A Conversation with Miles Jai

Can you please let us know how you identify?

Non-Binary, Trans-femme

What inspired you to start doing makeup? Any moments of gender euphoria that you can share around that?

I started doing makeup during my sophomore year in high school, but I started to really get into it around my junior year. The process of getting ready has always been exciting for me~. Back then it felt nice to be perceived as feminine, in between genders, or no gender at all. When my friends asked "so are you a he or she?" I would answer, "I'm just Miles" and my close friends just got it and never asked again. That was a really special moment for me.

How did you make the leap from doing makeup recreationally to YouTube fame?

I made a really chaotic video about people telling me to "like their status" and folks really seemed to like that and subsequent videos after that. I managed to retain an audience for a while, as I grew older and more opportunities came my way, my focus started to shift to beauty more. I really wanted to master the art form of makeup and transformation, as transforming is one of my favorite things to do!

YouTube can be full of comment trolls, did you ever worry about getting backlash when you started making YouTube videos?

Surprisingly not really! Youtube wasn't really popular back then, and if you were on it, you were kind of considered a loser to the general public. Like "Oh you're doing YouTube? Cool...(side eyes)". People didn't take it seriously until someone became a millionaire and celebrities started to join in. It was full of very small, interknit communities and once I had a regular video post schedule going, they were pretty easy to find. I also wasn't talking about politics, which made it really easy for anyone, even folks who probably didn't care for LGBT people, to watch.

When you’re working with companies, as a model or otherwise, what do you think organizations can do to be more inclusive of trans and gender nonconforming folks?

Definitely do background research on your model first, we normally have our pronouns and gender identity in our social media to clarify (and so we don't have to keep repeating ourselves haha). If we are talking specifically about modeling, it is important to also include the folks behind the camera as well. Seeing someone who is like me working on production side of things would put me at so much ease, cause I know there is at least one person who can really look out for me and might see what some others could over look.

Can you tell us a little bit about how things like tucking underwear make you feel?

I only wear tucking underwear when I am wearing really form fitting pants or when I feel like I'm dripping feminine energy that day. Not an everyday thing, but when I'm wearing them, I definitely feel 100% sexier.

What do you do/use to best affirm your gender?

This one is tough cause in my mind, I just am what I am! If I was stripped naked and shaved bald (I'm already bald, but that is besides the point), that wouldn't change a thing. Still non-binary. Still femme. I have always felt that way so STRONGLY, I don't think anyone can take that from me...but dresses, makeup, and wigs are definitely the sweet gorgeous cherry on top.

Why work with TomboyX?

As soon as I saw the undergarments catered towards nonbinary and trans folk, I knew I had to get involved. I don't come into contact with high quality brands like TomboyX very often, so I was flattered when I heard they wanted to work with me!

Any parting words or things that feel important to share that we didn’t touch on?

Stay safe out there!