The Unfiltered Story.
Meet the Founders
Hey there — we’re Jessi & Matt, the couple behind Gypsy Footwear.
This isn’t a side hustle. It’s our full-time mission, our future, and something we’re pouring everything into — one comfy, purpose-driven pair at a time.
- We design every product ourselves.
- We pack the boxes.
- We write the notes.
- We answer the emails (probably with a dog nearby).
Why We Write Every Note
And yes — the notes are on purpose.
At our house, giving gifts is personal. It’s meant to be celebrated.
Nobody embodies that better than our sister Erica — she’s legendary for her thoughtful gifts and even more so for the handwritten notes that come with them. Notes that make you feel seen, appreciated, and connected.
That’s what we want every pair of Gypsies to feel like. Even though we don’t know most of our customers personally, we want you to know how much your support means — not just to us, but to the animals we’re working to help. The note in your box? That’s our way of honoring you. Of saying: you matter. This matters. And thank you.
It’s not glamorous, but it’s real. And we love it.
What We Believe
Gypsy Footwear was born out of a simple but serious idea:
That shoes can be well-made, feel amazing, look great — and still be affordable.
That small businesses can do big things, if they stay focused on what matters.
Why “Gypsy”?
The name “Gypsy” was inspired by our first dog — a spirited Husky mix with a mind of her own and a heart of gold. That spirit is in everything we do, and it’s what inspired the name.
That’s why we give back to animal shelters with every order. We know what it means for an animal to get a second chance — and if we can help make that happen, even in a small way, we will.
Huskies, like Gypsy, are among the most commonly abandoned breeds — they’re beautiful, high-energy, and often misunderstood. We carry that with us every day, and it’s why supporting shelters isn’t just a feel-good footnote — it’s part of our company’s DNA.
The Next Chapter
Right now, we’re based in Florida — but the next chapter is already in motion. Soon we’ll be moving to Hayesville, North Carolina, where we’ll build the next phase of Gypsy Footwear.
The Adventure Bus Life
Adventure is a big part of our story. We bought and built our own adventure bus ourselves — and during the process met and connected with an incredible community of nomads that truly understand how to enjoy life. These people fit perfectly with our brand and can often be found supporting the great small-town communities we love.
When we relocate to Hayesville, we’ll be living in that very bus while we build out the ultimate Gypsy headquarters and a brand-new life in the North Carolina mountains.
Small Town, Big Heart
That small town, and the towns surrounding it, represent everything we love about small-town America — strong community, real values, and people helping people. You’ll find us (and Gypsy Footwear) at local festivals, community events, and anywhere folks are gathering to support great causes and enjoy the little things in life that matter most.
Why We Keep It Lean
We don’t waste money on fluff — because every dollar saved helps us:
- Deliver more value to you
- Give back to animal shelters
- Keep growing a brand that puts people and purpose first
We’re still building. Still growing. Still developing new products that fit our brand, our customers, and our ideals.
The Names Mean Something
You might’ve noticed that our sandals don’t have trendy, random names. That’s intentional.
Every Gypsy Footwear style is named after a woman who’s played a real role in our journey — someone who’s helped shape who we are and what we’re building.
Chloe is a friend who helped us develop our earliest products. She wore out the prototypes, gave us unfiltered feedback, and pushed us to make them better.
Melissa is both a sister and our best friend’s wife — a Melissa, like the shoe’s namesake, is the kind of person who gives blunt, honest critiques when we need it and overflowing support when we need that too.
Jessica? That’s Jessi — co-founder, heart, and sole of the company. (Pun fully intended.)
We don’t name our sandals with marketing in mind. We name them for meaning. And yes — we absolutely love it when a Melissa orders a Melissa.
It’s a good bet that whoever the next sandal is named after will have a direct connection to our lives — someone who’s made an impact on our story, our company, or our mission.
Who knows... maybe someday we’ll name a sandal after you.
If you're reading this, you’re already part of our journey.
And we couldn’t be more grateful.
Thanks for being here.
Let’s build something great together.
— Jessi & Matt