With an exceptionally comfortable construction, minimal lacing system, and smart leather and suede uppers, the Desert boot is rarely ever a bad choice to bookend your look with.

Dr. Martens 8-Eyelet Boots

Assimilated punk iconography can sometimes look a bit, well, naff (distressed patching, shoddy DIY safety pin customisation). But Dr. Martens classic 8-eye boot will always bring an instant edge to any outfit.

Known as style 1460 (after the date it launched, 1 April 1960) the shoes came about after Dr Klaus Maertens set about creating a boot with an air-cushioned sole after injuring his ankle skiing. What followed would leave a hefty imprint on everything from style to music to politics.

With a Goodyear-welted construction and clean, trend-proof design, a pair of Docs is the perfect choice for casual looks that show your historic menswear credentials. Just brace yourself for wearing them in.

Gucci Horsebit Loafers

The shoe of choice for discerning men from Pitti Uomo to Garage Nation, Gucci’s horsebit-adorned loafer is intrinsically linked to London’s Garage scene of the late 1990s and early 2000s, but its decidedly classier pedigree (mid-century Florence) is also undoubted.

Steeped in Italian flair, it’s a style born to be worn sans-sock with a neatly rolled-up trouser or a pair of nattily tailored shorts once the sun’s out.

The Horsebit’s clasped metal detail on the upper is a subtle but instantly recognisable mark of distinction, while its low-profile silhouette and smooth sole mean it looks just as handsome even when outside of Florence.

Accessories

Ray-Ban Aviators

Like many classics, there’s a story behind these teardrop-shaped glasses. First worn by pilots during the 1930s, the style’s large lens shape provided necessary protection from glare while flying, hence the name aviators.