Lee Holmes picks the six essential shoe styles no well-dressed man should be without

Men's shoes might not be analysed, idolised and fetishised in the way that women's are, but that doesn't mean they should be an afterthought.

Given that men's clothes tend to be plainer, accessories are often all the more important.

Shoes say a lot about the wearer, which is probably why bad ones are cited so frequently as a serious turn-off. A pair of functional clod-hoppers – the kind ordered from the back of a Sunday newspaper – warn any potential suitors that the wearer's idea of a good time is heading to an out-of-town PC World to compare games console prices. Garish limited-edition trainers, meanwhile, indicate latter-day Nathan Barleys. Long pointy shoes are pure X Factor reject: avoid the approach taken by a groom at a recent wedding, where one wag in the congregation noted his shoes were so pointy that they entered the church five minutes before he did.

A streamlined pair of brogues or loafers says cocktails, power and fun. Hello, Don Draper. At least they do on a date or at the office, but on holiday, not so much. Shoe success is about matching the style to the occasion as well as picking a good pair, as David Cameron showed last summer when he posed on a cliff path with Sam Cam wearing slip-on loafers with jeans. Note to Dave, smart-casual does not mean wearing something smart and something casual at the same time. Fortunately such footwear faux pas can be avoided by having a minimum of six carefully curated pairs to cover all occasions. Exercise restraint, look for modern classics, and don't just think in terms of smart and off-duty. There is a whole spectrum in-between – which is where styles such as desert boots and punched brogues come in.

Maintenance is also key. Sir Hardy Amies, in his classic ABC of Men's Fashion, made an elegant case for keeping shoes well-polished: "It should be noted that the surfaces of the materials in a man's costume ... are predominantly matt. The silk of his tie, and the leather of his shoe or boot, are welcome light-reflecting contrasts. This is just one reason why well-polished shoes are essential."

Six essential shoe styles


Popular since the 1950s, the loafer is synonymous with preppy Americana. Wear with chinos or shorts, and team with the obligatory striped sock for a timeless style. The ultimate loafer comes from Gucci. Launched in 1966, it conveys both casual elegance and smartness.

Gucci loafer, £1,240, www.gucci.com

Desert boots

Beloved of film stars such as Steve McQueen and more recent rock royalty Liam Gallagher, the desert boot is probably the most versatile footwear known to man. Perfect with both jeans and shorts, it's at its best when worn with a rolled chino. Feeling bold? Then wear with a casual suit to the office.

Office desert boot, £56.99 www.office.com

Tennis shoes

White tennis shoes are timeless, and owning a pair should be actively encouraged, if only to suppress the ever-increasing ubiquity of the fanciful, try-hard sportswear trainer. Not all tennis shoes are created equal; spend less than a tenner and they'll fall apart in under a week.

Superga tennis shoe, £40, www.my-wardrobe.com


Brogues earn maximum style points because of their versatility – they can be suave and sophisticated, or add a twist of eccentricity. Brogues suit jeans or a suit, and even brown brogues can work with black trousers – although perhaps co-ordinate with a knitted brown tie to bring the whole look together.

Oliver Sweeney brogue, £220, www.oliversweeney.com

Smart lace-ups

Choice is varied when it comes to the smart lace-up, so keep it simple by selecting a good black pair. Team them with jeans or a suit and they'll even be useful for the occasional black-tie dinner. Invest wisely and they could last you a lifetime.

Ndc shoe, £306, www.ndcmadebyhand.com

Deck shoes

As the name suggests, deck shoes were originally worn on boats, but they are no longer just for Sloanes and extras from 'Howard's Way'. More of a summer shoe, they can be worn comfortably with and without socks. Draw the line at wearing them with a suit – they're at their best when worn with skinny rolled jeans or chinos.

Asos "Quoddy" boat shoe, £159, www.asos.com