Proper Women: Strength, Style, and Holli Kenley

When Holli Kenley stood onstage last February and felt a crown settle onto her head, something profound happened. Old memories of painful criticisms and harsh judgments dissolved in an instant. Instead, she felt overwhelming joy.

It was not simply a crowning moment. It was a reclamation.

Holli is Ms. Senior California 2025, but that title is only one part of the woman she has spent a lifetime becoming: a therapist, teacher, speaker, TEDx presenter, and author of eleven books. Her work centers on healing, betrayal, loss, and the lifelong journey of finding one’s voice; a journey she has walked herself. “It is about finding my voice and helping others find theirs,” she says, describing the thread that connects all the chapters of her life.

For women who are navigating midlife and beyond with curiosity and courage, Holli is a compelling reminder of what is possible. She speaks with clarity, empathy, and a strong belief in the power of transformation.

The Journey Back to Herself

Holli’s path was not linear. Early challenges made finding her voice “at a young age… really difficult and hard,” she recalls. Through personal recovery work, she grew into her roles as teacher, therapist, author, and speaker.

This depth of understanding has shaped her view of aging. “As women age… we become invisible. We are not seen, we are not heard.” She reframes this as a beginning. “We are finding ourselves again and redefining ourselves again.”

When women say, “I am too old,” she offers another truth:

“Try this instead. I am not too old. I am pure gold.”

The shift invites women to see themselves with compassion and confidence.

Style as a Catalyst for Courage

Long before crowns and pageantry, Holli understood the emotional significance of clothing. Growing up with very little, she cherished the pieces she owned, and a brief stint in modeling showed her how style could influence confidence.

Today, her relationship with fashion is thoughtful and intentional. She gravitates toward pieces that convey dignity, maturity, and inner beauty, embracing the truth of who she is now. That authenticity is also why she encourages women to “step out of their comfort zones.” Whether it is a new color, a different silhouette, or something a bit bolder, she believes in trying what feels unfamiliar. “Part of finding your voice is being courageous.” Today, her own wardrobe reflects that courage.

The Jacket Moment

And then there is the jacket. The Boston Proper piece she wore to the Ms. Senior America pageant drew attention everywhere.

For Holli, that joy was not simply about the sparkle. It represented stepping confidently into a new phase of her life.

That experience mirrors what she appreciates most about Boston Proper. She believes the brand gives women permission to express themselves, to try something bold, and to rediscover their style voice. She loves that the pieces feel “age appropriate, classy, elegant,” and reflect the dignity she wants women to see in themselves.

Shop The Look

Over The Top Pearl and Rhinestone Embellished Shawl Collar Ponte Jacket Black Multi | $219.98

The Crown She Shares With Others

One of the most meaningful aspects of Holli’s reign has nothing to do with the title itself. It’s the ritual she created for other women. The revelation she experienced when her own crown was placed on her head inspired her to pass that feeling forward in the most personal way.

She brings small symbolic crowns to luncheons with women of all ages. She places each crown on their heads and tells them:

Many of the women become emotional, not because of the crown itself but because of what it represents. For many women, it is the first time in years that someone has looked directly at them and fully seen them.

This practice reflects Holli’s belief that inner beauty lives in the way we lift others up and help them step into their own strength.

What Comes Next

Holli is not slowing down. She is speaking more, mentoring more, and preparing to write her twelfth book. She remains active in the Ophelia Project, guiding young women toward confidence and resilience. She also continues to represent California with humor, grace, and sincerity.

As her journey continues, Holli plans to keep reaching for styles that align with the values she holds most dearly: elegance, maturity, dignity, and inner beauty. She loves that Boston Proper reflects those qualities in its designs, allowing her to feel both beautiful and honest to who she is today. Wearing clothing that mirrors her voice helps her step into each opportunity with clarity and confidence, the very qualities she encourages other women to embrace.

For women everywhere redefining themselves and stepping into their own visibility, Holli Kenley stands as a reminder:

Step confidently into your golden chapter with Boston Proper.