Prep

Obsession with J.Crew on full display

Oct 27, 2023

If you had to wear one clothing brand for the rest of your life what would it be?

Without hesitation, I would choose J.Crew. I am uniquely passionate about this brand because I appreciate the classic look, modern relevance and ease of its pieces. I love history, I’m nostalgic, and this brand seems to hit those notes with elements of modern freshness that I can’t help but buy into the brand (quite literally).

I recently finished The Kingdom of Prep: The Rise (and near fall) of J.Crew by Maggie Bullock. This book was the perfect mix between my favorite topics - fashion, history, and business. For most people my age, I don’t think they considered J.Crew “cool” until recently. Maybe they still don’t find it cool but one thing is for certain: J.Crew has managed to remain relevant for 40 years despite how much the world has changed. As the title states, J.Crew has been on the brink of existence a couple of times yet in 2023 they are experiencing a masterful comeback reminiscent of the early 2000s. The Company has been through two leveraged buyouts, an IPO, and Chapter 11 bankruptcy. This begs the question - why is J.Crew still relevant? How does any brand stay relevant in our throw away society?

My answer, and what Bullock describes in the book, is that J.Crew is familiar and authentic - like your favorite TV show or an old worn-in sweatshirt. What is interesting about looking at J.Crew’s history is in the periods where it almost failed, the Company distanced itself from the core look and in trying to accomplish this, the quality suffered too. This is a key business lesson: Pick something and be the best at that thing. J.Crew tried to get outside its core aesthetic and suddenly became less familiar and relatable to their most loyal followers. Sure, J.Crew has almost always been synonymous with “prep” but what makes it different is that I’ve never viewed it as ostentatious, but instead ease, casual sophistication.

The Company was built by a catalogue expert, Arthur Cinader, in the 1980s. It was Arthur and really his daughter, Emily Cinader, who turned the Company into a what was once known as “the American brand”. Arthur had neither a high school nor college diploma yet Bullock describes “[Arthur] was a student of everything, a voracious reader and observer who loved, as one friend put it ‘to roll around in ideas and concepts.’” Arthur’s early vision and surgical management of every detail from catalogue copy to quality of a rollneck sweater to the beams inside the 99 Prince retail location, were the foundation which Emily built upon to turn J.Crew into a household name. People were fascinated with Emily but then came Mickey Drexler, the merchant prince, and eventually Jenna Lyons, a fashion phenom. The personalities of J.Crew’s leadership team over the years are key to the transformation and growth it experienced across decades. You’ll have to read the book to really understand all the intricacies of these characters and I highly recommend doing so.

A few key elements stand out to me about this business which are fundamental to building any successful business in my mind.

Why
People
Timeliness

Why. If you found a business, you better eat, breathe, sleep whatever it is you’re doing. We’ve all heard the saying: people don’t buy what you do they buy why you do it. For Arthur and Emily Cinader, J.Crew style wasn’t something they aspired to, it was who they were at their core. The why wasn’t to create this preppy brand that people associated with wealth and New England summers on exclusive islands off Massachusetts. “The word they most often used to describe the look was “American” Emily had banished logos; she loathed all that status-conscious boasting,” writes Bullock. They wanted the clothing to be accessible and familiar, “…[for catalogues] the litmus test of a great J.Crew picture was: Does it feel real? Could it pass for a snapshot?,” writes Bullock. I love J.Crew for the simplicity and knowing what I do now about the founders of this business and their unassuming ideals I align with the brand even more so than before.

People. I’ve already touched on the key players that founded the brand and those that carried it forward through the decades. As Bullock notes, “…only Mickey and Jenna - are famously credited with leading J.Crew into a new golden era. But there was a team of heavy hitters behind them…they knew how to turn Mickey’s rapid-fire brain waves into full-fledged businesses.” The best businesses have incredible people in the right positions to efficiently generate the most success. The old saying “it takes a village” applies to more than raising children. I think it’s one of the key pieces of any successful brand but as Bullock keenly points out there’s a fine line between idolizing key players (CEOs, Founders, Designers, etc) making them the face of the brand and putting the right players in position to cohesively bring out the best in each other while embodying the brand to its core.

Timeliness. Every successful business is the beneficiary of its rise during a specific time in which that one thing was needed and sought after. Truly iconic and history defining brands - Apple, Nike, Tesla - are the disruptors, “ahead” of their time and benefitting from sufficing a need or solving a problem before the general public realized they needed or wanted this thing. While J.Crew hasn’t changed the world, I do think timeliness plays a role here. This is the benefit of a company that’s been around forty years, we see how time either helps or hinders. Bullock catalogues J.Crew from “the catalogue boom of the '80s to the specialty retail bonanza of the ‘90s, through the birth of online shopping, and into an era in which we shop from our phones that never leave our hands…” It is wild to see how fashion and shopping in general has changed in the last four decades.

It’s hard to succinctly write about a 325 page book that was full of poignant ideas around the way prep has been characterized over the years, how fashion has changed and how our background truly shapes us as leaders. I hope if nothing else this inspires you to think about the way you consume the brands you do and appreciate the work that has gone into keeping that brand relevant. Because I love J.Crew I’ve pulled together links to my current favorites and provided them below. Hope you enjoy!