“I’m a person of habits.”

I try not to travel very much for work. I do a little bit of inspiration travel once or twice a year, but I try to really limit that to be with family. Travel for me is very much about escape, relaxation, and getting a break from the craziness of my job and my life in New York City. I’m a person of habits, so once I found this place in Jamaica that we loved—Round Hill Hotel in Montego Bay—we decided to go out there every year. I love the ritual of that. Aside from that, pretty much all my trips are to warm-weather spots. I just can’t imagine paying money to go somewhere cold. I don’t like cold weather, and in New York I get enough of it, so when I have the opportunity to travel I always pick somewhere warm. I did just travel to Paris and I absolutely loved that, and I’m planning another Paris trip in the spring. But if it’s a family vacation then I like to be somewhere where we can just be relaxing and swimming at the beach.

“Everything we do is for our family.”

My husband’s desk is next to mine. We spend 24 hours a day together, basically. We actually met at work; it’s kind of the only thing we’ve ever known. It is nice, knowing that we’re both working for our family and that we have this shared goal: maintaining a nice work-life balance so we can spend as much time as possible with our kids. Everything we do is for our family. We have three kids, 10-year-old twins and a 7-year-old boy. My daughter has always been so interested in fashion and she has a really interesting sense of style that always kind of delights me when I see it. It really comes from her, it’s a very different sense of style than mine. And I love that. She’s not just a copy of what I like. My style is more feminine than hers, and hers is a little bit more sporty. Actually now for the first time, she’s able to fit into our smallest size shoe, which means she can wear our shoes for the first time. She loves it, and it’s fun for me.

“I’ve always had this love affair with shoes.”

I always say this but shoes were always my first love. As a kid, my mom would take me to buy one pair of party shoes a year (because when I was growing up, you used to actually get dressed up to go to your friend’s birthday parties). And we had this one little shoe shop in our town that I loved. I had a very glamorous grandmother with tiny size-5 feet so I could put on her high heels and her ball gowns. I also did ballet and I would love when I got a new pair of Capezio slippers each year. I’ve always had this love affair with shoes and I just could never stop thinking about them. And then I started working in design, initially in handbags, and later my husband and I decided to start a company together. He said that we had to start with shoes because ‘all you do is look for vintage shoes and try to find the perfect pair with the right toe shape.’ But I had never designed shoes before. He basically said to me, ‘Well, figure it out.’ So I took a 6-week course before we put the designs into work and you know it sounds kind of like a fairytale story now but that is how we started it. We got lucky; the stars aligned, we started this collection over 10 years ago and it got picked up by Bergdorf our first season. It just kind of took off right away.

“Everything I pack is accessories.”

When we go away to Jamaica, I bring like 10 pairs of shoes, which is ridiculous because I don’t even really wear shoes when I’m there. Everything I pack is accessories and I tend to build my outfits around the shoes that I want to wear. I pack that way, too. I’m a way overpacker. I generally check bags. We just launched a straw tote, and what I love about it for vacation is that it has this insert in the base you can just fold up so it’s packable. That way you’re not forced to use it as your carry-on or to smush it in your bag and then it breaks and it’s just not worth it.

“Pack accessories that you can wear to the pool but also dress up at night.”

Something we try to do with the designs at my company is make sure that there’s a lot of different uses for everything. My advice is to pack accessories that you can wear to the pool but also dress up at night. We have these ruffled slide sandals called the Birdie, it’s a beachy sandal version of one of our most popular styles. I love to wear a plank sandal like that by the pool, but then I’ll wear them with a really pretty dress because they still feel dressy to me. You can wear these shoes to a farmer’s market or to a wedding, even. I’ll pack our gold sparkle Lulu mule slides which I love and I’ll wear those out at night. I’ll bring a pretty dress from Batsheva, which is this brand that I’m completely obsessed with. She makes all these super ruffley dresses and I’m definitely packing that one. And then there’s a crocheted bikini from a company called She Made Me, which is an Australian brand. I have a Misha and Puff sweater that I’ll probably carry for the plane when I get chilly. And then there’s a pink-ish/peach-ish cover up by 9seed and that’s something great to throw over a bathing suit.

“I’m a total germaphobe, so I always bring hand sanitizer.”

In terms of a beauty routine, I’m pretty natural so I keep it really lowkey. I’m a total germaphobe, so I also always bring hand sanitizer. I like to be really comfortable, I’m not one of those people who can get super dressed up to travel. I usually bring something to change into so when we get off the plane we can put on something else. Sometimes my kids will just wear their pajamas on the plane and then I’ll have a T-shirt and a bathing suit for them ready to go and we’ll change in the bathroom on the plane. But maybe I’ll wear a flowy dress; I end up bringing Mata dresses a lot. I like to buy a couple of new bathing suits that are fun and exciting to wear and one or two new dresses to wear. And I usually have one of our suitcases packed with all of our newest samples—I’m usually going right when our resort collection launches so I have all this fun beachy stuff to wear.

“I always like to listen to podcasts on a plane.”

We don’t let our kids use iPads unless we’re on a plane so it’s actually really nice because they get so excited to be using them that they’re really quiet and focused the whole flight. In the case of going to Jamaica, it’s really nice to have four hours to myself where I really don’t have to take care of anybody. I always like to listen to podcasts on a plane. It’s nice to be able to close my eyes instead of watching something. If I’m listening to podcasts, I usually listen to “Fresh Air” and I love “S Town,” but I love to have my Kindle loaded up with a bunch of really good books. I also always have some sort of craft going on because the place we go is really chill and crafting helps me to almost meditate. A couple of years that we’ve been there I’ve done these overly ambitious projects for a school auction where I cross-stitched the faces of every single kid at my kids’ school onto a pillow and that took me so long, it was like the entire vacation. There were about 20 of them, and I cross-stitched the class hermit crabs on there, too.

Jessie Randall travels with a Bigger Carry-On in Blush.