The Most Important Question Facing the Modern Business Guy

I was recently in the US, on our annual back-to-school shopping blitz.  Usually, I’m the travel agent, chauffeur, sherpa, and wallet.  I do not typically partake in the shopping extravaganza.  I serve a specific purpose on these trips…get out of the way of my wife and daughters, and be prepared to pay, without asking any questions.   That’s the accepted, and expected, role of Daddy and Hubby on these family excursions.  Make sure there’s a pool in the hotel that’s more than 3 feet deep-(I learned that one the hard way), that there’s American money in the wallet (or at least easy access to it when we arrive), and that I’ve scouted out the nearest location of both IHOP and Chili’s.

I'm the mall sherpa

This time, while guiding my lovely daughters around JC Penney (my favourite US department store, by far), I spotted a pair of shoes.  A very suave pair of brown lace-up dress-shoes.  They were on sale (bonus), and they had a pair in my size (super bonus).  I tried them on, bought them, and slipped back into the rhythm of paying for my daughters’ purchases and carrying bags before they even noticed I was gone.  I’m a speedy and stealth shopper that way.

Spiffy brown shoes

The rest of the trip went according to plan, and we arrived home the next day, just in time to rip off the tags and start the first day of school.  As my daughters tried on their new clothes and new shoes and wondered what to wear on Day 1, I also contemplated my new shoes.  How nice they were.  How comfortable they were.   What suit to wear with them.

Piles of new clothes at Casa Slater after a US shopping blitz

What to wear.  OMG.  What to wear.  Being new to the brown shoe club, I had no freakin’ clue what to wear with brown shoes.  Well clearly a brown suit.  I don’t have a brown suit.  A beige linen suit?  Who has a beige linen suit?  Well, Roger Federer, for his days at Wimbledon.  That’s who has a beige linen suit.  I have blue suits.  Black suits.  And an ill-fitting grey suit.  And lovely new brown shoes.

Roger Federer can pull off a beige suit.  Betcha he's wearing brown shoes

I immediately felt like my wife every time I tell her that we’re going to an event that requires a dress.  With the exception that I was pretty sure that I didn’t need panty hose.  Staring at the closet wondering how I’m going to match these shoes with even one piece of clothing that I own.  How could brown be so challenging?   I have black shoes, just like every other dude.  And I also have a pair of ox blood loafers.

My oxblood loafers.  A safe choice.  I know how to wear them.

So I turned to a source that has never let me down.  It’s a little secret I call the world wide web.  I figured that if I had this question, some other guy, somewhere in the world has also had it.  So off to the interweb I went.    Well, as it turns out, when you google when should a man wear brown shoes you get 67 million responses.

67 million entries.  This is clearly a crisis

Yes it’s ok to wear brown shoes with a blue suit.  Yep, even with grey.  But never with black, and let me think about the grey again.  It depends what company you work for, and in what industry.  It depends which side of the Atlantic you happen to be going to work on, and for that matter, it depends on which side of the English Channel you call home.  OMG, I’m a schlub from Hamilton with a meeting in Toronto with an insurance company.  Can I wear the brown shoes or not?

Which shoes go best for a meeting with an insurance company?

So the 67 million responses effectively created 67 million more questions.  As it turns out, black shoes are black shoes.  Black.  White shoes are white shoes.  White.  Brown shoes are not necessarily brown shoes.  They’re Oxblood.  They’re Chocolate.  They’re Tan.  They’re Burgundy.  They’re Cognac.  They’re Walnut.  Holy Shit (coincidentally, another shade of brown).  Not only do I not know whether I can wear my dandy new shoes, I don’t even know what colour they are.

Who knew BROWN came in its own rainbow?

In my desperate search of the web, I learned that there is a long-standing controversy about brown shoes.  Who knew?  Well, clearly the 67 million searchers before me.  The one thing that seems very clear is that brown shoes are definitely out for a job interview.  This from a website called wallstreetoasis.com.  How could Wall Street be wrong?  I learned that in Europe they think Americans (and I’ll include Canadians in this too) look ridiculous wearing black shoes and a blue suit.  Well call me ridiculous, because I’ve been doing it for 30 years.

Old faithful, the black dress shoe.  Who knew you were ridiculous when worn with a blue suit?

I learned many things on my serendipitous trip across the web that day.  Some people think the belt has to match the shoes, while others think that’s an outdated fashion rule.  I did learn that your belt doesn’t need to match your shoes if your shoes are white bucks.  I also learned that white bucks are badass.  Thumbs up, Pat Boone!

Oh, please don't let white shoes be making a real comeback

I learned that the Queen’s banker, Cazenove, apparently never promoted anyone who wore brown shoes to work.   A sample of the comments related to that particular news story (yep, it's a news story) included:

·      Brown shoes are not ok in the city.  Never have been, never will be.  Remember,  never wear brown in town.

·      No brown in town

·      Brown shoes are fine.  So long as you work in IT

·      Maybe on a casual Friday in the summer if you’re wearing chinos, but never, ever, with a dark suit

·      As a young person, well under 30, not only would I never wear brown shoes, I also always wear a tie.  A gentleman should always present himself well.

Black shoes for the Queen's banker?  Black shoes for me.

So the long and the short of it is that I got dressed in my navy suit and brown shoes.  I took a long look at myself and changed to black shoes.  I immediately felt the stress drain away.  Ridiculous?  Maybe.  Stressful?  No way.  So off I went to the big city for my meeting with the insurance company.  I was met in the lobby by my counterpart.  He is far more dapper than I could ever dream to be.  He was wearing a summer-weight grey suit and what else?  Brown shoes.  And he looked swell.

I just don't think I could pull it off.