Style Tips from The Most Fashionable Men on the Planet

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Like a migration of exotic birds, a flock of the most fashionably dressed men on earth descend twice a year on a Renaissance city in Italy.

The location is Florence and these males arrive from all over the world, dressed in sartorial splendour, to attend the bi-annual, (in January and June) Pitti Uomo, a trade show featuring the latest in men’s clothing and accessories. Started in 1972, it’s considered one of the most pre-emenenient international fashion fairs dedicated to menswear and is held in the historic Fortezza da Basso, a fourteenth century palace once owned by the Medici family. Today, close to 25,000 visitors consisting of retailers, press, designers and other industry types from 100 countries attend the four day event.

With the popularity of street-style photography and bloggers in recent years, the world at large now gets to see what the attendees wear at this rather niche trade show.

There is a distinct look to these preening peacocks being photographed as they strut about the courtyard outside the fair. Men of various ages can be seen dressed and embracing the traditional elegance of classic menswear. Despite Pitti Uomo being a fair that extols all the latest and modern innovations in menswear, it is all the traditional hallmarks of gentleman attire that seems to be the most beloved.

From perfectly knotted ties that correspond with the right shirt collars, deftly fluffed silk squares in jacket pockets, jaunty fedoras, carefully curated wrist accessories to expertly cuffed trousers that show off some of the best wingtips and brogues, it is a splendid display of gentlemanly elegance brought up to date for the 21st century. And there-in lies the difference between these modern day dandies and their yesteryear brethren: these men might take dressing up to an art form but there is a studied effortlessness about their look.

The Italians have a word for it that has entered the English lexicon – sprezzatura – a nonchalance that seemingly conceals the conscious effort that went into creating it.

These men never look too contrived – despite the meticulous attention to small details – it looks right and works in today’s fast paced modern world. And best of all, it’s inspiring to see younger generations of men taking up the cause for dressing well.

Take a look at our slide show below for some style inspiration from the men attending Pitti Uomo this past week in Florence. 


Never underestimate the importance of a good top coat – it’s the first thing people will notice. In North American cities, we tend to opt for navy blue, black or grey coats – and there is nothing wrong with that – but an unexpected colour like salmon can be just the thing to make you stand out in the crowd.


Other hues to consider for winter instead of predictable black would be camel and white. It’s a classic.

Another classic combo is grey and winter white. It exudes a casual glamour and has a distinct air of opulence about it. After all, who dares to wear this much cream in winter but someone who couldn’t care less about dry-cleaning bills?

With any outfit, always add a touch of your personality, like this young gentlemen. He might sport edgy tattoos but have a penchant for classic banker stripe suits but he made it uniquely his own by adding some rocker looking bracelets.



In some cities, observers might look upon this gentleman a bit suspiciously but not in Florence during Pitti Uomo. Attendees with ever-increasingly wild facial hair has become a norm here. What separates him from some wild hermit type is that luxe looking leather backpack, the ultra-cool sunglasses and deft layering. Don’t be afraid to mix the casual with dressier items – like his denim jacket under his tweedy coat.


Likewise here, don’t be afraid to play a mix maestro. An unmatched waistcoat with a different trousers and brightly hued coat makes for a playful and interesting look. What makes it all work? Each piece – checked waistcoat, double breasted top coat, pleated trousers and poorboy cap – are all from the same train of thought. They are all classic menswear items but just put together in an unexpected way.


A grey suit with a navy blue overcoat would be considered very traditional and conservative business attire and one that is ubiquitous on the streets of major financial quarters in big cities. But this gentleman would be a mile ahead in terms of style compared to your average stockbroker. How so? First, there is the cut of this suit. Most men think loosely fitting suiting is the way to go for comfort. Not so. A razor sharp tailored suit like his makes you look leaner and not sloppy. The trousers should not fall in a puddle of fabric around your ankles. Stopping just at the ankle or a bit below is best – all the better to show off a polished double monk strapped shoe. Key note there: polished shoes. It puts the perfect punctuation to an immaculate outfit.

Don’t forget the small details. Use small accessories to add whimsy, humour or a touch of your personality to your outfit. Why should your driving gloves be basic black or brown? Yes, men are adding bracelets to their wardrobe – whether it’s the rubber kind you get for participating in a charity marathon or colourful beads you picked up on your last beach vacation – don’t save just for weekend wear but add to your suitings. As for a bag, explore other options other than a briefcase. An elegant leather portfolio case or leather knapsack are all stylish options today.

Every face deserves a great frame. When it comes to sunglasses, don’t forget the importance (the health benefits of protecting your eyes from UV rays) but also the style factor.  A great pair of shades can add allure, drama and wit to your look.