In her 1942 film You Were Never Lovelier, Rita Hayworth, AKA the ultimate ’40s pin-up girl, made waves for wearing a sheer dress that showed the faintest sliver of nipple in between floral embroideries. She would go on to completely bare her breasts in see-through dresses just three years later.

Singer and actor Marlene Dietrich was fond of illusion naked dresses in the ’50s. Sheer pieces were strategically embellished to cover up body parts. While performing on stage in the latter part of the decade, however, she wore an embellished Jean Louis gown that showed off her breasts.

Jane Fonda has always been iconic. Before she filmed the camp classic Barbarella in 1968 (which included a strip scene), the activist had already been serving nip in various fashion shoots. Here she is in 1965, posing in a see-through ensemble.

Jane Birkin, the OG it girl, was actual decades ahead of trends. In 1969, at the famed Studio 54, the actor rocked several of today’s buzzy trends in one — Mary Janes, the exposed thong, the naked dress, and exposed nipples. (She was also seen rocking her signature woven basket bag.)

Cher and designer Bob Mackie frequently collaborated on her flamboyant ensembles. Her 1974 Met Gala look, however, is arguably their most iconic. In fact, it’s been referenced several times since by the likes of Kim Kardashian and Ice Spice. The glistening feathered number was also utterly see-through — one of the most risqué looks to walk the Met Gala red carpet.

In the ’90s, another pop star and designer duo emerged: Jean Paul Gaultier and Madonna. Though the French creative was always boundary-breaking, he really found his muse in Madonna (his cone bras became the pop icon’s signature look).

In 1992, during a fashion benefit the designer held for amFAR (The American Foundation for AIDS Research), Madonna stepped out in a Gaultier dress that fully framed her bare breasts. It was a moment. Kardashian recreated this look to attend the designer’s show in 2022, but covered up with a beige bra.

Who could forget this outfit Kate Moss wore in 1993? The diaphanous silver slip was indicative of the decade’s minimalism while the contrasting black thong was a bold fashion touch.

That same year, Naomi Campbell also made fashion history when she strutted with a bare breast on the Chanel runway in a flowy lavender number.

Another runway moment made history in 1997 when Dior sent Shalom Harlow down the catwalk in a dress so sheer it looked like she was wearing nothing at all.

Lil Kim is the queen of nip-centric ‘fits. Remember the purple seashell nipple pasty jumpsuit she wore to the 1999 Grammys? Well, that same year, she went the sheer route and subtly exposed her breasts in a masquerade-inspired bra and skirt set.

In 1998, Rose McGowan walked the MTV Video Music Awards red carpet in a shimmery mesh halter dress that was completely sheer. It was also one of the G-string’s first red carpet appearances. The ensemble would go down in MTV VMA history.

Jennifer Lopez has always been a spicy dresser. Way back in 2001, she was already ditching lingerie at the most prestigious of events, like the Oscars.

In 2002, just a year after Baywatch wrapped, its star Pamela Anderson walked the red carpet in a sheer pink lace dress that exposed nip and thong.

Historically, athletes weren’t expected to be spicy dressers. In 2004, Serena Williams flipped this narrative when she attended the premiere of After the Sunset in a pink-and-red dress.

When Gwyneth Paltrows walked the 2002 Oscars red carpet in a sheer black gown by Alexander McQueen, her ensemble was dragged. “Everybody really hated [it], but I think it’s kind of dope,” she said in a 2021 Vogue interview. “I had a weird hangover about it for a while because people were really critical.”

The dress came full circle in June when Paltrow’s daughter Apple Martin wore the exact dress.

What does it take to be a CFDA Fashion Icon awardee? Iconic behavior, naturally. Rihanna, for example, received said accolade in 2014, and attended the event in a sparkly sheer number and stole.

Jenner is one of today’s biggest nipple-freers. In fact, she’s been flaunting nips for almost a decade now. The model first bared the nip in 2014, during Marc Jacobs’ NYFW show. It was doubly historical for Jenner since it was also her first-ever Fashion Week gig.

I would argue that Florence Pugh’s pink Valentino number, which she wore to watch the label’s Fall 2022 Couture show, is this decade’s most canonical nipple-flaunting look. She received tremendous backlash for this dress, which she immediately shut down. Even her response was epic: “Why are you so scared of breasts?”

It’s a feat to steal the spotlight during any Barbie-related event, because Margot Robbie always shows out. But Dua Lipa managed to do just that when she stepped onto the pink carpet in a completely see-through number by Bottega Veneta. This Barbie frees the nipple.

Doja Cat took freeing the nipple to unprecedented heights at the 2024 Grammys when she donned a sheer bustier dress that hung low enough to intentionally and radically flaunt her nipples.

The see-through fabrication also served to display her many tattoos — real and faux. The most shocking of which was an ode to her gown’s designer, Dilara Findikoglu, on her forehead.