Four (And One) Items I Regretted Wearing to My First Job

by Leda Marritz

It started with my interview, to which I wore a “nice” black T-shirt, jeans, and sparkly sandals that I borrowed from a friend of mine named Lessie. I was 22 years old and had no idea what I was doing.

In my defense, at the time I didn’t realize it was a proper interview; I thought I was just meeting up with someone to talk about a potential position.

But it was a proper interview, and fortunately it was with a lovely man, a distant connection of Lessie’s mom. Although he was the C.O.O. of the company, and wore a suit to work every day, he was generous enough to overlook my totally inappropriate attire. During our meeting he asked me what I was reading, and thank god it was something respectably interesting (I still remember: Out of Egypt, by André Aciman, which had been recommended to me by my brother).

During my first week at the job, my new colleagues took me out to lunch. It was August and plenty hot out, and I was wearing a top I considered cool — it was made of a mesh-like material, bright orange, and sleeveless, with an asymmetrical seam across the front. The kind of top you might wear to a party, but definitely, definitely not to work. I actually still have it and still like it, but when I think of wearing it to work, it makes me cringe.

I was aware that people in the office looked more professional than me — even the other 22-year-olds — and there were times when I felt awkward and embarrassed that I didn’t look as nice. A combination of thriftiness, rationalization (“I look cool in my own way”), and genuinely not realizing the importance of a baseline amount of polish kept me from running out and dropping my entire meager paycheck on a new wardrobe.

The office was near Astor Place, in New York, and my friend and colleague Valerie and I would sometimes go shopping at lunch. Valerie always looked so nice, so put together and trendy. Eventually, and with her encouragement, I made some small improvements, such as fancy jeans from Express (dark, slit pockets and a kind of sheen to them) and collared shirts.

Basically, a slightly upgraded version of my interview outfit.

Despite my best intentions, there were still a few mishaps. Like the time I bought a legitimately nice blouse from Banana Republic with a drapey neckline that I later realized was very revealing if I bent over even slightly.

After two years at my job, I decided to move on. I was leaving New York entirely and heading to San Francisco. I had learned enough to know that to get a new job, one where I was not being interviewed by a sympathetic friend of a friend, I might need to up my clothing game.

I asked a senior woman at my company, who was probably in her mid-30s at the time and who dressed very sharply, in elegant separates with stockings and heels, whether I should buy a suit.

“You’re moving to California?” She laughed. “Yeah, I would not recommend buying a suit.”

I didn’t. And that’s something I’ve never regretted.

“The Grindstone” is a series about how we work today by Billfold writers Leda Marritz and Stephanie Stern. Looking for advice? Want to see a specific issue covered in the future? You can email them here.

Leda Marritz lives in San Francisco. You can read more of her writing at