On paper, it’s not the greatest time to be a man, and dressing well can sometimes just reinforce those alpha-chauvinist stereotypes. But dressing properly can cut through the political noise. Here’s how to dress well to make an actual difference, via five smooth style icons from each decade. Starting with the 80s.

I was always the small, ugly one at school. Spots, big nose, and all. And from about the age of 17, I figured that the only way to survive was to use fashion and style to create a persona. And through, multiple doomed and frustrated attempts, here I stand as a testament to those early efforts – white hip-hop wannabe, cool raver, Levi’s only acolyte – minus the spots (unfortunately not minus the nose) and a self-supposed style guru.

My point is that there was resistance through most of the above stages. RESISTANCE to the way I looked and to the way I dressed. And sometimes that nearly (and later literally – that’s another story) brought me to my knees.

Kids who were either already good-looking and cool, or confident and/or aggressive enough make their way through the teen years of discontent. They didn’t like me. And as I got closer (with a little help from party pills – not to be advised) to breaking the mold of the high school loser label, I encountered more resistance.

Fashion, at its best, is all about resistance. It’s about an aesthetic and visual tension between the banal world we inhabit (and when I think about those mean kids now, I realize that they weren’t evil in their nastiness, just dull) and the realm of possibility.

The meeting point for most of us is at the relatively mundane level of the high street, train station, classroom, or office. And while these checkpoints do reign in the amount of radicalizing we partake of, they also create a fitting, sometimes striking counterpoint to the person we want to project.

Expect resistance if you want success. Here are five key male templates that have made a difference. Decade by decade

1. Don Johnson – Miami Vice


Sure, Johnson had the looks and charm on tap. And sure, Face from the A-Team, Richard Gere, and Steve McQueen all informed the Michael Mann alt-cop result. And yes, living on a luxury boat in Miami and driving a recommissioned Ferrari is hardly a disruptive style choice.


But see this – it was cool and slightly effeminate and – here’s the thing – he got away with in the office because it was only a jacket and a plain pastel t-shirt. Was he breaking the rules? Well, saide from not wearing socks, not really. Would he look like a chump cop? No.

Vincent Gallo – Buffalo ’66 Era


Galo’s media fire may have burned short and bright, and his breakout directorial and acting success remains his only hit and is itself plagued by valid criticisms. 

But Galo mastered, in the pre-social media age, the concept of hybridization to a male-centric t. Yes, blue eyes and a roman nose help, but far from being anyone’s idea of good-looking, the Italian American exemplified the power of agitation into silhouettes that encompassed cowboy, pimp, slacker, and all round anti-hero. 

And he could wear a suit. His aesthetic was ripped by pretty much every alt-a-lister: Johnny Depp, Jaquim Phoenix, Heath Ledger. Galo was the only one who looked like it was supposed to  – like he was trying by not trying.

Idris Elba – The Wire


Plenty of good-looking and well-dressed black men have graced the screen through the years, but none have so successfully captured the debonair spirit in a character so deeply flawed as The Wire’s Stringer Bell. For Elba’s character, dressing well was a prerequisite for elevation in a field where every pawn wanted a piece of the pie, in places where joggings and a t-shirt would have been so much easier.

Donald Glover

And in a complete sea change, actor, singer, and producer influencer Glover encapsulates the fast fashion quick change philosophy that pairs stars with trends via news feeds ala Pharrell (the first), Kendrik, Styles, Ocean, and Tyler. Glover is the simplest and most classically styled (MOST of the time). He understands that you don’t need to make radical wardrobe choices to make standout style statement.

Timothy Chalamet – The French Dispatch

Chalamet may well be a studio-bred star; the new Di Caprio-in waiting with $10 million per movie contracts lined up for the next 3 or 4 years. But he’s also a skinny Jewish kid with a shy persona. He exemplifies the gender-neutral wardrobe appeal and makes it his own, without ever looking like a 70s throwback.

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