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:

Monkstraps

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

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

Barroco

Beige Corduroy One Pleat Trousers

193 (TaxFree: 158)
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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.

Oxfords

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.

The immaculately-coutured Francesca Serafin greets me at the door of her studio in Milan’s leafy Ticinese suburb. Bedecked in a vintage Hermes skirt with shiny gold buttons, silk blouse and Louboutins she strikes a stylish silhouette. Serafin has turned what was initially a hobby creating pocket squares for friends into a fully-fledged business. Having graduated from the Bocconi Law School in Milan and initially working in law overseas, she soon realised the fashion side was more her forte and subsequently launched Sera Fine silk in 2015.

We’re here to narrow down our choice of top 5 tie knots, and who better to sit down with than Serafin who sells some of the finest ties on the market, procured from luxurious Como silk.  But before we delve deep into the elaborate nature of tie knot styles themselves and which ones rock our boat, it’s important to consider that the collar shape of your shirt has a bearing on how well your knot will fit once fastened. While style is important, comfort should not be compromised.

So once you’ve fastened the top button of your shirt, you want to be able to slip 1 or 2 fingers inside the neck line comfortably. You don’t want it to be too loose or equally too tight. If you’re hyperventilating you know you’ve gone too far. The collar gap on the shirt is designed for a specific reason so if it’s too big then there’s a risk that the collars crossover in the middle which is a sartorial no no.

Navy Blue Zig Zag V Point Knitted Tie Navy Blue Zig Zag V Point Knitted Tie

Serà Fine Silk

Navy Blue Zig Zag V Point Knitted Tie

91 (TaxFree: 74)
Out of Stock

There is nothing worse than a tie that is too short and flies at half-mast. So how is the correct length achieved and is it ok to have the back blade hanging slightly lower than the front like you see classic menswear dudes flaunt at Pitti, as though they’ve tied them the wrong way on purpose? Yes, it’s definitely ok – it’s a nuance of sprezzatura after all. I’d caveat that by recommending sporting a slightly high-waisted trouser. That way, even though the thinner side of your tie will appear longer, the wider side will still align with the top of your waistband, just as it should. And remember, the most aesthetic knots always possess a characteristic dimple which adds depth to the tie. A little tip, as you’re pulling the knot tight you can manipulate the shape of the dimple with your index finger.

As for the knots, the choice is endless – in fact it’s no exaggeration to define tying a tie as an artform. Whether you plump for an even or uneven shape tied with a small or large knot, largely speaking they can be categorised into two groups: those that have a greater deal of flair such as The Prince Albert, which is asymmetrical and those like the Half Windsor, which are symmetrical.

Sartorialee’s 5 favourite tie knots:

1. The Old Bertie 

I was a dedicated follower of the Four-in-hand, that was until I discovered the innate charms of The Old Bertie, said to have been the knot-du-jour of the Duke of Windsor who went on to become King Edward VII – but was affectionately known as Bertie to friends and family. You could be forgiven for mistaking it for a Half Windsor on first inspection. It’s a more complex knot to tie than initially meets the eye but with a little practice perfecting one will become second nature. The reason it gets top billing from me is that it’s more substantial than a Four-in-hand yet provides equal opportunities for symmetry and it works really well for sitting just on your waistband rather than too far below it.

2.  Four-in-hand

Second in line comes the Four-in-hand, which derives its name from the four-horse carriage. The knot resembles the way the carriage driver would knot his reins thus keeping four horses in hand or four in hand. It was popularised by the Four In Hand driving club in London which was founded in 1856. Often maligned as being the school kid knot, it produces a nicely-sized knot (which is neither too big or too small) and yields that essential dimple us sartorialists strive for. The Four-in-hand is a very versatile knot – I particularly like it when it’s teamed with a tab collar shirt but it’s equally at home with knitted ties.

