I remember it like it was yesterday. A few years ago, I was in hotel conference center in downtown Minneapolis at one of the premiere events for technology executives. It was a high-end event that attracted the top leaders in the area. I, along with everyone else, was wearing a suit. The lights dimmed, and the keynote speaker walked on stage. A hush fell over the crowd. It was Palo Alto Networks founder and CTO, Nir Zuk. He was wearing a t-shirt, jeans, and bright blue Adidas sneakers.

With full confidence, he gave a rousing speech about the future of threat protection then walked off the stage with a vigorous applause. I don’t remember the content of his speech, but I do remember his confidence and impact as an influential speaker.

He had a reputation. He had name recognition. He did not have (or need) a suit. For some time, I’ve pondered that experience. What does this mean? Did he not care? Did he think, “I don’t need to dress up for you, but you need to dress up for me”? Was it a completely intentional way of communicating confidence and progressiveness? Is it just a California thing? Or am I just over-analyzing all of this?

Rebels

I recently read the book Rebel Talent: Why It Pays to Break the Rules at Work and in Life, by Fransesca Gino. The premise of the book explores how successful leaders break with convention to succeed. She described how Mark Zuckerberg wore his signature hoodie to a Wall Street investor forum that resulted in the biggest tech IPO in history, peaking at $104 billion. Bill Gates and Albert Einstein had a similar sense of fashion.

I relate most to Steve Jobs in this regard. Unlike the others I’ve mentioned, he started off wearing a business suit while he was growing Apple to be the company it is. Only once he established his success did he switch to the black mock turtleneck and jeans that he became known for.

Dress for your day

The places I worked before CHS were pretty causal. I was used to wearing comfortable clothes to work every day. When I first came to CHS three years ago, it was relatively formal compared to the other companies in town. I had to go clothes shopping. About two years ago, we introduced a new dress code which was entitled “dress for your day.” This was empowering for individual judgement on what made sense for you. If you are spending all day with your co-workers, feel free to wear jeans. If you are meeting customers, or speaking to the board, you better kick it up a notch.

To this day, I wouldn’t really consider CHS a casual work environment, but it’s rather mixed. Everyone has their preferences, and some vary their attire more than others.

Don’t dress for the job you have, dress for the job you want

Perhaps you’ve heard this saying. It’s meant to convey upward momentum in the formality of your dress, if you want to advance in your career. Some of the tech geeks that I hang around with could interpret this quite differently and wind up in an disciplinary meeting dressed as Boba Fett.

Dress like a technology executive

It’s no secret that I see myself as on my way to becoming a really impactful technology executive. Unfortunately, I was tragically born without a sense of fashion. I’d much rather spend $800 on a new Lego Millennium Falcon, then on a new business suit. I even think I could get more business value out of the falcon, somehow. I have friends that are into fashion. They go shopping at places other than TJ Maxx. They have personal clothiers, whatever that means. It’s just not me.

I am admittedly in the land in-between. I do not have the self-confidence to wear a t-shirt, jeans, and bright blue Adidas on stage in-front of a crowd of business suits. I put on the suit when the occasion calls for it. I look formal in my LinkedIn profile and on my blog website.

I somewhat feel like Steve Jobs. I need to put on the suit until I have accomplished enough to where I don’t need to. I’m not sure if or when I will cross that threshold, but I know I’m not even close.

If I take the advice of Francesca Gino, I should embrace my rebel streak now, regardless of how uncomfortable it makes me and others feel. It could be the very thing that sets me apart and creates the success I’m looking for. Steve Jobs’ suit may have actually slowed Apple’s success. Perhaps Nir Zuk didn’t have the self-confidence to dress informally, but forced himself to because he knew it would make him more impactful.

What do you think? In all seriousness, I am not looking for fashion advice on this blog, so please don’t give it. Instead, I’d love your opinions on the dilemma. I’m convinced that many highly successful technology executives do not wear suits. Yet, of my free will, I don the suit when I feel like I should. Do you?

Ultimately, I’m taking the “dress for success” axiom and flipping it on its head. I don’t know if it works or not. Tell me what you think in the comment section below.