Dress for Success Golden Boy, But Wait... - a podcast by Fixed Cost Financial

When I began in the investment advisory business in 1986, we were expected to wear a suit. The same was true of the police department where I had worked previously, but a jacket and slacks were more common. Those who wore a jacket and pants at the advisory firm, however, were pushing it. I didn't push it, and thus I've always had two dozen suits of various weights for northern cold and Florida damp climates. The dress code was traditional but not as rigid as that of the 1960s, what some would call the Mad Man era. In the 60s, my father had several basic black and blue suits, many white and a couple of blue shirts, and many black and medium blue and red ties. All of his shirts were pressed, folded, and in thin plastic bags. Shoes were always black wingtips. The only flare was a white pocket stuffer, that was firmly held in place and presented a straight white line across the left breast.

Then the late 60s came along, and someone higher up said the company had lost its way by not keeping up. Leisure suits were expected to be purchased and worn. Younger customers expected a hip executive and the world was changing. My father struggled with the change, and didn’t like it.

I have a picture of friends and me from the 80s when the television show Miami Vice was popular. It’s a polaroid of four people about to go out for the evening, and it’s one of those that today brings out the comment, “what were we thinking?”

In March of 2019, Goldman Sachs announced that suits and ties were now optional. I found this announcement unimaginable as I know of several men who were dismissed for violating the dress code. In one case, while at lunch at a small diner in New York City, two traders took their jackets off as the air conditioning was broken and the jammed pack diner was extremely hot. A partner at the firm spotted the two, and upon their return, they were greeted at the receptionist desk with a security guard and a box for each containing their belongings. They were terminated and walked out the door. While jackets could be removed while working as a trader, a golden boy was never to be seen outside without their monk-like bespoke suit, shoes, and tie. I understand what some will go through with the new flexible dress code that favors a more casual environment.

The polished and pressed suited employee looks to be a thing of the past, at least for the next few years. This signals the firm grasp of a widespread change in workplaces across America. Although dress codes have relaxed, they are now more complex than ever, and I’ve dealt with the problem for decades. When it comes to administrative staff, I’ve resorted to a uniform shirt and solid color matching slacks at times. Why? Because I’ve had people at times who abused the flexibility and pushed the limits. I feel that there is always a need for a sense of uniformity and professionalism, no matter the level of formality, at all places of work. From the coffee shop to the bank, I sense there will be a growing trend towards corporate slacks and shirts. And it’s not like I’ve not seen this trend for years. While attending Network After Work events, I rarely see a man in a suit and tie, but the corporate polo is typical.

Clothing, coupled with demeanor, are outward expressions of self, beliefs, and lifestyle, and people today definitely resist regulation; unless you wear a red MAGA ball cap, and then for some you’re a punching bag.

When setting a dress code, it's essential to think about who you are, the circumstances, and the image you want to put forward. If a lawyer shows up for court in jeans and a T-shirt, there’s going to be a problem, but for the same lawyer attending a creative meeting for a startup, some may be fine with it, others not.

In today’s Connecting Dots podcast, I will discuss the opportunities for those who have mastered the art of adapting to the situation when both in and out of the office and how much of what many are struggling with is not new, just different as times change.

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