3.  The Prince Albert

Sometimes referred to as the Double Four-in-hand, The Prince Albert is an asymmetrical knot which builds on the foundations of a Four-in-hand instead of the Half Windsor. Despite the Royal connotations of its name, there is no evidence to suggest that Prince Albert, the Queen’s husband, ever actually wore one, so its provenance is shrouded in mystery. The beauty of this knot is that it can be as subtle or stand out as you like depending on how you adjust and tighten the knot. I’m conscious to always pull the knot quite tight though in order to achieve a shapely and polished appearance – revealing a more pronounced croissant-resembling overlapping curve effect.

4. The Oriental

Perhaps its appeal to me lies in its name (given my persuasion for all things South East Asian) but the The Oriental, aka The Small knot is in the top 5 of my tie knot armoury. For reasons unbeknown to me, its popularity has failed to make much of an impression in the western world. I suspect largely due to the fact that most men learn the four-in-hand when they first tie a tie at school. However, The Oriental is useful because it is similar in size, but is more symmetrical. If you’re a collar pin, collar bar or collar clip kind of guy then this is the knot for you – because the knot it yields is small enough to sit supremely snugly beneath.

5.  The Half Windsor

Symmetrical like the Windsor, but with a smaller knot – essentially a more modest version, although not as its name suggests, half the size. In fact it’s 75% of the size, making it a better proportional choice for taller men, as it uses less of the material than the Windsor. I’ve never been a fan of the former whose triangular knot I find a bit a bit staid and unwieldy but I make an exception for its cousin The Half Windsor. It’s a more formal style of knot better suited to a wider, heavier tie, which I think looks really rather at home with a spread-collar shirt – because its wider, chunkier knot fills the more substantial collar gap, particularly so when paired with a Morning Suit at weddings and other formal occasions. It also pairs nicely with point collars and button downs.

Editor’s Pick – 5 Silk Ties by Lee Osborne

Autumn/winter is undoubtedly my favourite season as it affords a wealth of opportunities for sartorial self-expression and is where the art of layering truly comes to the fore. While I’m always sad to bid farewell to summer, there’s always a tinge of excitement in the air as the leaves start to metamorphosise from their magnificent bold yellows and greens, through to their rich hues of burgundy and burnt orange. As the leaves tumble to the floor there’s no better excuse to embrace the great outdoors than to go on a country walk and rustle and crunch your way through them wearing a pair of brown suede boots, the way Gianni Agnelli would no doubt have done. Paired with cuffed grey flannels, a chunky knit and suede bomber of course.

Autumn/winter fires up my sartorial senses like no other time of the year. I literally cannot wait to burst open the vacuum packs that have been in hibernation at the back of my wardrobe for the past six months. One note of caution though before I begin. As warm and inviting as they may look, avoid the temptation of donning a bulky goose-down parka. It’s rare to find one that will flatter, instead of drawing comparisons with the Michelin man. A far more complimentary silhouette can be achieved by assembling lighter layers utilising pattern and texture to great effect.

These are the key items I turn to each year to add flair to my cold season ensembles.

How to layer a…

1. Suede Bomber

I’ve always considered the best staple pieces of menswear to be ones born out of functional necessity, and the bomber jacket is no exception. Steve McQueen was a big fan, and the bomber is as chic now as it was when he rocked up in the pitlane in 1971 film Le Mans – even more so in its rather suave suede incarnation. The original prototype was developed by Dobbs Industries strictly for the U.S. Air Force and Navy fighter pilots. It wasn’t until the late 1950s that the jackets first appeared in Europe. Revive McQueen’s swagger by pairing it with a chunky knit roll neck and cream cords, not forgetting the rubber-soled suede boots. And if you’re feeling bold, opt for yellow or rust goatskin suede such as these two great expressions from Atacama. With the exception of a patterned scarf, like this Arcuri diamond repeat-pattern blue wool and yak scarf, keep the remaining components of your look monochromatic.

