alessandro squarzi

Dress like an Italian: Alessandro Squarzi’s guide to summer style

We asked Alessandro Squarzi — fashion entrepreneur, vintage car collector and thoroughly nice guy — for his six top tips for dressing like an Italian, from shirting to shoes

It’s not fair really, is it? You spend a lifetime trying to establish a style for yourself, trying to corner the ‘cool’ market — and then someone like Alessandro Squarzi just breezes in. The Milan-based fashion entrepreneur epitomises the Italian idea of ‘sprezzatura’ — the studied, insouciant art of careless sophistication — and is one of the most prominent collectors of vintage clothes, cars, watches and motorcycles in Italy.

A good man, then, to offer up an Italian’s guide to dressing for summer. With sunny days on our dreary horizon, we’re excited to get out of the house, dress to the nines and begin socialising once more. And how better to make a style statement than by following the advice of one of the most street-shot fashion enthusiasts in Europe?

Explore the wonderful versatility of the t-shirt

We’ve been looking at the t-shirt all wrong — according to Squarzi, at least. The Italian doesn’t see the simple, humble tee as an underlayer, or a garment grabbed last minute when you’re in a hurry. He sees it as an opportunity to explore and express yourself with its many forms, patterns and colours.

“My first suggestion for the summer is to rediscover the beauty of the polo shirt,” Squarzi tells us. “Discreetly elegant garments, polo shirts will add a refined touch to your outfit. In this case, it is also interesting to play with colours and patterns: a beautiful monochrome or striped polo shirt is perfect for summer. Also in this season, I’ll always appreciate the simplicity of a white T-shirt. But, importantly, it must be excellent quality cotton.”

Dress like an Italian: Alessandro Squarzi’s guide to summer style

Orlebar Brown Espresso Polo Shirt

£115

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Dress like an Italian: Alessandro Squarzi’s guide to summer style

Fuoriuso White Castellani T-Shirt

£70

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Dress like an Italian: Alessandro Squarzi’s guide to summer style

Sunspel Riviera Polo Shirt

£90

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Go bright white — and very size specific — with your trousers

Dress like an Italian: Alessandro Squarzi’s guide to summer style

We Brits aren’t known for wearing trousers during the summer months. In fact, at the first glimmer of good weather, we tend to whip then off in favour of shorts — and then keep our legs out until the soggy end of September. Squarzi, unsurprisingly, has a little more taste — and gives us but one suggestion in this category.

“White jeans, of course!” the entrepreneur exclaims. “And even better if they’re selvedge. The most important thing with jeans in general, whatever the colour, is that the denim does not stretch and that the fit properly conforms to your body. The width of your trousers, in my opinion, must never be less than 19cm.”

Dress like an Italian: Alessandro Squarzi’s guide to summer style

J. Crew Straight-fit Stretch Chinos

£89

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Dress like an Italian: Alessandro Squarzi’s guide to summer style

Tod’s White Denim Jeans

£350

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There are plenty of lightweight jackets to choose from

As with our approach to shorts, jackets don’t feature heavily — even in their lightweight forms, come to think of it — in many Brits’ summer wardrobes. It can be hard enough convincing some of us to even wear shirts when the sun’s out. Squarzi, however, is a sucker for a good characterful jacket. And his list of approved styles is long enough for us all to find some inspiration.

“I’m always glad to propose a vintage military jacket,” says Squarzi. “Or a jungle jacket or a Solaro jacket. These garments can always give a refined allure to even the most basic outfit. For summer I also appreciate linen jackets, in a butter or khaki colour — I always find them to be beautiful.”

Dress like an Italian: Alessandro Squarzi’s guide to summer style

Fortela Carlo Safari Jacket

£500

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Dress like an Italian: Alessandro Squarzi’s guide to summer style

Ermenegildo Zegna Unstructured Linen Jacket

£1715

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Dress like an Italian: Alessandro Squarzi’s guide to summer style

J. Crew Wallace & Barnes M51 Jacket

£165

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Casual shirts can be long-sleeved, and Hawaiian prints are allowed

Dress like an Italian: Alessandro Squarzi’s guide to summer style

Shirts tend to swing wildly between formal and casual for most of us. They’ll either be starched-collar affairs, cuff-linked and worn with a suit and tie — or they’ll be wildly informal; furry and plaid for winter weekends or unbuttoned and garish for summer. Squarzi, however, suggests we stick to a middle ground.

“As far as shirts are concerned,” the Italian advises, “I always wear Texan shirts. Strictly long-sleeved though: the only short-sleeved shirts that I condone are the Hawaiian ones. And they can be colourful and fun — suitable for the summer and your most casual moments.”

Dress like an Italian: Alessandro Squarzi’s guide to summer style

Fortela Twill Texas Shirt

£160

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Dress like an Italian: Alessandro Squarzi’s guide to summer style

J. Crew Palm Print Shirt

£89

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Dress like an Italian: Alessandro Squarzi’s guide to summer style

Brunello Cucinelli Denim Western Shirt

£580

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Sandals still don’t cut it, so look for loafers instead

Flip-flops, be gone! Everyone already knew that the rubbery sunny weather stalwarts didn’t look good — but it’s taken Squarzi’s advice for us to kick our slider habit. Instead, the Italian suggests that you should invest as much in your summer footwear as you do in your winter boots. Just because they’re not as heavy-duty, he says, doesn’t mean they shouldn’t be well-made.

“During summer,” Squarzi offers as an alternative to sandals and flip-flops, “I am a great lover of loafers. I believe them to be the perfect option, for every occasion. That is, except perhaps, for the beach. In that case, I would recommend a sporty shoe — a simple Vans slip-on, for example.”

Dress like an Italian: Alessandro Squarzi’s guide to summer style

JM Weston Black Boxcalf Tassel Loafers

£865

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Dress like an Italian: Alessandro Squarzi’s guide to summer style

Edward Green Belgravia Loafers

£1020

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Dress like an Italian: Alessandro Squarzi’s guide to summer style

Vans Classic Slip-on Shoes

£55

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Accessorise according to how you feel, and make them practical

Dress like an Italian: Alessandro Squarzi’s guide to summer style

What springs to mind when you think of summer accessories? Sunglasses? A hat, perhaps? Broaden your mind. Squarzi certainly has. In fact, he’s currently all about the jewellery — and some practical fashion touches.

“Given the current global pandemic situation,” says Squarzi, “in my opinion a bandana is a personal touch to accompany a face mask. The importance of face masks is, at the moment, essential: we must understand that wearing the mask will be very important for everyone’s safety in the upcoming months. And, regarding other accessories, I really appreciate Navajo jewellery and, of course, watches. In these cases, I would suggest that you always wear something that best expresses your mood, depending on the day.”

Dress like an Italian: Alessandro Squarzi’s guide to summer style

Peyote Bird Canyonlands Cuff

£625

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Dress like an Italian: Alessandro Squarzi’s guide to summer style

Two Feathers Navajo Ring

£34.99

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Rather taken by that denim shirt above? We’re not surprised. They’re more refined than you think…

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