James Dobson is the designer and founder of the brand Jimmy D, and co-founder of the beauty platform Beauty Benders.

The lipstick economy feels like it’s in full effect – that old adage that during a recession people choose to treat themselves with the rush of a little luxury like a designer lipstick rather than a whole ensemble. Thinking about the lipstick economy has made me ponder my own complex relationship to that little waxy bullet of pigment, and a term that I have come to refer to as Lipstick Shame.

As I embarked on my beauty journey, I decided lipstick wasn’t for me. I put it down to my lips feeling a little small, and lipstick really spotlighting them. Looking back, I think it was a touch of… what's the term? Oh yeah: self loathing and internalised homophobia.

But as I nudged out of my comfort zone and began wearing eyeshadow more regularly, I felt the need to up the ante for my going out looks. Lips became the focus, albeit HEAVILY overdrawn or diffused out like they had been messed up after a make-out session.

One night fellow Beauty Bender Andre and I went to a local fashion designer’s party wearing lipstick and dishevelled wigs, and the crew of party organisers that met us on entry took one look and said, “hey guys, I think it’s time to leave”. Confused, we told them that we’d just arrived and they simply replied, “yeah, it’s still time to leave”. I immediately took off my wig, shoved it in my bag and could not get that lipstick off my face fast enough. Lipstick Shame kicked in.

Is Lipstick Shame, and shame around makeup in general, a universal feeling?

British fashion designer Charles Jeffrey can relate. “Lipstick can feel like this bold statement that pushes you into another realm, and I’ve had those times when I’ve questioned if it’s ‘too much’,” he says. “It’s that feeling of pushing the boundary and wondering if people are reading it as too femme or too performative, which can mess with your confidence. I’ve learned to lean into those feelings as part of my expression, but it’s definitely something that I’ve had to work through.”

Beauty influencer Niko Haagenson has felt similar. “I feel a lot of shame when I wear makeup around my family and often find myself hiding my face or averting eye contact. I refuse to not wear it, but I still feel insecure.”

I battle with my own self image (which in many ways I feel like makeup has helped with). Add to this societal ideas of how I should present myself in my 40s, while also having a burning desire to represent myself in a way that expresses who I am creatively, and it’s all a bit of a headfuck.

Also: binaries are boring but unfortunately still very much in effect, and nothing feels more coded as ‘high-femme’ than wearing lipstick. A disapproving look when I’m out or simply waking up the next day and re-assessing the selfies I took the night before can make me spiral into Lipstick Shame; the little cherry on the top of a makeup look which (my brain tells me) pushed things too far and made me a laughing stock.

Despite these complex feelings, there is an undeniable power to wearing lipstick. “It’s like an armour and art form combined,” says Jeffrey. “I don’t always wear lipstick because it’s such a statement for me, and I usually reserve it for the evening when I want to feel more intense. But when I do wear it, it feels like I’m fully committing to my look.”

I’m pushing myself to overcome my Lipstick Shame, with a tinted lip balm or even a swipe of MAC Powder Kiss lipstick during the day, blotted and gently diffused around the lip line (cos I still think my lips look to small if I’m confined to my natural lip border). I do all of this because lipstick can make you feel fucking invincible, it can make you feel sexy beyond belief, it can make you feel like some kind of Rococo aristocrat. Or, as Niko puts it, “Lipstick makes me feel like I want to kiss the world”.

I’m trying to untangle my thinking from the heteronormative bullshit we’re bombarded with and say “hey guys, I think it’s time to leave” to those feelings of shame that are stopping me from living my best lipsticked fantasy.

REALLY GOOD LIPSTICKS

Charles Jeffrey’s fave lipstick: NARS Powermatte Lip Pigment in Starwoman, $56

Niko Haagenson’s fave lipstick: Pat McGrath MatteTrance Lipstick in Elson, $75

Beauty Bender James’ fave lipstick: MAC Powder Kiss Lipstick in Werk, Werk, Werk, $49

Beauty Bender Andre’s fave lipstick: By Terry Lip-Expert Shine Liquid Lipstick in Red Shot, $65