Brick suede Bomber Jacket A1 Cary Brick suede Bomber Jacket A1 Cary

Atacama

Brick goatskin suede bomber jacket

851 (TaxFree: 697)
Out of Stock
2. Corduroy Jacket

Done badly, you’ll resemble a nerdy school professor. Worn correctly, corduroy will free you from every preconceived stereotype as well as keeping you stylish and warm this winter. I for one am pleased that Corduroy is back in vogue this season as it’s one of my winter go-tos. Corduroy is a cotton fabric that is twisted into thick ribs that are both hard wearing and soft.  Pair this Chelsea jacket from Vicenza-based outfitter Cruna with Claudio Mariani’s Gurkha tailored denims

3. Chalk Stripe suit

The holy grail of navy suiting, the chalk stripe is the height of cooler clime sartorial elegance. Simply pop a cashmere roll neck underneath it and a suede gilet (see more below) such as this one from Atacama on top and you’ll need no further accoutrements to stave off the chill. Again, brown suede boots that go slightly against the formal grain will gain you serious sartorial aplomb and have the great Signor Agnelli’s approval from above.

4. Gilet

The gilet for me is the unsung hero of A/W tailoring – it’s a garment shape that has been around for centuries which takes its name from the French word for cardigan. Its evolution can be traced back to the jerkin, favoured by European peasants in the 15th- Century. Worn as a sleeveless jacket, it was usually crafted out of leather designed to keep the wearer warm while not restricting freedom of movement. This is still the gilet’s main appeal today, but I would argue its versatility is equally important. It looks just as at home over a suit as it does over a sweater or cardigan. Atacama’s light and dark suede versions have got your back here.

Brown Suede Sleeveless Vest Brown Suede Sleeveless Vest

Atacama

Brown Suede Sleeveless Vest

720 (TaxFree: 590)
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5. Scarf

Scarves work wonderfully well as a constituent part of winter layering. My collection of scarves is bordering on my obsession with ties for the amount of them I own. I even wear linen ones in the summer. The scarf is the proverbial icing on the cake when we speak about winter layering and fundamental to pulling the whole look together. Much the same as jacket and tie combinations, stick to patterned scarves with monochromatic outfits so that the scarf is the star of the show. Likewise if your outfit’s busy make sure your scarf isn’t to avoid a pattern overload. Take this patterned gem from Arcuri as my case in point, likewise this delectable double-sided wool and silk offering from Sèra Fine Silk. For outfits featuring multiple checks or stripes plump for monochromatic versions, even better if they happen to be textured or subtly patterned like this Fumagalli 1891 wool and silk scarf.

Being able to nail the more casual side of your sartorial repertoire is not a God-given attribute most men are blessed with. It may be music to the ears of those itching to free themselves from their suited shackles, but the majority of men still shudder at the thought of the term business casual. I must say, I’ve always rather envied the small minority of men that seem to straddle, and I hate this term — the smart-casual divide — so seamlessly.

It was much easier for our forefathers of course, who donned suits 5-days a week and hardly gave it a second thought. Thankfully for them, the term business casual had not even been invented. But as our employers are loosening the knots of their ties all the more, the question remains: how do you rock up to the office (or perhaps — more topically Zoom Call — when working from home) looking less formal, but still sartorially-savvy?

Jackets

In terms of jackets that exemplify this dress code, it has to be the patch-pocket variety. Any other style screams suit jacket masquerading as a separate. Salernitan tailor Melillo 1970 have two which fit the bill here: their navy wool blazer is the timeless option, or if you hanker after something with a bit more texture and subtle dogtooth pattern then plump for the Pied de Poule with button-flap patch pockets.

Shirts

The aim of the game here is to err towards softer shirting fabrics. Swap your usual crisp white work shirt out for a pale blue Chambray polo in light indigo by G. Inglese for example. Cordone’s popover style polo shirt or even their rather suave Azure pale blue flannel shirt will work wonders. Dispense with the tie and instead wear a pocket square as a neckerchief in the nonchalant way Clark Gable once perfected. I’m really rather fond of Cordone’s new season wide striped cotton shirts too. Their warming autumnal hues will sit beautifully beneath either of the patch pocket blazers if you lean more towards a bolder pattern.

