Fashion is a vibe, and for Tosha Williams, it’s shining bright. The Nashville-based mom-preneur finds her joy in the bright, floral world of Lilly Pulitzer.
The brand’s origin isn’t rooted in the Black experience—Lilly Pulitzer was founded by the white orange grove heiress who wanted to camouflage the juice stains on her work dresses—but that hasn’t stopped Williams from feeling a strong connection to the eponymous brand.
“I’m a creative. I’m an art therapist by trade. So I’ve always been into the arts and love color and living out loud,” Williams tells EBONY.
Taking her love for everything Lilly P. a step further, Williams created The Pink Retreat. Every summer, hundreds gather to celebrate the brand and their love of a colorful closet. And yes, Williams is surrounded by other Black women who share her affinity.
The Pink Retreat, presented by Discover The Palm Beaches, just celebrated its fifth anniversary with an action-packed weekend at the Hilton West Palm Beach and throughout West Palm Beach, Florida. “It’s where Lilly Pulitzer lived and created her first collection,” Williams shares.
From walking tours on Worth Avenue to the highly-anticipated Afternoon Tea, “There’s a little of everything for everyone,” says Williams. “I love it when women are crying by the end of the weekend. I’ve had a couple say I didn’t even know I needed this. Having an opportunity for women to enjoy an inspiring, empowering and welcoming weekend together to make new friends and memories is our goal.” Williams is already gearing up for The Pink Retreat 2025.
EBONY sat down with Williams for an animated conversation about her love for sunshiny, brighter-than-life clothes and why everyone should feel welcome at The Pink Retreat table.
EBONY: When did you first discover Lilly Pulitzer?
Tosha Williams: I went to Loehmann’s about 30 years ago and found Lilly P. hanging on the rack. I was like, “Oh my God, what is this?” It was a patchwork shift dress. I tried it on, but it didn’t look good on me because I’m a curvy girl. I still wanted to know about the designer because I loved it, and I started seeking out more pieces.
How did you first connect with others who loved the brand?
There’s always been a thriving online Lilly P. community where we buy, sell and trade clothes. I was a stay-at-home mom and really couldn’t afford to just go into the store and buy off the rack, so buying, selling, and trading was an affordable way for me to actually get the clothes I liked. It’s a really vibrant community, and you have an opportunity to develop relationships with others.
Is that where The Pink Retreat was born?
I always thought there was no LillyCon. My boys were getting older, and I wanted to do something other than art therapy. But if I was going to do it, I wanted it to be on my terms and be the boss. I’m a very spiritual person and started meditating and praying. I kept getting this vision of a banner. And then, on one of the Lilly boards, someone suggested that we should get together and have a convention. I kept getting those nudges, so I created a Facebook group, and we started coming up with ideas.
Lilly Pulitzer isn’t a brand that people instinctively think is inclusive. Why everybody should feel like it’s for them?
When I was first interested in the brand, their shifts didn’t fit me. I’m not shaped like that, and it left a lot of us Brown and Black women out. It’s a blessing to have a relationship with Lilly and be able to have conversations about things that need to change. And they have, not necessarily because of me, but over the years, created more diversity within the shapes of their clothing. The Pink Retreat has introduced and allowed more Black women who wear Lilly P. to be more open about it. They’re like, “Oh, one of us is doing this.” I’ve had so many Black, Hispanic and Asian women say that because I’m a woman of color, they feel more comfortable coming to The Pink Retreat.
What are some of your favorite Lilly Pulitzer pieces?
I’m a kaftan person, so I love a good kaftan [Three’s Company] Mrs. Roper style, but also the ones that are a little more tailored. You can dress them up or dress them down. I have a few I’ve collected over the years. I also love the vintage pieces from Lilly Pulitzer White Label, as I’ve always had a preppy aesthetic.
How do Lilly Pulitzer and The Pink Retreat represent freedom to you?
I love to wear color and be bold. There’s freedom in living out loud, just giving yourself the space to unapologetically be yourself, which is why I wear it. I’ve had women come to The Pink Retreat who have said it’s harder to make friends as you get older. They come to the event, and they’ve met their new BFF. That’s what this is all about. This is about women reconnecting with themselves and connecting with each other, empowering women and letting them know there is a sisterhood, especially in this day and age. I think it’s important for us to have spaces where we can sit and laugh, hold hands, hug, and say, “I got you, girl.”