Diane von Furstenberg – designer, women’s rights activist, icon – has a life that lends itself to metaphor. This she knows.
She entitled her 2009 exhibition in Moscow Journey of a Dress, for example, because it told the story not just of her “aesthetic evolution” (from the invention of the wrap dress in 1974, at the age of 28, to her current much broader offering), but of her personal evolution – from young wife newly arrived in New York from Europe, through the years of burgeoning fame, her time at Studio 54, motherhood, divorce, remarriage, renewed success, and so on. She often says her life story has been “the journey of a woman”. So it shouldn’t have surprised me, really, that when I asked her what her favourite hobby was, she said, in effect, “journeying”.
OK, she actually said “hiking”, but the two are not so dissimilar. A hike, after all, is just a shorter kind of journey: a process of moving from one point to another under your own steam. DVF, as she tends to be called, does everything under her own steam.
She often says – has said to me when we met in the past – that she didn’t know what she wanted to do as a young woman, but she knew what she wanted to become: independent, confident, strong. The wrap dress, for her, was simply a means to this end; when her first husband, Prince Egon von Furstenberg, moved her to New York from Europe, she thought she needed something to do, so she asked a friend who had a factory in Italy to run up a little dress for her. Indeed, she is currently writing a collection of essays entitled The Woman I Wanted to Become. Little wonder that her literal journey reflects her lifetime journey: it’s the sort of pastime that doesn’t require any help from anyone, or even much in the way of equipment.
DVF began walking as a girl growing up in Belgium. “I had a good friend and she had a dog and we would walk in the forest,” she says. Later, at boarding school in Oxfordshire, “I would walk along the river. I was never that into team sports – they aren’t so big in Europe – but more independent activities, like swimming or skiing or hiking.” She first realised she loved hiking, she says, on the Italian island of Ponza, where there is a long walk between the village and a lighthouse. She didn’t really begin hiking in earnest, though, until she bought her house in Connecticut when she was 26. Called Cloudwalk, it is the place she feels most at home in the world.
It is also the place she wants to take me hiking. I begin my journey on a Saturday morning.
The area of Connecticut where Cloudwalk is situated (Diane inherited the name from the house’s previous owner, Evangeline Johnson of the Johnson & Johnson family) is heavily populated by fashion people. Oscar de la Renta and his wife Annette live about 10 minutes away and often come over to watch movies. Designer Bill Blass used to live nearby and the former fashion critic of the New York Times, Amy Spindler, also had a weekend house on a nearby lake. This is not a coincidence; they were all drawn to the area after visiting legendary artist and magazine art director Alexander Liberman and his wife Tatiana, who had a country house nearby. DVF is no exception.
“I went to visit,” says Diane. “I was just splitting up with my husband, and I had two little children.” (Her son Alexander and her daughter Tatiana, now 42 and 41 respectively, by chance have the same first names as the Libermans.) “I thought I needed a place to raise them. So I found an agent in the phone book, and called him and said I was interested in houses in the area. He sent me some pictures of various places, and one weekend I went with my mother and Kenny Lane [the jewellery designer], because he had to drive – I didn’t drive then – and we drove around and saw this, and I liked that there were a lot of little houses on it. Before we were out the driveway, I had agreed a $10,000 down payment.”
DVF bought the property, which has five buildings on it, just before her 27th birthday for $200,000. Since then, she has added parcels of land as well as a neighbouring farm. She now has just under 200 acres, on which she has a studio for herself and her second husband, Barry Diller (though “studio” doesn’t begin to describe the loft-like building, which includes an enormous library/office/screening room, a bedroom painted with fresco-like murals of the sky and trees, and his-and-her bathrooms); a main house for guests and dining; smaller houses for her son and daughter; a caretaker’s cottage; and a barn that DVF wants to convert into an indoor swimming pool “for when I am old”. There are also chickens, a vegetable garden and 120 apple trees. DVF paid off her mortgage on December 31 1999, as a “millennium present to myself”.
Cloudwalk is where she raised her son and daughter, having moved them to the farm from New York City when they were in middle school. “It was the year  Calvin Klein’s daughter was kidnapped,” Diane says, “and I wanted a place where they could be free.” The farm is a place, she says, where she has had “many lives. The children were small, the children were bigger, the children were gone, the grandchildren were there. There is one man, there is another, there is a husband.” But throughout it all, the land has been there, and she has walked.
Indeed, DVF walks every weekend, no matter where she is. She often walks the section of the Appalachian trail near Cloudwalk, though since her marriage to Diller in 2001, once a month, or once every six weeks, she and Barry take their yacht and hike on whatever island they happen to be sailing near. “Other than the Bahamas and the Maldives, pretty much any island is a place to hike,” she says.
