How to Wear Driving Shoes From the sports car to the sports bar, heres how to wear them
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.
6 Key Looks
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.
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.
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.
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 aqua-appropriate diving watch.
Add a couple of colourful bracelets and some classic sunshades and you can sip your Negroni safe in the knowledge you’re exuding Riviera chic.
The Beach Wedding
You are invited to s 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.
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.
Common Driving Shoe Do's and Don'ts
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.
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.