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(Opinion) You are Not Steve Jobs: Why You Shouldn’t Wear the Same Thing Every Day

If you are what you eat, as the saying goes, clothes have a similar impact: you become what you wear
By Sheree Gotuaco |

It takes only one chance to make that impression. Will you be ready when the opportunity presents itself?



There’s a growing trend in tech: Some founders are increasingly opting to wear the same outfit every day as a kind of self-imposed uniform. If they decide that their outfit is sandals, khaki shorts and a white-collar shirt, they’ll wear this no matter the occasion, from pitching to seasoned venture capitalists and leading business development with potential clients to interviewing employees and negotiating with government regulators.


This wardrobe minimalism in the tech world is of course inspired by Steve Jobs, who famously wore blue jeans, a black turtleneck and New Balance sneakers at all times, even when introducing category-defining products like the iPhone and iPad to legions of adoring Apple fans. Jobs adopted this get-up to reduce his cognitive load: Every minute he saved not thinking about what to wear every morning was a minute he gained for thinking about more important matters, like business strategy or product development.


While Apple products are still a consumer staple, it’s Jobs’ fashion sense that may be his greatest legacy, at least in the startup and tech world. Everyone from Facebook CEO and co-founder Mark Zuckerberg to Snap CEO and co-founder Evan Spiegel are donning their own signature outfits—an endless array of gray t-shirts for the former and a white shirt and black jeans for the latter—no matter what the fashion police may say. Further encouraging this trend are buzzy articles that espouse the virtues of wearing the same clothes every day, the implication being: Simplify your wardrobe, and you, too, young founder, can grow up to be like Jobs, Zuckerberg or Spiegel.


But things are not that simple. They, of course, never are. Back here in Asia, much of our workforce belongs to traditional businesses, where a lot of dealings and relationships are still primarily face-to-face. A young executive or one of his superiors may not want to be bothered to deal with wearing different clothes every day, but the people around him—his colleagues, his clients, his investors, his partner, and his subordinates—will still make decisions, oftentimes unconsciously, based on how he or she dresses: Is this a person I want to give my business to?



Does this person exude confidence and show the capability to close accounts? Should we spend on training this executive to represent our company in the international market? Is it worth investing my time coaching this person with an eye for a long-term future at the company? In other words, clothing makes the man or woman—and the impression.


Of course, the people who buy into the concept of wardrobe minimalism are true disciplines of the philosophy, so they will need more convincing beyond these gentle pointers. I would thus like to approach the argument on their own terms: The oft-mentioned “cognitive load” or “decision fatigue” that they believe they reduce through a signature outfit in fact actually exacts a high opportunity cost on their professional life: Yes, you’ll reduce friction in your morning routine, but you won’t arrive at some world-changing decision or insight in the few additional minutes you gain.


On the other hand, if you spend more time carefully thinking about what to wear each day, the investment you put in will generate exponential returns. No matter what these articles will have you believe, it does pay off to dress for the occasion. You will command the attention of investors or clients if you pitch to them in a proper suit, you will connect better with your employees if you’re dressed down for the after-hour beers, and you will sell more if you match the business casual attire of your enterprise clients.


The author, Sheree Gotuaco, says that when you choose not to think about your wardrobe, "Yes, you’ll reduce friction in your morning routine, but you won’t arrive at some world-changing decision or insight in the few additional minutes you gain."



If you are what you eat, as the saying goes, clothes have a similar impact: You become what you wear. As the respected designer Tom Ford says, “Dressing well is a form of good manners.” It takes only one chance to make that impression. Will you be ready when the opportunity presents itself? Will your team be? Will your family members be ready when they enter into the corporate world and vie for career advancement?



At every level of my professional life, I’ve witnessed the impact of fashion in action: All things being equal, the person who is able to present themselves better always nails it. The great thing about this truth is that a person’s style can easily be improved with proper advice, which is always free for the taking. That’s why it’s become my advocacy to help people dress better.


Through my fashion-tech company, Stylist in Pocket, we have helped countless people from different walks of life, different industries and different life challenges transform themselves solely through practical dressing advice. Their confidence increases, dressing up becomes fun again, and they save time and money by not having to shop outside their homes again. The experience is as gratifying for them as it is for our team of stylists. Because above even stocks, real estate and businesses, the best investment a person can make has always been and will always remain the one thing we far too often overlook: ourselves.  






Sheree Gotuaco is the CEO and Founder of fashion-tech company Stylist in Pocket (SiP), which provides free personal stylists with home visits within greater Metro Manila as well as helps individuals nationwide with its curated clothing parcels. SiP has helped thousands of Filipinos improve their sense of dressing, and in extension, their inner selves and their careers. Filipino professionals and their families interested in using SiP should visit their website to sign up, while business owners who want to avail of corporate styling workshops and services or uniforms are encouraged to send a message to

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