Trousers

There has never been a better excuse to embrace the drawstring trouser, they were positively made for business casual — particularly when they’re as chic as those on offer from Neapolitan trouser maker Sartoria Corrado. You really cannot go wrong with any of the colorways — whether you stay safe with beige or light grey or inject a bit of color into the proceedings with a playful burgundy. Don’t rule out corduroy either. If you’re more of a Lapo Elkann statement kind of guy, I dare you to embrace the camo-print single pleats — just make sure the jacket is plain.

Shoes

Trainers can most definitely be incorporated into a business casual get up, so long as they are of the premium leather variety in an off-white or navy — and most definitely not the type you go to the gym wearing. But if you really can’t lower yourself to the sneaker, then brown suede loafers or derbies are the fail-safe options — plain leather is a tad too dressy still.

The Finer Details

For scarves, more muted jacket tones cry out for playful patterned scarves to really pop. Stefano Cau’s exquisite Habotai silk scarves are the icing on the sartorial cake here. Serà Fine Silk and Fumagalli have intricate designs aplenty too which will make you the talk of the town. The former’s paisley and medallion styles are totally on point, as are the latter’s intricate Kashmir-inspired designs.

Be sure to trade up the briefcase for something a little less stiff and starchy. The DUST’s sleek leather backpack fits the bill perfectly here. As will any of Athison’s more malleable fabric buckle-up bags.

On Sale
The Dust Company Sleek Leather Backpack The Dust Company Sleek Leather Backpack

The Dust

The Dust Company Sleek Leather Backpack

401301 (TaxFree: 246)
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Athison Gray/Brown Alight Backpack Athison Gray/Brown Alight Backpack

Athison

Athison Gray/Brown Alight Backpack

690 (TaxFree: 565)
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If ditching your tie is too much to bear, and who could blame you for that, make it a less-pretentious bobbly knitted silk from Fumagalli or one of G. Inglese’s rugged shantung offerings (a highly-textured fabric that you can learn more about in the Introductory Guide to Italian Silk Ties).

The production of silk can be traced back to China, namely the Neolithic Yangshao culture of the 4th millennium BC. Silk, a fine, strong, lustrous fibre produced by cocoon-making silkworms, and subsequently collected to make thread and fabric, was confined to China until the introduction of the Silk Road during the latter part of the 1st millennium BC.

However, it didn’t arrive on European soil until the 1100s. During the time of the Second Crusade, 2,000 skilled silk weavers from Constantinople (now Istanbul) descended upon Italy and began setting up their businesses. Silk is the overwhelming go to fabric for gentlemen’s ties. Not only is it the strongest natural fibre, it’s one of the most durable fabrics out there, possessing a high tensile propensity which allows it to withstand a substantial amount of tension as well as an inherent elasticity allowing it to retain its natural shape.

Silk ties come in many shapes and guises of course as the items below will testify. Some you will be more familiar with than others. I’m going to run you through the basic rules, and how best to wear them. I’ll guide you through which styles suit formal and which styles tend to pair better with more casual attire.

Bear in mind that brighter colours and bolder patterns (such as those in the below image by Serà Fine Silk) are generally considered to be more casual, whereas smooth textures and darker tones have a more formal connotation. Much like the choice of a suit, parallels to the choice of tie can likewise be drawn: for instance, a richly-patterned, woollen patch pocket blazer is less formal than a plain suit in fine worsted, so a highly-textured shantung grenadine tie with a bold club stripe is less formal than say, a plain navy repp tie.

It’s important to consider the nature of the silk fabric. For instance, does it have a smooth or rough texture? This is a vital consideration as it impacts the way light is absorbed through the fabric (particularly so in a silk knit where you can literally see the light of day filter through it’s tiny pores) or reflected on a more shiny silk. There are 4 basic rules to keep in mind: tone, colour, texture and pattern. The importance of texture cannot be underestimated in the selection of a tie – partly because it is the most subtle and therefore easier to miss.

Printed Silk

Printed silk ties are created either on screens (utilizing a stencil pattern) or large-format ink jet printers which transfer designs on to what is typically a twill weave. They allow almost untold realms of creative possibilities and have been used to great effect historically by the likes of Hermès and Ferragamo to name but two. Stefano Cau’s Wild Ducks printed cashmere tie is a particularly fine example of the art, as is his Rich Paisley Double Face (with two different patterns on either sidein a lush debonair shade of turquoise with navy and egg-yolk yellow motifs inspired by 50s Americana.

