We’ll Never Stop Ogling Calvin Klein

When I say Calvin Klein, what springs to mind? Perhaps it’s a fluffy-haired teenage Brooke Shields, dressed in curve-hugging jeans, saucily speaking to a camera — or the simplest of slip dresses making its way down a ‘90s-era catwalk. It might just be a logo CK T-shirt at your local Macys. Or, if you’re a living, breathing human who’s been on the internet this last year: an oiled up Jeremy Allen White, frolicking around a NYC rooftop (as one does) in his tighty whities.

There’s no right answer to this question. But that just proves the mercurial appeal of Calvin Klein. Since launching in 1968 as an outerwear label, it’s evolved to something bigger than just a mere fashion house. It’s a far-reaching touchstone on multiple levels; a fashion brand, yes, but also a key player in the cultural zeitgeist of the last five decades. It’s given us countless celebrity campaigns, major runway moments, and red carpet placements from which to draw reference. And now, as another fashion month comes around, there’s another force shaping the company’s legacy: A debut collection from newly appointed creative director Veronica Leoni.

A veteran of Jil Sander, Celine (under Pheobe Philo, no less), Moncler, and The Row — and founder of her own label, Quira — Leoni is the first lead designer to come into the house since Raf Simons’ late 2018 exit, and the only woman to ever hold the position. Her collection will also mark Calvin Klein’s return to the NYFW calendar after a seven-year hiatus.

The event is poised to be one of the hottest tickets of the week, and why wouldn’t it be? There’s understandable anticipation of what Leoni (who, for her lofty pedigree, has never worked with such a commercially relevant label) will bring to the table with such massive resources behind her. It will be fascinating for fashion nerds to see how she adapts her specific sort of cerebral minimalism to a company that plays in both high and mass spaces — this means she, ideally, needs to thread the needle between forward-thinking clothes and pieces that appeal on a mass market level. However it plays out, though, this shift is sure to usher in yet another interesting chapter in the Calvin Klein history book.

Before we look to the future of Calvin Klein, though, let’s take a moment to look back at all the ways the label has shaped trends, style, and pop culture. Ahead, you’ll find nine of its most influential moments throughout the last five and half decades — here’s to seeing more in the seasons ahead.

A Brand Is Born

Calvin Klein the designer launched Calvin Klein the brand in 1968 with the help of $10,000 seed money and his business partner, Barry Schwartz. And while the label is now known by most for its underwear and jeans, it began with a focus on coats. “It took him until about 1975 to find his groove: casually elegant, minimalist sportswear in luxurious fabrics and neutral shades,” notes fashion historian Kimberly Chrisman-Campbell of the company’s early days, which saw near instant industry support (particularly from American Vogue). “That’s been the Calvin Klein brand identity ever since.”

Licensing Enters The Chat

According to BOF, Calvin Klein’s annual revenue had grown to $30 million within its first 10 years of business. This, of course, was thanks in no small part to the brand’s savvy way of making super simple, commercially viable items (like denim and lingerie) feel incredibly sexy and exclusive. By the end of the decade Klein had inked a licensing deal for several major categories (including shoes, sunglasses, and sheets) making it all the easier for the average non-industry shopper to engage and identify with the label.

The Thirst Trap Campaigns Begin

Sure great clothes will often sell themselves. But you know what really seals the deal? Adding some of the world’s most attractive models, celebrities, and athletes to the equation. This is something Calvin Klein discovered early on through his iconic “Me and My Calvins” commercials starring Brooke Shields, as filmed by famed photographed Richard Avedon. The series of controversial vignettes, in which the then-16-year-old spoke directly to the camera with wide-eyed innuendo, were debated as exploitive (and still are today, including by Shields herself in her Hulu documentary, Pretty Baby) as the model was both underage and portrayed an extremely suggestive manner. But there’s no denying the questionable footage brought in plenty of customers: Per reporting at BOF, Fortune put Klein’s annual income at $8.5 million in 1981 — just one year after Shields’ campaign debuted.

Then there was Calvin Klein’s first underwear ad with Olympic pole vaulter Tom Hintnaus, shot from below wearing nothing more than a very, erm, fitted pair of white briefs. “That thirst trap would serve as the template for four decades of button-pushing underwear ads, right up to the current Jeremy Allen White campaign, which boosted underwear sales by 30% in its first week and gave Calvin Klein the highest consumer engagement in the company’s history,” says Chrismas-Campbell. “Unusually, Klein has always put his print models under exclusive contracts, creating a distinctive aesthetic that he could stretch out over several seasons” This, agrees fashion historian and author of Westernwear: Postwar American Fashion and Culture, Sonya Abrego, has proven to be a very potent formula. “That was just such a, a huge moment in the history of advertising — and presenting men in such a sexualized way got a ton of attention,” she says. “The campaigns are kind of the same today, and people are still paying attention.”

