When we met the sassy Brit Grammy Award-winning R&B singer-songwriter Estelle Swaray back in New York three years ago at New York Fashion Week, her genuinely warm personality and humility left a lasting impression. How cool it was for us when the American Boy hit-maker returned to The Rock (she’s been here three times) for last weekend’s Caribbean FashionWeek. We caught up — poolside at the Courtleigh Hotel and Suites — and shared deets on relationships, family, and her latest album All Of Me.

What are you sipping?

A refreshing glass of tonic water with a wedge of lime.

We’re loving your outfit — who are you wearing?

Diane von Furstenberg trousers and this truly comfy Top Shop top.

Was music always your career goal?

I’ve always loved music, but I never spent years dreaming of becoming a musician.

So what came before the music?

(laughs) I worked in a supermarket packing shelves, before working in a record shop in Central London, and then did some freelance writing.

When did it occur to you that not only can you do music, but that people the world over were endorsing you?

It was after I realised my music was doing better than my jobs over the years. I did my first gig in a hip-hop club years ago and the reaction was overwhelming. It is still occurring. I was in Belgrade recently, a city I’ve never been to, and people were singing Come Over verbatim. It was an incredible moment.

Who would you most like to collaborate with right now?

Mary J Blige, I love her. She is both an inspiration and a mentor and I appreciate what she is doing and that she is a genuinely warm person.

What is it that changes people after that big breakthrough?

I believe it is the perception of what you think people expect you to be, in addition to being a human being. You should change and grow in whatever you do. However, you must be a good human being at the core.

Share with us one of your personal goals.

I need 10 more Grammys — that’s one of my goals right now.

Are you familiar with any Jamaican designers?

Yes, Gavin Douglas. He was dressing me even before I knew who he was. His creations are made for the stage.

Who are your other favourite designers?

Mark Frost, Nicholas Kirkwood, Diane von Furstenberg and Rachel Roy.

What’s the one thing you enjoy most about your career?

The opportunity to be here in Jamaica relaxing for a couple of days. I know I’m working, but I never take these simple, luxurious moments for granted.

Who are some of your Jamaican music references?

I grew up listening to Terror Fabulous, Buju Banton, Lady Saw, Beenie Man, and Bob Marley.

Tell us about your family.

My mum was born and raised in Senegal and my dad was born in Trinidad and raised in Grenada. I remember both my parents subscribing to the Rastafarian faith. They had long dreadlocks and enjoyed the music of Bob Marley and Dennis Brown.

Share with us your journey in putting together All Of Me.

It was the result of the end of an intense four-year emotional relationship and gave me the breakthrough and release I needed to grow to where I am in my life right now. It taught me to love and appreciate myself more, and to demand a certain level of love in return.

How important is it to be true to yourself and be successful at the same time?

Being true to myself sets me apart from everyone else. When American Boy was released, I knew it would be a hit. Not everybody thought so, but I knew what it was capable of and it was a huge success.

How important is it to stay connected to your fans?

It is very important. People who didn’t know me before only knew American Boy and it was essential that people the world over know that I had my own label, that I was working hard and was about to put out my third album. My social media connections give fans the real Estelle.

How have your years of performing in clubs all over London contributed to your success?

It has definitely built me as an artiste. I go to the clubs to enjoy myself and see what people are listening to and what they want to hear. It’s important that I remain connected to my roots.

Where do you see yourself five years from now?

In addition to acting, producing and directing, I need to do three more albums in the next five years as well.

So, we hear you’re interested in pursuing a film career. Which actor would you most like to work with?

I’d love to be in an Adam Sandler film. I love comedies and can appreciate a dry sense of humour. I’m also a big fan of British actor Noel Clarke.

What is the greatest highlight of your career to date?

Definitely the 2009 Grammy Awards performance with Kanye West. It could have been a disaster, but I took my time, sang on key and did not trip over myself. It was a true test.