There are only 5 acceptable boots to wear with a suit

After a long fall, it’s finally getting colder in New York City. That means we’re going to start dropping not-so-subtle hints about how a gentleman should dress for winter weather.

Footwear is key here. Yes, you want to be warm. Yes, you want to be comfortable. But you do not want to dress like a child at work.

With that in mind, we reached out to Jessica Cadmus, founder of The Wardrobe Whisperer and a stylist who specialises in working with professionals at the top of their game.

She told us that there are really only five kind of boots that are acceptable to wear with a suit.

“What makes a boot suit-worthy is its level of refinement. The first thing to look at is the tread. If the boot’s tread is high and jagged, most likely you are looking at a hiking boot, and those should not be worn with a suit. Not on Wall Street, at least. The sole/heel should be similar to a dress shoe,” she said. (The tread, if you don’t know, is the part of the boot that touches the ground.)

“Next, look at the construction. If you are noticing chunky elements like big grommets and heavy stitching and laces, chances are those boots are also made for the trail. The details of the boot you need are more elegant and muted, very similar to a dress shoe but with a high shaft,” she added. (The shaft is the height of the boot from the bottom to the top.)

There are five kinds of boots that meet these requirements:

The Chukka

This pair is from Paul Evans.

The Chelsea

This pair is from To Boot New York.

The Jodhpur

This pair is sold at Barneys.

The Brogue

This pair is from Crokett & Jones.

The Desert

This pair is from Marsèll.

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