What Are Driving Shoes And How To Wear Them in Style

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The driving shoe is an incredibly useful addition to your summer wardrobe. It is an elegant combination of the penny loafer’s dressiness and the traditional moccasin’s comfort. More urbane than the boat shoe and not as precious as the Belgian loafer, it sits perfectly within the sometimes dreaded smart-casual clothing category and is the only shoe you really need on a relaxed vacation to warmer climes.

Yes, it was intended as a tool to aid motoring, but the driving shoe’s classic design ensures it’s so much more than that, and as a result it can be worn in a variety of contexts. Whether you’re jetting off to a beach holiday or you’re after a dapper yet relaxed slip-on for the weekend, a pair of driving shoes may be what’s been missing from your footwear arsenal.

What Are Driving Shoes?

A driving loafer is essentially a moccasin-construction slip-on with a snug but comfortable fit. The defining feature are the small rubber pebbles that cover the sole and extend to the back of the heel – they are very flexible and provide added grip on the pedals. Designed to afford the wearer greater control while behind the wheel and to prevent heel-wear to regular shoes, they were easy to change into before driving due to the lack of laces.

Most serious, professional driving shoes are now closer in style to sneakers and have a combination of laces and Velcro but the classic style (like classic cars) has enduring appeal. They were traditionally constructed from suede or reverse-calf but now all manner of leathers and materials are selected.

How To Wear Driving Shoes

The Road Trip

This is what they were actually designed for in the first place, but like the biker jacket and morning coat, the original use is sometimes forgotten today. However, for the classic motoring enthusiast who wishes to be comfortable and elegant, a well-made driving loafer is a useful piece of kit. Wear with jeans, a tee and a quietly cool jacket. Add some aviator shades and a vintage timepiece and you are all set for the Mille Miglia. Or a trip to the local supermarket.

Florentino

Preppy Perfection

With their fancy European branding and connotations of sophistication and privilege, it is no surprise that the driving loafer has comfortably established itself within the contemporary preppy wardrobe – the successor to the original Ivy League look if you will. That they should be worn without socks only adds to their modern cult status in resort wardrobes.

Warm colors are ideal for combining with seersucker, madras, or linen shorts and the ubiquitous Oxford cotton button-down shirt. A NATO strap on your vintage watch and some Clubmaster sunglasses will ensure you are all set to summer in the Hamptons.

Massimo Dutti

The Business Trip

Driving shoes are the ideal shoe for business travel, especially by air – they are both light in weight and comfortable. They can be easily slipped off for security checks or naps, which is one of the rare circumstances that socks should be worn with them – your fellow passengers should not be subjected to your bare feet, nor the chemicals escaping from them.

Wear long, pale-colored cotton-blended socks and select a loafer in a dark, conservative hue. Chocolate brown suede is ideal and is formal enough to be worn with suits in blue or charcoal grey. An unstructured piece of tailoring in a high-twist worsted wool strikes the right note especially when paired with a plain soft blue shirt and dark textured tie. Have the trousers tailored with little or no break as drivers have only a low heel.

Mango Man

Poolside Chic

Drivers are the ideal vacation shoe and can navigate you through airports and smart dinners. But they are also sporty enough to wear around the pool or beach bar when teamed with your tailored swim shorts, knitted polo shirt, and an aqua-appropriate diving watch.

Add a couple of colorful bracelets and some classic sunshades and you can sip your Negroni safe in the knowledge you’re exuding Riviera chic.

Calibre

The Beach Wedding

You are invited to a summer wedding in a tropical location but subsequently, learn that the event is happening on an actual beach. This creates a sartorial dichotomy… of course, you know that your bench-made Oxford shoes will complement your wool, silk, and linen-blend suit to sartorial perfection but you are also aware that the combination of sand and salt could cause havoc with the leather and create some serious damage.

You have already spent a fortune on getting there, attending the stag do and buying a wedding present. If you have to factor in replacing shoes, you may need to re-mortgage. But you are not ready to throw the towel in just yet and you absolutely refuse to wear sandals or, worse still, flip-flops. You would never risk that combination and you are fairly certain that there will be a photographer present at the event.

Just wear your leather driving loafers without socks and problem solved. The rubber sole is practical in the sand and a little wear and tear will only add to their charm.

Mango Man

Eurotrash Casual

For summer spectator events, your pristine driving shoes are perfect for top-drawer entertainment at the likes of Wimbledon. Look to the Italians on how to get this look right and avoid the naff British uniform of too-tight beige chinos and blue shirt.

Slim-leg cotton trousers, a shirt made from a textured cotton and a 7-fold silk tie is the combination to aim for, and a blue hopsack blazer in the unstructured Neapolitan style will have the right attitude and buttons to complete the look. If the event threatens to be a little chilly, a single-ply Scottish cashmere slipover will add a stylish layer. Oh, and now would be the time to wear your Audemars Piguet Royal Oak.

Mango Man

Common Driving Shoe Dos and Dont’s

Dos

Keep your suede shoes clean with steam and a brush, but do not be too precious with them. They look better a bit lived-in.

Keep tissue paper in them when not being worn for an extent of time. This will keep their shape. Proper wooden trees are not required.

Try a different colour. Brown is classic but they are a great way to introduce blues and greens into your shoe wardrobe.

Don’ts

Ever wear socks (unless wearing for air travel).

Walk too much in them. They are great for strolling from beach to bar, or car to café but not for sight-seeing days in Milan.

Fret about the pebbles wearing out. Buy a new pair and keep the old ones to wear around the house and garden.

The Best Driving Shoe Brands

Tod’s

Tod’s was introduced in 1979 by Diego Della Valle who, as the grandson of a shoemaker, quickly introduced what would become the most famous driving shoe, the Gommino. Fiat magnate Gianni Agnelli wore Tod’s shoes to Fiorentina soccer matches, events which were widely televised, awarding Tod’s a cult status in Italy and overseas as a result.

Today the brand also offers a custom service, where you can elect to have one of its classic models realised in a leather and trim of your choice.

Car Shoe

Car Shoe was created in Italy in 1963 by Gianni Mostile and today, like back then, it has strong links to the world of classic motoring. The brand was purchased by luxury Italian house Prada in 2001 and has since collaborated with Alfa Romeo and The Driver’s Club.

Furthermore, it has been a constant feature at The Goodwood Revival, the annual celebration of the golden age of motorsport, with a ‘pop-up’ shop selling its merchandise. If you are feeling fancy it even offers a version in Crocodile skin.

Gucci

Whilst perhaps more well known for its classic horsebit loafers, Gucci makes a fine pair of driving loafers. Synonymous with the house’s elegant Italian roots, its designs range from the understated to the outlandish, with anything from classic black leather to shearling lined suede iterations – many feature the iconic horsebit snaffle over the vamp too.

Cheaney

Despite being one of Britain’s most prestigious shoemakers, with a history that dates back to 1886, Cheaney offers one of the most diverse footwear line-ups amongst any equivalent heritage brand. One such design you might not expect to find amongst its offerings is the driving shoe.

Made in different textures, all boasting their subtle hues, there is plenty to choose from, but the Hunt in dark brown grain leather is arguably the most elegant. It’s a smart take, with a penny loafer trim that makes it versatile enough to pair with either jeans, shorts or even a suit.