It’s often said that the best-dressed men are the ones who don’t seem to try. The operative words here are: seem to. This isn’t about a lack of effort. It’s about concealing whatever effort was required to look good, thereby giving the impression that looking good, for you, is the easiest thing in the world, an innate skill.

The Italians have a word for this: sprezzatura. There’s no easy English translation, but it’s been described as a kind of “studied carelessness”. Sir Hardy Amies, the mid-20th century couturier to the British royal family, touched upon the idea when he famously stated that “a man should look as if he has bought his clothes with intelligence, put them on with care and then forgotten all about them.” Like the Japanese concept of wabi-sabi, it’s a philosophy that finds beauty in imperfection: the odd rumple or scuff is something not just to be tolerated, but celebrated.

And there are few men who embody this attitude towards style as fully as Messrs Carlos Castillo and Jorge Navares. Over the past few years, the bearded duo behind the Spanish menswear label MAN 1924 have become a recurring feature on street-style blogs, their trademark look – relaxed tailoring, heritage outerwear and retro sneakers, all thrown together with an easy, off-hand sort of elegance – discussed, dissected and imitated by men all around the world.

As MR PORTER prepares to launch an exclusive collection of summer tailoring from MAN 1924, we thought it was high time we looked back on a few of their best looks. And who better to offer a little commentary than one half of the duo, Mr Jorge Navares himself?

Unless otherwise stated, all of the most recognisable photographs of Messrs Navares and Castillo were taken at Florence’s biannual menswear trade fair, Pitti Uomo. When they step out onto the city’s streets, the men behind MAN 1924 don’t just act as ambassadors for their own brand; over the past few years, they’ve garnered plenty of fans for New Balance, too. Part of the appeal of MAN 1924’s trademark relaxed tailoring is that you can dress it up or down, and what you’re seeing here is a prime example of the latter. “This is one of our more casual looks,” says Mr Navares. “Sometimes, you don’t feel like putting too much work into your outfit. You prefer something more comfortable.” The comfortable thing to which he’s referring is the brand’s Tomi trousers, seen here in a winter-appropriate cotton corduroy; the warm-weather equivalent, available now, is cut from a lightweight summer linen. “Wear them with sneakers and a technical parka,” says Mr Navares, “and you’re ready to rumble.” (Or, given that we’re talking about linen, should that be “ready to rumple”?)

This picture shows off the duo’s natural flair with texture and colour. On the right, Mr Castillo combines mustard corduroy Tomi trousers with a silvery-grey Harris Tweed Kennedy jacket, while on the left, Mr Navares employs a classic, always complementary palette of light brown, white and navy. Of particular note is Mr Navares’s double-breasted navy moleskin coat, a traditionally formal garment that’s worn here in a very dressed-down manner. (“This is something we do a lot,” explains Mr Navares.) As before, New Balance sneakers complete these two looks; as ever, it’s all executed with little apparent effort.

The summer edition of Pitti Uomo, which takes place in the blazing heat of June, is the Olympics of men’s summer style – and the MAN 1924 team are regulars on the podium. “We adore this layered look in summer,” says Mr Navares. “It gives you a kind of dressy-casual look ideal for hot weather.” Both men are wearing the brand’s unlined Kennedy jacket, which is available in a variety of summer-appropriate fabrics: Mr Navares (left) wears seersucker and Mr Castillo (right) wears a cotton and linen blend. Colour is key to the success of these looks: the natural shades of light ecru and terracotta really allow the rich texture of the fabric to shine through.

Back again at Florence’s Fortezza da Basso for the winter edition of Pitti Uomo, which takes place every January, this photograph shows Messrs Navares and Castillo adopting a rather different approach to style than in the previous image. “This is a wink to British street style of the 1970s and 1980s,” explains Mr Navares, who can be seen on the left wearing a trench coat in a big tartan check. Mr Castillo, on the right, wears an olive-drab cotton parka, a military coat synonymous with the classic 1979 mod movie, Quadrophenia. Mr Castillo has added a pop of contrast with a bright orange scarf – most likely one that he designed himself for Lovat & Green. “We find it interesting to bring up masterpieces from another time and dress them in a modern way,” Mr Navares says. “A good piece really makes a difference.”