Men in makeup: lawyer by day, glamour puss by night

It’s a Monday morning and I’m about to sit my exam in financial services regulation when my colleague whispers, “Seán, are you OK? Your skin looks… blue?”

The moment she asks, I know what she’s talking about. “Oh no, I’m fine,” I reply, as my mind flashes back to two nights previously. A few post-revision drinks had turned into a night out and soon I was being convinced by friends to go on to a club. This wasn’t possible, I said, because I had no makeup with me.

Then inspiration struck. “I can use this blue highlighter pen as eyeshadow – it’ll be great,” I said as I casually drew broad strokes of phosphorescent ink over my eyelid. Thirty-six hours and four futile showers later, I still look quite obviously painted as I prepare to recall what is a regulated activity under FSMA 2000. If I’m going to champion makeup, I think, I need to start making sure I do it properly.

I’m 26 and I’ve been wearing makeup for almost 10 years. In that time, the way I wear it, and what I’m choosing to express when I do, has changed. When I was a teenager, it was often secretive and experimental, but also, I guess, intended to shock. Now I’m so used to it, it feels less of a big deal. In the decade since I first started wearing makeup, I also realised I was queer (my preferred term for my sexual identity) and the friends I’ve made in adulthood are not really the type to be shocked by a man wearing makeup – in fact, I now know several guys who wear makeup, too (and usually theirs is much better than mine).

At the same time, I’ve embarked on a career in the City which, as drunk people in smoking areas frequently tell me, seems incongruous with the fact that I wear mascara at the weekend. Apart from being amused that they think I wouldn’t be able to just wash it off before going into the office (highlighter pens aside), this kind of reaction says a lot about how we categorise people – a man who wilfully chooses to look feminine might be fun, cool or interesting, but can’t possibly also be serious, understand fiduciary duties or use Microsoft Excel.

In many ways, I’m a cautionary tale. A homophobic dad of one of my school classmates didn’t allow his son to pick drama as an option in year 9, because he thought the department would be a hotbed of theatrical effeminacy. You’ve got to hand it to the homophobes: when they’re right, they’re right (they’re never right). Still, the first time I wore makeup was in a school play. We put on joint productions with the local girls’ school every other year, and in the intervening summers I was invariably selected to play vampiric countesses, lugubrious Prussian housewives and the odd French maid.

The first time a kohl pencil was applied by my friend’s mum to my upper eyelid, I blinked and flailed around, impaling my own cornea. Bloodshot and weeping, I looked less like a 17th-century noblewoman and more like an emotionally traumatised barmaid in a particularly intense EastEnders special. Since then, I have cowed my eyelids into submission with pencils, gels, powders, glitter, glue and tinsel (glued on to my eyebrows: it lends a whole new meaning to the word “browbeaten”).

Other boys I know who started wearing makeup in their teens found that the emo scene was their particular gateway drug. But, despite the pallid skin and dark hair bequeathed by my Celtic ancestors, I was naturally chipper and preferred mid-tempo R&B; a brief attempt at the emo thing didn’t work out.

I went to an all-boys school with quite a traditional uniform and dress code; while I had already started wearing makeup in my free time, my teachers and most of my fellow pupils never saw me with it on. University allowed bolder experiments. Of course, initially this was a disaster: I looked absurd. Gobbing in the face of subtle glamour, I attended tutorials at 2pm on a Thursday afternoon in metallic eyeshadow and blue lipgloss. While this did raise the odd eyebrow from my Renaissance literature tutor, I never felt it was a problem. (Was this because I did an arts degree? Perhaps other disciplines with more, er, conservative tutors would have encouraged visual self-censorship.)

There’s an entire period in 2008, still recorded in the far corners of Facebook, that I now refer to as “tuberculosis chic” – I had thought it was a great idea to go out in an array of red, pink and purple hues, like a sickly Victorian child. As you can imagine, this did wonders for my student sex life: it turns out no one wants to get off with Robert Louis Stevenson. Some of this was due not just to ugly colours, but to the fact that I was wearing makeup at all. And some of the most unpleasant comments came from gay peers. At best, I was flamboyant and fun, but certainly not sexual: a colourful eunuch. At worst, I was judged an attention-seeking embarrassment who made it harder for gay men to be taken seriously. This meant I wouldn’t wear makeup on dates because I believed they would be more successful without it. A couple of years ago someone I’d been dating for a few weeks told me he was fine with me wearing makeup but would prefer it if I didn’t wear it in front of his friends. He was promptly dispatched (I mean I ended it there and then, not that I killed him).

