Celebrity Style

From J.Los 00s-era gown to Olivia Wildes after-party naked dress.

In Hollywood, no awards show is more prestigious than the Oscars.

All that said, there are some outliers.

Olivia Wilde freed the nipple at the 2025 Oscars after-party.

Since the 90s, a select few daring dressers have pushed the boundaries of Oscars fashion.

Jennifer Lopez and Gwyneth Paltrow, for example, both wore see-through garments in the early aughts.

However, they went the high-fashion route, with voluminous skirts and subtly sheer tops.

Claire Danes at the Shrine Auditorium in Los Angeles, California.

During this years award show, there was one naked look that stood out among the rest.

Danes, however, paved the way.

It was minimalism at its finest.

Jennifer Lopez arriving for the 73rd Academy Awards.

Jennifer Lopezs Two-Tone Glam

At the 2001 Academy Awards,Lopez donned this two-toned concoctionfrom Chanel Haute Couture.

It was undeniably elegant.

Gwyneth Paltrows Romantic Rocker Vibes

The dress Paltrow wore to the 2002 Oscarswould become infamous for its bare qualities.

Gwyneth Paltrow during The 74th Annual Academy Awards.

It also happened to be completely sheer.

She paired it with something less low-key and a whole lot more daring: an itty-bitty halter bra.

Emily Ratajkowskis Silver Number

Queen of see-through ensemblesEmily Ratajkowski wore yet another diaphanous design at the 2023Vanity FairOscar party.

Cameron Diaz during The 72nd Annual Academy Awards - Vanity Fair Party.

Ive included it on this list as an honorary mention, for obvious reasons.

Instead of freeing her own, she covered them in glimmering crystals.

The effect was surprisingly elegant and reminiscent of an ancient Greek goddess.

Zoë Kravitz attends the 2019 Vanity Fair Oscar Party hosted by Radhika Jones.

Florence Pughs Delicate Peplum

Florence Pugh is the reigning queen of freeing the nipple.

From fashion week tothe Golden Globes red carpet, theOppenheimerstar is practically the face of the movement.

Anittas Glistening Gown

Like Pugh, Anitta also bared breasts in a shimmery gunmetal gown that was practically transparent.

Zoë Kravitz attends the 2019 Vanity Fair Oscar Party hosted by Radhika Jones.

She rocked the ubiquitous exposed undies trend with her strappy thong completely visible.

Her dress was the glamorous combination of all 2024s biggest trends.

Victoria Monets Florals

Also at the 2024 after-party, singer Victoria Monet joined the nights nip-forward ranks.

Emily Ratajkowski attends the 2023 Vanity Fair Oscar Party.

Her choice of black gown came equipped with a bustier that was sheer and sculptural.

And thats exactly what she did during at the 2025Vanity FairOscar party.

TheUncut Gemsstar frequently bares skin in her public appearances, strategically placing everything fromfeatherstobeltsto cover her top.

Sabrina Carpenter attends the 2023 Vanity Fair Oscar Party.

But you could still see most of her nips peek through from behind her mermaid waves and sheer fit.

This article was originally published onMarch 7, 2024

Florence Pugh arrives at the 2024 Vanity Fair Oscar Party.

Anitta attends the 2024 Vanity Fair Oscar Party hosted by Radhika Jones.

Victoria Monét attends the 2024 Vanity Fair Oscar Party Hosted By Radhika Jones.

Olivia Wilde freed the nipple at the 2025 Vanity Fair Oscars after-party.

Julia Fox wore a see-through hair dress to the 2025 Oscars after-party.