because life doesn’t fit in a file folder
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I Have One Lilly Pulitzer Dress

“Being happy never goes out of style.” ~Lilly Pulitzer

 When I was in middle school, the pretty girls took off their Fair Isle sweaters in May. They sloughed their turtlenecks with the little whales on them and switched up the covers on their Bermudas bags. Spring meant sunshine and tulips and daffodils and lovely lightweight dresses.

One day, I dared to ask a pretty girl where she found her colorful sleeveless shift.

“It’s not from here,” she said, crossing her arms in front of her very flat chest.

“But where did you get it?”

This particular pretty girl – let’s call her Courtney — flipped her hair and caught it in one hand, a move I could never master.

“It wouldn’t work on you,” she said. “It’s a Lilly.”

Cover of The Official Preppy Handbook
Cover of The Official Preppy Handbook (Photo credit: Wikipedia)

That night, I consulted my Official Preppy Handbook. It showed a photograph of a similar looking dress to the one Courtney had worn in school that day. The handbook stated that Lilly Pulitzer clothing was a “must-have” item for all “preppy” women.

In middle school, I didn’t care that my mother made kick-ass matzah balls.

I just wanted to be a prep.

Looking at myself in the mirror, I thought about Courtney’s words. A little Jewish girl with a big nose, I’d never look good in a casual shift dress. I’d never rock pale pink lip-gloss. At summer camp, when I got off the sailboat, my hair was a frizzy triangular mess. I’d never look like I’d spent the day relaxing on the yacht. Who did I think I was?

About five years ago, I was in Florida shopping with my friend, Jan, when we passed a Lilly Pultizer Shop. I’d never seen one before. We don’t have Lilly Shops in Western, New York. Why would we? We wear sleeping bag coats for most of the year.

Anyway, Jan encouraged me to go in. She may have physically pulled me through the door.

I didn’t think I had any business being there.

But I sifted through the yummy racks filled with whimsical fabrics.

How can you not love orange elephants?
How can you not love orange elephants?

I heard Courtney’s voice in my head.

What was I doing? I was still that Jewish girl. And now I had boobies. Big ones. How was I ever going to fit into anything Lilly? It was ridiculous.

Jan handed me a pile of dresses and commanded I try them on.

And there was this one.

When I came out of the dressing room, the Lilly ladies made a fuss.

{But, you know, they work on commission; they’re paid to smile and coo.}


I looked at myself in the mirror, and I liked the way I looked.

I’m no socialite.

And I’m decidedly unpreppy.

But I bought it.

Because screw you, Courtney.

It works on me.


Lily Pulitzer passed away last month, on April 7, 2013 at the age of 81. I am confident her legacy of brightly colored fabrics featuring flamingos & seals & peacocks & turtles & elephants & hippoptamuses & flowers & flowers & flowers will live on forever. A believer in the power of whimsy, I like to think we would have been friends.

• • •

May 14th marks the beginning of my 4th year in the blogosphere. Come back next week because I’m giving away a Lilly Pulitzer handbag, baby!

In the meantime, tell me about something you never thought you could wear/do/be, but you did it anyway!

tweet me @rasjacobson

120 thoughts on “I Have One Lilly Pulitzer Dress

  1. You know, I read this when it was posted via FB, but I suppose I never commented. It’s a super cute dress I could never wear because I don’t think Lily makes stuff in my size. But you look awesome in it! :>

    1. This is the beauty of a handbag. Anyone can look and feel fabulous holding it. 😉

  2. Insert “Wolf Whistle” here.

    (selfish comment to gain an additional entry for some silly handbag that I have no chance of winning)

    1. Actually, you do look super hot Renee, so there is that also…

  3. I had a similar experience a couple years ago while vacationing in Ft. Lauderdale. I walked by the Izod/Lacoste store and gaped at the gorgeous, up-scale Country-Club clothing and thought, what on earth would I find in there that I could afford/would fit/would look good in? Then I spied the sign with the magic words written on it: “SALE” and I thought, “What the heck?” My daughter and I nonchalantly entered the pristine store with the white walls and shelves and perused the merchandise. An adorable red and white striped polo caught my eye, along with its accompanying mini skirt. I carried them back to the fitting room and traded them for the shorts and t-shirt I currently sported. Oh! They fit perfectly! And, talk about cute! Then the sales girl spotted me twirling around in the 3-way mirror and told me, “Did you know all our sale merchandise is an additional 30% off?” No, actually, I did not! Woot, woot! I am now the proud owner of a fun Izod ensemble and every summer I look forward to wearing it. I hope you have many more years of fun wearing your own Lilly (she is next on my list of wardrobe investment pieces!)

  4. I did I similar thing. In middle school in started out the year wanting desperately to be a ‘hipster’. I came from the type of family’s that wears Lilly Pulitzer. I don’t mean to brag, but many could consider me to be a ‘socialite’. Growing up in eastern New York, plenty of people wore that kind of stuff, but you had to know what it was. I stopped my whole hipster act in the first or second week of 6th grade. I decided my whole life would revolve around VS PINK. In the third quarter of middle school, I noticed how many boys and girls wore Vinyard Vines. And that’s where it all started. I went online and looked and looked at their clothes, sometimes crying about much I wanted to be one of those girls. My mom told me those girls are ‘preppy’. I WANTED SO BAD to be a ‘preppy’ girl. I looked up stuff online and on YouTube and found out what the brands were, how to wear what you have and bassicly how
    to live THAT life. My parents bought me two Vinyard vines sheep shirts, a VV tee shirt, and Lilly Pulitzer shorts. Now, I’m a ‘preppy girl’ all the girls think of me as the Cpurtney chick (I’m much nicer than that btw) as I type this, I’m wearing a lIlly shift, pearls, and jacks. I even saw how the preppy girls all played field hockey. So, now I play field hockey. I was scared at first to try and be one of them. But being that person is great! If you have a similar issue like me with trying to fit into a group, just go for it. What’s the worst that can happen, everyone who you want to be like doesn’t like you? Everyone else will still think of you as one of them.

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