From ‘slutty little glasses’ to thigh-high boots: 9 Jonathan Bailey looks we thought were wicked
Bailey is not just pushing new fashion looks; he's pushing for LGBTQ+ rights – but doing so in a very stylish way
By Aaron Sugg
Over the last two weeks, Jonathan Bailey has gone viral once again, for not just one, but two new fashion looks that have sent the LGBTQ+ community into a stylish spiral.
When it comes to turning looks, Wicked star Bailey never fails to catch his fan’s attention. The Olivier Award-winning actor has become a style icon, known for turning heads at red carpets and more recently, spreading legs in editorials.
1. Thigh-high leather boots
If you are wondering what we are talking about, he recently (18 June) left fans breathless in a photoshoot by Sharif Hamza for The Hollywood Reporter, where he posed in thigh-high leather boots with a man-spread “wider than Sharon Stone in Basic Instinct,” as one fan put it… Please see exhibit A on the second slide of the carousel – viewer discretion advised: the boots are high, not for the faint of heart.
Another said: “In the words of Glinda: Oh, Oz!” — and frankly, we at Attitude agree. He slayed the house down boots (pun intended).
In the caption of the post Bailey said: “@hollywoodreporter – a total honour” but really the pleasure was all of ours sitting at home who got to see the photos on his Instagram grid.
2. “Slutty little glasses” – Jonathan Bailey
In Jurassic World: Rebirth, the seventh dino-sized drama in the Jurassic Park franchise, the Orlebar Brown model plays Dr. Henry Loomis alongside co-stars Scarlett Johansson and Mahershala Ali as mysterious covert operatives.
But while the plot might be prehistoric, Bailey’s fashion sense is anything but extinct. At the London screening, he gave the people what they wanted: “Slutty little glasses.” Safe to say the look had us roaring.
In an interview with Entertainment Tonight, Bailey teased us: “I might just wear my little glasses…” He did. “Really slutty.” Then he set the trend for summer 2025: “Let’s have the summer of slutty little glasses.”
Forget Hot Girl Summer, it is Slutty Paleontologist Summer now, and Dr. Loomis is not just digging up dinosaur bones, he’s digging up compliments.
In a promo shot from the movie posted to his Instagram grid, fans flooded the comments with glasses emojis. One commented: “The tiny little glasses are essential to the plot.” Another: “Those slutty little glasses — I need to be sedated.”
3. A nod to Oz
@outmagazine If I could click my ruby red shoes three times, I’d wish for a night with Fiyero! 👠✨ Feast your eyes on #JonathanBailey serving stunning looks on the #Wicked movie press tour. Follow our 2024 #Out100 honoree down the yellow brick road at the out.com to check out his wickedly hot styles. 🔥 🎥: New Vision/Getty Images 🖊️: @Raffy Ermac ##wickedmovie #fiyero #lgbtq #celebstyle #redcarpet ♬ original sound – Out Magazine
Now, we could not possibly talk about Bailey’s most iconic looks without following the yellow bricked-up road over to his Wicked red carpet moments. Bailey really knows how to generate a buzz for whatever film he is starring in, and this look was no exception.
Bailey, who came out publicly as gay in 2018, plays Elphaba’s charming classmate Fiyero in the 2024 film Wicked. At the Wicked LA premiere in 2024, Bailey, in a playful nod to Oz, wore a custom Versace Tin Man-inspired look.
Safe to say, someone needed to oil him up.
He wore a silver chainmail shirt, crisp white trousers and scarlet red Dorothy-inspired ruby slippers. Fans’ knees were left trembling, shaking harder than Dorothy’s heels trying to click her way back to Kansas.
4. Short-shorts
How could we possibly cover the Wicked promo tour without drooling attention, sorry, drawing attention, to Bailey’s short-shorts moment? At a photocall for Wicked in Australia last year Bailey looked tall, dark and handsome in an all-black ensemble as he posed next to co-stars Cynthia Erivo and Ariana Grande.
