ollowing bankruptcy in the late ‘70s from his first apparel business, The People’s Place, Tommy Hilfiger set out to master not only the creative pulse of fashion, but also the business of commerce. By this time, preppy style had manifested into a class of its own, with aspiring designers opening doors to wealthy clientele left and right. With the style originating from upper-class Ivy League college students on the East Coast, it drew inspiration from popular New England sports like sailing, fencing, golf and polo. Preppy became so much more than a fashion statement, it was (and is) a culture and lifestyle. So, how exactly did Hilfiger go from bankruptcy to iconic, internationally-recognized, “preppy American luxury”?

The Making of a Fashion Icon

The Birth of “Tommy Hilfiger”

In 1985, Hilfiger decided to pursue his creative dreams once more, founding Tommy Hilfiger Corporation with the help of Indian fashion mogul Mohan Murjani. Being from the East Coast himself, he wanted to create a classically cool, American lifestyle brand with its own preppy twist.

ss active wear hilfiger blog quote

Knowing he would need to make a profound mark in the industry to beat out the competition, Hilfiger partnered with advertising genius George Lois. Lois created a risky campaign that compared the then-unknown Hilfiger with household names Ralph Lauren, Calvin Klein and Perry Ellis on a billboard in Times Square—and it paid off. Almost overnight, consumers knew the name “Tommy Hilfiger”. Just three short years later the brand had already made $25 million in sales. By the ‘90s, Tommy Hilfiger was an industry pioneer blending fashion and celebrity through tour sponsorships and ad campaigns.

The George Lois Tommy #Hilfiger Times Square ad comparing Tommy to fashion icons Ralph Lauren, CK & Perry Ellis, proves it's good to take risks in #advertising.CLICK TO TWEET

Learning From Growing Pains

The rapid growth that catapulted the brand to success in the ‘90s eventually resulted in its downfall through market saturation, ultimately cheapening the brand. After a strategy shift and acquisition in 2010 by one of the largest global apparel companies PVH, Tommy Hilfiger was able to rise to the top of the fashion industry once more. In 2017, Tommy Hilfiger brands global retail sales reached about $7.4 billion. And, most recently, the brand was honored by Fast Company as one of “The World’s Most Innovative Companies” for Style.

American Cool Style With a Preppy Twist

What is Preppy Style?

Preppy style can be dated all the way back to the early 1900s when a group of privileged men at Ivy League schools created a new look focusing on leisure and athletics. Geared toward the middle and upper classes, the clothing was a display of wealthy culture—deeming the fashion “American luxury.”

How to Master the Look

The look itself is inspired by a clean-cut appearance and classic hues and prints, with Tommy Hilfiger being the modern style icon. The brand aims to focus on consumers between 25 and 40 years old with a household income of at least $50,000, remaining on trend with millennial buying patterns of “affordable luxury”. Some recent ambassadors for Hilfiger include five-time Formula One® World Champion Lewis Hamilton and model Hailey Baldwin.

Here’s a look at some of our favorite ways to master, as Hilfiger himself calls it, “classic American, cool style with a preppy twist”:


A button-down gingham shirt paired with boat shorts or chinos.


To play up the look, throw on a quarter-zip over any button-down.


In the summer, wear a fitted dress and tie this chambray button-down around your waist. In the winter, throw a sweater on over this top and pair with riding boots.

We’re excited to announce the addition of the Tommy Hilfiger brand to our ever-growing, elite collection of wholesale apparel. You can check out the entire line of new Tommy Hilfiger styles on the S&S Activewear website!

Jan 14, 2019
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