I met with an executive who walked into my office wearing similar pants. She was fantastic but something about the ripped jeans and why she considered that appropriate for our meeting makes me have second thoughts about working with her. Am I overthinking this?

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Well I see you’re a creative director. I’m not really sure what that is but it sounds artsy and eccentric. Lol. Is that the type of field you work in? If so I guess that’s fine. But like if this is accounting or law or consulting, etc then maybe yeah it’s weird.

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What if you dress super matronly with bad shoes? Am I allowed to judge you because I find this in terrible taste? Get over yourself.

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I’ve learned that those who dress outside the norm are typically more empathetic and have a holistic view of life. First impressions are the worst impressions - maybe she invests more energy into her internal self than external and is brilliant.

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She got to where she is, likely, by being fantastic and she did not let outdated, often gendered rules about dress get in the way of building strong relationships and doing great work.

Focus on what matters- who she is, her ideas, and your collaboration.

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You are definitely overthinking it.
A: as a creative director suits are not always appropriate
B: those jeans probably cost more than what you are wearing - ripped != worn out. It’s not a sign of disrespect. Would you have had the same reaction if there were no rips but had specialist appliqué applied?
C: dress standards have changed especially since Covid and work from home, even banks/finance have tended to relax dress codes unless seeing external clients.

I would be asking yourself why did you think they were inappropriate??

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I think so. I don’t think that what people wear dictate their abilities to do their job. If she’s nice to work with and is capable, I don’t really see the issue.

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Is this a client? She can wear what she wants. If she's an exec at your company, the ranks would imply she's senior to you and it's not worth picking a fight over her pants.

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I don’t know that I understand the scenario, but I didn’t hire a vendor once because of how the account director presented himself over a zoom meeting when he knew my senior executive was in attendance. He was arrogant, a poor listener and showed up wearing a shabby t-shirt, like he just rolled out of bed. Appearance mattered in this case.

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