Ayana Wellington-Pitterson, the thrifty commander

Ayana Wellington-Pitterson may have left Trinidad and Tobago to live in the US when she was 12, but decades later, her recollection of the country of her birth remains strong, as are some of the practices she learned from her modest childhood.

“I could walk my way through the path on how I got to school. I went to San Fernando Methodist; I remember some of my teachers’ names. I remember that I got skipped so I could take Common Entrance exam, but right when results were coming out, we moved. I remember the food and the beaches. Oh, how I loved the beaches...

“I remember how you had to go outside looking like you put yourself together, no matter how poor you were, because dressing well was and still is a sign of having good manners,” even on a tight budget, she told WMN.

The move and the culture shock were stressful at the beginning, but Wellington-Pitterson, the eldest of six children, adapted, worked as hard as she had to and is now a Judge Advocate General (JAG) Commander in the US Navy.

“I never envisioned coming to this country (US) at all. We moved to the Bronx, I went to middle school, high school, and then college and law school in New York.

“Then I decided I wanted to get out of NY badly, but wanted someone to pay for it. I wanted to see more of the world and the US.”

She applied to and was accepted into the JAG Corps the year after finishing law school. And although she passed both the New York and Connecticut bar, she has never practised civilian law a day in her life.

“After that it was five weeks of indoctrination school that taught about being in the navy – how to wear the uniform, the rules and etiquette of being an officer – then ten weeks at the Naval Justice School, where you learn the practice of military law and what you would be doing as a military lawyer, which is different than the civilian side.

“Then you go to your first command. My first command was in Jacksonville, Florida, where I was a prosecutor.”

She is now based in San Diego. Her job entails offering legal advice to the commander in charge of the entire fleet of surface vessels for the Pacific.

“It’s me and two other attorneys – I’m the deputy right now.”

She said while the Navy in general is mainly male-dominated, there are a lot of women in the JAG Corps.

“But African-American at my level, there are only three at commander," which in itself can be challenging, as she has found that explaining her thoughts can sometimes be a little frustrating – something with which she has dealt since she joined the navy.

“I’ve been in the navy for 18 years…I have non-African American and female mentors who I am close to, but it’s sometimes very lonely because my way of thinking is not going to be a white woman’s way of thinking. I’m an immigrant, grew up in NYC, was poor, so I’m going to see the world in a different lens, even though we’re wearing the same uniform.

“It gets a little easier, but not less frustrating.”

She had failed to be promoted to the rank of commander a few times, but she has never blamed it on the fact that she is black or female. She believes it was because of some of the career “detours” she may have taken because she didn’t have proper guidance.

“Whereas if you have the right guidance, you’ll know how to avoid those detours. I am female and black, but I would say that there were things in my life and career that if I had to do it all over again, I would have made a few different decisions, so that I would have a different resume.

“I still have another rank to go – captain. We’ll see how that will play out when that time comes.

“For now I’m not really worried about the promotion, I’m focusing on doing the job I’m doing to the best of my abilities because I want to be one of the best. I want people to be able to say, ‘Hey, Commander Pitterson – you should call her on this, because she is one of the best SJAs (staff judge advocates) we have out there.’”

Wellington-Pitterson told WMN she has no regrets about joining the JAG Corps, as she has had experiences and learnt lessons she would not have had otherwise.

“You know there are some of the things you learn that you cannot teach? That ability to get up and do what you have to do, without allowing things to keep you down, is not something you can teach anyone. You have to learn it through experience…

“In the navy there are so many things that come at you – the fact that we have to move every two-three years, new city, new house, getting kids into schools, making new friends, getting babysitters, finding neighbours you can rely on – these things are what some people do once or twice in their lifetimes, I’ve done it eight times,” the mother of two teenagers said.

Her children, she said, are “in that emotional teenage world right now, with the moods and everything else. You know how that can be,” she sighed.

Fortunately for her, her husband works from home and understands and accepts what being married to a woman in the military means.

“We got married about two days before I checked into my first command. He’s been through it all – the joys and the stresses. He has been a trouper. It’s important that the family be on board with what you’re doing. The kids too have adapted well to our life.

“We’ve had our bumps, but it hasn’t been extremely difficult for us to manage.”

And in as much as she is all in when it comes to her career, she gives her all to her life outside of the navy.

“I have a huge social media following for my thrift shop, Thrifting Divas, that has grown to over 100,000 members on my Facebook, IG and YouTube…I started blogging in 2013 on thrifting, wearing thrifted fashion, and how you can look amazing without spending a lot of money. I started showing people how I put together my outfits with thrifting. Ninety per cent of my closet is from second-hand clothing,” although she can afford to buy her clothes brand-new.

She believes this is something she learned from the Caribbean and it is a skill she finds very useful in trying to be consistent with the content she posts.

“Back then (in TT) you ironed your clothes before you went outside, no matter how poor you were – it was wash, dry, iron and walk out.

“You don’t have to have a lot of money to look and feel amazing.

“I always encourage women not to wait, do it now. Don’t wait for that new job, or to lose weight. The platform I’m trying to build for women is that now is now.”

She said Thrifting Divas brings balance in her life.

“I have the navy, my family and I have this side business that is flourishing and is part of who I am – being able to serve my country and being able to serve me.”

Wellington-Pitterson said she's given her husband and children a taste of her Caribbean life, and they love it. Their last visit was just before the covid19 pandemic began.

“We stayed in Trinidad for a bit, then went to Tobago for a little bit. We stayed with my aunt, Joanne Archie (Police PRO), for a while and that was so much fun.”

As far as her career goes, Wellington-Pitterson said she can retire when she has served 20 years in the navy, but nothing is yet set in stone. If it decides it wants to keep her on as captain, it will be considered.

"But I’m not stressed about planning out every step of my career any more. As long as I enjoy it, when the time comes to go, I’ll know.

"For now, I just want to be the best I can be.”