Why boots come out on top of shoes, and how to work Chelsea boots, hiking boots, desert boots and chukkas into your wardrobe.

Before there were shoes, there were boots – just watch the movie Gladiator if you don’t believe me. Fast forward 1,800 years from the Romans to the Victorian era and contemplate the kind of footwear that made sense when horses were the predominant method of transport. For almost all of human history, men have worn boots, and although we can now get by with mere shoes thanks to the fact that modern life involves so little ordure, there are still good reasons to wear them.

The most important reason is obviously that they look good. This season, nothing looks better than Chelsea boots, the current style favoured by the fashion set, who is giving them a new relevance by wearing them with slim jeans and nylon bomber jackets. However, we like to match our boots to our circumstances; nothing will look as right as a pair of hiking boots if you’re in the country for the weekend, and nothing will look as cool as a pair of brown suede boots if you’re wearing a grey flannel suit. To explain why, we’ve drawn up MR PORTER’s ultimate guide to boots – where we analyse every style, and show you how to wear them well.

**BOTTEGA VENETA **Suede Chelsea Boots

These close-fitting ankle boots, with their convenient elasticated sides, follow a design patented in 1851 by royal boot maker Mr J Sparkes-Hall. Fast-forward 165 years, and these boots now come with a varied collection of associations, from the blue-collar credibility of Australian workwear, to the aristocratic trappings of jodhpur boots. Tobacco-coloured suede boots with crepe soles look great with blue denim during the day, while leather versions work better in the evening.

Wear them with

OFFICINE CREATIVE Harvard Suede Desert Boots

Chukka boots resemble Chelsea boots, but come across as more casual thanks to their laces. Smart chukka boots look good with tailored trousers, while desert boots – a variation on the chukka – combine extreme comfort with a casual elegance. The latter were invented by British shoemaker Mr Nathan Clark after he saw British soldiers serving in Egypt in WWII wearing soft, locally-made suede boots with crepe rubber soles. Launched in 1950, his desert boots were a radically casual option at the time, but have become a menswear staple. Try a pair with jeans and a tweed jacket for a “sprezzy” look.

Wear them with

VIBERG Hiker Whole-Cut Leather Boots

As with so much athletic-wear, elegance is the cost of progress – contemporary hiking boots have many virtues but they don’t look as good as well-polished leather versions. Old-fashioned hiking boots, with their distinctive D-ring eyelets, are unimpeachably masculine and feed into our fantasies of wintering in a log cabin, chopping firewood with an axe and spending cosy evenings drinking Japanese whisky by the stove. These are best worn with selvedge denim jeans, a chunky rollneck sweater and a buffalo-checked jacket.

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YUKETEN Suede Desert Boots

Moccasin boots are as American as apple pie, and represent an evolution of the styles worn and the stitching techniques employed by Native Americans. Today, they’re part of a look that’s rich in vintage appeal, and in which the quality shows through thanks to the emphasis placed on patina and wear. It’s cool to have a new pair of moccasin boots, but it’s even cooler to have a 20-year-old pair. So, best start today. Follow Mr David Beckham’s example and wear them with slim dark jeans, a flannel shirt and a vintage motorbike.

Wear them with

JOHN LOBB Abbott Suede Jodhpur Boots

Short of donning high-heels, nothing makes an impression like a pair of dress boots. They take many forms, from highly polished black-leather pairs that sit well beneath a business suit to textured brown models that look best worn with a pair of cords. If you’re going to visit snowy climes on business any time soon, then formal boots with chunky soles should keep your feet dry and warm, while still looking the part. Alternatively, take your inspiration from Mr Gianni Agnelli and wear a brown suede pair with a grey flannel suit.

Wear them with