An outsider’s take on how the preppy brand remains relevant, retains exclusivity—and comes back down to earth

Disclaimer: I don’t own a single item of Lilly Pulitzer merch. In fact, for a long time I poked fun at the bold, bright, and sometimes gaudy shift dresses that are iconic of the brand.

But somewhere along the line, without me even realizing it, my view of Lilly Pulitzer shifted (pun intended!). 

But why? How?

It’s hard to find answers to these questions without first exploring why I and so many others found ourselves feeling disconnected from the brand to begin with.

Perhaps it has something to do with the aura of exclusivity surrounding it. Lilly Pulitzer has always been associated with the upper class—after all, the designer herself was very much a part of it. Lilly Pulitzer has been a brand long favored by the likes of the Kennedys, from Jackie O (Lilly’s former classmate) to Kick and Kyra.

Then there’s the fact that Lilly Pulitzer stores exist inside places like Ocean Reef Club, a private community in Key Largo, Florida, where just the initiation fees can run upwards of $200,000.

There’s also no question that Lilly Pulitzer has become the de facto uniform of sororities, exclusive by their very nature. Take a peek at any southern sorority rush week vlog and you’ll see that Lilly is ubiquitous. The brand is so popular with sorority sisters that the company even launched a (short-lived) sorority collection in 2010.

“The Lilly look” doesn’t come cheap—a dress can easily set you back $200; a half-zip can cost $100; even a t-shirt will run you $50. The brand never repeats prints. And with the prints being so distinguishable, it’s easy to spot a repeat wear. So, women who like Lilly end up buying lots and lots of Lilly.

But the exchange taking place here between customer and company is more than just one of money for goods. I’ve always asked myself: do people really love Lilly Pulitzer clothing? Or do they like the statement that wearing Lilly makes on their behalf? Or is it that they love being part of the community that Lilly Pulitzer fosters? Because let’s be honest: the community is strong.

There are Facebook groups like Friends That Lilly and Styling My Lilly that serve as social forums for lovers of the brand. Fans share photos of themselves on Instagram dressed in their Lilly Pulitzer, using hashtags like #lifeinlilly.

In the weeks leading up to Lilly Pulitzer’s semi-annual After Party Sale, the company taps influencers to announce the sale dates, reveal what items will be included, round up their picks into shopping guides, and advise their readers on how to devise a game-day strategy.

To purchase Lilly Pulitzer is to buy into the friend group.

To Lilly Pulitzer’s credit, though, it hasn’t relied on its established customer base of card-carrying preps to keep it going. In 2015, the brand partnered with Target to sell affordable versions of Lilly Pulitzer items—everything from clothing to accessories to homeware. The collection, which consisted of 250 items that were limited in quantity to maintain a sense of exclusivity, sold out in stores and online within just a few hours of its launch.

It goes without saying that Target, one of the largest retailers in the world, has a wider reach and higher convenience factor than the Nordstroms and Lilly Pulitzer boutiques through which the company normally sells. But Target also caters to a different crowd: their typical customer is a millennial mom whose household income is $80,000. By offering a change to price and place, even if temporary, and by staying true to the Barefoot Princess’s down-to-earth spirit, Lilly Pulitzer has been able to reach a whole new customer base and initiate them into the Lilly lifestyle.