The Mentorist

Can’t Take My Eyes Off You: Dressing for the Office

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Had they called each other that morning to coordinate outfits?

I walked into the conference room and, for a moment, thought I’d caught the second act of Jersey Boys.  There stood our CEO, surrounded by members of the company’s executive team –- four of whom were wearing virtually the identical outfit as our leader.

I probably wouldn’t have thought twice about this if I’d walked into a meeting at my old law firm:  Pinstriped suits and rep ties were worn by everyone of the male persuasion.

But the dress code at my new company was decidedly ‘free range,’ allowing people to wear most anything that wasn’t nailed down.  (Oh, the days!)

Interestingly, these five guys were having none of that freedom:  Each wore a striped, long-sleeved dress shirt; a black leather belt with brushed silver buckle; straight-legged, medium-wash blue jeans; dark socks; and newly polished, black calfskin oxfords.  Apparently, the only deviation tolerated within this Gang of Five was the color of shirt stripes.

The other men in the room had ‘busted loose’ and put on whatever they darn well felt like wearing.  Or could it be that they just didn’t ‘get it’?

I looked for some pattern in the situation:  Why were these four executives, in particular, playing the Four Seasons to our CEO’s Frankie Valli?  Why not some of the other men, instead?

I soon realized that the group of followers comprised the CEO’s hand-picked successor, that successor’s successor and two other ‘C’-level officers decidedly under-qualified for the ‘top dog’ positions they’d found themselves in.

In other words, the CEO’s doo-wop boys were the two next most powerful executives in the company and the two executives who were probably least qualified to do the jobs they’d been assigned.

Did dressing like the CEO help influence – at least, subliminally — the CEO’s choice of successors in the chain of command?  And did it help — albeit, subconsciously — boost the CEO’s regard for the two strugglers?

I say, “You betcha!”  (And this is before taking into account that all five of them drove the same make of car….)

The anthropology of workplaces fascinates me.  I believe that, by adopting an anthropologist’s observational habits vis-à-vis your office’s culture, you will start making choices that are better ‘thought-out’ — and that will lead to consequences you’ve been able to anticipate and plan for. [See ]

A part of workplace anthropology involves studying the tribal dress:  How is the leader decked out?  Who else has adopted that dress?  What status do the adopters have in the leader’s eyes?  How much power?

Once you’ve figured out the answers to these questions, you can consciously decide whether you also want to adopt the leader’s dress.  And — if you don’t — you can make a considered prediction as to the career benefits (or costs) of wearing a distinctively different set of duds.

The extent to which my four colleagues mimicked the CEO’s dress was laughable.  (Don’t they ever yearn for solid-colored shirts…?)  Nonetheless, your workplace image will improve if you adopt a watered-down version of their dressing philosophy.  Try following these two ‘rules of thumb’ when deciding what to wear to the office:

  1. The ‘Already Promoted’ Rule

    Dress like the people who are one level above you on the company’s org chart.

    You want to be promoted, right?  If so, start looking the part.  That way, the people you’ll need to sponsor your promotion will have an easier time envisioning you in the new role.

    You don’t have to ‘matchy match’ others down to their shirt stripes.  But your choices of what to wear should fall within the same categories as theirs:  They wear blazers?  You wear blazers.  They wear loafers?  You wear loafers….

  2. The ‘Print Ad’ Rule

    If you’re a woman and everyone at the next level is a man, ask yourself this question when deciding what to wear:  Could I appear in the same print ad campaign with these men and look like I ‘fit’?

    how to dress for the officeIf the answer is ‘yes,’ you’ve discovered the female version of your workplace’s tribal costume.

    Whether the men in your office dress like they just stepped out of a J. Crew catalog or an Armani ad, you should look like you belong in that same photograph.

Of course, rules are made to be broken — strategically. Someday, I’ll tell you about the time I wore Jimmy Choos into a conference room full of docksiders….

Author: Jane E. Owens

Jane E. Owens, The Mentorist’s chief blogger, has spent her career immersed in the business and culture of corporations and law firms. A former general counsel and corporate lawyer, Jane is fascinated by those who thrive (as well as those who don't) in the professional world – and, through her mentoring practice, hopes to increase the ranks of the former. To learn more about Jane or suggest topics you'd like The Mentorist to discuss, go to:

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