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Jack Dorsey’s footwear evolution: An investigation

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.

Mark :(

Mark 🙁

Image: Christophe Morin/IP3/Getty Images

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 wore this to hang with Anna Wintour, so....

Jack wore this to hang with Anna Wintour, so….

Image: Phillip Faraone/Getty Images for WIRED25

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.

From a June 2007 company profile.

From a June 2007 company profile.

Image: Kara Andrade/AFP/Getty Images

Spotted: loafers.A 2009 meeting of technology executives at the US State Department.

Spotted: loafers.A 2009 meeting of technology executives at the US State Department.

Image: getty images/mashable composite

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!

Jack hypnotizing beautiful celebrities with his shiny shoes.

Jack hypnotizing beautiful celebrities with his shiny shoes.


Hangin' with Obama in those freshly polished pointy toes (2011).

Hangin’ with Obama in those freshly polished pointy toes (2011).

Image: ImageCatcher News Service/Corbis via Getty Images

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.

Flexin' in a 2009 company profile.

Flexin’ in a 2009 company profile.

Image: Thomas SAMSON/Gamma-Rapho via Getty Images

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.

Who the hell tailored these pants?!?!!? (2010)

Who the hell tailored these pants?!?!!? (2010)

Image: Brian Harkin/Getty Images

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

It gets better.

It gets better.

Image: Dimitrios Kambouris/WireImage

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.

Not mad at this!

Not mad at this!

Image: D Dipasupil/WireImage/Getty images

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.

Party on top, ho-down below.

Party on top, ho-down below.

Image: Kevork Djansezian/Getty Images

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

A 2013 lewk.

A 2013 lewk.


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!

Honestly don't hate it.

Honestly don’t hate it.

Image: John Chiala/CNBC/NBCU Photo Bank via Getty Images

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.


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.

Jack's Cannes 2017 outfit is Kanye approved.

Jack’s Cannes 2017 outfit is Kanye approved.

Image: Francois Durand/Getty Images for Twitter

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!!!!!!!!

Cute kicks.

Cute kicks.


V. Sleek

V. Sleek


All black 'errything.

All black ‘errything.


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.

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HBO’s Twitter account just burned Jack Dorsey


Image: Hindustan Times / getty

Nothing brings out a perfectly workshopped diss like a little cross-industry promotional opportunism. 

We were reminded of this fact on Jan. 10, when, in celebration of the 20th anniversary of the show The Sopranos, the HBO Twitter account announced it would dish out Sopranos-inspired nicknames. And you better believe that Twitter CEO and “conversational health” guru Jack Dorsey wanted in on the fun. 

“In honor of the 20th anniversary of The Sopranos, I’m handing out Soprano nicknames today,” read the tweet from HBO’s main account. “Who wants one? FYI if you tell me your first name, this is way easier for me.”

Dorsey replied with an emoji of a person raising his right arm, and the word “jack.”

HBO was apparently happy to oblige, and hit the man who was most recently accused of some pretty serious Myanmar-related ignorance with a nickname all his own. 

World, meet “Jackie No Edits.”

The nickname references the misguided desire of misinformed people to force Twitter to implement an edit button. This is a bad idea, but an OK burn as far as burns go. 

Dorsey, for his part, quickly changed his profile name to “jackie no edits.” And thus, the corporate cycle was complete, and we could all go back to our peaceful online lives

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Jack Dorsey and Twitter ignored opportunity to meet with civic group on Myanmar issues

Responding to criticism from his recent trip to Myanmar, Twitter CEO Jack Dorsey said he’s keen to learn about the country’s racial tension and human rights atrocities, but it has emerged that both he and Twitter’s public policy team ignored an opportunity to connect with a key civic group in the country.

A loose group of six companies in Myanmar has engaged with Facebook in a bid to help improve the situation around usage of its services in the country — often with frustrating results — and key members of that alliance, including Omidyar-backed accelerator firm Phandeeyar, contacted Dorsey via Twitter DM and emailed the company’s public policy contacts when they learned that the CEO was visiting Myanmar.

The plan was to arrange a forum to discuss the social media concerns in Myanmar to help Dorsey gain an understanding of life on the ground in one of the world’s fastest-growing internet markets.

“The Myanmar tech community was all excited, and wondering where he was going,” Jes Kaliebe Petersen, the Phandeeyar CEO, told TechCrunch in an interview. “We wondered: ‘Can we get him in a room, maybe at a public event, and talk about technology in Myanmar or social media, whatever he is happy with?’”

The DMs went unread. In a response to the email, a Twitter staff member told the group that Dorsey was visiting the country strictly on personal time with no plans for business. The Myanmar-based group responded with an offer to set up a remote, phone-based briefing for Twitter’s public policy team with the ultimate goal of getting information to Dorsey and key executives, but that email went unanswered.

When we contacted Twitter, a spokesperson initially pointed us to a tweet from Dorsey in which he said: “I had no conversations with the government or NGOs during my trip.”

However, within two hours of our inquiry, a member of Twitter’s team responded to the group’s email in an effort to restart the conversation and set up a phone meeting in January.

“We’ve been in discussions with the group prior to your outreach,” a Twitter spokesperson told TechCrunch in a subsequent email exchange.

That statement is incorrect.

Still, on the bright side, it appears that the group may get an opportunity to brief Twitter on its concerns on social media usage in the country after all.

The micro-blogging service isn’t as well-used in Myanmar as Facebook, which has some 20 million monthly users and is practically the de facto internet, but there have been concerns in Myanmar. For one thing, there was been the development of a somewhat sinister bot army in Myanmar and other parts of Southeast Asia, while it remains a key platform for influencers and thought-leaders.

“[Dorsey is] the head of a social media company and, given the massive issues here in Myanmar, I think it’s irresponsible of him to not address that,” Petersen told TechCrunch.

