#AskPedro – What is professional yet functional attire?

This question comes from reader Tom:

I work in a public school and I was wondering as I look around at the other male teachers, what is appropriate, professional yet functional attire? I don’t want to always be in khakis and a polo, yet a suit and tie are overdoing it. Does it really matter? I know our young males need role models, but I’m not sure if my appearance really matters in that respect. 

My response:

I think a lot of men, most actually, ask themselves these questions all the time. How to look well-put together without overdoing it. And does it matter?

Let me start with the latter: it absolutely matters. And we know it does. After all, we groom ourselves, we take care of our homes, we dress well for our best friend’s wedding. Why? Because we know that visuals communicate, from first impressions to a sense of professionalism and occasion. And there is nothing wrong with that. What’s wrong is if we reserve our judgement to just what we see.

In your situation, you want to convey to your students that they matter. You’ve made an effort to dress well (not necessarily “up”) because they are important to you and what you are doing together matters. Not only will you be sending a positive message to your students, you will show them that a grown up is resourceful enough to take care of themselves. Dressing well suggests that you have other aspects of your life in order and that you are not just winging it.

Now, I’m not suggesting that we use clothes to cover up our real selves. That’s why it’s important that whatever you wear you are comfortable and it’s as close to your personal sense of style as possible.

One issue that I run into all the time is that guys feel there are opposites of dress: sloppy casual vs sharp suits. Instead, there is a third approach, which I call “tailored casual.” Outfits that aren’t suits or ties, but are well made, fit superbly and make you look sharp without looking formal. The thing is, I think a lot of guys don’t even try because they are afraid of failing and looking even worse.

Building a sharp and solid wardrobe doesn’t happen overnight. It will take time to assemble these pieces and probably some trial and error to find the look you like. Plus, it ain’t cheap. Building a quality wardrobe will cost you, as it should. The lesson is to invest a lot in a few items: you will look better switching between two excellent pieces than five mediocre ones. To get started, I think sports jackets are a must. You can dress them up with ties or dress them down with open shirts and sweaters.

Another staple for me is the button-down shirt. Brooks Brothers has some of the best around, especially the “new” old ones. The great thing about the button-down is that it is inherently casual – the buttons were added to the collar points, after all, by polo players who didn’t want them flapping around while they played. The shirts look great under sweaters (a cardigan or Shetland crew neck is highly recommended) or jackets or even just on their own.

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Casual. (I love my Shetland sweater.)

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In terms of trousers, I am a big fan of khakis and not just in khaki brown – dark green, red and blue are excellent alternatives. However, most fit very, very poorly. So you’ll need to try on quite a few to get the right fit. Another option, a step above khakis, is flannel. Because of its matte finish, it looks more relaxed than worsted wool, so it’ll go great with a sweater but it’s nice enough to work with a jacket. Grey (mid or dark) is a classic option, although brown looks fantastic too, and more casual.

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Full-rise trousers.

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And finally shoes. Shoes are very, very key to this. Any fantastic outfit can be ruined if your shoes are cheap and poorly maintained. I would strongly recommend spending most of your money on two great pairs of all-leather shoes. Then regularly moisturise, cream and polish them.

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Carmina Vegano from @leatherfootemporium

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Circling back to why all this matters, I remember a story Bruce Boyer told on his recent visit to Toronto. He talked about going to the ballet and looking around at all the people dressed in hoodies and old jeans. This bothered him because the people on stage had literally shed blood and tears to put on this event. It was the highest form of their art and their passion. Couldn’t the members of the audience live up to that effort just a little bit? How about acknowledging how special the evening was with clean, sharp looking clothes? Our society, sadly, is quickly moving away from this idea of occasion. And that is why, Tom, I think it is so important that you set the tone for your students.