The LadyLike Profile — Olivia Connors

One of the most prestigious of all things TG for many years gone by was to be picked as a LadyLike Profile girl. Over the years many ladies told their stories to LadyLike and we shared them with the readers. Since the untimely demise of LadyLike magazine we have begun to present some of the features and articles here on TGF that did not make it to the printed page and the magazine stand. Here is the very last official Profile from LadyLike magazine — Olivia Connors.

Vital Statistics

Residence: Born in Chicago and now reside in a suburb of Chicago.
Profession: Semi retired but I still dabble in house flipping, insurance and retail sales at Transformations by Rori (plug).
Age: I’m an early Baby Boomer. I think I’ve seen the miniskirt come and go three times.
Height: 6 foot even and I wouldn’t change that.
Weight: I work hard to keep myself in the 170 to 180 zone.
Shoe Size: “Big Foot” size 12, but I’d look funny with a size 8.
Perfume: Currently, Kenneth Cole, Black.
Makeup: Max Factor foundation, Maybelline Mascara and the rest is from Transformations by Rori.
Favorite Clothes: Classic and Black, or Black and Classic.
Favorite Place: Acapulco, Mexico.
Favorite Activity: I do so many things, I don’t really know if I have a favorite… everything is good.
Favorite Movie: There are so many great movies, but I’d have to pick Pulp Fiction… it’s real life.
Favorite Music: I am a rock and roller at heart.
Turn-ons: A great dress, cocktails and a great dinner.
Turnoffs: Liars, pedophiles, cheap people and the Beatles.

The Interview

LL: Welcome to LadyLike, Olivia!

O: Thanks so much for inviting me to be the Profile Girl.

LL: The pleasure is all ours. You’re well known in the community as the lady who is in charge of the Be-All in Chicago. Is Chicago your hometown?

O: I was born and raised in Chicago and now live in a suburb of Chicago.

LL: Do you have any siblings?

O: I am the middle child of 5 with Italian Father and an Irish Catholic Mother. And people wonder!

LL: What was your childhood like?

O: My life as a child was fairly normal. I was just an okay student, did a year or so of college and then came the draft notice. That was the only time I purged. Thank god I had a small wardrobe.

LL: So you got caught in the draft?

O: Yes, I spent two years in the Army and 13 of those months in beautiful Southeast Asia.

LL: Thank goodness you made it back to the States after those thirteen months. There were far too many who didn’t. But, back to you. When did you first feel the pull of femininity?

O: In the womb!

LL: That is early.

O: Seriously, I swear I was still peeing in my diapers and I knew something wasn’t right. It was warm down there, but it just wasn’t right.

LL: When did you first try on femme attire?

O: I can remember trying on my first pair of shoes at about four years of age. One of my aunts caught me trying on her daughters shoes while I was staying with her when my parents went to Florida. They fit good and looked pretty neat. They were red.

LL: So you became fixated on red shoes at the age of four?

O: You’d think I have a closet full of red shoes but I don’t own one pair.

LL: Were you able to dress up at home when you were young?

O: As I mentioned, I had an older sister and as the years went on I gained two more sisters so I always had a selection of clothing as a child and teenager. My closet was a big old shipping trunk in the basement of our flat in Chicago. I’d sneak downstairs at appropriate times and get all dolled up… well as much as I could, and prance around the basement practicing “the walk”. What a time I used to have.

LL: Sometimes trans people have trouble in their youth due to the way the idea of dressing can intrude upon your thoughts at almost any second. Describe how being TG affected your youth.

O: I probably could have been a better student and in turn had more opportunities in the work place as an adult but, as you say, I was constantly preoccupied with this gender confusion. But I did okay. As mentioned, I had a normal childhood and I was an okay student. However I did graduate high school from a summer class with a bunch of other goof-balls.

LL: So you hung around with the slacker crowd. I guess back then we would have said you were a juvenile delinquent?

O: I used to hang with a typical bunch of guys and girls but we did it all, from the underage drinking, street racing, nights in the park, nights on the lake front, nights in the slammer — the whole thing. I was not a weirdo. In fact I was considered the unspoken leader of the group.

LL: The leader of the pack?

O: You could say that. No way was I ever a preppy kid, or by today’s definition, a geek. I was on the street and definitely a greaser, pompadour and all.

LL: That is hard to imagine. From street fighting greaser to lovely lady. That’s part of the fun of gender shifting, though. Where you ever caught dressed when you were young?

O: Oh my god, was I ever. One late summer day while my father was changing the screens for storm windows stupid me decided to get dressed in my personal space in the basement.

LL: And that was where…

O: It was where my father stored the screens and storm windows! HELLO! Today it would be a cry for help, back then it was a good beating and “what the hell’s wrong with you, do you want to go to a girl’s high school?”

LL: Now there’s a question most of us would say yes to.

O: I wanted to scream yes, but I could see the disappointment in my father’s eyes. The drama with my mother went on for months. She could have started the second Chicago fire with the vigil lights she burned over this.

LL: What else could a good Irish Catholic woman do? Did they ever get over it?

O: As an adult I became my parent’s favorite son and I held the family together for a long time, and was always there for my parents. Now I let my sisters do it since my dad has passed.

LL: When was your first time out in public as a female? Where did you go and what did you do?

