Holding Your Own: The Story You Tell with Your Outfit Choices
What I'm packing for his family reunion
This year, I did a rare and unusual thing: I bought clothing for fall, while it was still 100 degrees, real-feel temperature.
In France.
Over the years, in observing women in New York City, the minute the temps fall, she has fashionably whipped out ‘of the moment’ style for the season and I’m still wrestling with an ill-matched sweater over a slinky summer weight dress.
So this year, I decided to *grow up* and plan ahead.
Matt’s family reunion is in Milwaukee in mid-September.
I white boarded the outfits for the four days. The temperatures are forecast to be between 60-81.
I follow this process for 3 reasons:
I map outfits to activities. This way, I also don’t forget a key item, like a strapless bra (which I did once, for an evening gown, and spent the day searching in an little Irish town for what ended up being a very pricey replacement)
I don’t “overpack.”
It cuts down on the decision fatigue.
So below, you will find
The flight/travel day. I’ll wear the same outfit on the outbound and inbound.
A networking breakfast in town.
Must-have visit to the Milwaukee Museum, designed by Santiago Calatrava and vintage shopping.
The family reunion, comprised of time on his parents’ farm and the supper club.
💪🏼 But here is the other thing I have realized: Outfit choices are more than just a reflection of your personal style—they tell powerful stories to the world about who you are, what you value, and where you're headed.
So here goes.
Why the Story You Tell with Your Outfit Choices Matters
In professional settings, the way we dress can either reinforce or undermine our message. Whether you’re stepping into a boardroom, presenting at a conference, or leading a team meeting, your outfit is part of your personal brand. It’s the first impression before you even speak a word, setting the tone for how others perceive you.
But beyond first impressions, your attire can also be a form of silent communication, conveying confidence, creativity, and attention to detail. It can show that you respect the occasion and the people around you, and that you are intentional about how you present yourself.
So next time you choose an outfit, think about the story you’re telling. Is it aligned with your goals? Does it reflect the message you want to convey? Because in the end, what you wear is not just about looking good—it’s about embodying the professional and personal narrative you’re proud to share with the world.
I want to build an unforgettable personal brand. Can you help me?
Absolutely, You will never regret building a powerful personal brand. It unlocks magic and opportunities that you have yet to access. I often say, think of Anna Wintour. If Vogue Magazine fired her tomorrow, she still has a powerful personal brand that far outshines Vogue. I outlined the 7 steps I took to build my personal brand in this cheatsheet.
You could download it for free here:
https://joyadass.lpages.co/how-to-build-a-powerful-personal-brand-and-how-i-did-it/