12 of the Smartest Men’s Shoes for Party Season

Crockett & Jones Hamilton Chelsea Boot, £895

Crockett & Jones Hamilton Chelsea Boot

Smart enough to wear with an evening suit and practical enough to be worn on an icy evening? That of course means a Chelsea boot – and the Hamilton from Crockett & Jones has a serious pedigree there. Celebrating 60 years of James Bond, the Hamilton is actually a style taken wholesale from the shoemaker’s 1962 catalogue. It says a lot that it’s just as appealing today, with traditional straight cut elastics and flexible shoulder insoles for comfort, and a classic round toe for that 007-worthy classicism. Keep them in black to keep things formal and you have a pair that’ll last you a good 60 years or so.

Available at Crockett and Jones.

Oliver Sweeney Luisetto Shoe, £279.20

Oliver Sweeney Luisetto Shoe

While the tactile grained leather of this single monk strap shoe is elegant in the extreme, it’s a pair that’s actually built for comfort. The deerskin is incredibly soft, and rather than a stiff board inside, Oliver Sweeney has used a softer leather sock. It means that the entire shoe is deceptively flexible and more than comfortable enough to keep you on the dancefloor all night. The fact that its buckle makes it more interesting than your standard Oxford is the icing on this particular festive footwear cake.

Available at Oliver Sweeney.

Joseph Cheaney & Sons Spitfire II Derby Shoe, £375

Joseph Cheaney & Sons Spitfire II Derby Shoe

A more militaristic take on the classic, open-laced Derby, the Spitfire II is based on an archival design from pilots’ shoes of World War II. It’s basically a formal shoe with a more practical, industrial feel and a watertight construction that’ll have you singin’ in the rain, especially with the chunky sole. The Kudu leather is taken from the African antelope and as each is hunted naturally, you may well find scars and scratches, lending to its more weather-worn look. With its high pitch angle, the Spitfire II is also an incredibly comfortable shape, and even if it’s not as formal as other Derbies, you can wear it with anything – up to and including a military uniform.

Available at Cheaney.

Thom Browne Harris Tweed Uniform Shoe, £640

Thom Browne Harris Tweed Uniform Shoe

Sometimes you just want to be the centre of attention and for you, there’s this eye- catching take on a classic silhouette from New York label Thom Browne. The Italian- made pair uses the kind of Herringbone Harris tweed you’ve probably got hung up in your wardrobe somewhere, in this instance in a light grey. Practical? The uppers are made from 100% wool with a calf leather lining, so not entirely. That doesn’t stop them being one of the coolest pairs of party-ready shoes around. The Manhattan party scene won’t see these coming.

Available at Thom Browne.

MYRQVIST Ängsö Black Suede Shoe, £239

MYRQVIST Ängsö Black Suede Shoe

Forget ‘the usual’, this pair of loafers from Scandi-slanted, Portuguese-made shoemaker MYRQVIST is more distinct than your old penny loafers could hope to be. Each shoe is dominated by the large fringe tongue for a flash of flamboyance, complete with a contrasting single monk strap in different grained leather and a bright silver buckle. The Charles F. Stead suede is water repellent for practicality, and while the soles are relatively stiff, they’re Goodyear welted, meaning that these will last more than long enough to become a core part of your new signature look.

Available at MYRQVIST.

Edward Green Charles Loafer, £825

Edward Green Charles Loafer

A fine leather loafer with the shape and comfort of a slipper (Edward Green’s own Albert slipper to be exact), this sleek, svelte shoe is as minimal as you can get, letting the supple veg-tanned Arno calfskin do the talking. Its matte finish is understated and more contemporary than most slipper-adjacent footwear and makes for a pair that you can wear as confidently with a business suit as a smoking jacket. Just make sure you wear some statement socks to go with them. It’s party season, after all.

Available at Edward Green.

Grenson Hanbury Double Monk Shoe, £445

Grenson Hanbury Double Monk Shoe

Colours are great; suede is great. But for that classic eveningwear, dinner jacket look, a high-shine pair of black shoes is a go-to – and the bookbinder leather on this pair from Grenson will look phenomenally sharp in low light. Despite the formal look of the high shine, the leather’s easy to look after, and the double monk buckles make a solid point of difference (and eye-catching flash of silver) when compared to your standard patent leather lace-ups. With a flash of red on the sole to match the leather lining, the Hanbury is a classic evening shoe any man can pull off.

Available at Grenson.

George Cleverly Melvin, £575

George Cleverly Melvin

If you’re going to opt for something a classic as a plain black Oxford, you may as well go with one of the most important names in British shoemaking: George Cleverly. The shoemaker’s best known for their intense bespoke experience, but their ready-to-wear offers all the same quality just without all the fittings and extra time for manufacturing. In this instance that means a wholecut shoe with an elegant silhouette, matching black Goodyear welted soles, and just a touch of broguing on the toe. These are a tried-and- true classic – and for good reason.

Available at George Cleverly.

Gucci Jordaan Loafer, £645

Gucci Jordaan Loafer

The horsebit loafer is a classic design and Gucci is its originator – so if you’re thinking about that particular breed of shoe, you may as well go to the source. This particular pair however are anything but the norm. They may still have the gold-toned emblematic hardware, but the dark brown suede with Gucci’s Square G across it is a different look entirely. They’re not for the faint-hearted but their eye-catching look – complete with contrasting plain brown leather – is incredibly attractive. As are you when you wear them. We assume.

Available at Gucci.

Herring Markham Two-Tone Oxford Shoe, £360

Herring Markham Two-Tone Oxford Shoe

A classic style done in a decidedly modern way, Herring has taken the stalwart men’s classic and draped them in burgundy calf leather. That leather is hand-finished individually by the same Portuguese factory as Carlos Santos, meaning the two-toned, fume shading will never look exactly the same from shoe to shoe. Paired with a proprietary blue sole and a chiselled toe, the Markham has all the features you’d expect from a pair of bespoke formal shoes for a far more accessible price. They’re not cheap; far from it, but for a pair this good looking they’re less than you might expect.

Available at Herring Shoes.

Berluti Alessandro Demesure Scritto Leather Oxford, £1,740

Berluti Alessandro Demesure Scritto Leather Shoes

Quality Italian shoes don’t come more high-quality or Italian than Berluti. This pair of dark, charcoal brown leather Oxfords come in the iconic label’s signature Scritto leather, embossed with what looks like Renaissance-style lettering. Paired with a lustrous patina, the Alessandro balances a classical, pared-back silhouette with all the hallmarks of a truly luxurious shoe. Pair with a bespoke evening suit with a svelte Italian cut for a look worthy of the Milanese fashion elite.

Available at Berluti.

Vivvant Oliver Blue Oxford Shoe, £285

Vivvant Oliver Blue Oxford Shoe

What’s life without a splash of colour? The beautiful blue of this pair from London-based Vivvant is an absolutely stunning colour, dark enough to be considered formal, but more than a few well-heeled steps above your usual black pair. Made in Florence with all the Italian craftsmanship that entails – including a hand patina process that means each shoe is unique – the Oliver’s a more confident twist on a menswear classic. It’s obvious why Vivvant would want to sign it off with their signature triple V stitches on the back.

Available at Vivvant.

About the author

Sam Kessler

Legend has it that Sam’s first word was ‘escapement’ and, while he might have started that legend himself, he’s been in the watch world long enough that it makes little difference. As the editor of Oracle Time, he’s our leading man for all things horological – even if he does love yellow dials to a worrying degree. Owns a Pogue; doesn’t own an Oyster Perpetual. Yet.

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