The Very Best Smart Shoes For Men (Even Those Who Don’t Do Smart)

There are two types of men in this world: those who relish any opportunity to stride around in a pair of polished Oxford shoes, and those who consider their least battered pair of canvas trainers to be a la mode. Regardless of which camp you belong to, an understanding of the different types of smart shoes will improve your nous immeasurably.

Whether it’s for the corporate workplace, a family wedding, a big job interview, or even just because you want to be a little smarter for 2020, every man requires a pair of smart shoes at some point. When that time comes, it pays to know your Derbies from your dress boots.

What to look for in a pair of smart shoes

It’s been a rollercoaster, reader. From the early-noughties appetite for pointy, pleather winklepickers (we’re no longer hungry, by the way) to the resurgence of square-toed slip-ons, the hunt for respectable footwear can be a tricky one. You need to know what to look for. Thankfully, the recipe is simple: you just need the key elements.

“When thinking about buying a pair of smart shoes, quality is paramount,” explains Paula Gerbase, artistic director of historic shoemaker John Lobb. “A Goodyear welted sole is the first box to tick. A pair of shoes with this type of construction will last years if cared for, so make sure to choose something classic yet modern to lengthen its lifespan.”

For the uninitiated, Goodyear welt is the oldest, most durable method for attaching a sole to the actual shoe. It involves running a lockstitch through the upper, insole and welt, while using a separate stitch to attach the outsole. It’s sturdy, makes repairs easier and is widely regarded as a hallmark of quality.

A Goodyear welted sole is the first box to tick. A pair of shoes with this type of construction will last years if cared for, so make sure to choose something classic yet modern to lengthen its lifespan

Equally important is material. Leather uppers and leather soles are the obvious choices. The sharpest smart shoes are almost always a combination of these two elements. Get the toe shape right too and everything else will fall into place.

“A lace up with an almond-shaped toe in a black calf upper and classic leather sole, for example, will always look good and can evolve with your style,” says Gerbase. “Wax the toe to a mirror finish to achieve heightened sharpness for an evening look. Or, work a burgundy or brown shoe cream into the leather to create a depth of colour.”

Finally, invest in a pair of hornbeam shoe trees made to fit, and use them after each wear. This will ensure the leather stays faithful to the original shape and your smart shoes remain at their best.

Smart Shoe Styles


best smart shoes for men

The Oxford is the definitive dress shoe. You can enlist this formal favourite for almost anything: date night dinner, smart-casual, work suit and so on and so forth. That’s because it’s one of the most ubiquitous options, defined by a closed lacing system (and a shape that, when in patent leather form, are the recommended shoes for black tie dress codes).

Grenson

SHOP

Gresham Oxford Shoes, £385, grenson.com

Church’s

SHOP

Dubai Oxford Shoes, £450, mrporter.com

John Lobb

SHOP

City II Oxford Shoes, £970, matchesfashion.com

best smart shoes for men

Assuming you’re not in a life of servitude as m’lord’s butler, patent leather Oxfords are perhaps a little too formal. That’s where the Derby shoe comes in: a relaxed cousin of the latter that’s most at home teamed with tailoring, but still a worthy part of smart-casual looks.

To the untrained eye, the Oxford and the Derby might look pretty similar. But the difference lies in their lacing systems. Where the Oxford uses a closed system, the Derby features an open one, with each set of eyelets sitting on top of the vamp and left unfixed at the bottom.

John Lewis

SHOP

Italian Leather Derby Shoes, £80, johnlewis.com

Mr P.

SHOP

Suede Derby Shoes, £345, mrporter.com

Ami

SHOP

Chunky Derby Shoes, £370, matchesfashion.com

best smart shoes for men

Don’t discount the brogue. Though a chequered history placed it front and centre of 2004’s indie crisis, it’s still a solid smart shoe proper. Featuring decorative panels and intricate hole-punched patterns that were originally intended to let water escape when crossing marshland, these country classics are also much less formal than plain Oxfords or Derbys.

But that’s where things get confusing, because both Oxfords and Derbys can actually be brogues. Strictly speaking, a brogue is simply any type of smart footwear that features the hole-punched detailing, known as broguing. It’s therefore possible to have an Oxford brogue, a Derby brogue or even a brogue Chelsea boot (oh, the madness). The key thing to look out for is the level of detail: the less broguing, the more formal the shoe.

Magnanni

SHOP

Dark Brown Leather Brogues, £290, harveynichols.com

Tricker’s

SHOP

Bourton Leather Brogues, £415, mrporter.com

Burberry

SHOP

Lennard Perforated Brogues, £590, matchesfashion.com

best smart shoes for men

Monk strap shoes can trace their roots to 1500 BC, but the mid-2000s saw a smarter version march from the friary into the smarter circles of menswear. Their offbeat strapped fastening and streamlined silhouette made them an instant hit, especially among the flock of Pitti peacocks.

Occupying the middle ground between a dress shoe and a loafer, the monk strap shoe is a slip-on at heart, but one that retains the tongue and vamp commonly found on its lace-up counterparts. The real USP though is the wraparound strap and buckle in place of laces. Yes. That bit is the monk strap.

Reiss

SHOP

Gelder Monk Strap Shoes, £195, reiss.com

Brunello Cucinelli

SHOP

Suede Monk Strap Shoes, £720, mrporter.com

Sons Of London

best smart shoes for men

Today, London’s outer south west suburb is filled with soulless coffee franchises and £19 gin and tonics. However, back in the Sixties, Chelsea was at the heart of London’s fashion renaissance; its capital of cool, and still the spiritual home of one of the most rock-and-roll smart shoes around.

Created for Queen Victoria (but made cool by The Beatles and Mick Jagger), the Chelsea boot is a King’s Road icon and a timeless alumni of the Swinging Sixties. Today, chunky soled versions have become popular, but if they’re to be worn smart, it’s best to go for a traditional, low-profile leather sole.

R.M. Williams

SHOP

Craftsman Chelsea Boots, £350, mrporter.com

Tod’s

SHOP

Suede Chelsea Boots, £675, matchesfashion.com

Reiss

SHOP

Tenor Chelsea Boots, £195, reiss.com

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