Advice | September 19, 2016 9:00 am

The 10 Essential Men’s Boots for Fall

The best styles from day to night, office to out-of-doors

It’s almost boot season.

We checked the calendar.

So, before you step outside at leaf-crunch-o’clock wearing boat shoes (or worse, sandals), let’s get you outfitted in something proper. To that end, we’ve rounded up the 10 best boots of the fall, as categorized by style and use case. From hoofin’ up a mountainside to shakin’ it at a autumnal wedding, there’s a perfect pair to tie every look together.  

If a boot could be your best buddy, it’d be the chukka. Wear ‘em anywhere.

AM: Heschung Genet Suede Chukka Boot
PM: Nisolo Emilio Chukka Boot

Shining or sedate, light or dark, it’s damn near impossible to not look tony in a chelsea. Wear ‘em when you know people will be looking.

AM: Common Projects Suede Chelsea Boot
PM: Church’s Houston Leather Chelsea Boot

Tried and true. Hearty. Robust. Invest wisely in a lace-up and you’ll want to take ‘em to the grave. Wear ‘em everywhere — just not with a suit.

AM: John Varvatos Rivington Wire Boots
PM: Want Les Essentiels Montoro Boots

It’s bound to come down sooner or later. Stay prepared. Stay polished. And keep a pair of these in your car or under your desk.

Scattered Showers: Blondo Damien Waterproof Wingtip
Cats and Dogs: Swims Charlie Boot

If you’ve ever tried to hail a cabbie at shift change to meet some friend over on the West Side Highway, you know what an urban hike is. And as for the real mountain-man variety, we’ve got you covered there, too. Wear ‘em when you’re pounding the pavement or traversing the peaks.

Urban Hiking: Heschung Richmond Buckled Full-Grain Leather Boot
Hiking Hiking: Danner Mountain Pass