Jackie Iulo: Sag Harbor’s 14-Year-Old Freshman on Transitioning to Her True Self

She was born Jack. She is a twin. And she has lived in Sag Harbor since the age of seven months, when her family moved there from Park Slope in Brooklyn.

Today Jackie Iulo is a confident, outspoken transgender 14-year-old girl, about to enter her freshman year in high school at Pierson. She loves fashion, art and, like most kids her age, she has her idols — Lady Gaga tops the list.

“I saw her at a concert in 2017 and just became transfixed,” says Iulo, “No pun intended on the trans part, but I just fell in love with her and her music. She is just so incredible.”

Also incredible, is Jackie’s presence, her confidence and, yes, her lip-synching — she competes regularly in lip-synching competitions and recently knocked the crowd off their feet with her lip-syncing performance of Barbra Streisand’s “Don’t Rain on My Parade” at the recent Out East End Impact Awards — where Iulo also received the Youth Leadership Impact Award.

How did Jackie Iulo transition from Jack to Jackie? And what is life like for her as a transgender teenager living on the East End?

We spoke with Jackie, as well as with her mother Lisa Iulo, via telephone from their home in Sag Harbor. Their honesty, insight and affection for each other and this community made an impression. [This interview is primarily with Jackie and, where it applies, we’ve included her mother Lisa’s input.]

How was this process of transitioning for you — what did you feel and go through?

It is a huge question in society — how young people discover themselves so early because their minds are still growing. It was so natural, I didn’t even question it in a way, I was attracted to it — I loved it. I just loved being myself.

What did you love?

I was just naturally attracted to a lot more feminine things in a very natural way, as in, “I’d rather that be the color pink, I’d rather that be Barbie, or dresses, high heels.” I was more attracted to just being more a girl every day — I would always kind of make up feminine names, I would always play pretend as a girl. I’d always had my sister dress me up, I always wanted to be with girls, like in pre-K.

How young were you when you first recall feeling different?

Officially, when I started really becoming Jackie, it was in third grade — after I got my ears pierced — because I was afraid to go to school [as a boy] with my ears pierced because I’d be judged for being masculine [with earrings]. It really happened when I went to my mom and I said, “Hi, I really want to be Jackie. I want to wear this, and I want to do it every day.”

Lisa, was it a surprise to hear your child say this — how did you react?

Lisa Iulo: She was always flamboyant … always twirling around. She was playing little league and twirling in the field. … I indulged it because I didn’t care — you want to play with a doll, go play with a doll. You want to throw on a dress when you come home, go for it. And people were like, “Oh, it’s a phase,” but I just knew it wasn’t a phase. I thought that she was going to be a gay man, a flamboyant gay man.

Then she wanted to grow her hair out, so she grew her hair out, and as she got older she was looking more girl-like but she came to me at the end of third grade and said, “I want to be Jackie. I want to dress like a girl.” I didn’t quite know what that meant because she was so young, too. I just said, “OK, you can do that. I’ve got to go talk to the school; we’ve got to talk about this. I want everyone to be on the same page.”

How did it go at school?

Lisa Iulo: They were so supportive, and this was a first for them (Sag Harbor Elementary School and now Pierson Middle-High School). And for me — just flying by the seat of my pants, too — it was all about everybody feeling comfortable and accepted and the same with the middle high school. They’ve got her back big time, and it was kind of a seamless transition in terms of Jackie’s friends because they were all like, “Yeah, so she’s been a girl since she was little.” They didn’t bat an eyelash.

Jackie, you have an older sister (17) and a twin brother — how did they handle it?

We were all very young — my sister was like, “Oh yeah, Jackie loves playing dress up. She would dress me up, and she would put makeup on me and do my hair. … My sister is incredible; she is so smart. … I’m so lucky.

My brother — I know he thought there was nothing wrong with it — he never really questioned it, he just kind of went with it, really. I’m sure he knew something was going to happen at one point.

Lisa Iulo: Having twins, because she is a twin, personalities were so vastly different, and I think maybe that was why I kind of had the feeling like this was not a phase, this was engrained in who she was. I’ve always said this from my life growing up which was full of love but not easy — it’s harder not to be happy in this life, and you’ve got to be happy and you have to be really thrilled with who you are. Those two things are going to make you succeed.

Jackie, what was your Dad’s reaction to you transitioning?

Both my parents had almost a background with always being accepting even before I came around. My dad is incredible, really. I think he is so supportive, and I love him to death. … He grew up in time when being gay and trans was “bad” … in the Catholic religion and at the church, gay people were a sin. Gay people aren’t a sin — just to clarify. All his life he had gay friends during the (AIDS) epidemic who died. He was just always a very accepting person.

Did you go to counseling to try to process it?

No, I did not. I just did what I really needed to do … and luckily I was accepted with very open arms by my school, my parents — so it was a lucky, very smooth transition, and I’m very grateful for that.

Did you have any resistance?

There have been a few incidents. I feel like with every trans person, in their life there will be incidents. But I feel very lucky to say out of the many, many trans people in the world that I have way less. … I happen to have a very big personality, so I do express who I am in every way.

