"Because most of all, dressing well requires knowing oneself."
Fast Company recently released a new initiative: Best Dressed in Business
They NAILED it and underscores what we call Intelligent Style: Their list of ‘best dressed’ highlights true diversity in STYLE, not fashion or trends, as well as leadership and what it looks like to show up as a leader.
“Because most of all, dressing well requires knowing oneself.”
You may not resonate with everyone’s style.
That’s OK, you don’t need to.
But, they can still inspire you.
One of the first questions we always ask a new client or member is ‘Who is your Style Icon?”
This doesn’t have to mean a celebrity — as this list illustrates — rather anyone you know whose style who inspires you.
When you consider this question, think about what it is about their style that inspires you. Because it’s not really about the clothes. It’s how you’re perceiving them in their clothes.
For instance, Michelle Obama is a common response we get to this question for our Member's profiles.
But that can mean SO many different things.
It can mean classic and confident.
It can mean bold and intelligent.
It can mean inviting and powerful.
And, Michelle Obama is an excellent example of Intelligent Style for another reason: She navigates the dance of dressing for the audience AND for herself flawlessly every time.
Meaning, she’s respectful of the occasion and the audience while not sacrificing herself. A lot of the history of ‘executive presence’ is based in ‘shoulds’ an ‘appropriate.’ It’s about fitting in. But true leadership can’t be about fitting in. It’s about creating buy-in. And you can only do that if you build trust. And you can only build trust if you are truthful. And you can only be truthful if you’re in alignment with your values and vision.
Consider what Dara Treseder shares about the POWER of Style, interviewed by Elizabeth Segran:
What’s the best piece of fashion advice you’ve ever gotten?
My mother told me, “dress for you.” That simple truth shaped everything. Fashion is comfort, not just physical but emotional. When you feel at ease in what you wear, you move differently. You lead differently. Confidence is the most powerful thing you can put on.
We’re heading back to the office, back to our conferences and our board meetings soon, so let's put your Intelligent Style into action.
Intelligent Style Exercise:
Take a second to consider these Best Dressed. What would YOUR Best Dressed profile say?
(Hint: Focus on your next level — what are people saying about you? What is the energy you bring to the room? How do others react to your presence? What is your vibe? There are no wrong answers.)
And if you’re ready to take the next step to bring your Best Dressed to life, we have different paths to meet you where you are:
🖤 Rebrand – You’re stepping into a new chapter (promotion, business shift, new stage of visibility). This is our CEO 1-1 VIP experience—an in-depth transformation of how your style reflects your leadership with Boutique Box CEO Catherine Cassidy.
🖤 Refresh – You mostly like what you have, but it needs a tune-up. A few intentional updates, edits, or fits. This is the 1-1 fitting—available in Chicago or virtually.
🖤 Rebuild – Your current wardrobe just isn’t cutting it. Nothing feels like you. This is where the Boutique Box Membership shines—curated, customized style delivered to your door.
🖤 Reinvent – You are beginning to position yourself for your next level. This is where our soon-to-launch Intelligent Style 101 program supports you in building confidence and clarity with your current closet. You don’t need more clothes, yet.
Not sure which is right for you? Join Catherine LIVE on September 2nd for Reinvent & Rise: An Intelligent Style Activation