Ahead of fashion’s most scrutinised red carpet, we asked some of the industry’s chicest insiders how one actually dresses for the Met Gala.

Some people count down to their birthday. Or the next time they’ll see their highly non-committal, long-distance boyfriend. Or that holiday they can only technically afford because Amex exists and Klarna is loyally carrying the rest of the load.

But for the fashion crowd, there’s really only one date circled in red ink. One night that arrives with the sort of quasi-religious anticipation usually reserved for christenings or Beyoncé drops: the first Monday in May. Formally, the Met Gala. Otherwise billed as Fashion’s Biggest Night.

Held each year at New York’s Metropolitan Museum of Art to celebrate the opening of the Costume Institute’s spring exhibition, the evening, once a gala, has become a kind of cultural pageant. Hollywood’s brightest stars ascend the museum steps dressed bigger, stranger and more theatrical than usual, courtesy of fashion’s most ambitious ateliers, all attempting to interpret the theme placed before them.

This year’s brief: Costume Art.

What follows, inevitably, is the annual ritual – a frenzy of pop-culture obsessives and fashion darlings (including us) poring over every hemline, reference and rhinestone with a fine-toothed comb. Think of it as the ultimate post-party debrief.

So before this year’s big night kicks off, we asked some of fashion’s most stylish and well-versed insiders for their 411 on the art of dressing for the Met Gala.

Olivia Singer Writer, editor and creative consultant

What’s your all-time favourite MET Gala look?

Much as I am profoundly entertained by the competitive theatrics of the 2020s, there’s something really chic about when everyone just used to dress in normal but fabulous clothes – SJP in tartan McQueen in 2006, Kate Moss in Marc Jacobs in 2009, Mary-Kate and Ashley in a wealth of fabulous vintage. But my favourite year for the red carpet was, perhaps unsurprisingly, the Comme des Garçons year: Stella Tennant, Michele Lamy, Rihanna, Caroline Kennedy… everyone looked fantastic.

Which designer–celebrity duo would you love to see this year?

Anyone with Matthieu Blazy’s Chanel. I hope he does something fun, and he has some fabulous ambassadors. I’m excited to see what Ayo wears.

What’s one do and one don’t for this year’s theme?

Don’t be basic; I hate when people have things that light up or transform into other clothes – it’s not drag race. Do, if you can and aren’t on a contract, support young talent!

Osman Ahmed Writer and fashion editor 

What’s your all-time favourite MET Gala look?

I know it’s fashion’s Super Bowl and it’s more of a costume party in this era of virality, but I’m a big fan of when the Met Gala was a sort of fashiony-uptowny-museumy event and people looked like they were having fun, picked their own outfit and there were just a few arrival photos, not in HD focus. I think women who wear vintage to these kinds of things are always the chicest and most mysterious. Tina Chow in an antique Fortuny robe or gown; Mary Kate and Ashley in their treasure trove of vintage; Jessica Stam in what we would now call “archival” Dior Couture, back in 2007. Miuccia Prada in whatever exquisite Pennisi jewels she brings out of her vault. Shout out to Cher and Diana Ross, too, because they really laid the blueprint for the kind of theatrical dressing we see now, and somehow always looked like they weren’t in a costume. 

Which designer–celebrity duo would you love to see this year?

I’m probably most excited to see who (and what!) Jonathan Anderson, Mathieu Blazy and Haider Ackerman are bringing to the table. I’d also love to see some younger designers and independent labels being worn by women who love their work and maybe strike up a longer lasting relationship outside of transactional brand contracts. Again, I’d love to see women in vintage that they own, rather than from an “archive”. 

What’s one do and one don’t for this year’s theme?

I guess it’s about the body this year. I am a little afraid because nothing is more of a battleground than women’s bodies in a public arena. There’s such a wealth of designers — both from history and really exciting, young designers — whose work explore the body in interesting ways. Not just naked dresses! I guess it’s also about art, so I’d love to see people doing what great art does best: conveying something profound about the world we live in now. That said, maybe the most radical thing is for people to wear what they love and makes them feel like the best version of themselves in what must be an anxiety-inducing environment. Can you tell I just read Famesick? IYKYK. 

Jodie Hill Creative consultant and editorial director

What’s your all-time favourite MET Gala look?

It’s not even really a “look,” more just this image that comes back around every now and then. Charlotte Gainsbourg and Maggie Cheung at the 2007 Met Gala, both squatting in the bathroom, smoking. Charlotte’s in Balenciaga by Nicolas Ghesquière and Maggie’s in a fur bolero and long black dress. 

