Style icon is a bit of a hackneyed term these days. You’ll often hear it uttered by overzealous fashion commenters to describe any Hollywood A-lister capable of tying their own shoelaces. Occasionally, it’s justified. Clint Eastwood, Steve McQueen or Cary Grant, for example. But even the most immaculately turned-out celebrities still can’t hold a candle to the inarguable king of style icons – the style icon’s style icon – 007 himself.

Despite being a fictional spy, James Bond’s impact on menswear has been very real. And far from covert. Rarely one to be swayed by trends (aside from the odd safari jacket or baby-blue flannel romper suit), 007 has always been a vehicle for classic tailoring, effortlessly cool casualwear, luxury timepieces and some of the best black-tie looks you’re ever likely to see on screen.

But while the core elements of Bond’s look have remained over the years, his style has never been static. Each actor to play the part brought something new to the table, lending further depth to Bond’s wardrobe.

From Moore’s racy, fashion-forward take on 007 to Daniel Craig’s super-sharp Tom Ford suits, we look back at the six main Bond actors, recount their greatest style moments and decide how they rank in terms of their sartorial prowess.

6. Timothy Dalton

Stepping into the shoes of one of the public’s favourite Bonds, Roger Moore, Timothy Dalton had his work cut out for him. He played the role twice between 1986 and 1994, and while License To Kill and The Living Daylights were both critically successful, the same cannot be said for Dalton’s wardrobe.

Dalton’s broad-shouldered power suits and pleated baggy trousers were a sign of the times and haven’t aged particularly well. He tended to come across as if he’d been forced into his tailoring instead of having been born to wear it like Connery or Craig. Plus, his overall look was in stark contrast to the flair and flamboyance of Moore before him.

Still, he did have his moments. For the prior 12 years, Bond’s casualwear had been anything but understated. Dalton changed that by bringing a bit of his own sartorial stylings to the role. The safari jackets and camp-collar shirts were out, replaced by oversized outerwear, high-waisted pants and deck shoes.

A more relaxed take on casual Bond, but by no means a bad one.

Key Style Moment: Beige Bomber In Tangier

Dalton’s Bond took Tangier police on a chase while wearing a beige bomber, navy polo, baggy pleated chinos and deck shoes. It’s a simple look, but one that sticks in our minds nonetheless.

5. Roger Moore

Over the course of 12 years, Roger Moore played Bond a grand total of seven times. He was the longest-running Bond and an undeniable style icon. However, while menswear dandies will wax lyrical about him being the most stylish Bond, his tendency to favour brash and ballsy attire over anything classic and timeless puts Moore somewhat at odds with our core style philosophy.

Moore’s Bond was a bit of a playboy. All about the girls and less about the missions. Still, that’s not all he was interested in. You only have to take one look at his outfits to know that this was a man who took his style seriously.

The camp humour that defined UK film and television during Moore’s tenure allowed him to be far more daring than his predecessors. He introduced double-breasted tailoring to Bond, favoured open collars, wide lapels and snatched waists, and did wonders for the sales of safari jackets worldwide. In fact, the latter became something of a signature piece, appearing in five of his seven films.

Key Style Moment: Double-Breasted Blazer in Corfu

While he often lived dangerously in terms of style, Roger Moore’s Bond did have his classic moments. For instance, this double-breasted blazer, stone gabardine pants and blue shirt look.

4. Pierce Brosnan

Pierce Brosnan was the fifth actor to play James Bond, appearing in four films between 1995 and 2002. He took Moore’s over-the-top, fashion-forward aesthetic and Dalton’s relaxed suiting and flipped the script. This was Bond’s return to refinement, classic tailoring, and even wearing a tie.

Brosnan’s Bond was all about the sharply cut, form-flattering tailoring, a lot of linen and even more Brioni. He knew how to nail Riviera style in his light-coloured summer suits and pastel shirts, and his neatly coiffed hair was a masterclass in good grooming.

