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#HowTheyDoDapper: Olivia Hill

by Priya Pappu |

Olivia wears the Harvest twilly.

Olivia wears the Ruth twilly.

Olivia wears the Harvest twilly.

Everyone meet our dear friend, Olivia Hill. We were reminded last week, at the Nashville SC photoshoot, of just how wonderful it is to be in Olivia's presence. She simply exudes happiness.

And why wouldn't she? Happiness goes hand in hand with living your best life.

Olivia is certainly doing that . . . and making memories along the way. 

After we met Olivia and heard her incredible story, we were inspired. Olivia references her grandmother, Ruth, as one of her key inspirations, not only in terms of style, but grace! It was from this tribute that our Ruth Twilly was born. This encapsulates what Clifton+Leopold is about. 

"Her grandmother would never get to see the freedom she felt. But they had one thing in common: they were both willing to walk away from the life they knew, to be the woman they were meant to be."


It just felt right to end our #HowTheyDoDapper Pride Month Series with someone who inspires us as much as she does. Read on to meet our stunning friend, Olivia!


Name, pronouns: Olivia Hill, she/her

Find them looking dapper in: Nashville, TN

Tell us a little bit about the story you're writing in your Clifton+Leopold: 

I am a Trans Activist. I spend most of my awake time advocating for the trans community.

My journey started when I was very young. I felt like I was me until about age 10. Thats when I got the the talk that I could no longer dress up like myself. I had to wear boys clothes. My mother also took me to a psychiatrist for two years, to teach me that I was a boy and I had to act, dress and play like a boy. It wasn't until much later in life that I gained the courage to step out as my true authentic self.

Once I discovered Clifton+Leopold, I wanted to adjust my style. The kerchiefs really help me do that and feel feminine and fashionable. It's that added flare that puts energy into my spirit.

My grandmother was very active in the fashion industry. I believe when she checks in on me that she is very proud of my style.

Complete this sentence: I love the C + L ___________ because _________: 

I love the C+L kerchiefs because of their superior quality and fabulous style.

What is currently atop your C + L wishlist? The Dawn kerchief.

It's a Saturday! What are you doing?

Hanging out somewhere downtown, being social!

Your ultimate dapper icon: My grandmother, [Ruth], she had amazing style & class.

It's quitting time on any given day. What are you sipping on?

Good whiskey or a fruity tropical drink, it depends on my mood.

A dance party is not complete without (song or artist): 

Rain on Me - Ariana Grande & Lady Gaga

Tell us, what makes you feel dapper?

Being dressed up at a dance party, with the right shoes and perfect lipstick.

Can you share a favorite Pride memory, what you're looking forward to most this month, or what Pride means to you?

I remember my first ever Pride! 22 June 2019. I was in the Parade. As I walked down the street carrying the banner from my employer, people started cheering. They continued to get louder and louder the further down Broadway we went. It really hit me emotionally. As a newly transitioned woman, I felt as if everyone on that street was accepting me and cheering, "YOU MADE IT!!". I cried most of the parade. Tears of joy streamed down my face and I thought to myself, I AM FINALLY ME!

Imagine your greatest wish. Whatever that would be. To be president, Miss America, CEO of a major corporation, and then suddenly you are walking down Broadway and it hits you that your dream came true. I AM ME!

Where can we find you on the internet?





Olivia, you are an inspiration to everyone that it is never too late to be your true, authentic self! Thank you for sharing your courageous story with us. We are so proud to have you as a part of our community! That story of your first We may have shed a tear typing that into this blog post.

We've been featuring LGBTQ+ members of our C+L community for a special Pride edition of #HowTheyDoDapper all month long. View the other features here!

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