When in doubt, overdress.

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This sage advise is not from me but from fashion mogul Vivienne Westwood. She does have a clear conflict of interest but I’ve long learned that this philosophy can save the day.

To some, how we look shouldn’t and doesn’t matter but my experience has been that people do judge a book by its cover. That’s just a human trait.

This topic may seem a tad superficial but I think that appearances are important at work. A book shouldn’t be judged by it’s cover, but often is. So, I recount below three times when I felt underdressed and thought I should have known and done better. Hence my mantra, when in doubt, overdress!

The time at a trade show

Once in my younger career, I was part of the team mandated to help prep our stand at a trade show in Germany. The show started on a Monday so myself and colleagues joining from France and Germany had to fly in during the week-end to prep the stand on Sunday. Having done this many times before, and often on my own, I knew what it involved. Trade shows before opening day are complete construction sites. The halls are busy with builders building stands, littered with boxes and crates, in deafening noises of hammering, power screw driving, shouting, and all that in a sweaty environment. To put it simply, it’s not glam. In this occasion therefore, I showed up in sweats and snickers. Literally. And no make-up of course, because why? I knew that it would be a tiring and sweaty affair. There was work to be done, like unpacking all boxes with marketing material, set everything up on the stand, and make sure we had everything set-up, the fridge, locker room, plugs in the right places, screens. This also required as it usually does lots of walking up and down the aisles to meet the various services and vendors on site to make sure everything is set-up for the next day. Well, let me tell you that my five other colleagues, men and women, were all dressed in business casual attire. As if they didn’t know what they were there for! It goes without saying that I got some judgemental looks from a couple of them when they saw me. At that time I felt out of place even tough I was dressed appropriately for the task at hand, I felt under-dressed and after some reflection I was actually under-dressed. This was a work task and what I failed to consider is that even in such moments, I am still at work. My other colleagues dressed as if at anytime, the big boss could have showed up just to check how things were going. And he could have.

The time flying for business

I had a Monday flight from London to Vancouver, so a long haul. 9h40 to be exact. That morning I made my way to London Heathrow airport by tube. It was a long journey with a change at South Kensington station to get from the District Line to the Piccadilly Line to Heathrow. I was in the morning rush hour and while walking the busy underground hallways to reach the Southbound platform of the Piccadilly Line, I came face to face with… my boss! He was going to work, and I was going to the airport. This was a most embarrassing moment for me. I was dressed in thick leggings, an old jumper and comfy – but worn-out – ankle boots. I had no make-up on – which shouldn’t be a problem – and my glasses on. But worst was my hair. I am a black woman, so to avoid my hair drying on the plane I had “styled” it in 4 big plaits and wrapped the edges with a silk scarf that I usually wore for sleeping. Oh, this was bad. I looked like I was in my PJs. But really I just wanted to be comfy for the flight. I could see the look of confusion on my boss.

– Hi Mimi, where are you going?

– Oh hi John, I’m on my way to the airport to catch my flight to Vancouver.

– oh yes, of course….

Then he proceeded to look at me from head to toe, still confused but wished me a good flight and a good meeting over there. At that time I was really caught off-guard. I thought, well I am flying and meeting any customers until the day after my arrival so all is good. This is my time. I need to be comfortable. The thing is this was a business trip. This was work time. I should have been wearing comfy business clothing. Who knows who you’re going to meet on your journey? Well now I knew… you could meet your boss!

The time at a sales meeting

We had a sales meeting and the dress code was casual but everyone came in dressed to impress and I was dressed casual… I can’t believe that with all my experience I had fallen for it it again. In the grand scheme of things, it’s not the end of the world, but it’s a big deal of you feel uncomfortable or out of place.

One last time, say it with me. When in doubt, overdress!

Disclaimer: my experience is that, especially at work, a book is judged by its cover. However, I certainly don’t advocate that we should focus entirely on how we look to others.

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