Likewise Silvio Fiorello’s red and blue paisley design which employs a rather unique special silver metallic screen printing effect, designed to catch the light, adds an extra touch of luxury and sophistication. Having said that paisley is considered slightly less formal because of its playful swirling patterns so straddles the smart casual divide supremely well.

Serà Fine Silk and Cordone 1926 have beautiful examples of printed medallion ties. Sera’s light pink version is a divine partner with a light blue shirt (cotton for business, chambray for casual) and navy suit while the latter’s unregimented offerings (especially the polka-dotted) are a beautifully contemporary statement piece if you deem the former a touch too elaborate.

Wear with: a plain white or blue shirt or even better, a lighter Bengal stripe or something with a larger yet subtle check — the larger amount of spacing which a more expansive check affords will contrast well with the more intricate, closely-held pattern of the tie. The canvas to display such delights should be a dark navy or grey flannel suit to allow the colourful hues to really pop this autumn.

Shantung Silk
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G Inglese Silk Shantung Tie with blue background G Inglese Silk Shantung Tie with blue background

G. Inglese

Hand-refined 100% Blue Silk Shantung Tie

129103 (TaxFree: 84)
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G Inglese Silk Shantung Tie with dark green background G Inglese Silk Shantung Tie with dark green background

G. Inglese

Hand-refined 100% Silk Shantung Tie

129103 (TaxFree: 84)
Out of Stock

Otherwise referred to as raw silk or dupioni silk — Shantung features irregularities and knobs from raw silk threads providing a more casual look and feel that looks fantastic with the right outfit. It derives its name from the Shantung Province of Eastern China, which is sometimes also referred to as Shandong. G.Inglese’s 5-fold hand-refined 100% brown silk tie is a great case in point here and I love the dainty little mother of pearl button stitched on the back.

Given the slightly more relaxed (while remaining smart) feel a Shantung silk tie exudes, and depending whether you opt for a brown or a navy colourway, an Oxford button-down shirt and plain-coloured patch pocket blazer worn on its own, or full suit in navy or olive will earn you those enviable sartorial stripes (navy with olive, brown with navy).

Grenadine Silk

Originally produced in Italy, Grenadine is a weave characterised by its light, open, gauze-like feel, woven on traditional jacquard looms. Nowadays, only one fully-fledged jacquard operation remains, that of Fermo Fossati in Como which has now has a monopoly on such things. Sadly, jacquard weaving is a dying art nowadays which makes it all the more appealing to the connoisseur. Stefano Cau has an enviable collection of the very finest exponents of the loom, particularly this navy/ecru striped number.

Grenadine is super versatile and goes with just about anything. The early incumbents of grenadine were plain colours, but nowadays playful stripes and dots have entered the foray. While wearing grenadine brings an understated panache to sharp tailoring in my eye, it can look equally impressive with a soft-tailored blazer and jeans.

Knitted Silk

A knitted tie possesses an admirable three-dimensional quality which adds great texture to an outfit. Fumagalli’s wonderfully-named Mosaic Crunchy Effect tie is my pick in this particular category. Similarly to its cousin Shantung, a knit exudes a more relaxed vibe. The fact that they’re made from a high-twisted silk yarn means they’re crinkle resistant, so they have the added benefit of being great for travel. Compared to the average silk tie, people tend to take note when you wear one — mainly due to the fact that they remain one of the lesser-spotted varieties.

I owe a debt of gratitude to my late Grandfather who introduced me to the delights of knitted ties at a young age – although I didn’t know it at the time. But it had a subconscious effect on me and I’m a big advocate of knitted ties worn with tailoring. Although a knit works well with a blazer — it really doesn’t matter if you chose to team it with a pair of chinos or off-white flannels, it remains a great anchor to the whole ensemble — I’m equally at home wearing mine with a Harrington jacket and a rather louche sweater draped across my shoulders for a more relaxed dressed-down look.