They both represent everything I love about cinema and fashion coming together. Each had an ongoing relationship with Ghesquière, at Balenciaga and later, Louis Vuitton. What I like about them is that they never feel too “done.” They move between everyday dressing and red carpet without seemingly changing anything. It’s so effortless and chic. Especially Charlotte, she was always seen wearing a full look with heels and a bare face, still completely herself and slightly dishevelled in the best way. Like she got dressed in low light and didn’t check again. That image has something the Met’s lost a bit. It feels loose, a little bit irreverent, slightly chaotic. I think everyone misses events where celebrities would show up for their own night, not the production around it. Nowadays, the gala could use a bit of the mess and attitude: someone sneaking out for a cigarette instead of another step-and-repeat.

Which designer–celebrity duo would you love to see this year?

Honestly, anyone who keeps it simple and actually looks like themselves. I always like when there’s a real alignment between the designer and the person wearing it, something that feels lived-in rather than staged. Lately it’s all getting a bit overworked, like everyone’s trying too hard to have a moment, and it just ends up feeling noisy.

What’s one do and one don’t for this year’s theme?

Do: Stick to who you are. You can feel when something’s been forced, and it never lands the same. At the end of the day, a leopard can’t change its spots! Even if the styling tries to say otherwise.

Don’t: Please, no more naked dresses. We’ve seen it. 

Ameli Lindgren Founder of Nordic Poetry

What’s your all-time favourite Met Gala look?
It has to be Rihanna in Guo Pei (2015). Not just because of the spectacle, but because it felt genuinely archival-like something that already belonged in a museum. That’s the benchmark for me: when a look doesn’t just reference history, it becomes part of it.

Which designer–celebrity duo would you love to see this year?
I’d love to see Bella Hadid in a true John Galliano moment-either a custom Margiela or something that taps into his late ‘90s Dior energy. She understands silhouette and attitude in a way that feels very collector vintage, not costume.

What’s one do and one don’t for this year’s theme?
Do: Commit fully-reference a specific era, a specific archive, a specific idea. The best looks always feel researched, not just styled.

Don’t: Play it safe in “expensive minimalism” unless it’s exceptionally cut. There’s nothing worse at the Met than a look that could pass for a very good dinner outfit

Brenda Weischer Fashion influencer and writer

What’s your all-time favourite MET Gala look?

Solange in 2018 for “Heavenly Bodies: Fashion and the Catholic Imagination” wearing Iris van Herpen Fall 2012 Couture, added with a durag that had “MY GOD WEARS A DURAG” written in the back. She is my all time favourite Met Gala guest overall. There are not a lot of images of it online, the durag had to be spread in order to read it.

Which designer–celebrity duo would you love to see this year?

Maybe with her unlimited resources, Lauren Sanchez Bezos could resurrect McQueen? 

What’s one do and one don’t for this year’s theme?

I think more importantly than dressing the part is using the platform, one of the most covered red carpets in the world, to speak up for things that matter. You could directly address the hosts, too! 

Ariana Sheehan Founder of ARO archive

What’s your all-time favourite MET Gala look?

Cher 1974 , Lil Kim 1999 and Cardi B 2019.Hard choice but definitely Cher, I just love that woman!! 

Which designer–celebrity duo would you love to see this year?

Something interesting please! Like Valériane’s Indépendantes De Coeur dressing Dennis Rodman. I like the hard with the soft, or something London based? Martine Rose x Rihanna and A$ap Rocky? I’m not into ‘celebs’ – boring! What even is that lol.

What’s one do and one don’t for this year’s theme?

Don’t do wearable ‘paintings’ or attached pieces of art. Art is for the walls and clothes are for your back. I HATE ‘funny’ clothes or outfits. Do hire a stylist that knows what they’re doing and watch Matt Kings’ Met Gala in’s & outs!

Abigail Hazard Wonderland’s Fashion Editor

What’s your all-time favourite MET Gala look?

Sarah Jessica Parker wearing Alexander McQueen Met 2006. Both of their looks!!!

Which designer–celebrity duo would you love to see this year?

A Stella McCartney x Taylor Swift Met Gala step out would make the Swifties quake however unlikely. I am looking forward to seeing who Glenn Martens dresses for Margiela.

What’s one do and one don’t for this year’s theme?
Do: Zone in on a specific reference. From what I’ve read, the exhibition is divided loosely into three sections, and I want to see an interpretation of less desirable beauty standards like the aging body.

Don’t: Play it safe. Anything themed should make you go all out, make an effort to nail the theme, whether the look gets you a best dressed or not.

Words by Moira González and Ella Bardsley