Tipsy Good-Time Gal Struts in Stilettos

Holly Dunlap, who wears a perma-tan, gold and exclamation marks, grew up in Scottsdale, Ariz., where her mother forbade her to wear black. “I grew up wearing basically all pink and green until I was a teenager,” she said.

Dad was a real-estate developer; Mom covered the house head to toe in Lilly Pulitzer. “It was a Lilly Pulitzer playhouse!” Ms. Dunlap said. There was golf, sailing and horses: “I rode English and Western. My boots were really nice.” Winters in Palm Beach and the Bahamas. Her father was recently voted one of Arizona’s 10 best-dressed men by a local paper. “My dad’s closet is insane,” said Ms. Dunlap. “He has pink pants with green frogs on them. Bright purple blazers. Yellow pants with turquoise turtles. He’s kind of known in town as the guy with the wild style.”

Today the blond, 5-foot-10 Ms. Dunlap is a shoe designer; she’s opened Hollywould stores in Nolita and Palm Beach. This winter, she’s adding a clothing line. Her shoes also sell at Barneys New York, Saks Fifth Avenue and Bergdorf Goodman. She has the distinction of designing the most practical $600 stilettos you can find: They have a special heel and foot bed that is springy and padded so you can run around in them. In other words, they are sexy shoes you can get roaring drunk in.

Which brings us to Ms. Dunlap’s Web site, in which she keeps a running diary of her life as a 32-year-old single party gal with an apartment on Washington Square Park and one in Florence and 400 pairs of shoes. A recent entry:

My mom hates it when I talk about drinking on the diary. She says it makes it seem like all I ever do is go out drinking, which really isn’t true. In fact, only twice in my life have I ever had so much to drink that I actually made myself sick. The first time was when I was 15 years old, at a party on the last day of school my freshman year in high school in Arizona. Too many Bartles & James fruit punch wine coolers really did me in, which isn’t too surprising considering the quality of the beverage. The second and only other time I have ever drank so much I got sick was Tuesday night. Oh, what a night.

Her wild, albeit WASP-y ways started early.

“When I was 16 years old, I took summer classes at F.I.T. in New York. I lived with two teenage models in Hell’s Kitchen and worked as a cocktail waitress at a blues bar,” she said. She met a fellow named Harrison Kravis, whose dad was billionaire buyout specialist Henry Kravis, who at the time was married to society couturier Caroyln Roehm. Soon enough, Ms. Dunlap had herself an internship working on Ms. Roehm’s designs for the “Ivana power-lunch ladies.”

She was paid in shoes. Those were, she said, the first “really nice shoes I owned other than my riding boots. All my other shoes were flip-flops and sneakers. Well, that and a few pairs of Candies.

“At that time, New York was a totally different place,” she said. “There was no enforcement of the drinking age; nightclubs like Disco 2000 and Club USA went until 9 a.m., and everyone was crazy. The day I arrived at F.I.T., I made friends with some gay boys who showed me the club scene and spent the rest of the summer enjoying being away from my parents. My first night out, I actually met Lou Reed and Mick Jagger, and from then on it was crazy every night. At the time, everyone in the club scene had club names, like Richie Rich or Walt Paper. So I was nicknamed Hollywould.

“I was actually really responsible,” she said, “but I can’t imagine how on earth I convinced my parents to let me move alone to New York when I was 16!”

Her fashion horizons quickly expanded. “In my punk-rock phase-when I wore black, against my mother’s wishes, and dyed my hair pink-I totally fell in love with Vivienne Westwood,” she said. “And I always loved Christian Lacroix, kind of in secret. He used to be my favorite designer.”

She went on to the Rhode Island School of Design, but after one year transferred to the Paris campus of the Parsons School of Design. She got a place in the 10th Arrondissement and applied for an internship at Lacroix.

“I worked there for free for a year!” she said. “I had pink hair. The suits at the company thought I was crazy.”

She also worked for the Paris office of British designer Vivienne Westwood. “They’re really good friends!” she said of Ms. Westwood and Mr. Lacroix. “Eventually he said to me, ‘She probably needs help in London-if you go, you will go with my blessing.'”

And off she went. “Once I’d moved to London to work for Vivienne, I got caught working illegally, which I didn’t even know I was doing,” she said. “I literally got caught at Heathrow coming back from Paris with all this luggage. No one knew that my work visa had expired. Six months!”

Holly went to Hollywood, where she got a job as a stylist for the photographer Peggy Sirato, “who is kind of like an Annie Leibovitz.” She stayed a year.

“It was kind of nice being out there. I’d been working nonstop since I was 17,” she said. “For the first time I wasn’t working seven days a week. I really got to enjoy life, L.A. style. I could wake up and go roller-skating on the beach!”

But then her roots came calling.

