CEOs and successful businesspeople like to have fun too.
Some are fashion forward. Some are more reserved. And some just seem to not really care or don’t really have a clue about fashion.
Dress For Success is a friendly term in the business world. It’s a good rule for life. You don’t want to give people a reason to not trust you or to think that you’re goofy or things like that. The clothing you wear and the fashion choices you make do give people something to think about your character whether you like it or not.
With this one we’re going to have a fun time and just look at some of the…let’s call itinteresting…fashion choices from successful businesspeople.
1. Sam Walton In A Hula Skirt
Sam Walton was the founder of Walmart. He lived and breathed retail. He got his start long ago and eventually started his own chain and that became Walmart and he found a formula that he could replicate over and over and it worked all over the world. It’s one of the great American success stories.
And one day on Wall Street Sam Walton came out in a full Hawaiian outfit complete with hula skirt. It was his fun personality and his willingness to poke fun at himself while also showing off the culture and closeness of the Walmart company.
Here’s the official video of the fun event.
2. Gary Kelly’s Halloween Costumes
Apparently the CEO of Southwest Airlines, Gary Kelly, likes to dress up for Halloween. He’s been doing it for several years and one of his recent bests was dressing as one of the Beatles. He looks great and carries on a tradition in the company of having fun and not being afraid to dress up and look a little silly. Former CEO Herb Kelleher was also known to have fun and once dressed up as Elvis.
It’s all in good fun.
3. Bill Gates Granny Glasses
Bill Gates never seemed to shy away from the “Nerd” label. And that’s pretty cool. Being smart. Being curious. All those things are cool in my book. Bill Gates helped to change the world. He brought computing to the masses and he’s still out there working to do great things.
Over the years he’s always had a variety of different glasses. The granny glasses look was a pretty good one. Maybe he was inspired by John Denver from the ’70s who probably helped to popularize those spectacles.
4. Gussie Busch The Cowboy
Gussie Busch was one of the CEOs of Anheuser Busch. He was known to be a fun loving guy that loved being around people. He was talked into buying the St. Louis Cardinals and became a huge fan. He was known to wear a cowboy hat and cowboy boots along with all the regalia while cheering on the team. He would even get on an old school wagon and steer the clydesdales around the field to rev up the team and the fans.
Great stuff.
5. Mark Zuckerberg’s Hoodie & Sandals
Mark Zuckerberg really became one of the first Millennial CEOs when he came to prominence with Facebook. I respected his willingness to not sell Facebook in the early days. I respected his insistence to continue as CEO. And he’s always done it the way he wanted and that includes his fashion choices. He always wore that dark hoodie with those Adidas sandals. I don’t know if he still wears those, but in the last ten years I’ve seen other very successful Millennials wear hoodies just like Zuck.
6. Richard Branson…as a woman
Richard Branson is obviously very successful. He’s outgoing. He loves giving back and he just seems to love his life. He’s had success in numerous areas of business starting in music and getting into other areas including the airline industry. And that’s where this fashion choice comes in. Richard dressed up as a female flight attendance. You gotta love a CEO that can poke fun at themselves as a way to build a culture.
7. Elon Musk’s Biker Vest
This one is pretty cool. He does seem like a pretty cool guy. He’s a good dress. He has style.
Elon Musk wore this leather vest that is like a motorcycle vest. With a few more patches you could see him maybe being a visitor on the set of Sons Of Anarchy or something. I bet they would have respect for all he’s done in the business world.
8. Chase Carey’s Amazing Mustache
I admit that I don’t know much about Chase Carey. He’s very successful in business. I’m just in awe of his amazing mustache.
9. Walt Disney’s Fedora
We don’t really wear business attire hats anymore. But in Walt Disney’s time it was very fashionable and cool to wear a fedora. And he wore it really well. There are several pics of him out there in a hat like this, but this one is pretty cool. The man that brought happiness to the masses also knew how to look pretty cool. Today maybe not so much, but you never know.
10. Rand Fishkin’s Yellow Shoes
I think he’s worthy of being on a list like this. Rand Fishkin is one of the biggest names in SEO. I believe that SEO is as important as ever. Rand has told the story before about why he wears yellow shoes. It’s a way for people to recognize him when he’s speaking or at conferences and it’s kind of morphed from there.
Here is a full blog post and video on it.
Final Thought
Some of these were conscious decisions. Some weren’t. It goes to show that the term Dress For Success can mean different things for different businesspeople. You can have fun. You can be serious. You can stand out or blend in. Maybe it’s just about being yourself and being comfortable in your own skin.
