Man about town or casual day-tripper? Country-man or city-liver? Whatever your style, shoes can make or break an outfit – wearing the same generic pair to work, play and weddings is definitely not putting your best foot forward. Use this guide to get to grips with what to wear, when.

Wearable with any kind of suit, tuxedo or even a pair of jeans, the leather Derby shoe is your popular all-rounder. Easily confused with the Oxford shoe, Derbys have a similar shape but with an open lace section for a more relaxed fastening and wider fit. They were originally worn by country gentlemen in the Victorian era but hit city fashion at the beginning of the twentieth century, and they’ve been a staple shoe ever since. Smart, flattering and timeless, every man needs a trusty pair of Derbys – it’s worth investing in both a black and brown pair.

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This is your traditional, go-to formal shoe, first made popular by students at Oxford University (explains the name) throughout the 1800s. Lightweight with a narrower fit, Oxfords have super-neat closed lacing. With the toe cap version, you’ll find detailed stitching across the front section, which can be a different colour leather to create a smart two-tone design. Wear every day to the office, shine them up for a wedding, or match them with smart chinos.

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Brogues take pride of place in the shoe hall of fame. Worn by many generations of men, they have a sturdy look and the leather has distinct perforated detailing on parts of the toe, heel, quarter and vamp in varying patterns. Brogues and tailored tweed are a great match if you want to work a vintage look at a wedding or weekend celebration. A little trivia for you: the perforated holes were initially created in Ireland to help drain water from the shoe when men were wading through the country’s rural landscape.

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Originally designed for King George VI as a comfortable house shoe, loafers are now a popular choice for almost any kind of occasion. Made from suede or leather, they’re laceless with a low-cut design and fabric threaded through the upper shoe to flaunt a front tassel. Great with shorts or cropped slim trousers, you can easily dress loafers up or down.

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Unlike standard lace-ups, the monk shoe has a buckle and strap fastening for a more striking look, while still keeping you firmly in formal territory. Similar to Derbys in their structure, monk shoes are very comfortable to wear all day into night. Opt for soft fabrics and wear a contrasting jacket with daring patterns in your tie and pocket square for a stylishly offbeat look.

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The most formal design of all, you’ll need these to wear with a tuxedo or tails for a wedding or awards ceremony. Buff your dress shoes to show off their signature high-shine finish, and choose either a plain or brogue pattern – sticking to the classics is the simplest way to faultless style.

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