Jon Stein, 33, is chief executive and founder of Betterment, an online investing brokerage and advisory company, which he started in 2008. In 2010, it won TechCrunch’s Best Start-up in New York award.
Jacket and tie by Windsor Custom
Windsor Custom is a New York company that makes its clothes in a bar called the Ainsworth. You actually go to the bar to get everything tailored. I love this label because I want to support New York-based companies like ours.
This is a navy blue knit blazer with a colourful white, black and red lining. I don’t wear a blazer except on days when I have a presentation or meeting. Or Fridays. We have “formal Fridays”, the opposite of casual Friday, since start-ups are so casual and I don’t want us to be “kids in jeans with flip flops”.
Cardigan by Club Monaco
My wife works at Club Monaco so now half my wardrobe is Club Monaco. This is super comfortable and I can wear it to a board meeting or to a dinner.
Shirt by Save Khaki
I got this during a sample sale. What isn’t Club Monaco in my wardrobe is mostly Save Khaki. The shirts are quite fashionable and form-fitting but light enough to wear to a professional meeting.
Jeans by DL1961
I almost always wear jeans to work. Even when I presented on stage to a thousand people at the NY Tech Meet-up, I wore jeans because that’s the tech look in New York. I’m big on the idea of uniforms. I went to a high school where we had uniforms and it’s great to get up and not have to think about it. A shirt and jeans is exactly that.
Watch by Gucci
This is as simple as it can be in terms of watches. I keep things simple so I wear silver a lot. This was a gift from my grandmother. It suits what I do for work because it’s simple enough to wear every day but to wear a watch gives you an air of professionalism.
Shoes by Esquivel
They’re comfortable and dressy. I almost never wear sneakers to work even though everything else I wear is more casual. You can be judged by your shoes so having good ones at work is important.