
February 28, 2026
The “Dress for Success” Myth or Why the “It Is Better To Look Good Than Feel Good” Approach Doesn’t Work!
After addressing graduating students this past week at Northwestern University in Chicago, I was approached by four young men wearing beards, asking me if they should opt for a “clean” look. In other words, should they shave their beards?
I explained that I rarely see executives in senior positions sporting facial hair. However, if this is important to them, I advised that they should choose either an industry that embraces total freedom in dress or enter the workforce looking the part, become super successful, and then grow the beard.
Now this seems like fairly straight forward advice yet, in my answer, there is a much deeper and more pertinent consideration upon which all of us need to reflect. Whether you’re looking for your first job, a promotion or changing an established career path, you must align your personal values with those of the industry and ultimately the company with whom you choose to work.
Whenever someone points to the “dress for success” axiom, what we are inevitably embracing is what I call the “when in Rome” mindset. Specifically we are being advised to “dress the part” for the job, the company, and the industry, and if in doubt, “err on the side of conservatism”.
Once again, this sounds both reasonable and simple. But here is the question . . . how do you dress to fit in while still being true to your authentic self? Ultimately it is ‘who you are’ and ‘what you stand for’ that will enable you to pick the right career path as well as navigate the inevitable challenges of a changing market to reach your pinnacle of personal success.
In this regard, I am reminded of the advice offered by a senior executive from a global corporation.
Based on this individual’s extensive and diverse experiences spanning many countries and positions over a 23 year career, she stressed the importance of knowing who you are when she told me the following:
“It is important to recognize that positions, responsibilities and even cultural circumstances will change over the course of time. Therefore the key is to be true to oneself. In essence if you know and have a true sense of what you value and for what you stand, even though situations can from time-to-time become challenging, the constancy of knowing who you are will enable you to adapt to those changes.”
Now within the context of the above statement, you might look at how one chooses to dress as being little more than superfluous window dressing in the overall scheme of things. However if you are not comfortable with how you look or feel, it does not matter what others may think as you are not going to have a good feeling about yourself.
This is the reason why, in all the years I have helped my clients elevate their visual presence, I have never referred to the need to dress for success. I prefer to coin the phrase “Dress for Opportunities.” I can remember talking to a male executive who when faced with a challenging negotiation wore his “power suit.” This sentiment is also reminiscent of the episode of Everybody Loves Raymond when brother Robert wanted to wear his “lucky suit” to an interview with the FBI. When their mother ruined Robert’s lucky suit, forcing him to wear something else, he was anything but confident. I can only wonder what would have happened with the executive had his power suit not been available.
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This takes us back to my four bearded young friends, and how their decision would affect their career paths. If having a beard were that important, then choosing an industry that embraces total freedom would allow them to fit in while still being true to who they are. However, if their beards were simply fanciful fashion statements, then shaving to accommodate the sensibilities of a more conservative job market will not pose a personal conflict. Either decision is the right decision as long as they are being true to themselves.
In the end, caring about how you are dressed is a sign of respect for others—and of most importance – yourself.
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