“I saw an ad in the paper for the Lilly Pulitzer head-designer position, and basically I brought them my portfolio, which has nothing to do with Lilly at all-all sorts of things that didn’t apply, like my designs at Lacroix,” she said. “But then I did a little special project for them, which showed pictures of me from my birth to, like, whenever wearing Lilly. And right in the middle is this family picture, from Easter: 30 family members-men, women and children-on the steps of my grandparents’ house, all of them head to toe in Lilly. They saw the picture and they were like: ‘She’s in!'”

She moved to Philadelphia, where Lilly Pulitzer was based. The company had been out of business for several years; in the early 90’s, two Harvard Business School graduates named James Bradbeer and Scott Beaumont, bought the name and relaunched it. In came Holly. She was 25 and head designer.

“I used to fly down to Palm Beach to hang out with Lilly for inspiration,” she said. “Most of what we did was lie around the pool drinking margaritas. Which was wonderful.”

She was credited with revamping the Pulitzer line, helping to bring it its current haute-hip status. But she cooled on the environment. “The trouble is that their stuff wasn’t sexy enough for me,” she said. “I kept trying to make it sexy-shorten the hems of the skirts, things like that-but they wouldn’t have any of it.

“At one point during my time there, I realized I had to be my own boss,” she said. “I started teaching myself Italian with tapes. Just before I flew to Italy, I had been in touch with the Italian Trade Commission about shoe factories. They gave me a list of about 30, all of which had reservations about taking on a fledgling company like mine, until I found one small factory that was willing to work with me.”

She still spends seven to eight months a year in Florence. She opened her Nolita store with its candy-striped awning in autumn 2002, followed by a branch in Palm Beach in 2003. Her parents recently became investors in Hollywould.

“My mom and dad still mispronounce ‘Ralph Lauren,'” said Ms. Dunlap. “They just basically want me to get married, have kids and quit this shoe-business nonsense! But recently my dad’s been getting really good. We were watching some awards show a few months ago, and he said, ‘Holly, is that dress that girl is wearing by Vivienne Westwood?’ And he was right!”

She appeared on the fashion radar in 2002, when she was nominated by the CFDA for the Perry Ellis Award. The ceremony was being held at the New York Public Library, and Ms. Dunlap found herself embroiled in a protest outside the entrance.

“I was really drunk, and everyone who knows me knew I was drunk, and there were these protesters outside who looked like PETA protesters, and they had my head on a stick,” she said. “So I went over there to ask them why they had my head on a stick. They told me they were protesting Perry Ellis, whose name was on the award I had been nominated for. So I was like, ‘O.K., whatever, but that picture? Where did you guys find that picture of me? Because it’s really flattering! Can I get my picture taken with you guys holding a stick with my head on top of it?’

“Someone saw me making friends with them and wrote about it. I thought the whole thing was a bit silly, so I wrote to them explaining that I just drunk. What’s wrong with making friends when you’re drunk? Frankly, I think it’s smart to go to fashion parties and get drunk!”

Indeed, when in New York, Ms. Dunlap is rarely far from a boisterous bash.

Not to mention when in L.A. A recent diary entry:

I can’t put my finger on it, but somewhere between Star Shoes and the next club was where my drunken dialing began. I called everyone on my phone rolodex including … say it isn’t so … yes, my Secret Crush. This is someone who I am too shy to even look in the eye, let alone speak with, let alone call, especially at 3am NYC time. I have often seen his name in my phone and thought, Hmmm I should really delete that ….

She declined to say more about her secret crush and added that there’s no man in her life at the moment.

“It’s really hard to date while I’m doing this,” she said. “This sort of job just doesn’t allow you to keep a boyfriend-I’m always leaving town! And Italian men don’t really cut it for me. I found that everything one hears about Italian men is true .”

She hasn’t had much luck with New York men, either. From the diary:

From the Versace store I somehow ended up in a taxi full of young men with accents and we headed to Amy Sacco’s Bungalow Eight. Now, I do know that Rena’s party was full of handsome eligible men and I was probably sharing a taxi with most of them, but for some reason whenever I go out on the town I forget that I am single and in need of a boyfriend/husband, and the only boys I talk to are either gay, 19 years old, the help, or worse yet: the gay 19-year-old help. Upon arrival at Bungalow Eight I immediately found a crowd of 19-year-old boys and practiced my hip-hop dance moves ….

She said Hollywould is breaking even but insists she’s hardly living large.

“I’m living like a student!” she said. “Although a few months ago, after flying cattle for years and years, I put my foot down and said, ‘My customers are spending $600 on my shoes, I’m selling to Barneys, Saks Fifth Avenue and Bergdorf. I think I’m allowed to fly business now!'”

Tipsy Good-Time Gal Struts in Stilettos