7 Footwear Styles Every Man Should Own

It’s often said that the first time you meet someone, you’re judged on a number of factors – with three of the main counts being your hair, your handshake and, arguably most important, your footwear.

Whether it’s a job interview or a first date, if you’re hoping for approval from a prospective employer or potential love interest, you’re probably not going to get it when they glance down to see a rather sad-looking pair of battered old winklepickers.

“But there’s too much choice!” we hear you cry. With a seemingly never ending array of footwear styles available both in stores and online, shopping for shoes can be overwhelming. Fear not, with the help of some of the biggest names in British shoemaking, we’ve whittled down the bulk to seven essentials.

The Black Leather Oxford

There is no golden rule or set formula for building the ‘perfect shoe collection’, as tastes are bound to differ. However, it pays to be ready for every eventuality, and that includes ones involving suits. In which case you’ll need a black leather Oxford.

To get technical, the Oxford name refers to a closed-lace shoe, where the quarter (the piece of leather which the laces go through) is stitched under the vamp (the front part of the shoe). If you can run your finger underneath the last two lace holes, what you actually have is a Derby shoe.

It might seem like a needless thing to point out, but the lacing system is what gives the Oxford (or the Balmoral, if you’re in Scotland) its snug fit and clean finish, making it the most formal shoe type of all.

What To Look For

“An Oxford should be worn with grey or black formal trousers,” says Grenson creative director Tim Little. “Make sure the toe shape is right. Too pointy and you look like a spiv, too round and they look clumpy. A nice almond shape is what you’re looking for.”

Recommended Brands

Affordable: Aldo, Clarks, Topman
Premium: Dr. Martens, Kenneth Cole, J.Crew
Luxury: John Lobb, Crockett & Jones, George Cleverly

The Brown Leather Brogue

While broguing may sound like a dance class for men with too much time and testosterone on their hands, it’s actually a time-honoured shoemaking technique that you’re probably already familiar with.

These perforations, which come in several different designs, were originally designed to let water out while the wearer was wading through boggy Gaelic farms. But here’s where things get complicated: because broguing is a technique rather than a shoe itself, Oxfords can be brogues, as can Derbies and wingtips.

As a general rule, more holes equals more casual. So if you’re looking for something the will take you from the boardroom to the bar, opt for a semi-brogue, which lacks the W-shaped toe design.

What To Look For

“Brown brogues are a true British classic and every wardrobe should have a pair,” says Little. “Look for a round toe on a chunky sole to wear with jeans, or a more elegant almond-shaped toe with a leather sole to wear with a suit.

“Tan is the classic colour, but if you want to be more discreet, try a darker brown. Look for leather that appears burnished as it looks more luxurious and will get better with every polish.”

Recommended Brands

Affordable: Marks & Spencer, Dune, River Island
Premium: Oliver Sweeney, Paul Smith, Ted Baker
Luxury: Church’s, Tricker’s, Thom Browne

The Suede Loafer

Despite being synonymous with dressing like JFK, the invention of the loafer has nothing to do with the preppy Ivy League, nor the humble loaf of bread (shoe-naming is often a very literal business, after all).

The first pair on record was designed in the early 1930s by a Norwegian named Nils Gregoriusson Tveranger. He based his Aurland shoes on traditional fisherman’s slip-ons and Native American moccasins, and in turn these formed the basis for the iconic Weejuns by American cobbler G.H. Bass.

Complete with a diamond-shaped cut-out, the penny loafer has survived almost unchanged since then, alongside smarter tassled and horsebit versions. Though leather is a common choice, soft suede is arguably the more versatile option.

What To Look For

“The classic aesthetic of a suede loafer lends itself to more tailored attire and can be worn with socks, or without, for a sharp summer look,” says Mr Porter senior shoe buyer David Morris. “If you’re after a smart-casual style, try a suede penny loafer in a dark brown or tan that can be worn with a pair of slim-leg chinos or shorts.”

Recommended Brands

Affordable: G.H. Bass & Co., H&M, Zara
Premium: Brooks Brothers, Reiss, Charles Tyrwhitt
Luxury: Gucci, Cheaney, Edward Green

The White Leather Low Top

Observers of men’s style love to talk about the biggest and best sneaker trends of the day. But if most had to choose just one to immortalise, there’s more than a chance it would be the white leather low top.

The slick style has been typified in recent years by the Adidas Stan Smith. First introduced in the early 1960s as the Robert Hallilet, the shoe picked up its current moniker in 1978, but only over the past decade has the white tennis shoe has become ubiquitous.

Today, every brand worth its salt has its own take from sporty to ultra-minimal, to be worn with everything from shorts to tailoring.

What To Look For

“If wearing white low-tops with a suit, keep them as pristine as possible,” says Little. “Other than that, they truly do go with everything.

“To keep your sneakers clean, avoid wearing with raw denim, but that’s the only real no-go. Pair them with flannel trousers and a merino sweater for a smart-casual vibe, or with chinos and a bomber on the weekend.”

