What would you wear every day if you could wear anything? We're talking no limits, not from bank accounts or corporate wardrobe requirements, not those snarky writers from US Weekly or the sexy lady judging the size of your 401k by the validity of your Rolex.
One man in particular has had that choice over the years. He's Bill Gates.
In the past several decades, Bill Gates has been seen in jeans, ties and suits, but at the end of the day, there's been one look he's come home to. It's the sweater. With a buttoned shirt under it. For over 20 years, this has been the signature calling card of one of world's most powerful men. (That, and those $7 haircuts.)
And you know what's crazy? Men's Vogue tells us that it's fashionable.
Ned Martel is a Deputy Editor over at Men's Vogue and he was kind enough to stare at many pictures of Bill Gates that I sent him. When I got him on the phone, we discussed the matter, starting with some shots from a 1985 Microsoft publicity shoot.
"Sweaters..." I hear Martel think out loud. "The thing that strikes me is that...you didn't need to dress in the '80s like you were well funded to get funding...it was the opposite—if you presented yourself as pinstriped, you might not be seen as the upstart worth getting behind."
And such may be true even today. When is the last time you saw Kevin Rose sporting a triangle hankerchief that matched his tie? But where Martel described the look as "I'm too busy to think about wearing a suit," it's probably been generalised in modern terms to "I'm too cool to wear a suit."
We flip to a newer shot, this time taken just last year. (It's our lead photo of the piece, minus that Voguesque spoof cover art.) Sweater. Collar. Same thing, right?
"This is more expensive," Martel points out immediately. "I think it's like a purple cashmere v-neck. That's probably a bit of a luxury he would not have even sported in his youth...Like he got married and got a life. It's more dad-like."
But something else changed, too.
"His glasses are more grown up," Martel says. "The change that you see in his face because of that. It is a reflection that he's thought about."
The word "fatherly" comes to mind again.
"It's a different way of announcing your place in the establishment of American billionaires. I think you see that subtly in the way he dresses because it began as a little bit rebellious and it's matured into a way that's said it had a payoff."
So the wardrobe payoff after several billion dollars is wire-frames and cashmere. But is that fashionable? What is a sweater and collar, after all? It's certainly is not a cutting edge trend, nor is it quite a timeless classic.
"Any guy with confidence and a sense of how he wants to present himself is a fashionable guy," Martel explains. Finally, a justification for that plaid shirt my wife hates.
But before I let Martel off the line, there was one last point to be settled. Gates vs. Jobs. No OSs. No fancy keynotes. Just. Wardrobe vs. wardrobe.
(Ed note: Of course, this photo is, like, the one time Gates isn't wearing that damn sweater.)
"Comparing their clothes is like comparing their accomplishments—they both helped together to define an era," Martel explains. "And the fact that we even have an indelible sense of how they've looked of the years means it worked." [Men's Vogue]
Cover art by Richard Blakeley.