That said, there was always something a bit corporate-executive-at-the-company-Christmas-party about him whenever he donned a tuxedo. Which, for a character so closely associated with black tie, was a shame. Still, in terms of warm-weather tailoring, no other Bond has done a better job, past or present.

Key Style Moment: The Herringbone Linen Suit

Brosnan’s Brioni suit with a blue Turnbull & Asser shirt and Church’s monk-strap shoes in The World is Not Enough will always be our winner.

George Lazenby

Although he only appeared as James Bond once, George Lazenby managed to cram a lot of style into 142 minutes. The Australian actor divided opinion and was criticised for not being a good actor. However, even the most ardent critics would be hard-pressed to pick fault with his wardrobe.

OK, perhaps the ruffled dress shirts weren’t the best thing anyone has ever worn on screen. But aside from that, Lazenby’s looks have stood the test of time. In reality, the Australian had a distaste for tailoring, but you’d never know it from watching him. His suits were far more in line with what’s popular today than the likes of Connery or Moore, favouring a close fit, soft shoulders and natural sleeve heads.

Although it’s only fleeting, one of Lazenby’s looks that deserves a mention is his cream linen suit when he checks into the Palácio Estoril hotel. With a pastel pink shirt and navy knitted tie, this outfit is one of our favourite Bond looks, displaying a perfect balance of colour and contrast.

Key Style Moment: Autumnal shades

His brown cashmere bomber and orange roll neck combo in On Her Majesty’s Secret Service almost makes up for the two – that’s right, two – ruffled-front dress shirt he wore in the same film. Almost.

2. Daniel Craig

Our most recent Bond first appeared in 2006’s Casino Royale. His slightly rugged look contrasted his predecessor Pierce Brosnan’s ultra-polished appearance, but his suits were arguably some of the sharpest we’ve seen.

From form-hugging Tom Ford tailoring to equally form-hugging swimming trunks, Daniel Craig has brought us some of Bond’s most memorable looks. His slick tailoring is the perfect blend of classic and modern, and his sartorial chops are unrivalled in terms of casualwear.

Whether it’s a Barbour jacket and knitwear in the Scottish countryside or a down bomber jacket and classic hiking boots in the Austrian Alps, Craig’s Bond was a master of casual style. He made a plain polo shirt and chinos look as classy as his white tuxedo, and nothing he wore ever looked forced.

Key Style Moment: Action In Austria

Craig’s Tom Ford knitted-sleeve bomber, Agnelle leather gloves, Tom Ford stirrup pants and Danner Mountain Light classic hiking boots in Spectre made us want to update our winter wardrobes.

1. Sean Connery

The people’s favourite, and ours too. Sean Connery set the template for that quintessential James Bond look with his classic English tailoring, restrained colour palette and general classiness. The first time he appeared on screen he was wearing a tuxedo and, at that moment, history was made.

Connery kept colours simple and let the tailoring do the talking. Grey, in particular, was a favourite choice. He wore three different grey suits in Dr No alone. Even so, his outfits were far from dull. This was thanks partly to the skilled hand of Conduit Street’s Anthony Sinclair and part to the fact that Connery understood how to use texture to bring a look to life. From shiny wool and mohair to fuzzy flannel and dupioni silk – Connery’s outfits were always full of tactile touches.

He wasn’t without his outlandish moments, though. The one that immediately comes to mind is the blue towelling romper suit he famously sported in Goldfinger. Still, whether you think it looks good or not, it inspired countless contemporary luxury resortwear brands. Orlebar Brown even made a tribute to it as part of the label’s 007 collection.

If nothing else, it showed us that Connery’s Bond can be both daring and debonair, which clinches the top spot for him in our eyes. RIP, Sean; your legacy will live on forever.

Key Style Moment: Bond In Black Tie

The first time we see Connery he’s wearing a tuxedo in Dr No. It was an Anthony Sinclair dinner jacket with satin shawl collar, Turnbull & Asser shirt and bow tie. It’s a moment that will stick in our minds forever.

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