Last week, a member of my Advisory Committee, Tom Leisle, suggested I attend the Young Professionals week of activities. Since by no stretch of the imagination am I a young professional, I was perplexed about what to wear. Apparently, time had caught up with me and now I would to be the oldest person in the room.. How on earth did this happen?

When I asked my friend Amy Egan if I should blog on this topic, she said definitely – what woman doesn’t wake up with the question of what to wear? And the question is more important especially when a woman reenters the workforce or pivots careers.

The History of My Professional Wardrobe

Growing up in Appleton, I went to Catholic schools and wore a uniform all day. Also, I was in a family that played sports and attempted musical instruments. Aside from the school uniform, outfits consisted of clothing worn to races, games, or practices.

Going to college in Saint Louis opened my eyes to life in a bigger city, especially one where there were so many cultural events to attend. Also, being further South, people dressed better and I learned the value of my clothing and how fun it was to dress up. My college roommate explained to me that jeans were not an everyday staple – she only owned one pair. I was blown away by this!

Then, I moved to Spain for a few semesters abroad. Prior to my departure, my friends from Spain sat me down for an important conversation. They politely explained to me that in order to have a nice time in Europe, the correct clothing was required. They explained that Americans who do not dress appropriately do not like Spain. And since it was their country, and I was their friend, they wanted me to have a good time and like their country.

So, I took their fashion advice and had a few great few years in Europe armed with the correct attire. Just as my friends had warned me, I learned right away that I must look a certain way to be acceptable, and dressing up was a statement about who you were. You were checked from top to bottom every time you entered any establishment – to ensure that you were worthy and you fit the bill. Jeans definitely had to be Levi’s and the right socks and shoes were a necessity at all times. I tried to break free of the clothing rules some days, only to be completely stared at all day long and pointed at with people saying “Americana!” when acknowledging me.

When I moved to Chicago and worked downtown on Michigan Avenue, being fashionable was key. Every day I dressed the part while viewing the latest trendy styles in the storefronts. It was fun, but short-lived.

I landed a job in the suburbs in Sales at Motorola, a company where engineers are the majority. Being in Sales, it was clear the pagers and pocket protectors worn by the engineers could only be improved upon. Fashionable yet conservative outfits were helpful to improve the company image in front of customers.

Many years later, I moved to Milwaukee and became a stay-at-home mom. Dressing up was not on my radar screen. I constantly needed to change my clothes (3x a day) caring for small children or because I was in between clothing sizes being either pregnant or post-partum. I just needed something that fit (for the next month at least)!

After my kids were in school, I started attending events with entrepreneurs and wondered what other women were wearing. I soon found out that there were no other women. Every meeting I went to was filled with men and I really was not interested in their fashion choices.

Throughout my life, there had always been a dress code to follow, whether I was in school uniform, strolling Michigan Ave., or attending playdates. Now I was at a loss – there didn’t seem to be a dress code for people like me.

My Entrepreneurial Style

So, that leaves me to last week. I went to a meeting with the Young Professionals. Being the oldest person in the room was definitely something new. I had to move my wardrobe again, try to look like the woman in her 40s who started her own business and should be taken seriously. And how exactly do female Coworking Space owners look?

So, my friend demanded I answer the question of what I wore as she said everyone would be wondering. I went with skirts and a shirt, or pants and a nice shirt, all with the handbag and coat to dress it up. It think it worked. It feels good to choose my own dress code that fits my new career and personal style – one that I determine myself.

Just when I thought it was over, this morning, in the coworking space, we discussed clothing choices for Spring and how our outfits for the day looked on each of us. The clothing discussion will never, and should never, end when women are together. Our journey continues.

What’s your professional style? We loved discussing our fashion choices in our co-working space, and would love to have you join the conversation. Contact me to schedule a visit.

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