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How To Figure Out What To Wear To Work


I was in a wardrobe conundrum. What does one wear to a summer outdoor wedding when one is over fifty? When choosing a look, how does one account for possible humidity, potential hot flashes, and a pandemic dependence on flip-flops with arch support? 

Four hours at a local mall was a waste of time. My only purchase was a cookie.

woman shopping

On the wedding day, I stood in the elevator in a black dress with a blazer, defeated. This was an old work outfit. A woman who appeared to be my age entered the elevator and looked me up and down. "Going to a wedding?”

"Yes," I replied. "Do you think this outfit is okay?" I was looking for reassurance from a stranger.

"What's the attire?”


"Hmm, that can be anything from a prom dress to shorts. I've got a wedding tomorrow. Same thing. I'm wearing capris pants. It's probably wrong, right?”

"I don't know.”

"You look nice, but I'd call that business casual.”


We went our separate ways. She was right. I was more business-y than cocktail-y. My fellow wedding attendees in their gauzy floral sundresses were polite and did not mention it.

Now I'm in another wardrobe conundrum. After years of working from home, I shall return to an office setting.

I used to know how to dress for work and was rather good at it. In days of yore, business attire was my jam. Blazers, blouses, skirts, and suits—no problem! But that was one-thousand years ago, also known as the nineties. These days, business attire is a spectrum, and I do not know where I fit.

woman in casual outfit sitting at her desk's guide to business attire outlines six versions of the most common business attire. Six. It begins with casual attire. Casual attire allows for T-shirts and jeans. If you want to wear open-toed shoes, go for it. While I'm a fan of my flip-flops, I just don't feel pulled together enough in beachwear at the office.

I step up the ladder to smart casual. In this dress style, you're adding a trendy extra to your casual outfit. Trendy is obviously my problem. Perhaps I should climb to the next tier, to business casual. With business casual, khakis are a staple. I hate khakis. This leads me to the top two tiers, business professional and business formal.

coworkers looking at laptop

Let's start with business professional. describes it as, "A traditional form of attire used in more conservative settings or companies with strict dress codes. You might wear business professional in industries like finance, government, or law. Business professional clothes should be well-fitted and may be tailored to fit you specifically." Okay, this is one I recognize. I used to dress this way. This might be it.

A look at the next tier, business formal, tells me that one only need to dress in business formal for award ceremonies, benefits, or other evening events. Okay, so that's out too.

With edicts of the business professional style in mind, I prepared for a meeting at my new work and grabbed one of the standby classic suits that hang in my closet. It was stiff, too formal, and as my mother used to say, "I looked like I was trying too hard." Those old suits don't suit me anymore. Business professional doesn't fit me in this stage of life, even though I am going into the office.

See? A conundrum.

coworkers walking down staircase

Then I found this quote from designer Miuccia Prada, "What you wear is how you present yourself to the world, especially today when human contacts are so quick. Fashion is instant language.”

My wardrobe, my instant language, as it were, needs to say, "Hello, I'm happy to be here, but it isn't my first day. I'm experienced." My attire needs to communicate that I'm in my fifties, but confident! It needs to show that I'm up-to-date but also not swayed by passing fads. I want to wear classic clothes but also demonstrate that I understand it's not 1998. And above all else, my wardrobe needs to be free of Spandex.

I had no choice but to invent a category. Get ready, office, Business Mrs. Roper has entered the meeting. Let's get to work.