Personal Style, Part III: Confidence & Context

This is the third installment in a series about events that shaped the way I dress. These stories may or may not be relevant to you but hopefully they offer a perspective that isn’t often seen on the internet. Previously: Part I, Part II.

If you’re reading my blog then you’re probably someone that puts some thought into what they wear. It’s a sad truth that many men do not dress as well as they could or as well as was expected historically (although there has certainly been growing momentum to change this). Here in California, most men dress very casually in and outside of the office. It takes some serious guts to go against the grain. Being “that guy” can be hard at times, especially when you’re first learning about clothing. When you dress well it is often interpreted by others as an open invitation to remark and critique; nobody comments on what the frumpy office drone is wearing, but once you start to make a change people often seem more comfortable in commenting on your attire. That’s why dressing well takes confidence.

At the same time, it’s important to keep in mind the context that your clothes are in. Although “dressing for yourself” is a great thing to do, it’s important to remember that the way you dress (whether good or bad) will change the way people think of you and interact with you.

A couple of years ago I was an intern for a firm in San Francisco. After years of construction work over the summer I was eager to work in a white collar environment and dress the part. I made a point of wearing a tie every day, even though ties were virtually nonexistent in the office of 300 people. I assumed that my tie-wearing was a move that showed I was a professional and could be taken seriously, but instead it did the opposite. It showed that I was not well tuned in to the office environment and was more interested in my own wardrobe agenda than the acceptable office attire. My tie-wearing made me stand out, and not in a way that an intern probably should. I later found that one of my managers expressed concern to a coworker that I was “uptight” because I insisted on wearing ties (anyone who knows me well knows that this couldn’t be further from the truth). In my attempt to fulfill my role as a professional I had unwittingly isolated myself and effectively done the opposite. Fortunately, my hard work paid off and I was able to land a full-time job at the firm; however, my “professional wardrobe” was not as beneficial as I had hoped.

It does take self confidence to dress well but it must be done within the context of the environment you’re in. This is something that has taken me a long time to realize and is something that I’m still working on. I assume that dressing elegantly is a skill that comes with time and experience, and recognizing that hopefully means I’m on the right path.

There is a difference between “that guy who always looks nice” and “that guy who is always too dressed up.” They way you dress should be guided not only by your personal interests but by the situation you’re in. After all, the guy that wears velvet slippers to the office isn’t really any more stylish than the guy who wears sandals.