Mamas We Love: Jen from Jen’s Pirate Booty

One small souvenir purchase during a trip south of the border, and the rest of Jen’s Pirate Booty is history.

When she first started her career in fashion, Jen Rossi’s customers quite literally bought the clothes off her back. Today, Jen is a trendsetter in her own right, owner of her own brand and mother of three beautiful children. We are always fascinated by the strong, driven, hardworking women who surround us, so we decided to learn more of her journey and what lessons she picked up along the way. 

Was fashion always something you aspired to be part of?

I have loved fashion my entire life! I was always playing dress up in my Mom’s and her friends’ closets and loved doing fashion shows for whoever would watch. All throughout junior high and high school my walls were covered from floor to ceiling with tears of Kate Moss, Claudia Schiffer, Christy Turlington, Naomi Campbell and Helena Christensen. Guess this gives away my age! :) I made a ton of my own clothes during high school and my early twenties. I even made tags for a clothing line called “RockstarLA,” but never ended up doing it. I moved to San Diego in the late 90s and lived across the street from a super cute clothing store that was owned and run by a ton of young, stylish and cool twenty-somethings. I would go there every day, run my hands through the racks, try on clothes and just dream of having my own store and own clothing line. A couple of years later, at 20 years old, I moved back to Malibu and walked into a brand new boutique called “Planet Blue” and was hired on the spot! Just a year into my time there, I was promoted to buying and continued to buy, run, work and manage the stores for the next 14 years!! It was SUCH an incredible experience and the breeding grounds for where I am today!!

Tell us a bit of what brought you to create JPB.

During the time I started JPB, I had a very awesome, demanding, busy and full-time job, while doing a few other side ventures. So I wasn’t particularly looking to start something else. Yet, I also couldn’t turn away and ignore it when it was happening. It just grew very organically and somehow, by some miracle of grace, here we are, 12 years later and still going strong!!!
In my late 20s, I was traveling in Mexico and bought a beautiful gauzy tunic that resembled something Janis Joplin or Stevie Nicks would wear. I could not walk 10 feet without being stopped and asked what brand it was. People were so drawn to the flowy, effortless, bohemian, beachy, 60s/70s look and feel. This was right before e-commerce websites and social media made their mark. So fashion wasn’t moving a million miles a minute. Trends had time to ease their way into the market, marinate, flourish and stick around. There was also no access to seeing every single thing that everyone was wearing, in every small, remote town or massively populated country across the globe. So to me, my customers and everyone in my circle, this was new and fresh and we ALL wanted a piece. Or 10 pieces. :)
I wore my piece to work one day and everyone who walked into the store wanted to buy it!! So what did I do? My Mama and I jumped into my car, went back to Mexico that weekend and brought back as many pieces as we could find!
I made a quick handwritten invoice, put them into the store on consignment and sold hundreds in just a few days! Our customers were buying them off our backs! We would sell one, put another color on, then out the door it went! So back to Mexico we went. In between trips to Mexico, I started a wish list for customers awaiting the next shipment, and there must have been hundreds of names on that list, including many huge celebrities and socialites!
At some point during all of this, while wearing a piece, I was tapped on the back by a buyer for one of the biggest stores in NYC. She asked where I got my tunic and I told her the story. She asked if I could go get some for her. So again, on my 2 days off from my busy, busy job, off to Mexico we went!! And finally, after another trip or two across the border, I decided it was time that I source this beautiful, sheer, sexy, raggedy, Piratey fabric myself and start designing and producing my own collection. Thus was born this colorful, ever-changing, wild and crazy, fun and exciting journey into the world of fashion design!
I never went to school for it. My journey is my education. And to this day, I am still learning, still making mistakes and still being stopped nearly every single time I wear a piece of Jen’s Pirate Booty.

What’s your secret to balancing motherhood and a successful business?

I am a Libra ~ my sign is the Scale. Balance. So I guess ,because of the Libra in me, finding my balance IS a very key and integral part of my being and my success. I am the Mother of 3 incredible little girls and, above all, they are my greatest gift, my passion, my joy, my home, my heart, my blood, my breath and my water. So besides making time for Jen’s Pirate Booty and all of the love and energy that goes into it, making time for my family, my friends, time to travel, time to do yoga, meditate, go to the beach and time to LIVE and just BE in the moment, has always been a priority of mine and a mantra that I live by. I have always worked hard and played hard, giving myself that balance that I need. I worked to save up and go traveling! Then I would come back to Malibu, have very little money in the bank and then start the cycle all over again. So now, I have set myself up so that I can pretty much work from anywhere on the globe ~ as long as there is Wifi. MOST of my best collections and designs were ignited from being in a different country. That’s when the magic happens and I am most inspired and most open to allow my creativity to flow. And of course, none of this would be possible if I didn’t have the love and support of my family, my friends, my showroom and my incredibly hard-working, loyal and insanely creative team at JPB. Thanks to everyone who helps create space for me to find my balance and time to travel, be a very hands-on, hard-working and present Mama, wife, daughter, sister, Auntie, friend, designer, entrepreneur and business owner.

Favorite vacation spot?

I absolutely love Thailand. It stole my heart many moons ago and has been luring me back ever since.

Why “Pirate Booty”? Where did the name come from?

At my very beginning, I had to make an invoice for Planet Blue, and I had to put a company name on it. I didn’t have a brand, I didn’t have a name. I didn’t even have a company. This all happened so quickly, without any prior planning. I pretty much wrote down the first thing that came to my mind and it was “Jen’s Pirate Booty,” because of the way this entire journey began. I was buying and reselling. “Pirating Booty.”.It just seemed right.
At that time, Johnny Depp and Keith Richards were two of my biggest fashion icons. They were beachy, boho, rock-n-roll dreaded Pirates, living life to the fullest, dripping in tarnished jewels, draped in shredded Gauze and traveling the world. I loved the look, vibe and feel that the word “Pirate” gave off and have remained true to that essence throughout all of my years designing.

Name three pieces of clothing every woman should have in her closet.

A Goddess, Boho, Drapy Kaftan, a kickass pair of jeans that make your booty look amazing and a beautifully worn-in, story holding, vintage tee. Oh, and something made from sequins! Can’t ever forget the glitz and glamour and sparkle and shine! More is more for me. Ha! No Marie Kondo’ing in my closet.

And, we have to ask, did fans really buy the clothes off your back when you were starting out?

They sure did! All day, every day! Repeat customers would walk into the store, just to see what the girls and I were wearing and literally buy pieces off of our backs! It really helps to see how clothes are being worn and styled, as opposed to hanging on racks. And nobody seemed to care that we were wearing them. They actually appreciated it and loved this concept. It was one big, happy, fashion-obsessed family!

Wearing: Jen’s Pirate Booty x Free People Exclusive Pixie Mykonos Kaftans for mommy and for kids. 

In honor of Mother’s Day, we collaborated with Jen’s Pirate Booty to create two “Mommy and Me” pieces. Shop them and the rest of the collection here. 

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