I tend to let the back blade of my tie hang loosely behind the front — and never thread it through the keeper loop as I find it too regimented. The tip of the tie should always sit comfortably below your waistband — don’t fall for the schoolboy error of tying your tie too short as the blank void it leaves across your stomach is not a good look.

It’s all well and good having an amazing tie, but how you tie it is of equal importance. My advice would be to keep the knot classic and simple. My personal favourite is the four-in-hand which I pretty much wear exclusively as I love the shape and the dimple it creates below the knot. But it’s ok to try something different every now and then with something like The Prince Albert — if you want to stand out but in a subtle attention-to-detail kind of way. I would avoid anything too intricate as it will look like you’re trying too hard, which goes against the whole notion of sprezzatura (see my previous column) when you’re supposed to be.

Most of the year I tend to err on the side of 3-fold, untipped, hand-rolled lighter-weight ties, but as we’re approaching autumn it’s ok to break out the odd 7-fold tie – a style which came to prominence in the late 19th century. In some quarters it’s held up as the pinnacle of luxury neckwear thanks its abundant use of fine silk and the intensive manual labour required to create each one. Cordone 1956 have rendered some rather wonderful examples of this style. I’m particularly fond of their Diamante collection, it’s so devilishly difficult to chose between them though, but I’m drawn to the rakish charm oozing from its Green and Azure colourway. Teamed with a double breasted cashmere blazer, it’s a real case of Duke of Windsor eat your heart out.

The coat of arms of the city of Porto proudly attests to being “ancient, very noble, always loyal, and undefeated”. Indeed there is a warmth about the city its inhabitants want you to cherish. It’s the kind of place where if you happened to approach someone in the street to ask directions you could easily end up having dinner with them, dancing late into the night or at the very least sharing a glass of the city’s finest export, port wine.

Sure, Porto oozes history on every corner, its churches, streets and even its railway station are a testament to it, festooned as they are with eye-popping azulejo tiles, but it has its finger firmly on the 21st-Century pulse. You’ll stumble upon a host of unexpected finds. From former shopping centers taken over by musicians who repurpose old shops as rehearsal studios; abandoned warehouses metamorphosed into cool concept stores and curated spaces; edgy street art, to beautifully manicured gardens and fantasy glass palaces, all imbibed with characteristic Portuguese love and dedication. I guarantee a three-day trip will sow the seed of a lifelong love affair and leave you pining for a return before you’ve even left.

DAY 1 — SATURDAY

Impress the locals by ordering a cimbalino (coffee) to accompany your pastel de nata at Vogue Café, a joint initiative between The Fladgate Partnership (of Taylor’s port fame) and luxury publisher Condé Nast. Attached to the Infante do Sagres hotel in downtown Porto, it boasts exquisite décor which feels like it has been lifted directly from the pages of the iconic magazine. Open daily 12-11pm.

The Gastronomic Experience offered up by 2-Michelin starred chef Ricardo Costa at The Yeatman is a sensational 12-course affair showcasing minimal interpretations from a genre powerfully influenced by surf’n’turf, as well as crafting food artistry from Portugal’s rich bounty of regional ingredients. As views go, it’s hard to beat the 180-degree panorama of Porto’s glittering cityscape spread across the facing river bank. The notion of table time limits don’t exist here thankfully, leaving you to leisurely savour each and every delicious morsel, totally unhurried. 

Complete a memorable evening by stopping off for a nightcap at nearby Enoteca 17.56, a chic wine bar owned by Port producer Real Companhia Velha. Not only does it possess dreamy views back across the River Douro towards Porto,  but there’s even an interactive museum on the lower level which charts two centuries worth of port production.

DAY 2 – SUNDAY

Make a beeline for Foz, a chi-chi ocean-facing neighbourhood where people-watching is a prerequisite. Sunday’s were designed for ambling around the bounteous grounds of Serralves, the green lung of Porto, a cultural institution designed by Álvaro Siza Vieira, a salmon pink Art Deco edifice which would not look out of place on Miami’s Ocean Drive. Have a relaxed lunch on the terrace at Praia da Luz, overlooking the Atlantic Ocean rollers, before spending the afternoon reclined on a sun lounger on the beach sipping on white port tonics.

