How to rock the boot look this winter

EDGAR's fashion expert on how to pull off classic boot style this Fall/Winter season.

November 22, 2016

While the options for most men’s shoes remains the same throughout the year, with only colours and materials changing, there are some styles that you can pretty much only wear right now, in autumn and winter. The obvious one is the boot.

This is a bit of a touchy topic because not all men are comfortable wearing boots unless they are of the functional variety. Some shy away from boots for their everyday style altogether and that’s a real shame. Wearing the right pair of boots with the right outfit can bring a level of sophistication and sartorial mastery that’s not quite there in any other shoe type. 

Here are a few quick and dirty tips to pulling off the boot look this season in style, because it’s not a question of should you wear them, but of how.

The perfect boot

If you’re new to boots the best option to go with is ankle length; it is the least intimidating style for boot noobs. There are lace-ups, zip-ups, Chelseas and cowboys, so depending on the look you’re going for – formal, casual or rugged – you can choose the appropriate style. 

The perfect trousers

This goes without saying, but I’m going to go ahead and say it anyway. When looking to incorporate boots into your daily wardrobe you should have the correct cut and fit of trousers to wear with them. Stick to slim-fit pants that hug your thighs and legs. You can maybe go with skinny jeans if you have emaciated twiggy legs or are Russell Brand. But don’t be the fashion fool who wears flared trousers with boots, or anything for that matter. Get your head out of the late '90s and stop thinking flares are ever appropriate, period.

Crop or cuff

Because boots go higher than normal shoes, your regular length trousers are guaranteed to look funny when you wear them together. Pick up some cropped pants or cuff your normal trousers to the proper length so that the break falls just right on the topmost part of the boot. There should be about an inch of overlap between the pants and shoes – no more, no less. 

When deciding between cropping and cuffing, cropped hems will look sleeker and more formal, and they will go perfectly with Chelseas for a clean silhouette. Cuffed pants will work with more urban boot styles. It’s also more practical because you don’t have to stick to a fixed length – you can cuff as high or as low as necessary.

Never tuck

The reason the previous tip exists is so people won’t have to commit this atrocity. Trousers tucked into boots has never looked good, and we still despise the B-list celebs who made it a thing in the late noughties. 

There are a few exceptions to this rule, however. Maybe you’re an equestrian rider. Perhaps you’re crossing a marsh in Wellingtons. Or maybe you’re walking in snow and the only way to keep your pants dry is by tucking them into your snow boots.

If, however, you’re wearing UGGs, you might as well tuck your face into your boots to save the embarrassment. As a rule of thumb, in the Gulf there is no need, or forgivable instance, where you should be caught in those furry monstrosities. 

This article originally appeared on and is reposted here with the author's permission.