Meanwhile, it’s been strange to observe a rise in the mainstream marketing of products aimed at men – marketing which also feels it has to apologise to and grapple with the fragile concept of masculinity. Take, for example, the truly woeful portmanteau “guyliner”, which no one in their right mind would use. Similarly, it’s hard not to roll a heavily kohled eye at the fuss over celebrities such as Johnny Depp, Jared Leto and Russell Brand wearing eyeliner – after all, they are comfortingly roguish, seemingly gender-conforming heterosexuals. More interesting is Eddie Izzard’s red lip, American pop star Adam Lambert’s statement brows and the painted face of outre club promoter and stylist Daniel Lismore, who takes male makeup to a level way beyond the kind written about excitably by fashion magazines.

It’s supposed to be fun: the range of style options available to men is already woefully narrow. Wouldn’t a world in which getting ready for a night out was about more than picking from a cupboard of identikit Zara shirts be more thrilling for everyone? Guys, believe me, there’s no quicker way to shake off the fog of the working week than a smoky eye and a nude lip. If you’re looking for a simple starting point, just put a bit of dark brown eyeshadow along both lash lines. Don’t you feel sultry already?

On a Friday night, people usually flee straight from the office to a bar, but I like getting ready to go out in a group, at my house or a friend’s. My mum has always described applying her makeup as painting on a blank canvas, and it is a metaphor I have inherited. It is highly ritualistic. I’ll sit in front of a mirror and apply liquid foundation with a brush. Then I’ll impose a subtly different structure on my face using blusher, and feel myself transforming into a creature of the night (makeup does look best under club/bar lighting, after all).

My makeup kit now probably fills a small carry-bag: liquid and powder foundation, bronzer, black and neon eyeliners, several pigment eyeshadows and a range of angled brushes. I’ve never been one for lipstick, but a friend recently introduced me to purple lipliner, which I hope to try at some point. The dream is to buy one of those expensive all-in-one kits with brushes that come with their own shampoo – but, you know, times are hard.

Of course, there are occasions when I choose not to wear makeup. I don’t wear it at work-related events, perhaps out of a latent sense of conformity. I do think if I wore it in a similar way to that of a female colleague, low-key and office-appropriate, I should be able to.

In my previous job, I once saw my boss on a Saturday, at a Christmas market. I was wearing pink glitter under my lower lashes. I hesitated before going over to say hello, before realising that this kind of self-policing would make me feel worse than any kind of socially awkward repercussion. And he was a little surprised, but it was fine.

In truth, how makeup fits in with my job is the least of my worries. I’m much more concerned about safety on the street. Walking through east London wearing false eyelashes and mascara in the middle of Pride is one thing, but travelling home on the night bus is another. Even in daylight, children in parks shout at you, men follow you down the street; sometimes it’s just silent staring, sometimes it’s demeaning questions. It is always threatening.

It would be easier not to have to take face wipes out at night if I want to feel safe walking to the bus stop alone. But there are plenty of positive reactions, too. Even if you’ve done your makeup so badly you resemble the Cheryl Fernandez-Versini waxwork after a devastating fire at Madame Tussauds, nice people will still compliment you. Some strangers are so desperate to prove how totally, earth-movingly OK they are with a man wearing makeup, they’ll cross a room to tell you how great you look. And I’m not ashamed to admit this kind of cheap validation is wonderful.

You can also tell yourself semi-sincerely that there is a nobility to it all – your Instagram selfies are not just a byproduct of your own vanity, they’re defiantly challenging the gendered status quo. You, my friend, are a bold freedom fighter. Yay, though I walk through the valley of the eyeshadow of death, I will fear no evil. Or something.

• This article was amended on 21 March 2019 to remove some personal information.