What 20 Years in Business Taught Shoshanna Gruss About Failure

by Aria Darcella

Shoshanna Gruss celebrated a major milestone earlier this year — the 20th anniversary of her brand. The Daily Summer caught up with the founder of Shoshanna to reflect on two decades of chic, inclusive fashion, and her take on the most stylish women in the world.

How far have you come since you have launched?
The collection has grown and matured with me. It’s definitely reflected my life. When I first started, it was full of youthful clothing, and now we reach a wide range of ages and sizes. My confidence in it all has grown as well. We have really stayed true to what we set out to do, which was to develop a clothing line that’s inclusive of more body types and celebratory of women’s bodies.

In what ways were you innovative?
In 1998, nobody was talking about different body types. People were saying, “We don’t really need that.” But I know you do, because I am the customer. That really hit a nerve. We were one of the first swim lines to sell separates in cup sizes the way we did. Now pretty much everyone sells bikinis as separates.

Is it daunting to put that much of yourself into the business?
I am the customer, and I want to stay the customer. That is how I test the temperature of everything. Would I wear this? When you feel that passionately about something, it makes sense. Shoshanna is my name, and I want to produce the most beautiful quality clothing that people are going to wear. I can’t pass it off like it has nothing to do with me, because it has everything to do with me. I still love it, too. I would say it saved me at certain points of my life as well. We all have our ups and downs, but I always have my business to turn to and put myself into. It has always been such a positive source for me.

What were some of the challenges in the early days?
I was so driven when I first started. When I think back, I can’t believe that I had the gall to do something I really had no background, no idea what it was. My dad used to always say, “You don’t even know what you don’t know.” I made probably 100 wrong turns and a million mistakes in the beginning. But to me they weren’t really mistakes — they were just times when I hit a wall and turned a corner.

Do you have any favorite pieces that you have designed over the years?
The swimwear, for sure! It was such a struggle growing up to find something that was even sort of cute. Anything that did fit me on top looked like something I could share with my grandma. I love that we make these pieces that range from size A through DDD and fit such a broad range of bodies.


Hat Attack x Shoshanna Caymen tote in gingham, $138

Your company employs 25 women. What is it like being in that space?
It’s very natural for me to be around these amazing, talented women, but we have had men work with us over the years. I hire the people in my office because of their talent, and because of the confidence that I have in them.

How do you navigate your work/life balance?
I’m a full-time mom, but I do work full-time. My dad is my hero, but he went to work. I don’t think he felt any guilt — nor should he have. But I do [feel guilty], not being everywhere. [Especially] being a single mom, actually. But it’s well worth it. I wouldn’t do it any other way.

What are your favorite things to do in the Hamptons?
I’m a beach girl. There’s nowhere I’d rather be than in the ocean. I’ve always liked to soak up the days in nature. Swimming, walking, gardening, relaxing, playing with my kids. In the summer, they usually go to camp. I try to work out and work, but mostly I’m home. Some mornings I will drive to Ocean Road to watch the sunrise, straight across where my house is. I live in North Haven, which looks out over Shelter Island, and we have the most unbelievable sunsets. My bedroom faces the sunset and whenever I’m changing to go to a party or something I always get caught up in the sunset. Once in a while I’ll go out and meet up with friends, but I love sitting outside and reading a book.

What are some tips for entertaining at home?
I use a company called The Culinistas. They’re almost like Uber for an at-home chef. They cook and set up the menus; they’re amazing. If I’m just doing something casual, I like to pick up food from the Hampton Market in Sag Harbor or Round Swamp Farm to make it easier on myself. I do not like formal dinner parties in the Hamptons. I will do almost anything to avoid that. I just like being outdoors—simple, easy, clean food, friends, cold drinks — that’s what I envision and fantasize about all winter long.

Who are some of your style icons these days?
Cate Blanchett. She always wears things that are fascinating, fun, and tailored to perfection. I also like to see people in the street. I am always interested in how people put together their look, especially when traveling.

What city has the best style?
Italian women on the Italian Riviera. The shoes are always a little bit different. They wear good jewelry to the beach, and it’s not too much or too understated. It looks like it’s been in their family forever. Their hair color is great, and their skin is always a little too tan but beautiful. They look like they are on a movie set!


Hat Attack x Shoshanna sunhat in Ditzy Blossom, $115

Got any big vacation plans this summer?
I’m going to Spain for 10 days, and then I’ll be back for July 4th. Then I’m in Sag Harbor for the rest of the summer.

Do your travels inspire your designing at all?
Always! I was fortunate to travel when I was growing up. We spent a lot of summers out of the country. I had a good global understanding when I was younger and was always intrigued by other countries and people. Now I travel as much as I’m able to with three little kids.

Tell us about working with Saks Fifth Avenue!
Saks is one of my longtime customers. We were talking about the 20th-anniversary collection, and Saks asked if they could have it as an exclusive. They put a lot of their support behind it. They are a wonderful partner, and I love working with them and shopping there.

How did your collaboration with Hat Attack come about?
They approached us, and it seemed like a natural fit because we are heavily involved in the swim and beachwear business. I don’t like to do things that feel forced. The timing for this was perfect — it felt natural and organic.

Who would be some of your dream collaborators?
I would love to work with a hotel or a beach resort. It would be an excuse to be on a beach for work!

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