I’m very lucky to say I am a confident person so when these incidents happen, I am not like shaken or affected, but I always think about how other trans people, if this happens to them, they can be affected. Not only do I think for myself, but I think for others because I can stop it from happening. 

What is your circle of friends like?

Very mixed. I have met some of my very best friends in the whole wide world who are trans but I do still have many friends who are not. … I’ve met lots of people like myself, and it’s been really awesome.

Is it a process of coming out again and again or not — how do you present?

I’m out to my whole school … because I did it in the middle of the year. In third grade — I just did it in one day. If you really think about the Hamptons local life, it is small … everybody knows everyone. … I’m not one to go up to someone and say, “Hi, I’m trans.” It’s in the discussion — they’ll be like, “Oh, are you trans?” and … I’d rather not say no because they’ll find out anyway, probably through somebody else — or they might just get confused. When I’m in other places, like not here, I don’t like “sell it” or I don’t really say it, but to the people who know, I just kind of live life.

Do you want to date someday? Who are you attracted to?

Dating? In a way it can scare me, really. I know I’m young but life has changed — young people are interested and want to. Especially going into high school. I’ve never dated someone. I’ve never held hands with someone. I’ve never kissed someone. I’m a proud “non-held-a-hand person.” … I identify as female, and I’m attracted to male and female. Dating does worry me a little bit, especially when they’re not trans. It will be a discussion no matter what, because it does affect it in different ways.

Are you going to go through a surgery?

I probably definitely will get the surgery. 

What do you say to those who say you are “too young” to know you are trans?

What I always say is, “Are you trans? No. Then you don’t know what that feels like.”

What does it feel like?

It’s so hard to say, because I feel like it’s different for so many trans people. I would say it is, in a sense, … like, “This doesn’t feel right. I know there’s something.”

What doesn’t feel right?

Like dress. I feel like clothes are a huge way of how people express who they are, and when I would wear sweatpants and a sweater with a baseball on it, I’d want to rip it off. That was the number one thing I hated. I don’t know why, I love clothing. I have a really cool shoe collection (laughs). … And my hair — I wanted my hair to be long when I was younger. I’d try to braid girls’ hair out of nowhere.

Talk about school, what you are involved in?

In the 6th grade I came into the GSA (Gay Straight Alliance) which was good, and pre-COVID it was exciting at the time. I was too young to be in it — I was 11 and the age was 13 — so I went to one meeting and they let me in, luckily. … We’d go the LGBT Network (at the Old Whalers’ Church in Sag Harbor) and watch videos and just hang around and have a good time.

What are your interests?

I’m interested in fashion … I do fashion competitions. I’ve made looks out of trash bags and out of COVID masks. I say get yourself some hot glue and rhinestones and you’re golden. … I like social studies, I like art. I like science a lot. I lip sync. I like to decorate my room — I love my room so much I feel like it’s kind of a way to show who you are, that’s why I’m always making posters and getting stuff for my room at T.J.Maxx.

What do say to kids who might identify and/or believe they are trans?

I’d tell them, “Just do it.” Not like in the Nike quote, just be who you are. I’m not saying it’s simple, because it’s not … it affects not just yourself but everyone around you, family and friends. This is your child, this is your friend, and even though your child is young, you know what’s best for yourself, they know what’s best for them. … If they are trans, there will still be very intense things that happen.

What kinds of intense things?

It might be them dealing with hateful people. It might be dealing with depression because of body dysmorphia. It’s not always a worrying journey, it’s a really exciting one — because your child is happy they can be themselves. If you do not accept your child for who they are, they will be either more miserable than they are not being themselves and being even sadder because you are not letting them. 

Would you say you’re fearless? What gives you that courage?

I fear many things. Facing your fears is courage, and I still have my own problems. I battle with thinking — my overthinking is really bad. … Everybody has their own issues, but facing them — and not getting rid of them but learning how to live with them — will make you a better person and a stronger person.

What do you fear the most — what are you really afraid of?

I’m afraid of death — it scares me a lot. And Lady Gaga ending her music career really scares me, too. (laughs)

Lisa, what are your fears, as a parent?

Lisa Iulo: There are a couple levels of fears. … When she initially said she wanted to be a girl, I didn’t know that at that point she was going to want to do the hormone blockers or the estrogen. She does the puberty blockers, and she starts the estrogen next year … so fear of the medications and the surgery — that worries me because she’s going to have to be on medication for the rest of her life. … The other worry … I’m not going to always be here to protect her; she’s going to have to go out into the world. … There are a lot of really horrible people out there and, yes, I worry about that a thousand percent. But at the same time I’m going to let her do and be who she is — I have to.

Jackie, what are your dreams and wishes?

My dreams, I guess, are to one day be known for something impactful — by being funny, being inspirational — something impactful whether it be known forever or known for a period of time. And my wishes are to meet Lady Gaga and to make everybody just feel safe and happy with who they are and make everyone know they have a friend, and that friend is me.