The Scent Of Success

The imagery around CK One perfume in the 1990s is now considered a defining part of the decade, but at the time, it represented a sharp turn in the aesthetic of the advertising landscape. Shot in black and white with several of the era’s defining models (including, most notably, Kate Moss), the campaign — much like the clean, crisp unisex fragrance itself — stood in stark contrast to the decadence of the 1980s. “The tone of the CK One ads was such a big deal back then,” says Abrego, who says the casting in particular was “very creative and edgy” for the time. “Yes, there were famous models, but also non-models.” She continues to note that many of the featured models were extraordinarily thin, which drew criticism for promoting the rising “heroin chic” look of the ‘90s, but also is a marker of Klein’s ability to adapt his vision to the ever-evolving moods of fashion. “The photos are black and white, but his actual product stayed the same.”

All In On Kate

Kate Moss was not just the face of Klein’s hit CK One perfume, she also became a the face of Calvin Klein denim and underwear (alongside actor Mark “Marky Mark” Wahlberg) and a regular at the label’s NYFW shows. Her relationship with the house not only made her an international star, but played a major role in reviving her career when it tanked over alleged drug issues in the early 2000s: Calvin Klein was one of the first brands to offer her work — a major contract in spring of 2006 — after allegations of cocaine abuse put her professional life on pause.

A New Creative Direction

In early 2003, Klein sold his company to Phillips-Van Heusen (now known as PVH Corp.) but stayed on as a creative consultant as Gucci alum Francisco Costa stepped in to design womenswear. Costa stayed fairly true to Klein’s clean and pared back approach to design throughout his 13-year tenure with the house, while bringing in some of his signature touches: artsy prints, gauzy layers, and elegant draping.

A Belgian In New York

It cannot be understated how the fashion industry completely lost their collective minds when Raf Simons — a Belgium-born designer and member of the famed Antwerp Six with high profile stints at Jil Sander and Dior — was appointed the creative head of Calvin Klein in 2017. Fashion royalty holding court at the scrappy, indie-label filled New York Fashion Week? You bet there was clamoring to get seats at the show. To some, Simons totally delivered the goods: Insiders were delighted by the European lens through which he filtered Americana classics — color blocked cowboy shirts, square-toed Western boots — but the line did not resonate commercially. So in 2018, Raf skipped back across the pond (and eventually to Prada, which he now co-designs with Miuccia) and Calvin Klein took a catwalk hiatus to focus on what it does best: selling simple staples via provocative and playful ad campaigns.

50 Years In Business

As Calvin Klein celebrated its 50th year in action, it looked to a new generation of beautiful it boys and girls to star in a mega-watt campaign selling a special anniversary collection. This buzzy cast included Kendall Jenner, A$AP Rocky, Liu Wen, Troy Silvan, and — perhaps most notably — high profile couple Justin and Hailey Bieber. The resulting commercial and editorial got a fair amount of buzz (because who doesn’t enjoy looking at famous people stripped down to their skivvies?) but nothing reaching the level of attention of the days of Shields or Moss. That level of collective hysteria, however, was soon to come.

A Bear Market

In what might be its most genius marketing move in decades, Calvin Klein enlisted actor Jeremy Allen White as its latest ambassador in 2024. Fresh off the success of his show The Bear, Allen White was definitely already percolating around society’s collective consciousness. But it was his shirtless, sweaty campaign — especially the commercial to go with it — that pushed him to new levels of notoriety. If you’ve watched it once, you’ve likely watched it subsequent five times as well. (No, just me?) The mega-buzz this generated for the brand, paired with some canny red carpet placements (such as Zendaya in Rome promoting Challengers, a very on-brand movie for Calvin Klein all about sports and sex) and new celebrity partners (including singer and dancer Jennie Kim of BLACKPINK, and actor Greta Lee) have teed it up nicely for a triumph return to the fashion month stage this month. I, for one, am rooting for the label to do big, thrilling things on the runway in the years to come. But whatever happens, there’s comfort in knowing one can always count on Calvin Klein for eye candy and great underwear.