewa, Redwing, and Frye.

Red Wing Iron Ranger

Chippewa Rugged 6′

j&m bootds

Dress Boots:

Dress boots are usually made with a leather sole, and have a thin and polished high-quality leather upper. They go very well with slacks, suits, and sometimes jeans. In most cases, this type of boot isn’t rugged and can require a little bit a maintenance – just like a quality dress shoe would. In our opinion, dress boots almost always look better than dress shoes when it’s cooler outside. Johnston & Murphy and Allen Edmonds are definitely some of your better options here.

Allen Edmonds Dalton

Johnston & Murphy Tyndall Cap Toe


Do’s and Don’ts

*As a general rule, leather uppers are a must. If you’re planning on hiking, mesh or canvas is acceptable.

*Try to keep it vintage, if it looks trendy and modern, your $300 boots may fall out of style next season.

*Stay away from moccasin toed boots (occasional exceptions), square toed boots, and pointy-tipped boots.

*Keep in mind that leather and crepe soled shoes are not nearly as sturdy as rubber and cork soled shoes.



Wedge: a trendy, new look. Stay away from these boots with a platform heel of sorts unless you are okay wearing older trends. This look may not be around much longer. But we kind of like it.

Flat: the standard for dress shoes. Usually best for casual as well. Although comfortable and flexible, these soles will not hold up to the elements as well – especially in snow and rain.

Lugged: Lugged boots are boots with the large tread on them that look similar to a tire. They are great for the winter months, and have great traction and durability. Usually three-quarters to an inch in depth will be plenty for even the roughest of conditions.