A man's guide to wearing boots this winter

EDGAR's fashion expert explains how to pull off the classic boot look this season. 

November 30, 2015

With arrival of the Fall and Winter seasons comes a range of new pieces to add to your shoe collection.

While most of men’s shoes remain the same all throughout the year, with only colors and materials being changed, there are some styles that you can pretty much only wear right now. One of them 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, 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. 

It’s not a question of should you wear them, but that of how you should. Here are a few quick and dirty tips to pulling off a pair of new season boots in style!

The perfect boot

If you’re new to it, the best pieces to go with are ankle length. In fact, the best looking ones are made in this length because it is the least intimidating to wear 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. 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 about wearing flares, 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. Tucked pants just do NOT look good.

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 you’re wearing UGGs, you might as well tuck your face into your boots so people don’t ever see you sporting them on the street. As a rule of thumb, in Dubai, there is no need, or forgivable instance, where you can do this. 

Jim Joquico is founder & editor-in-chief of La Moda Dubai and Fashion Chameleon. Visit lamodadubai.ae and fashionchameleon.ae