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DRESS TO KILL: STYLE TIPS FROM BIG MAN MOB BOSS TONY SOPRANO

  • 3 min read

There are countless websites dedicated to it. Numerous Instagram pages. Heck, auction house Christie’s even flogged it. That’s right. In this article we’re talking about the most quintessential big man style ever. We’re talking about Tony Soprano’s big man wardrobe.

In case you have been living under a rock, Tony Soprano is the fictional mafia mob boss and eponymous main character of the most perfectly crafted TV series ever: The Sopranos. Tony, played by the late, great big man James Gandolfini, is not your average Italian mobster alpha male. His character is at turns melancholic, child-like, full of vengeance and soulful. And it was Gandolfini’s acting mastery that enabled him to excel within this role and enshrine Tony as a big man anti-hero for the ages.

tony soprano big man

The. Best. TV. Show. Ever

If you’re anything like me, you just had to map out a project for yourself during the eight thousand or so hours of Lockdown in 2020. Maybe you turned to home renovating. Maybe you used your allotted exercise hours to get in better shape. Maybe you picked back up the habit of reading. I chose something else. I chose The Sopranos.

And, after serious amounts of bingeing the HBO show which set the tone for modern TV, I can now officially declare that I am in love with Tony’s wardrobe. I mean what’s not to love? The tailored suits, amazing polo shirts, great looking loungewear and pleated pants all smack of a confident swagger and a harkening back to the good old days when big men dressed classy.

tony soprano

Big Man Tony

In The Sopranos, big men are no joke. The big guys in Tony’s crew (Bobby Baccalieri, Big Pussy, Vito et al) are not to be made fun of nor are they caricatured as lazy, unattractive or weak. They are unfailingly complex characters. And as big men, they are inherently relatable. I mean, I wouldn’t want to hang out with them anytime soon. They aren’t the most upstanding bunch of guys getting about. With friends like these, who’d need enemies, right? These guys could double-cross you without a moment’s hesitation. And then you’d have to kill them.

Come to think of it, I would hate being in Tony’s shoes as a mob boss. Owning a pair of his shoes on the other hand, well that’s a different matter.

Gandolfini as Tony Soprano was a perfect example of the adage that it's not just what you wear, but how you wear it. As Esquire put it:

"Tony's clothes all looked like they came from The Men's Wearhouse, but they fit him well, and he looked good in them. He took an obvious pride in the way he looked”.

With all of that said, let’s now take a quick look at how you can steal a bit of the Skip’s sartorial splendour and update your big men’s wardrobe.

tony soprano big man

Interesting shirts

Tony Soprano generally opts for nicely detailed polo shirts. He seems to always choose interesting shirts that sit perfectly between being too plain and boring versus going completely over the top. Tony exudes a level of confidence in his big man frame that allows him to wear really interesting shirts and look good at the same time!

Pleated slacks

The Skip’s choice of shirts are strong enough to shine on their own, However, what really sets them apart is that, almost always, he tucks them into a pair of really nice pleated dress pants. Here, tailoring is important. Tony’s pants sit slightly tapered. They narrow around the calf and are finish just above his ankle. Bada bing, bada boom!

Jackets

“Refined” but not formal, “casual” but not dull. Combining a great looking interesting shirt with a pair of pleated slacks is beyond reproach. However, there comes a time and place where you need to class things up a bit. This is where a jacket comes in. Not only will a jacket work with an interesting shirt tucked into pleated slacks, it’s also versatile enough to be paired with a great jumper.

So, there you have it. Tony Soprano might be a fictional TV character, but what a character he is: charming, sexy, sinister, relatable, funny, tragic and utterly compelling. And whatever the occasion, whether it’s hanging out with his crew, taking his wife to dinner or conducting mafia business, Tony is always dressed to kill. We big men would do well to emulate his effortless style.

By Anthony Cheadle

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