3 Boot Styles Every Man Should Own For Fall/Winter 2018

Boots are a fall/winter staple and the right pair (or two) should be versatile enough for a variety of outfits and occasions. I think Chelsea boots are more of a spring/summer style so we’re focusing on shoes that will get you through the colder, wetter months of the year and work better with heavier clothing.

One thing to remember, look at boots as an investment, good ones aren’t cheap, but properly taken care of they can last you many years. There are a ton of options out there and we’ll include our picks, but we’ve narrowed it down to three basic styles that you should have in your closet.

Desert/Chukka Boots

The most versatile and least seasonal, you can wear these nearly year round. They’re light and comfortable and work well with both casual looks (jeans, chinos) and more dressy looks (with sweaters and blazers).

Picks

Zegna

Allen Edmonds

Clark’s

Budget-Friendly Clarks

Johnston Murphy #1

Johnston Murphy #2

Work Boots

What you probably think of when you think of boots, these are more rugged and have thicker/chunkier soles. The look great with jeans and chinos and will get you through the colder months and weather with ease. They can come in a variety of styles, some very casual, others a bit more dressy.

Picks

O’Keefe

Red Wing Beckman

Allen Edmonds #1

Allen Edmonds #2

Wolverine 1000 Mile

Danner Jack

Dress Boots

Yes, you can and should dress up your boots. Just make sure you’ve got the right styles. Think of these like the hightop versions of your dress shoes. They should have a thinner, dressier sole and nice leather. Look for them in cap toe or wingtip versions. Formality note: some dressier styles come with a bit more tread (called a lug sole) which can still look good with dressier clothes, but it will make them slightly less formal.

Picks

Edward Green

Brooks Brothers Peal & Co.

Grenson

Mezlan

Allen Edmonds #1

Allen Edmonds #1

Aldo 

Calvin Klein