To complement his already daring choice of leg-baring bottoms, he paired the look with an almost-sheer black long-sleeve polo shirt, sleek black loafers and sunglasses. (Though not quite as “slutty” or “little” as the ones he wore in Jurassic World).
In an Instagram post featuring the look, one grateful viewer said: “God bless those awful shorts… daaaaang!”
Another joked: “Bailey has more defined lower limb muscles than the human anatomy model at our medical college.”
5. The wet look
In Bridgerton season 2 Bailey played dashing Viscount Anthony Bridgerton. A fashion moment we all enjoyed from the Netflix series, although maybe not intentional, was when Bailey emerged from a lake in a soaking wet white shirt.
Instantly iconic, the scene made waves across fan pages, leaving one admirer hot under the collar, they said: “Jonathan Bailey in a wet shirt might just be the cause of climate change.”
Bailey was no stranger to tight-fitting costumes throughout the season. In a press conference attended by RadioTimes.com, he revealed he once “ripped” the crotch of his costume while filming an especially intense fencing scene.
Who does not mind a bit of sword fighting?
6. Flower boy
At the 2024 Met Gala, Bailey served flower boy. In a classic meets camp tailored white blazer with sleek black lapels, black trousers and glossy dress shoes you could practically see the press camera flashes in.
But it was the floral drama that truly stole the show. Two oversized pink-and-white blooming flower embellishments. One perched delicately on his hip, the other blooming boldly in place of a tie.
You know what they say: ‘Think pink to make the boys wink.’ But there was no blinking when watching Bailey walk up the Met Gala stairs last year. We did not want to miss a moment.
7. Bearing arms at the afterparty
@jaiglezphotos #JonathanBailey Arriving To The Hotel #MetGala #Exclusive #ForYou #Paparazzi #JaiGlez ##2K24 #NYFW #ShotOnIphone #📱 ♬ original sound – Jai Glez
In the evening of the Met Gala last year, Jonathan and Bridgerton co-star Phoebe Dynevor changed their gala wear for something showing a little more skin to the Loewe Met Gala after party.
In a white tank top and matching white jeans, he held the actress’s hand, leading Dynevor, 29, past the crowd. Unsurprisingly, Jonathan posted the picture of the two of them. I mean when you look that good you would be silly not to! Admirers took to the comment section once again; one standout comment, that I am sure we can all relate to, said: “I wish to hold hands with you.”
8. Drink your milk
Now, Something to give your belly butterflies — even if you are not lactose intolerant: Bailey with milk dripping down his chin.
The actor launched his foundation, The Shameless Fund, last year with a thirst trap and a cause. To promote the launch, he wore a custom Loewe T-shirt with the phrase ‘drink your milk‘ stretched across his chest, in a nod to the steamy LGBTQ+ drama he co-starred in, Fellow Travelers.
In the show, Bailey’s character, Tim Laughlin, has a thing for milk (take that as you will), and in one particularly memorable scene, Matt Bomer’s character uses the phrase as foreplay.
Us at the office tend to drink more oat milk, but we think Bailey might have just converted us back to the lactose.
9. Milk gives you wings
@attitudemag FRIDAY FEELING 🤩 #JonathanBailey ♬ Ludacris Vs Kylie Cant Get You Out Of My Fantasy – cvvor
Last but not least, before you fly off to stalk Bailey’s Instagram, let’s throw it back to this viral moment. If you can tear your eyes away from his angel eyes and focus on the wings… Jonathan really knows how to ruffle a few feathers.
Wearing his iconic ‘Drink Your Milk’ campaign tee, we can only assume the milk gave him wings. One fan commented, “He should’ve been in Saltburn,” referring to the large strap-on wings mounted on his back.
If we saw Jonathan Bailey drinking Jacob Elordi’s bathwater, it would get more than just our wings fluttering…