From Jennifer Aniston's bra-free reputation on Friends to Kendall Jenner's sheer runway debut, look back at these braless fashion moments on National No Bra Day.

For years, women have been inching away from painful underwires and going braless. From the <a href="https://www.bbc.com/news/world-45303069">so-called bra-burning feminists</a> of the 1970s to the more recent <a href="https://www.nytimes.com/2019/11/22/arts/design/instagram-free-the-nipple.html">#freethenipple campaign</a>, women have ditched the lingerie as an act of liberation. Especially now, with the pandemic affecting our day-to-day style&mdash;namely, contributing to our lack of energy to uphold perceived style rules&mdash;the bra has changed from daily armor to an optional accessory.&nbsp;
Looking at the past, it's no surprise that we&rsquo;ve found our way here. Celebrities and models like <a href="https://www.lofficielusa.com/music/young-photos-madonna-birthday-80s" target="_blank" rel="noopener">Madonna</a> and <a href="https://www.lofficielusa.com/fashion/young-kate-moss-90s-style-runway" target="_blank" rel="noopener">Kate Moss</a> have made many a memorable fashion statement sans bra. Here, L&rsquo;OFFICIEL rounds up the best braless celebrity style moments in history.

Beloved Hollywood actress <a href="https://www.lofficielusa.com/film-tv/young-jayne-mansfield-photos-sophia-loren-playboy" target="_blank" rel="noopener">Jayne Mansfield</a> was a sex symbol ahead of her time.&nbsp;The blonde bombshell&nbsp;stole the spotlight at a 1957 party being thrown for Italian actress Sophia Loren when she showed up in an eyeful of a dress. The low-cut satin number left little to the imagination, and had Loren side-eying her cleavage in a now-famous photo. <a href="https://ew.com/article/2014/11/03/sophia-loren-jayne-mansfield/">In a 2014 interview</a>, Loren remembered, &ldquo;Look at the picture. Where are my eyes? I&rsquo;m staring at her nipples because I am afraid they are about to come onto my plate.&rdquo;

Jayne Mansfield

In 1992, Jean-Paul Gaultier held a fashion benefit in honor of amFAR, raising $700,000 dollars for AIDS research. The celebrity-studded event was a night full of fun, freedom, and, of course, Madonna baring it all, removing an oversized jacket to reveal only a buckle-adorned harness bra.

Madonna

Lead singer of Blondie, <a href="https://www.lofficielusa.com/politics-culture/debbie-harry-young-photos-blondie-punk-icon" target="_blank" rel="noopener">Debbie Harry</a> remains a rock icon through both her music and &lsquo;70s punk fashion. Vintage tees with no bra were a staple on and off stage.

Debbie Harry

Lil&rsquo; Kim&rsquo;s one-shoulder purple jumpsuit and seashell pastie duo, designed by her stylist Misa Hylton, was a hit at the 1999 MTV VMAs. The silhouette cemented itself in the entertainment and fashion industries; Miley Cyrus paid tribute to the look on Halloween in 2013, and designer Anthony Vaccarello included a single breast-baring little black dress&mdash;paired with a bedazzled pastie&mdash;in his debut Spring/Summer 2017 collection for Saint Laurent.

Lil' Kim

The everlasting success of Friends helped ingrain&nbsp;effortless &lsquo;90s style&mdash;high-waisted jeans, baguette bags, slip dresses, sneakers&mdash;into our current outfit repertoire. But the nipple as a fashion accessory is arguably the sitcom&rsquo;s most influential fashion contribution, even surging the fake nipple trend in 2017. Though <a href="https://www.vogue.com/article/jennifer-aniston-justin-theroux-aveeno-beauty-wellness-friends-hair-reese-witherspoon">Aniston once admitted</a> that she did in fact wear bras when filming the show, Friends&nbsp;has undoubtedly inspired us to go no bra when slipping on a tee in the morning.

Jennifer Aniston

Braless looks have long been a runway regular, seen in collections from Chanel, Prada, Dior, and Versace for decades. In Sonia Rykiel&rsquo;s Spring/Summer 1991 show, Tyra Banks showed how chic bra-free can be, wearing a mesh top under an oversized suit.

Tyra Banks

<a href="https://www.lofficielusa.com/fashion/jennifer-lopez-best-red-carpet-looks-young-bennifer" target="_blank" rel="noopener">Jennifer Lopez</a>&rsquo;s 2000s Grammys look, an emerald chiffon Versace gown with a hip-length V, went down as the first viral dress in history. The buzz was monumental for J. Lo and Donatella Versace alike, and the two reunited on the Milan runway to debut an updated version in 2019.

Jennifer Lopez

When <a href="https://www.lofficielusa.com/fashion/rihanna-best-met-gala-looks" target="_blank" rel="noopener">Rihanna</a> graced the 2014 CFDA Fashion Awards to accept her accolade&nbsp;for Fashion Icon, there was no question why she was the pick. Her Swarovski crystal-adorned naked dress, a custom piece by Adam Selman, exemplified raw Hollywood glamour.

Rihanna

<a href="https://www.lofficielusa.com/fashion/kendall-jenner-highest-paid-supermodel" target="_blank" rel="noopener">Kendall Jenner</a>'s first major runway was walking for <a href="https://www.lofficielusa.com/fashion/marc-jacobs-heaven-cultural-zeitgeist-fashion-collections-trends" target="_blank" rel="noopener">Marc Jacobs</a> at 18 years old. Her catwalk debut made headlines for the bra-free ensemble and extreme beauty look. Since then, Jenner has been a staunch #freethenipple advocate, making her love for going braless public for years, whether running errands or on the red carpet.&nbsp;

Kendall Jenner

While attending <a href="https://www.lofficielusa.com/fashion-week/valentino-fall-winter-2022-haute-couture-rome-runway-photos" target="_blank" rel="noopener">Valentino's Fall/Winter 2022 Haute Couture show</a> in Rome, <a href="https://www.lofficielusa.com/film-tv/dune-part-two-details-trailer-cast-timothee-chalamet-zendaya-florence-pugh" target="_blank" rel="noopener">Florence Pugh</a> arrived in a <a href="https://www.lofficielusa.com/fashion-week/sheer-haute-couture-runway-looks-florence-pugh-dress" target="_blank" rel="noopener">sheer pink gown</a> from the brand's pink <a href="https://www.lofficielusa.com/fashion-week/valentino-fall-winter-2022-pierpaolo-picciolo-runway-photos-pfw" target="_blank" rel="noopener">Fall/Winter 2022 collection</a>. While many were stunned by the actress's breathtaking style moment, some social media users made less than kind comments about Pugh. The Don't Worry Darling star called out <a href="https://www.lofficielusa.com/pop-culture/florence-pugh-body-shamers-backlash-valentino-sheer-dress" target="_blank" rel="noopener">body shamers on Instagram</a>, saying, "It makes me wonder what happened to you to be so content on being so loudly upset by the size of my boobs and body..? [...] <span style="background-color: transparent; font-family: inherit; font-size: inherit; font-style: inherit; font-variant-ligatures: inherit; font-variant-caps: inherit; font-weight: inherit; letter-spacing: 0px;">It has always been my mission in this industry to say &lsquo;fuck it and fuck that&rsquo; whenever anyone expects my body to morph into an opinion of what&rsquo;s hot or sexually attractive."

The 11 Best Braless Moments in History

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