Jack Dorsey’s sneaker style is the story of Silicon Valley growing up

At the last real day of CES (before Kanye showed up and tried to make the vacant halls of Thursday a “thing”), Twitter CEO Jack Dorsey held a public discussion to clue us all in on his efforts to make Twitter better.

But hey! Forget the hate speech, Nazis, account-muting, and general directionlessness of Dorsey’s social media devil child for a sec. What the people really wanted to know about were Jack’s SHOES.

So what exactly was Jack wearing that fateful day? Well, good people, the shoes were Rick Owens Island Dunk hightop sneakers, in a nice sun-dried tomato color. The style sells online for between $400 and $2,700, depending on their material and availability. 

The orange high tops are just one pair of several high-end statement sneakers that Dorsey has worn out in public in the years since he was reinstated as Twitter CEO, which has contributed to his image as Silicon Valley’s most fashion-forward executive. The competition, admittedly, is not particularly fierce.

Dorsey’s kicks are usually by the cool kid designer Rick Owens, cost hundreds of dollars, and are pretty dang fashionable. Paired with his billygoat beard and minimalist, all-black, drapey garbs — also often made by Rick Owens — Dorsey appears to be quite a high-end streetwear aficionado.

But it hasn’t always been this way. 

In the 12 years since Dorsey cofounded Twitter, he has morphed from a loafer-loving tech bro into a label allegiant hypebeast; he appears to have traded boat shoes for high tops, Toms for Yeezys. And after a thorough investigation, Mashable has determined that Dorsey’s footwear evolution really took hold in 2015: the year he was reinstated as Twitter CEO.

Sure, Jack is the CEO of one of the platforms that’s looking like it’s contributing to the demise of America; just Thursday, a rare candid interview with Jack revealed that he is unable to muster concrete answers to the many problems plaguing and questions about the future of his platform.

So other than for the fun of clowning on Jack — which is, of course, always a joy — why should we care about the aesthetic indulgences of one Silicon Valley fuccboi? After all, Dorsey’s footwear metamorphosis is probably just the tale of a once-nerdy coder learning about prestige brands, developing his personal style, and having the unseemly gobs of money necessary to get that outfit right. 

“Dorsey has had his own style for a while, and he continues to evolve,” Victoria Hitchcock, a lifestyle and fashion consultant based in the Bay Area, said. “His high tops are perfect symbol of bigger picture.”

Then again, Dorsey’s kicks could show something more. They stand in for the changing nature of the fashion industry, in large part thanks to the social media of Jack’s own creation. And, moreover, for tech workers’ relationship with fashion, largely thanks to all the money and attention Silicon Valley continues to get these days. 

“We’re kind of having a trickle up effect,” Lawrence Schlossman, the former Editor-In-Chief of the now-defunct (but beloved) snarky menswear blog, Four Pins, said. “It used to be what happens on the runway is what you’re going to see on the streets. Now, there’s this reverse osmosis.”

Today, Schlossman said, streetwear and high fashion are in many cases the same thing; the Rick Owens sneakers are an example of this high-end streetwear trend in action. And as Silicon Valley’s wealth and profile have increased, that fashion industry change has had an impact on the way tech CEOs, employees, and streamers alike, are dressing. 

“Specifically in the last 18 months, the tech titans haven’t been afraid to stand out,” Hitchcock said. “They’re spending more on luxury items and statement pieces, and you definitely see it in the low tops and the high tops.”

“A lot of those guys are super into Yeezys and Off-White Nikes and Supreme,” Lawrence said of YouTube streamers and esports stars. “What would be considered a traditional nerd guy is now latching on to these status symbols.”

Streetwear and the tech uniforms might sound different, but the clothing  staples are fundamentally the same: t-shirts and hoodies and sneakers. So it’s no wonder that the streetwear aesthetic has made it to Silicon Valley, in an entry-level way, through brands like Allbirds. 

Jack’s version of streetwear-inspired style is the high-end luxury version of a fashion industry trend tailor made for the tech world.

Jack is part of a universe that the world has watched grow from upstart college students to power brokers. There has been an increasing presence, interest in, and therefore scrutiny of Silicon Valley in the culture at large. So as these companies grow up, perhaps their executives aim to display both relevance and dare we say… swag?… in the limelight. And, more recently, maybe cool kicks can ground a tech exec like Dorsey when faced with the possibility that their technological inventions ruined America. 

“Shoes are an easy way to ground your style,” Hitchcock said. “Footwear is a fun, luxury indulgence that allows you to stay ‘light on your feet’ and express your creativity and not be weighed down.”

Or, even when everything’s wrong, at least you’re outfit is right.

Here’s the evolution of Jack Dorsey’s footwear game.

Loafers are Dress Shoes: The early Twitter days (2007 – 2009)

Every tech executive has a set of embarrassing photos from when he was damn baby, new on the tech scene. (Have you seen the Jeff Bezos globe photos?)

For Jack Dorsey, early company profile photos reveal that he was into boot cut jeans. And his shoes of choice were square toed loafers. Yikes.

The Square era was the pointy era: Jack’s shiny dress shoes (2009-2012)

In 2008, Twitter replaced Dorsey as CEO. Around the same time, he became a more high-profile figure — often attending events with celebrities and politicians — and was also into wearing very shiny dress shoes!