“We are both very happy being alone,” she continues. “We like to do things by ourselves. But this way, after the hike up, on the way down, we talk.” Not that her trails have to be so exotic; she also hikes on her own land. She spent years, she says, walking Cloudwalk looking for the place she wanted to be buried. “I started when I was 26,” she notes. She found it a few years ago – a secluded hill by a field located through the woods from the main buildings – and has secured permission from the state for its use. Currently, she is constructing a “meditation garden” with curving stone walls around the space. She thought she would have it all enclosed, but now she isn’t sure; she may leave it open on the downward sloping side to embrace the view.
“I called my son the other day and told him I wanted to be buried on my stomach, because that’s how I sleep,” she says. “But now I think I’ve changed my mind; I think I want to be able to see the vista.”
The hike she decides to take me on is not on her property, however, it’s in New Preston, a nearby town that is famous for being the place they filmed Friday the 13th Part 2. The trail, which leads to Pinnacle Rock, runs off a hillside road up to a 360-degree view. DVF drives to the beginning of the trail in her Bentley (she now likes to drive) and parks at the base. She has brought Evian water and ski poles to use as walking poles, and is wearing her own-brand jeans – this season’s, white with a black flower print that manages to look vaguely zebra-like – and Loma hiking boots, though normally she says she hikes in leggings: “When it gets rough, it’s good to have your legs covered.” She also says she picked this hike because it isn’t too challenging, and so it’s a good walk when you are going with people whose ability is unknown. (That would be me; though I have a past that includes hiking through the hills of Nepal, and day hiking in the Alps, it’s never really come up in our conversations before, which have mostly centred on her collections.)
A few years ago, DVF and Diller hiked the Inca trail, in Peru. “There were about 17 of us,” she says. “We didn’t have the boat that year, so Barry arranged the whole trip. We did the trail in a day, and then we did some rafting, and you know, the first thing they tell you on the raft is if you fall off, just lie on your back and go with the current until they can fish you out. So we get on the raft and – Woosh! The first thing I see is Calvin [Klein, who was on the trip] going off the raft. I thought ‘Oh no, he will die, it will be our fault!’ But he was so brave, he was fine. A lot of the other people on the trip had been intimidated by him, but after that he was a hero.”
The week after our hike, DVF is going to India to speak at a Hindustan Times conference, and then on to Nepal, where she is going to hike to the Everest base camp (she thinks) with Kathmandu-raised American designer Prabal Gurung. One of her favourite hikes is up Stromboli, the Italian volcano. (I’ve also done this one: you can look down into the smoking crater.)
Hiking, she says, “is always an adventure: we always get lost, or something goes wrong.” Once she and Barry were hiking in the Balearic region of Spain, and couldn’t find their way down. “Every time we went over the hill – there was more hill. My boots were falling apart and we had taped them together with a bandage, and Barry was getting very scraped up, and I really thought, ‘that’s it, we are going to be stuck here for the night,’” she says. “But in the end we made it back to the boat.” She isn’t afraid of much, and she sets a brisk pace.
“Walking is my time to think,” she says as to why she likes it so much. “I like to climb – I’m a goat, a Capricorn. I also think it’s a good way to talk to people. When my son was little, he used to say, ‘Mom goes on walks for two reasons: to hire someone or to fire them.’ It’s true, I often ask people to walk with me when I want to talk to them about serious things. I think it’s much better to have those conversations when you are moving. At work, sometimes I take people for walks on the High Line, which is right by my office – often if it’s a young person and we are having a career discussion, for example. It puts them at ease, and there is a finite length to it.”
When Diane hikes she does not pause to examine trees or pick flowers or commune with nature; she is oriented towards the goal, which is the summit. When we get to the top – a flat rock with a panoramic view of the neighbouring countryside – she sits down and sighs. Below us is Waramaug Lake. “That was Amy [Spindler]’s house,” she says pointing at a house on the water. Spindler died in 2004 of a brain tumour. “We came here to sprinkle her ashes. I think about her more than most people, probably, because of this place, and because she meant a lot to me. When I relaunched my business in 1997, and was feeling very insecure and small, her enthusiasm helped enormously.” She turns and looks in another direction, at another point in her life.
“My son used to run around this lake when he was in school: eight miles,” she says, and turns again. “The water is very good to swim in; it makes your hair feel really wonderful. It’s like swimming in rainwater.” And then she turns again, forward down the trail, and starts off, striding down the mountain, propelled by her own momentum into the future, the rest of us trotting behind.
Vanessa Friedman is the FT’s fashion editor