Footwear every man should have

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.

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