Those in the know head to neighbouring Matosinhos for dinner — gravitating towards Rua Heróis de França, hailed as the finest street on which to eat fresh fish in the whole of Portugal. Beat a path to the supremely old school Salta O Muro for mouth-watering octopus rice, glistening sardines, and sole — a rarity to experience fresh, but here in the north it’s the norm. Wash it all down with a bottle of Muralhas de Monção, a crisp, slightly spritzig white Vinho Verde from the eponymous white wine-producing wine region which resides between Porto and the Spanish border.

DAY 3 — MONDAY

Add a WoW factor to the start of the new week by heading to the recently opened World of Wine in Vila Nova de Gaia just across the Douro river from Porto. Ideally walk there from the Cais Ribeira navigating a path across Porto’s iconic Dom Luís I Bridge, designed by a student of Gustav Eiffel. When CEO of the Fladgate Partnership Adrian Bridge was considering ways to extend the tourist season in Porto he dreamt up the idea of World of Wine. Costing a cool €100 million, the 8.5-acre site sees the total regeneration of former port wine warehouses already in Fladgate’s possession at the foot of The Yeatman. It celebrates not only Portugal’s contribution to port and table wine, but also cork and olive oil, not forgetting its influence on the fashion industry as an acclaimed producer of clothing and footwear. Speaking of which, menswear aficionados will be in their element in Quarteirão Bombarda, specifically the backstreets in and around Rua Miguel Bombarda where cool vintage clothing, local designer’s ateliers, cutting edge art galleries and quirky bars and eateries abound. Be sure to visit the Jardins do Palácio de Cristal en route, which, as well as affording panoramic vistas of the River Douro, this botanical garden is one of Porto’s most cherished hideaways — boasting beautifully lavish lawns interwoven with sun-dappled paths fringed by cascading fountains, sculptures, and elaborate magnolias.

Stopping for a tea (of which there are over 300 different varieties) at boho Rota do Chá, is an absolute must. Created by Miguel Ortigão in 2003, it’s located within an old house on Rua Miguel Bombarda — a mystical oasis of inner-city charm which boasts one of the most beautiful gardens in the city: a place which overwhelms your senses to such a degree that you could be forgiven for thinking you were somewhere far more exotic like the Orient – from which it’s interiors take such divine inspiration.

WHAT TO PACK

Porto’s temperate oceanic climate ensures pleasantly warm and sunny summers. With this in mind, light layers are the order of the day.

Three jackets and a suede gilet will see you through all eventualities for a stylish weekend. A navy patch-pocket blazer can be alternated elegantly with a yellow or green Bengal stripe shirt, while a double-breasted check jacket will add pizzazz over a Chambray denim shirt.

Two pairs of high-waisted trousers — in teal and white — will pair seamlessly, particularly as the white pair will double up with the navy jacket too. Save the jackets for pre-dinner evening strolls along the quayside, and wear suspenders with an open-neck shirt and trousers during the day time to eschew a sophisticated, yet relaxed vibe.

Each garment can be accessorised for a more elevated evening appearance with the addition of patterned pocket-squares and silk scarves. The navy jacket needs something more elaborately colourful in the breast pocket, while a simple folded white square will add a nonchalant nuance to the check jacket.

For something slightly less formal, try an unstructured Sahariana jacket in a neutral beige to compliment all the other hues contained in your weekend bag. A brown suede gilet is an equally effective layer.

If I had to pack one pair of shoes, it would be brown tassel loafers, which look the part either dressed up or down, even with tailored shorts.

No article on Italian menswear should begin without referencing that oft-quoted sartorial term sprezzatura – defined as “a certain nonchalance, so as to conceal all art and make whatever one does or say appear to be without effort and almost without any thought about it”

But how do you go about assembling items in your summer wardrobe and look like you’ve subconsciously just thrown them all together? It is important to invest in quality items from the outset: classics crafted by artisans for a timeless longevity of style. Products so well made that you’d be proud to pass on to the next generation. 