Luxe life clues: Jack was an aspiring fashionisto (2009-2013) 

Jack’s been wearing luxury items, and taking some fashion risks, for a while. It just hasn’t always… worked out that great.

Look at this hideous Hermès belt.

Look at it.

Even if this luxury item is objectively terrible, he is also starting to experiment on the footwear front, just still in the realm of pointy and so, so shiny.

But he still needs… some help.

What is this? Boot cut jeans? Spiky hair? DIY Mandarin Collar? Justin Bieber?????

Get some better arch support, bro: Jack’s everyday footwear (Early 2010s)

In contrast to a lot of his flashier looks out at public events, in the early 2010s, the shoes he would wear at work or having fun were similar to what any other San Francisco tech worker would wear. Even if they were, uh, sometimes inappropriate.

(These are not running shoes??)

In the early 2010s, Jack sure did love his Toms. 

And boat shoes:

And Chucks:

Jack Dorsey, CEO, and regular guy!!

Popped collars and cowboy boots: fashion puberty (2012-2014)

In public, Jack was starting to make some fashion statements, and busted out some “cool” “pieces” like a leather jacket and round sunglasses. But in the shoe department, nothing was going on.

Here’s Jack looking pretty good in 2012, with some sort of popped/Mandarin collar style he repeated several times.

During this time, Jack was capable of dressing with more flare than his pure suits and fleece days. But his look was still mainstream. And filled with bootcut jeans and actual cowboy boots.

Cowboy boots can be rad. But, just not… like this.

Things in public might have looked a little awkward for Jack in the early 2010s. But like any pubescent teen, he was learning about what he liked… online! As early as 2012, he began showing his appreciation for the designers that would comprise his late 2010s uniform. He just hadn’t gotten up to wearing them head-to-toe in public yet. 

Also, he still loved J.Crew.

The Beard Appears: The bell-weather signs (2014-2015)

Dorsey appears to have flirted with stubble for a couple years in the early/mid-2010s. But by the end of 2014, he committed to the Beard. What the heck does this have to do with footwear? The beard was a crucial step in his transformation from clean cut start-up kid to founder with an *aesthetique*.

“They both are in the same ilk, in the same vein,” Hitchcock said. “With some of these up and coming titans where they don’t want to stand out, they never have, so the safest thing is a shoe. Or facial hair.”

Here’s the first pic Dorsey posted of himself on Twitter with the beard.

He even went full billygoat for a time in 2015, though the beard would be subject to various trims over the next few years. Here he is during a June 2015 media appearance. Even his mom complained about it. Aww, Jack really was growing up!

At this point, Dorsey also appeared to begin following the fashion industry currents as he moved his personal style away from loafers and Toms to colorful Nikes — and actively started expressing his “mood” through streetwear.

(BUT WHAT IS THE CUT OF THOSE JEANS WITH THOSE SNEAKERS. SEND HELP.)

Gateway shoe: Enter the hypebeast (2015)

Just after getting reinstated as Twitter CEO, Jack not only finds himself back in power — he finds his street style. 

In October 2015, he’s pictured wearing shoes from a designer he’s already said he admires: Rick Owens.

Here he is in Island Dunk high top sneakers in tan. The world takes notice.

“I wouldn’t be surprised if sneakers were his gateway drug into the world of Rick Owens,” Schlossman said. “I see it all the time. Footwear is the biggest category for men, luxury footwear. Most guys build their outfits foundationally. And a lot of that starts from the ground up.”

Once you pop the fun don’t stop: Jack’s footwear game escalates (2016-2017)

The cowboy boots must be hiding in the back of the closet, because Jack is wearing skinny jeans, opting for Yeezy’s over Nikes, and his high tops are Rick Owens — not Converse — now.

Do these orange babies look familiar? Jack actually debuted the sneakers he wore to 2019’s CES in 2016.

“Rick’d Out”: Jack finds his favorite designer, and nothing was ever the same (2017-present)

In 2015 Jack Dorsey found Island Dunk high tops. By 2017, he wore Rick Owens kicks to almost every public event. By our count, he owns at least:

• Island Dunk high tops in two colors.

• Cap toe and non-cap toe slip ons from the DRKSHDW collection.

• These leather sock shoes, that he wore to hang with the Prime Minster of India. 

• Maybe more!!!!!!!!

He is, as Schlossman put it, “Rick’d out.”

Cult Leader: How Rick’d is too Rick’d? (2017-present)

Every disruptor faces a backlash. Jack upped his footwear ante and developed a personal style in recent years. But some have wondered whether he’s put a toe or two out of line.

A 2017 Business Insider article indignantly pointed out that he wore “strange shoes” to meet with — GASP — Goldman Sachs CEO Lloyd Blankfein. 

Jack has been seen wearing these cross-foot thongs a few times. But apparently baring his toes while in the presence of a banker went too far.

Hitchcock thinks these sandals are actually high end and expensive, too. They have a similar look to luxe and custom sandal designers like CoStume National, Jutta Neumann, Officine Creative, and Cydwoq.

Still, Jack’s style of oversized black drapey shirts, leather sandals, and even these shorts, prompted my colleague to describe him as looking like a “cult leader.”

But hey, if finding fashion Jesus for Jack means actually looking like Jesus, godspeed. We’ll take cult leader over bootcut jeans and loafers any day.

Now if only Jack could be as clear headed about how he should make over Twitter, too.