Recommended Brands

Affordable: Nike, Superga, Adidas
Premium: Common Projects, Grenson, Polo Ralph Lauren
Luxury: Gucci, Givenchy, Tom Ford

Retro Trainers

Today, a pair of running shoes can pack as many tricks and treats as the electronic rectangle in your pocket. Which is great for actual running, but not so much for styling out the weekend.

Fortunately, it’s pretty easy to travel back in time, sneaker-wise, to an era where runners were bold, colourful, and dare we say it, fun.

Retro styles like the Nike Cortez and the Adidas Gazelle are easy to pick up, with newer brands like Novesta, Spalwart and Walsh doing decent impressions of kicks from the 1970s and ’80s.

What To Look For

“Retro sneakers continue to stand the test of time thanks to their simple design and comfort level,” says Morris. “Styles like Vans’ canvas sneaker and Prada’s Milano are all versatile options for a dressed-down office look or a relaxed weekend vibe.

“Worn best with black or indigo denim and a classic T-shirt, these trainers add a touch of nostalgia to an everyday look.”

Recommended Brands

Affordable: Vans, Superga, Novesta
Premium: Nike, Adidas, Reebok
Luxury: Prada, Balenciaga, Veja

The Leather Lace-Up Boot

A robust pair of boots is a formidable addition to any wardrobe, if for no other reason than they’re often built like the proverbial brick, well, you know.

Having shod the feet of soldiers, farmers and countless types of labourers, leather lace-ups will withstand whatever is thrown at them, be that an oil slick or the odd coffee spillage.

Reassuringly robust features like Goodyear welting and triple-stitched seams, found at brands such as Grenson and Red Wing, mean that a good pair will last a lifetime if cared for properly.

What To Look For

“Make sure the leg is soft otherwise they will be painful to wear,” advises Little. “Stick to the workwear theme with rugged twill trousers rolled up. Smarter, slimmer-soled versions can also be worn with a suit, provided that the trouser leg is sufficiently narrow and cut to the ankle.”

Recommended Brands

Affordable: Clarks, John Lewis, Dune
Premium: Red Wing, Dr Martens, Oliver Sweeney
Luxury: Grenson, Cheaney, Moncler

The ‘Goes With Anything’ Chelsea Boot

“Chelsea boots are a classic that will never go away,” says Little, which is fair to say seeing as they’ve been around since the mid-19th century.

Originally designed by Queen Victoria’s shoemaker J. Sparkes-Hall as an alternative to lace-up riding boots, the Chelsea takes its current name from the well-heeled London borough where they became popular in the 1960s and 1970s.

Look for pairs made from just two pieces of leather or suede, a sign of good craftsmanship, and as Little suggests: “Make sure the elastic at the ankle is strong, as it’s always the first thing to go and is difficult to repair.”

What To Look For

“Chelsea boots works especially well with jeans or tailored, slim fitting trousers with a slight crop,” says Morris. “If you’re going to wear yours with formalwear, make sure the colour of your boot is complimentary to the colour of your suit and opt for a slimmer sole to keep your look streamlined.”

As versatile as they come, this is a shoe that doesn’t need to be kept too pristine, as the odd scuff or scratch only infuses them with a rock ‘n’ roll recklessness.

Recommended Brands

Affordable: ASOS, H&M, Marks & Spencer
Premium: Kurt Geiger, Dr Martens, Dune
Luxury: Saint Laurent, R.M. Williams, Crockett & Jones

4 Expert Shoe Care Tips

Few men know footwear like Tim Cooper. As a third-generation shoemaker and cobbler-in-chief at Oliver Sweeney, he knows not only about the importance of traditional craftsmanship, but that a good shoe can be made even better with the right care. These are his 4 expert tips to live by.

Pick Your Polish Well

“Choosing the right polish for your shoe is simple – always read the label. A good polish should be composed of natural ingredients like beeswax or carnauba wax. These components nourish the leather in the same way a moisturiser does your skin, preventing it from getting dry, cracking, and losing its lustre.”

Prolong Their Life

“Once every four to six months, take some time to apply a rich conditioner to your shoe before the polishing process to prolong their life and get the best out of the leather. I’ve experimented with many different materials for polishing, but an old pair of tights gives a fantastically shiny finish.”

Use Protection

“Whether it’s shoes or sneakers, use a hydrophobic spray to protect against the elements by keeping water molecules away from the top layer of the material. If you’ve worn them in the rain, allow the shoes to dry naturally, fill the toes with newspaper and whatever you do, don’t put them near a radiator or an open fire.”

Keep It Clean

“Always clean excess dirt from your footwear to prevent further damage. For general cleaning, use warm water, a clean cloth and a soft bristle brush. For more difficult areas, use leather cleaner product with a clean cloth and brush. Then, remove the cleaning product with a damp cloth and allow to dry.”