Perfecting the art of separates is paramount – it’s not necessarily about the volume of clothes you have, but choosing items which work well together in a capsule wardrobe. Start by investing in a linen shirt – and I’m suggesting two different styles here which will transport you from beach to bar and all eventualities in-between. The key to it all is dressing-down traditional formalities.

The first is a short-sleeved camp collar shirt – which can be worn to the beach in between swims and look stylish with tailored swimwear. Go for a neutral tone which will pair well with any repeat pattern swimmer. It will also look just as great tucked in for an impromptu alfresco lunch with a pair of linen drawstring trousers and espadrilles. The beauty of the camp collar is that it sits super nicely under an unstructured jacket (with the collar folded over the lapels) which will elevate your look for that elegant evening stroll along the corniche.

Alternatively, if you’re opting for a slightly more formal look, trade it up for a collared striped linen shirt – with the cuffs folded in a laissez-faire fashion over the jacket sleeves. You can even throw a tie into the mix just before you sit down to dinner, and dispense with it again for that sultry stroll back to the hotel. A knitted silk or grenadine fabric will work wonders, or if you’re game for something a little more playful a medallion or diamante repeat pattern to contrast with the more muted tones of your outfit.

As jackets go, you should err on the unstructured side – it remains smart but will ensure comfort is key in the extreme heat of the Italian summer – as it’s softer on the shoulder and not cut quite so close to the body. One of the key pieces for SS20 is the safari jacket which offers a stylish alternative to the classic tailored blazer. I particularly love a loosely belted khaki coloured safari. A pair of cream trousers are key to pulling the whole look together and will pretty much go with any other colour you decide to sport. With that in mind, it really doesn’t matter what colour the jacket is if it’s paired with more muted tones. If you’re a confident embracer of colour, think along the lines of teal, mustard yellow or burgundy, with wider lapels and patch pockets to make it feel less suity – the lighter the fabric the better, preferably linen or linen with cotton in the blend. All of these sit well with earthy tones so you can’t go wrong. If the jacket is worn over a camp collar I’d keep the pocket square plain white or cream (if at all), and upgrade it to something a bit more ornate for the evening.

If I was to choose one pair of cream trousers I would opt for the Gurkha style waisted type with 2 pleats – because I think they look equally as good with a t-shirt as they do with a more formal shirt, tucked in to not only show off the high waistband, but your inner debonair. 

You could argue against the case for knitwear in an Italian summer, but the only type you’ll really need is to adorn your shoulders – as lightweight a cotton or wool as possible, and ideally a cable-knit to add texture into the mix. Alternatively a lightweight scarf in a bold zesty shade such as yellow or orange can add sartorial swagger to a plain linen ensemble.

As for shoes, stick to suede loafers or monk straps where possible as they’re less associated with business – not a word you want entering your vocabulary when you’re on digital detox on the Amalfi Coast – and definitely worn sans socks in holiday season. If you insist on wearing socks, make them super lightweight with a dandy shadow rib to complement your upper half.

Bresciani 1970 Cotton Socks in Purple Moss Bresciani 1970 Cotton Socks in Purple Moss

Bresciani 1970

Bresciani 1970 Cotton Socks in Purple Moss

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Out of Stock

And you’re going to need a stylish bag to stow it all away in. I’m a big fan of the classic leather weekender as it can be carried by hand or slung over your shoulder in equal measure and is stylish to boot. Unlike its wheeled carry-on cousin (although these do have a place when you’re flying, but you’ll be doing that much less this year, right?) will not aggravate the locals as you tow it along the cobbled streets disturbing the peace. Don’t scrimp on this detail as a smart investment here will pay dividends ensuring the bag will age as gracefully and stylishly as the late Gianni Agnelli, the playboy of Italian style who sought after every moment as if it were his last – and whose sprezzatura has influenced sartorialists the world over ever since.

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