The Confidence Paradox

Recently we stumbled across an Instagram account that made us stop in our tracks. Bloodyhell! Who is this guy here, in killer heels and tailored suits, unapologetically taking up space in the middle of a busy city?

He is bolder than bold. He knows how to do this. 


Jules and I were seriously impressed by his fabulous act of rebellion, in dressing how he damn well pleases, and looking amazing for doing so. He exudes so much confidence that it’s easy to look at him and know that he is that ‘different sort of human’ - the type who are teflon-coated and impermeable to self-doubt. They can do anything they want, it’s easy for them. 

So, when we saw his post the other day about how scary it can be, simply to be who we are, we had a few questions we needed to ask him about confidence and about how it feels to give yourself permission.

We wanted to ask Ray at what point he acknowledged a desire to wear something that as a man, he wasn’t ‘supposed’ to wear, and how did he feel in himself?, firstly acknowledging it and later, acting upon it. We wanted to hear about his internal feelings, not how other people reacted, but what the impact was like for him. 

He told us that he was completely uncomfortable as a really young man. He was working for Disney and although people have later told him that he appeared almost scarily confident, he was living with a deep level of discomfort in trying to fit into a guise that he knew wasn’t wholly representative of himself. 

He always had a love of the aesthetic and design of ‘women’s things’,but it wasn’t until his 40s that he started to care less about what other people thought and began to see that it was more important to stand up for what you believe to be right in the world. 

Ray does not consider the things he chooses to wear now to be cross-dressing, he doesn’t believe that bits of material and leather have a specific gender assigned to them, so it’s not cross-dressing, it’s simply wearing what you want. And we love him for calling that out.

We firmly believe that the term 'cross-dressing' does not apply to what we do at Moot, or what we want to see in the world for all humans and the choices that they should be free to make. There’s nothing ‘cross’ - it should wholly belong to you regardless of gender, you're not taking anything across into a realm that shouldn't be yours. 

Ray talked about history and how it was in the 30s and 40s, when even in Hollywood, women wearing trousers was considered scandalous. His own mother called the local newspapers and started a revolution of her own when she was turned away from her job at an international bank for daring to come to the office in trousers. She ushered in a change of policy  - attitudes to clothing can and do change and as a society we need to be challenging rather than blindly accepting of the status quo. Covering your body in a particular cut of material should be as inconsequential from a gender perspective, as which cutlery you use, or which phone you want to put in your pocket. 

Although Ray speaks beautifully and eloquently about ‘all clothing being nothing more than a costume’ (he’s an actor, you can actually hear the talent), he admits that he still has days when he feels nervous. “No one wants to be laughed at” he said. But he knows from experience that when you stand tall and walk about as if you had every right to be this damn fantastic, that the world will believe you. He tells us about living on a street in New York where there is a huge highrise development underway and how he knows that the builders are watching him as he struts down the road in his heels each day. He laughs as he tells us that after a while, they stopped him to say that they thought he had amazing legs and he always looked great. Proving that even if you’re not 100% sure that everyone is going to like what you’re doing, you get respected for your boldness, noticed for your bravery and admired for breaking the drudgery. The paradox being that you will gain real authentic confidence, by pretending to be confident even if you're hiding a bubble of fear. 

Ray’s overwhelming message to us through the few questions that we asked him, is the importance of authenticity. As an actor he knows that if you’re playing a part and it’s coming across as less than authentic, people won’t want to watch it. He says it’s the same in reality. 

Authenticity is a duty he feels he can serve, at his age - quite unbelievably he’s in his early sixties - he wants to help anyone to realise that living in ‘Shame is dangerous and terrible. It makes you feel alone.’ He admits that he was very fortunate to have been raised in family who taught him never to be ashamed, a spectacular gift to have passed to a child. 

 ‘Being you is powerful and important’ he ends. And we could not agree more. 


Follow Ray on Instagram at @hewearsheelsandhose


  • Myopic Bookworm

    A refreshing read. I am longing for the expansion of the range of clothes that is considered appropriate for a man to wear without it being considered some kind of attempt to be female. But I haven’t yet got past the end of the drive wearing a skirt, except a kilt. (Isn’t it odd how a skirt on a man is fine as long as it’s a very specific length and cut?!)

  • Tom

    What a bold human.

    And I can’t take my eyes away from the sexiness. I’m almost ashamed of my thoughts. (Almost.)

    P.S. — I am so glad I discovered this site.

  • Deirdre

    Being of the Theatre myself, these lyrics from The King and I come to mind:
    “Make believe you’re brave
    and the trick will take you far.
    You can be as brave
    as you make believe you are.”
    And the there is the RuPaul quote:
    “We’re all born naked. Everything else is Drag.”

  • Paola Padovan

    Bravo Ray for being so fiercely authentic. I have known him for years and can attest to what a wonderful human being he is. To know Ray is to love him. Great article about a fabulous person.

Leave a comment

Please note, comments must be approved before they are published