What if the secret to timeless style has nothing to do with following trends?
This week on The Iconic Midlife, I'm joined by legendary fashion designer Cynthia Rowley, whose career has spanned more than four decades and over 100 runway shows. But this conversation goes far beyond fashion.
We dive into why women over 40 should stop dressing for trends, how confidence evolves with age, the power of reinvention, and what it really takes to stay creatively relevant in an ever-changing world.
Cynthia also shares behind-the-scenes stories from dressing Hollywood's biggest stars, including a hilarious first meeting with Katy Perry, her philosophy on personal style, and why curiosity—not trends—is the key to looking and feeling your best.
Whether you're reinventing your wardrobe, your career, or your next chapter, this episode is a reminder that your style should reflect who you are—not what's trending.
In this episode, we discuss:
• Why there is no "right" trend to follow
• How personal style changes—and improves—in midlife
• Staying creatively relevant after more than 40 years in fashion
• Why women should stop saying, "I can't wear that."
• Building an enduring brand without chasing trends
• The difference between reinvention and constant evolution
• What working alongside her daughter, Kit Keenan, has taught her
• Behind-the-scenes stories from dressing celebrities
• The unforgettable first time she met Katy Perry
• The fashion "rules" women over 40 should completely ignore
Connect with Cynthia Rowley
Instagram: @cynthiarowley
Website: https://www.cynthiarowley.com
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Because midlife isn't the beginning of the end...
It's the beginning of your most iconic chapter yet.