O: You know, I’ve been out with the gender organizations for around twenty years. But like so many of us I used to test the outside world all by myself. First time I ever went out — wow! I can’t even remember the actual first time but let me share with you one of my early ventures. It was record cold in Chicago, something like 20 degrees below the big zero. I was living in an apartment with my spouse and she was working the night shift as a nurse. Perfect! I got all dolled up and went for a walk in the neighborhood with the shortest skirt and coat anyone could wear and white patent go-go boots. I saw about three cars, one of them full of kids and the hoots and howls were heard around the world. I must have looked ridiculous.

LL: Other than some embarrassment over the hoots and howls, how did you feel?

O: Absolutely fabulous! I’ll never forget it along with so many other private outings. You’d need a separate publication just for those stories.

LL: Did you have a TG support group to support you while you were coming out?

O: You know if someone tries to do this solo they are nuts. I found Tri-Ess through a local radio station… the disk jockeys were making nothing but fun about Tri-Ess. I, on the other hand, almost drove off the road while listening. Anyway that was my first experience with an organization.

LL: Just goes to show that the old public relations cliche about there being no such thing as bad publicity is true. Tri-Ess benefited because the DJs made fun of them. Did you stick with Tri-Ess?

O: Only till I found my true home, Chicago Gender Society. I joined CGS in 1988 and eventually worked my way to vice president for two years and then President for four years. It wasn’t hard. All you had to say was, “okay, I’ll accept the nomination.”

LL: Oftentimes it’s hard to get folks to step up to leadership positions in the TG support world. How did you like your time being an officer?

O: They were the best years of my life… no doubt. It was a great and very successful ride, mainly because of the people I had around me. We all just clicked… it was almost flawless.

LL: It’s great when you get that kind of synergy going. You seem to have preserved it in the organization of the Be-All. Tell us about the Be-All. Where did it originate?

O: The Be-All originated twenty five years ago and the credit for this wonderful event goes to Naomi Owen who still remains active on the board in an advisory position. The Be-All used to travel between five different midwest cities with Chicago being selected every five years (naturally).

LL: JoAnn and I attended once when it was in Cincinnati. How did you become active in the Be-All?

O: I had attended many Be-All’s in the early ’90s and came away saying — wow!. I was President of CGS in 1999. It was my second year in office and we had already made some great things happen. I, along with Julie Johnson and Robin Papecke started the annual Garden Party. I also got the CGS annual pageant resurrected after five or six years of dormancy and those were huge local events with upwards of 150 in attendance and 12 to 18 contestants. The productions were first class so CGS had acquired lighting and staging equipment and it was quite elaborate. Then came the gift of the Be-All.
Since Chicago Gender was so successful, the Chicago chapter of Tri-Ess came to us with an offer. It was their turn to produce the 20th anniversary and they were short of funds and people. Julie Johnson, Robin Paepcke and myself decided to bring CGS into the picture if we could lock down two consecutive years. That in itself, changed the entire dynamic of the conference. It is now it’s own entity, a registered 501C3, and the second largest gender conference in America.

LL: Will it ever go on the road again?

O: It’s in Chicago and will be until someone can prove they can do it better. Last year we celebrated the 25th anniversary in ‘true style’ with over 400 in attendance. I can’t say enough about the staff and volunteers, supportive presenters, vendors and most important, the attendees. It’s a wonderful thing… every piece of it.

LL: What do you do when it’s not Be-All time? What do you do for fun?

O: When it’s not Be-All time, we’re planning for next year’s Be-All. Seriously ask anyone who runs a conference. It’s constant. And what could be more fun? That pic of me laying on my butt is from the 90’s when I was a “member only”, I had nothing but time, but you know what… the involvement with Tri-Ess, Chicago Gender Society and the Be-All has been the best thing that ever happened to me.

LL: How do you think the community has grown in the years that you have been out? What can transgender ladies do to help the growth continue?

O: I believe we have grown tremendously. We are out. But please, keep in mind, if you venture out your door, you are acting as a representative of the entire community. Look the part, look your age and act appropriately. Women are the beautiful species. If you don’t realize it, they do, and they always have been the kingpin of the family unit, and I believe the corporate world. Remember, don’t ask the boss, ask his secretary… she knows it all. Women are a gift and if it’s in your cards to emulate the female gender, do it with intelligence, class and style.

LL: How do you feel you’ve developed, personally? Who do you credit with helping you on your femme ride?

O: I have to acknowledge my wonderful part time boss and friend, Rori of Transformations. I have worked as part of her staff for the last 7 years and it has been a wonderful experience. She has entrusted me to operate her store for one to two days a week for years. This has been an experience I could write a book on. It’s a dream come true. I’m not quitting so don’t send in your resumes. Anyway, there would be a long line of local folks in front of you.

LL: You heard it here, girls. No job openings as long as Olivia has the gig.

O: I’ve have always had wonderful support from everyone in the community and I have to put my spouse on the top of that list. She has been supportive from day one. She was my childhood sweetheart and still is. Don’t just “tell her you love her”, tell her what’s happening.

LL: When did you let your spouse in on your other life?

O: I did it before we were married and it’s worked very well. We’ve been together now for, I don’t know, maybe 35 years? The last couple of years have been difficult with health issues for her but we’re surviving.

LL: We could probably go on for many more pages but we have to wrap it up. Do you have any final thoughts to share with our readers?

O: I’d really like to say thank you LadyLike magazine for this opportunity. This is just another dream come true. We are all getting older and that’s one of the reasons I wanted to do this article. Age can be a beautiful thing… let’s just all keep positive in our thoughts and presentations and pack on the moisturizers.

LL: Any thing you’d like to do that you haven’t done yet?

O: I’m going shopping for red shoes… what took me so long?

© Kathy Richland Photography

Category: Transgender Fun & Entertainment