Making first impressions

Photo credit: Lenny Gilmore

A client recently texted me for some advice on what to wear to a unique situation outside of his typical work environment. Usually for his daily career in media, he wears a suit and tie and I’m rather proud to say looks quite sharp. But he was having some trouble deciding what to wear for an important meeting with a local politico outside his office that would take him to multiple locations throughout the day on a weekend. 

I’ve found this is a very common area where many men struggle to know what to wear. We have a good idea of what to wear bumming around the house, for days at the office, and for special formal occasions. Those are circumstances that are easily defined to the point of almost being formulaic. When a dress code is known, it’s a snap and requires no thought. 

But it’s those in-between situations that tends to trip you up. What’s appropriate for an outside the office work event? What if it’s on a weekend versus after-hours on a weekday? What if the dress code is the dreadfully indecipherable “be yourself”? Can I wear “dressy jeans”? 

I’m convinced this area is where most attempts to be stylish fail. The lack of direction means you don’t have a good frame of reference to build from when putting together an outfit. The result is often a mishmash of super casual and too formal, putting yourself in a no man’s land. There is time for experimentation, but this is a time for certainty.

Before I ever wrote about clothing, I found myself in this predicament. Working for the Illinois Senate communications department, there were days when the legislature was in session and I knew what I would wear: a suit and tie. But it was the off days that had no dress code that I found myself stumbling, wearing a polo and baggy khakis (untucked) and running sneakers. Unsurprisingly, I failed to make a great impression with the lobbyists and their clients I ran into at work. I looked like a sloppy intern. 

The lesson I eventually learned was to just dress up. Wear the suit and tie, even thought it wasn’t required of me. If I was going to meet someone in the context of work, it became important to me to always appear professional. You don’t get a second chance to make a first impression. 

I understand not everyone will need (or want) to wear the same worsted wool dark suit for these outlier events that come up in their lives. Perhaps it makes sense to get a suit in a more casual fabric like cotton or with a bolder pattern. Or simply have a sport coat and odd trousers on hand. But experience tells me that as you navigate your industry over the course of your career, you’ll get better at gauging the temperature and expectations of these sorts of things. And more importantly, you won’t regret being a bit overdressed; but you will feel uncomfortable if you are underdressed. 

I reminded my client he always looks great in his suits and is always confident wearing them. I told him wearing a suit will give him that same confidence outside the office at this meeting. 

“Suit it is,” he replied.