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My Love-Hate Relationship With Lilly Pulitzer

I gradually realized that even the perfect clothes wouldn’t help me fit in — and that I didn’t want to.

Photo: JP Yim/Getty Images

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For a brief period during my tween years, the single most important thing to me was acquiring a Lilly Pulitzer skort. Now would be a good time to disclose that I was what you might call a country club rat. Every summer, I spent approximately eight hours a day at a country club in suburban New Jersey. I’d start the day off with golf lessons in the morning, then transition to the pool, where I’d play dibble and eat frozen Snickers in my American flag tankini before changing into a Speedo for evening swim meets. It was privilege. It was very nice.

The club was historically white, Anglo-Saxon, and Protestant, so much so that every week in July, it emptied out when my friends went on their Presbyterian church’s youth trip. There were one or two Jewish families, and then there was mine, with slightly darker skin that tanned well and names that the swim meet announcers couldn’t pronounce. No one was quite sure about us, nor did they care until 9/11 happened and Iran (which one of my friend’s mom explained to her as “the country next to where the terrorists are from”) became a hot topic.

Denim wasn’t allowed at the club, so my go-to uniform was a pair of khaki shorts, which I’d wear at the required knee length for golf, then roll up five inches as soon as I dropped my kids-sized clubs at the pro shop. I had a steady repertoire of solid-colored polo shirts, and with the occasional addition of a grosgrain ribbon belt, I looked like an ethnically ambiguous Gap Kids model. My outfits, however, paled in comparison to those of my peers. Sure, their shorts didn’t have pockets deep enough to hold four golf balls, but they had patterns: bright blue monkeys hanging on yellow chandeliers, pink lobsters holding hands with sea turtles, lime green alligators floating on lily pads. How did all the other girls get the memo to wear pastel-printed golfwear? Why didn’t anyone tell me?

I told my mom about their outfits, and in return she told me the story of Lilly Pulitzer, a Florida housewife who had a juice stand and wore colorful dresses to disguise the fruit stains. I asked if I could get “something Lilly Pulitzer” (anything would do), and she immediately said no. After weeks of cajoling and a promise to take the recyclables out, my mother comprised: I could get my something Lilly Pulitzer, but it had to be from eBay.

Thus began my preteen eBay addiction, defined by late nights in front of the family computer waiting for auctions on “NWT kids size 12 Lilly Pulitzer” to end. I ended up getting a “like new” skort that was a patchwork of different patterns. It was my gateway drug, and I spent the next few summers saving my money for Lilly Pulitzer apparel, some secondhand, others from signature boutiques with names like Palm Tree in Paradise and Splash of Pink.

I fell hard for the brand’s manufactured idea that transforming your life into a permanent four-star vacation is as simple as wearing dresses with dancing frogs. Lilly Pulitzer represents a certain lifestyle, one that I dabbled in by consequence of belonging to a country club that I never truly felt a part of, and not just because my dad had an accent and a woman once mistook my older sister for a locker room attendant. Many of the parents at the club had grown up in similar social circles — a group of men had been in the same college fraternity, while another had gone to the same New England summer camp — and belonging to a country club was par for the course. To my parents, it was an opportunity that only became available when they had the money to afford it. It was a nice amenity, but it wasn’t woven into the fabric of our family. And yet, the lives of my summer friends seemed better than mine because country club life came so naturally to them — their parents bought them pretty clothes (not from eBay), drank martinis before dinner, went to Florida for long weekends, and used “summer” and “lunch” as verbs.

A few years after I had grown out of my beloved skort, my family went to Florida. We had never been and my parents wanted to see what all the fuss was about. We stayed at a fancy resort where the people were whiter, richer, and dressed in more pink and green than I had ever seen in New Jersey; I had reached Lilly Pulitzer mecca. Like my own country club routine, it reeked of privilege, but a different, deep-seated type in which being waited on and dressing for dinner wasn’t part of being on vacation, it was a rule of life.

My family didn’t know what to do with ourselves. We didn’t have the right clothes, so we left the resort for every meal and spent most of our downtime people-watching in the lobby. On the last day, we ditched the resort and went to Miami.

My love affair with Lilly Pulitzer ended on that trip to Florida. Maybe all the other hotel guests led the happy, endless-vacation lives that their clothes suggested, but I was homesick for my family’s values, where vacation was a break from hard work and wealth was self-made. The thing about Lilly Pulitzer is that she wasn’t a mere juice vendor — she was a socialite whose husband owned the citrus groves that supplied her stand. Plenty of people can wear Lilly Pulitzer, but you can’t just sign up for that martini-sipping life; you have to be born into it. It’s the kind of life where privilege is taken for granted, and I was raised to know that it shouldn’t be.