Sartorial Know-how9 February 2022

10 Leather Shoes That Will Set You Up For Life

In the first of a trio of articles on investing in leather goods to compliment your wardrobe, our resident style shrink Lee Osborne, AKA Sartorialee highlights the leather shoes that will transport you in timeless elegance from the office to a stylish night on the town.

My wife reckons I’ve got more shoes than Imelda Marcos. I may well have,  but a man can never own enough shoes. My only caveat to this would be to ensure whatever you do buy are of sufficient premium quality. Buy cheap, buy twice is the old adage and I’m a firm believer in that footwear and fast fashion don’t go hand-in-hand, but timeless purchases from skilled artisans is the footprint for our future. There really is no middle ground if you’re serious about footwear. Just like a bespoke suit, investing in quality will pay dividends for longevity. Here are my top 10 styles no sartorially-inclined gent should be seen without – many of which are On Sale right now, so there’s never been a better time to strike:


Single monks (in case you’re wondering, the name is inspired by a similar style of footwear worn by monks in the Middle Ages) have appealed to me more as I’ve matured and wearing them in place of Oxfords or Derbys will give you serious sartorial gravitas. Albeit in a subtle, attention-to-detail kind of way: these black single monks by Fabi offer a sleek silhouette when teamed with a navy or charcoal grey suit. If you’re combining them with a more casual outfit then plump for brown.

Double monks

I’ve always been a fan of double monks, despite the general consensus in menswear circles that they’ve had their day – I disagree, but I will admit I wear them slightly less often but that’s probably because I’m spoilt for choice nowadays. Another style that crosses the smart casual divide with aplomb. They elevate a chalk stripe suit, just as much as they do chinos and a quarter-zip sweater. These brown suedes are more of a loafer/monk cross but I like them.


Loafers come in many guises and whilst I love a penny loafer as much as the next guy, I’ve found myself gravitating more and more towards the Belgian loafer of late  – a supremely comfortable hand-stitched piece of artisanship inspired by the original design crafted in Izegem, Belgium and characterised by their miniature bow at the top of the vamp. 

These blue patents make me want to break out into a rendition of Marc Cohn’s Walking in Memphis – the well known track in which the singer/songwriter gives us an insight into his footwear penchants – ok they were suede, but you get my point). If only we could board a plane right now. Having said that, a black penny loafer is the only shoe that could convince me to stray from brown (I know, shock horror, right?) – it screams understated elegance.

Driving Shoes

While I’m not the greatest fan of driving shoes worn nine-to-five, I do advocate them for the purpose for which they were originally designed – for driving.  In what seems like a former life now due to the pandemic, I travelled a lot. 

It’s my go to shoe for when my foot engages with the accelerator, it passses muster even at check-in after a long road trip. But once I’ve settled into my room, I’ll slip into something slightly more formal like a suede penny loafer to head down to dinner in. The only other time I’d condone them, worn sockless of course, would be heading to the beach with a polo shirt and swimmers as they’re smart enough for an alfresco lunch at the beach club.

Premium sneakers

While I’m a fan of white premium leather sneakers, they are a devil to keep clean. Instead opt for something such as this vintage-style calfskin sneaker from Barracuda which exudes a beautiful burgundy patina – the fact it has a neutral-coloured crepe sole will mean it won’t show the marks nearly as much either. It will look just as at home worn with drawstring trousers and a cashmere hoody as it will with a soft-tailored suit worn with a white t-shirt.

Chelsea boots

If I had a penny for every wife or girlfriend who asked me which style of shoes she should buy for her other half, I’d be a rich man. I swear it. I almost always recommend a brown suede Chelsea boot, purely because of its versatility to be worn with smart and casual items alike. I’ve picked out a burgundy example here from Fabi, which features subtle brogue embellishments, just because it’s a slight twist on the traditional brown or black and neutral enough to wear with almost any outfit. I love them worn with a suit and cashmere roll neck just as much as I do with tailored jeans and a Trialmaster jacket.

Laced suede boots

Most men would be content with a suede chelsea boot, but I love a laced-up suede boot just as much as the great Agnelli did. He famously wore his with suits, as I have occasionally done in his honour, but I tend to pair mine more with dark jeans or beige cords with a chunky sweater topped off by a navy pea coat. In terms of sprezzatura, these are a no brainer.

Beige Corduroy One Pleat Trousers Beige Corduroy One Pleat Trousers


Beige Corduroy One Pleat Trousers

193 (TaxFree: 158)
Out of Stock
Split-toe Norwegians

A variation on the Derby, I love the split toe because, well,  it’s a bit different – what’s more, it’s crafted from two pieces of leather which meet in the middle of the toe cap which I’ve always been rather fond of. I like this particular rendition of the design by Fabi featuring a chunkier sole as they bear a passing resemblance to the Paraboot Michael,  one of the original and most revered shoes ever created by the legendary French brand.


As ubiquitous as they are, and somewhat unfairly referred to as a ‘schoolboy shoe’ by the unenlightened, there’s no denying the continued appeal of the unobtrusive, timeless Oxford. Besides, you can wear them to work as well as Weddings teamed with a Morning Suit. Just as much as you can pair them with black tie if you don’t happen to own velvet slippers or patent dress shoes. It’s the footwear equivalent of that old British catchphrase ‘it does what it says on the tin’, and certainly doesn’t shout about it.

Hiking boots

As much as you yearn to traipse your prized Agnelli suedes through lake and mountain, your common sense ought to guide you towards shoes more befitting of the terrain, such as these Trekking Boots from Barracuda which fuse the very finest calf leather with state of the art technical fabric. Besides not looking out of place with your retro one piece for après ski shenanigans and long country walks, they look rather cool with denim, a quilted gilet and merino wool beanie.

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