Tune into the cooler season with Valentino’s bold boots. The Italian label’s suede number is a sassed-up version of the classic Chelsea, featuring the signature Valentino pyramid metal studs matched with a sheeny black upper. Match these babies with a biker jacket and inky jeans for an all-black autumn look that’s sure to strike a rocker chord.

Available at Matches Fashion

When work calls, answer with Edward Green. The British cobbler offers handmade monk-strap boots in scorched tan suede. The Ravenstone model is luxe enough to wear with suit or trouser separates, and is built for hustling between a meeting and lunch and meetings again, thanks to the comfortable Dianite rubber sole with inbuilt grip and traction.

Available at MR.PORTER

See also: Gentleman's Guide: 5 Ways To Spot A Quality Tailored Suit

As luck would have it, Lanvin is bringing back its lace-up ankle boot for autumn. Fashioned from grey leather and supple calfskin, the luxury boot features a casual round toe, front lace-up front fastening, and a chunky low block heel. Comfortable and cool, play around with contrast-coloured laces for an injection of personalised attitude.

Available at FarFetch

Gucci is stepping out with punkish panache this season with the Show Queercore boots. The Italian brand’s black leather brogue boot – with heritage-style perforation - gets a makeover with tartan tweed patches and a tiger head burnished buckle clasped across the toe. Pair these bad boys with ripped jeans and a bright-coloured sweater or even patched-out jacket for an added rebel twist on heritage-style boots.

Available at Harrods

See also: Gucci Men's Tailoring Party

For the urban industrialist, Salvatore Ferragamo’s Work Boot is the ideal shoe for comfort and durability. And, for a factory boot, it’s incredibly stylish—just note the leather ‘scale’ trim on the boot’s backstay. In a chocolate-caramel hue, the suede lace-up also boasts a protective round toe and lugged rubber sole for extra traction. Not a workman’s boot exactly, but they’ll make you look the part.

Available at Bergdorf Goodman

A nod to British shoemaking, the Sharp brogue boots from Grenson are a men’s style staple (much like a wool overcoat or slim blue jeans) and should be added to one's winter collection. The tan calfskin hue and perforated Derby design pairs well with office attire, or simply with selvedge denim and a crisp shirt come the weekend.

Available at Lane Crawford

Far too fancy to be worn on the ranch, Berluti’s Chelsea boots are made-in-Italy and cut from hand-polished Venezia leather in a plump burgundy. This tapered-toe design has elasticated side gussets and a smooth leather lining that provides an incredibly comfortable fit. Plus, the oxblood hue is distinguished and different, great for special occasions when you want to a touch of colour to a black or grey suit.

Available at Neiman Marcus

After a pair of boots that are ready to hit the ground running? Motorcycle jacket maker-turned-fashion house Belstaff has us hooked on its Alperton boot this season. Crafted in Italy from black leather, the boots’ burnished finish creates a vintage appearance, worn in but certainly not worn out. Pull tabs and a lace-up front offer a secure fit, and sturdy lug soles allow for travelling: by foot or by bike.

Available at MR.PORTER

Crafted from hand-aged, hand-dyed calfskin in a rich sapphire blue, Santoni’s double-buckle ankle boot fuses all of the finest heritage features of men’s footwear—monk shoe, brogue and boot. Perfect for a formal event (they’ll brighten up a neutral pant) or worn off-duty with a cardigan and cotton chino, the boot features double gold-tone buckle fastenings and a decorative patina.  

Available at Harrods

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