By: Pam Perry
Who says you have to fade away after 40? Ola Jackson is here to tell you: Absolutely not.
She’s the founder of Your Stylish Ways, a bold lifestyle brand that speaks directly—and unapologetically—to Black women over 40 who are aging on their terms. Forget slowing down. These women are leveling up. And Ola is leading the charge.
After 35 years in business, including a celebrated run in public relations, Ola didn’t just reinvent her brand—she redefined her purpose. Today, she’s a fierce advocate for midlife reinvention and a voice for women who are tired of being ignored, underestimated, or invisible.
“I created Your Stylish Ways because I didn’t see us,” Jackson says. “Women over 40. Black women. Bold women. Women who still have dreams, style, purpose—and who refuse to let age define their destiny.”
Her pivot wasn’t just professional—it was personal. After decades of helping other women grow their brands, Ola looked in the mirror and knew it was time to shift gears. She wasn’t done. Not even close.
That realization birthed a movement built on four words: “Yes, At My Age!”
This is the rallying cry of the women who follow her. Women who have raised children, built careers, survived storms—and are now choosing themselves. Choosing joy. Choosing bold fashion. Choosing solo vacations, new businesses, self-care, self-love, and second chances.
Ola gets it because she’s lived it. She built her business while raising a son with autism, balancing boardrooms with caregiving, red carpets with late-night worry. That grit and grace show up in everything she does—and in every piece of content she creates.
Through Your Stylish Ways, she delivers more than style tips or self-care inspiration. She delivers truth. Connection. Community.
“We’re not talking fluff,” she says. “We’re talking real women facing real challenges and deciding we still deserve to shine.”
And shine they do. Each year, Jackson hosts her signature event, “Yes, At My Age and Thriving!”—a soul-nourishing gathering that brings nearly 100 women together to share their stories of reinvention and resilience. There are tears. There’s laughter. And there’s the undeniable energy of women reclaiming their time, voice, and vision.
This isn’t just about aging gracefully. It’s about aging powerfully.
And the world is watching. Ola has racked up honors like the Talk Magazine Woman of Distinction, SBA Business Champion Award, and Pittsburgh Black Media Federation Legend Award, to name a few. But accolades aside, it’s the inbox messages and DMs from women saying, “Because of you, I finally said yes to myself,” that fuel her mission.
“I want women to know—just because you’ve hit 50 or 60 doesn’t mean you’ve hit the end,” Jackson says. “It might just be the beginning of your most fabulous, fulfilled, and fearless chapter yet.”
And she’s not stopping anytime soon.
Ola’s future vision includes expanding Your Stylish Ways into a full lifestyle brand with signature products, national tours, and media content streamed across platforms. With support from The New Network TV and a fiercely loyal online tribe, her message is clear: Midlife is not a crisis—it’s a calling.
Photo Courtesy: Corey Lankford / Ola Jackson
As for what sets YSW apart? Ola doesn’t play into tired narratives. You won’t find shame or shrinkage here. What you will find is a space where confidence reigns, curves are celebrated, wisdom is revered, and style has no expiration date.
If you’ve been looking for permission to reinvent, permission to pivot, permission to live loudly—here it is.
“Often we’re told to ‘act our age,’” Ola laughs. “Well, this is what 50, 60, and 70 can look like—and it’s fly. It’s fierce. And it’s far from finished.”
So if you’re a woman over 40 wondering if it’s too late to start again, dream again, shine again—listen to the voice of Your Stylish Ways.
It’s whispering what you already know deep down:
You’re not done yet.
Ready to join the movement?
Visit www.yourstylishways.com and follow @yourstylishways on Instagram for style, sisterhood, and next-level midlife magic.
Watch the journey unfold at www.onyxwoman.com and visit their YouTube channel. https://www.youtube.com/@TheNEWNetworkTV. Media Inquiries: ola@onyxwoman.com
