Jack Dorsey regularly wears a Dior Homme cotton poplin reverse collar shirt, making an iconic design a consistent everyday look.

Jack Dorsey regularly wears a Dior Homme cotton poplin reverse collar shirt, making an iconic design a consistent everyday look.

For those who don’t tweet or swipe credit cards through a small white cube, Jack Dorsey is the creator, co-founder of Twitter, and is the founder and CEO of Square, a mobile payments company.  He’s 36.  And he has style worth profiling.

Jack Dorsey cares about aesthetics.  Whether it’s a product’s design, or its ease of use, he sees that design should be visually pleasing and efficient.  When it comes to the products that  computer scientists design, Dorsey has been critical, saying that what they are building is “terrible.”  I don’t think he’s made such a comment just to get more ink.  He gets plenty of that.

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But I do believe, after studying his style, Jack Dorsey’s words are hardly lip service.  When it comes to his personal public style, he definitely shows that he is into the very best designs, styles, and brands that reflect his design philosophy.

Dorsey’s developing an iconic style of his own by tapping into iconic designs by top fashion houses.  Take his favorite choice of dress shirt, designed by Dior Homme.  Its reverse collar in cotton poplin is modern, sophisticated, and minimalistic.  Photographers have captured him wearing this shirt many times,. He has also worn it for TV interviews.  It’s no ordinary shirt, despite its simplicity.  And it defines the public persona of Jack Dorsey.

Jack Dorsey wearing Hermes, a brand that stands for the ultimate in luxury, but also in design, quality, and construction.

In addition to wearing Dior Homme, he wears clothes from Prada and Hermes.  He has been photographed in an Hermes jacket with a stand up collar that was turned down by a photo stylist.  According to a public relations specialist familiar with that photo shoot, the stylist effectively changed the precise design for the photograph. This displeased Dorsey.  I admire his respect and reverence for excellence in design.

To be sure, Jack Dorsey is not running around to photo shoots for endless media and publicity.  There’s no doubt that he wears clothes beyond impeccably tailored jackets and suits.  After all, the young, super successful entrepreneur and CEO used to have scruffy facial hair, long unkempt bed hair, and a nose ring.

Jack Dorsey doesn't always wear tailored clothes and suits. Even in sportswear, his choices represent his very particular personal style and aesthetic.

Jack Dorsey doesn’t always wear tailored clothes and suits. Even in sportswear, his choices represent his very particular personal style and aesthetic.

No matter what he wears now, he came a long way from looking like a rebel child.  After all, Square processes $10 billion on an annualized basis, according to a recent Los Angeles Times article.  Before you take a swipe [sorry, the pun was irresistible] at Jack Dorsey’s carefully crafted personal image, it’s crucial to the Square brand that the man behind the company looks like he can be trusted to handle what could very well be your money.

Dorsey’s wardrobe choices help an onlooker think that he is precise and thoughtful.  More than that, his clothes seem to represent an idea of taking time honored ideas and modernizing them.  His apparel choices are of the moment, yet they represent a sense of timelessness that comes with clothes that are not trendy.  I think he’s one of the most thoughtful and stylish men in Silicon Valley.