“Twitter isn’t as widely used as Facebook but that doesn’t mean it doesn’t have concerns happening with it,” he added. “As we’d tell Facebook or any large tech company with a prominent presence in Myanmar, it’s important to spend time on the ground like they’d do in any other market where they have a substantial presence.”

The UN has concluded that Facebook plays a “determining” role in accelerating ethnic violence in Myanmar. While Facebook has tried to address the issues, it hasn’t committed to opening an office in the country and it released a key report on the situation on the eve of the U.S. mid-term elections, a strategy that appeared designed to deflect attention from the findings. All of which suggests that it isn’t really serious about Myanmar.

Jack non-apologizes for his tone deaf Myanmar vacation tweets

Excuse me, is that a nose ring?
Excuse me, is that a nose ring?

Image: Drew Angerer/Getty Images

Add Jack Dorsey’s name to the running list of white men who have issued non-apologies in 2018.

On December 8, the Twitter CEO shared reflections on his recent meditation retreat to Myanmar, a country whose army is killing and raping Rohingya Muslims “with genocidal intent.”

Some criticized the blind-eyed and tone deaf seeming thread in the days that followed. Now, Dorsey has issued what he called “more color” on his trip to Myanmar “given the resulting conversation.”

Dorsey took a 10-day silent meditation retreat to Myanmar to practice Vipassana meditation, which Dorsey described as a way to “hack the deepest layer of the mind and reprogram it” through pain and deprivation. He visited Myanmar because the practice originated in the country.

Putting aside the grossness of a billionaire visiting a third world country specifically in order to deprive himself of the worldly goods he so easily comes by, people criticized Dorsey specifically for the way he described Myanmar, and his unique position as a tech CEO.

See, the Rohingya genocide isn’t just any ethnically targeted mass-murder. In August, the United Nations found that Facebook had played a significant role in spreading the hate and disinformation that led to the expulsion, murder, and rape of Rohingya Muslims. The New York Times has gone so far to describe it as a “tool for ethnic cleansing.” From the UN’s final report, issued in September:

The role of social media is significant. Facebook has been a useful instrument for those seeking to spread hate, in a context where, for most users, Facebook is the Internet. Although improved in recent months, the response of Facebook has been slow and ineffective. The extent to which Facebook posts and messages have led to real-world discrimination and violence must be independently and thoroughly examined. 

Facebook was the primary social media vehicle for fueling the Myanmar atrocities. But Twitter has also come under fire for enabling the hate speech that contributes to real-world violence in other instances. Twitter has taken steps to curb hate speech, but critics have specifically taken Dorsey to task for not acting more decisively to stamp out hate speech on his platform.

Now, for Dorsey to visit a country currently wracked by the consequences of hate and violence in the social media age, and to not even acknowledge it, smacked of insensitive privilege, and at least some deep irony about the Silicon Valley bubble.

So Dorsey apologized, sort of. He said it was a “purely personal” trip for him, only focused on meditation. He shared his perspective that Twitter is a place for people to “bear witness” to the Rohingya murders. And that he wants to continue working with NGOs and others for “feedback on how to best improve.”

Sorry, but how Twitter can improve is just not the point. Dorsey is able to shut out the turmoil and violence of the world he helped create by taking part in á la carte tourism and spirituality. Meanwhile, those less fortunate are reaping the consequences in the same country in which a tech CEO chooses to vacation. A non-apology that, most generously read, focuses on what Twitter can do now, subsumes social media founders’ complicity in creating the reality, which they have the luxury to escape.

Should Jack be allowed to take a vacation? Sure, it’s been a tough year, to say the least. But, in Myanmar, he happened to do so in spectacularly tone deaf fashion. So maybe a little “feedback on how to best improve” is sorely needed.

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Twitter’s Jack Dorsey gets roasted for his ignorant tweets about Myanmar

More than 600,000 Rohingya refugees have flooded into Bangladesh to flee an offensive by Myanmar’s military that the United Nations has called “a textbook example of ethnic cleansing."
More than 600,000 Rohingya refugees have flooded into Bangladesh to flee an offensive by Myanmar’s military that the United Nations has called “a textbook example of ethnic cleansing.”

Image: Kevin Frayer / Getty Images

Twitter CEO Jack Dorsey shared with the world what he did on his most recent birthday: travel to Myanmar and do a 10-day silent meditation.

Dorsey made a thread on Twitter explaining the experience, and hundreds of people chimed in to remind Jack of the genocide happening in Myanmar that’s been perpetuated by social media, how funny it is that he paid money to get bit by mosquitos, and his general rich white guy privilege.

Of course, Jack took the idea of Vipassanā and translated it into terms that tech people are familiar with, using words like “hack” and “reprogram.”

Some people on Twitter compared Dorsey’s experience of embracing pain to their experience on Twitter, where harassment continues to run rampant and negativity permeates every aspect of the platform.

Another person pointed out how some people really don’t have the option to meditate on their pain, and instead are forced to live and work with it because they can’t afford healthcare.

One Twitter user compared Dorsey to Gavin Belson, the villainous businessman from the show Silicon Valley who literally goes on a trip to meditate in Asia only to return to his normal capitalistic ways when he returns to Silicon Valley. Classic rich white tech guys stuff.

One of Dorsey’s more universally funny tweets in his thread was one where he shared that he’d been bitten over 100 times by mosquitos, and that’s pretty hard not to laugh at. People love schadenfreude.

The most egregious part about Dorsey’s Twitter thread is his willingness to ignore the genocide happening in Myanmar, which either he somehow wasn’t aware of or just decided not to mention.

You gotta be aware of this stuff, especially when you’re tweeting it out to hundreds of thousands of people on your own information-sharing platform.

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