Robb Report Australia


Six timeless shoes every man should own

Shoes, like much of menswear, have changed immensely over the last 40 years, with styles like the ultra-high platform shoes of the 1970s coming in and — thankfully — going out of style.

Some shoes, however, have earned their keep as some of the most well-loved and iconic designs of the past four decades. The following six styles, spanning from elegant monk straps to laid-back sneakers, have cemented themselves as wardrobe classics of the modern man.

Driving Shoes

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Driving shoes are one of the few footwear styles to have first emerged within the last 40 years and withstood changing tastes and passing trends. Since launching in 1979, the Tod's Gommino moccasin has become one of the must-have styles in a shoe collection.

Today's version from $US425 to $US645 (about $A580 to $A880) still features treads specifically designed for better driving grip and comes in hundreds of colours, including a classic brown leather and suede styles in rich autumnal colours. (


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The highly detailed style first originated in the Scottish Highlands, where brogues were added to leather shoes to serve as drains for bog water. In the past four decades, the brogue has shed its utilitarian roots, with designers focusing on intricate details and luxurious materials.

Church's two-toned version, $US745 (about $A1020) and subtle brogues from John Lobb , $US1495 (about $A2040) offer modern, elegant takes on the classic shoe style. (;

Chelsea Boots

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Named for the swinging London group that popularised the boots in the 1960s, the Chelsea boot was the footwear of choice for mods, rock stars like the Beatles, and punks.

To keep the style modern, look for a pair with a low heel and sleek sole, such as Bally's minimalist black version, $US995 (about $A1360), John Lobb's earthy suede style, $US1835 (about $A2500) or Church's subtly brogued wingtip boots, $US614 (about $A840) (;;

Monk Straps

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These laceless shoes, first used by monks as a sturdier alternative to their traditional two-strap sandal, have long been a popular choice of footwear. In the past 40 years, they have lost their often-squared toe, making them infinitely easier to style with suits and jeans alike.

Bally's black double monk strap and deep burgundy single monk strap styles both offer subtle, but modern takes on the shoe, $US725 and $US995 (about $A990 and $A1360). For something bolder, look to this royal blue pair from Santoni, $US970 (about $A1330). (;


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First introduced in the 1950s, the iconic Gucci horsebit loafer has defined the evolution of this versatile shoe style. Although the style changes slightly with every season — highlights include a short-lived platform version in the '70s and last year's controversial fur-lined slip-ons — the classic black version remains a timeless option, $US695 (about $A950).

For a modern update on the classic tasselled loafer, look to Santoni's intricate two-toned style, $US910 (about $A1240), or Church's luxuriously minimal black option, $US405 (about $A550). (;;


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In the 1970s, brands like the sportswear giant Nike tapped into the sartorial potential of the sneaker, creating a style very similar to the ones shown here, $US110 (about $A150) that were designed to look as good on the court as they do off.

Gucci was the first fashion house to reimagine the shoe as a luxury item, sending a style very similar to these playfully minimalist sneakers, $US110 (about $A150) down the runway in the '80s.

Bally's cream-and-red high-tops, $US495 (about $A675) are a modern nod to the 1985 Air Jordan 1 , which is largely credited with sparking the so-called "sneakerhead" movement. (;;

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