Jay Calderin

Founder & Executive Director, Boston Fashion Week




What is your idea of perfect happiness? A quiet mind. Cool breezes. Church bells ringing in the distance. The smell of fresh cut grass. A hammock.
What is your greatest fear? Not mustering the courage to do the right thing when I experience fear.
What historical figure do you most identify with? At the moment I feel a great sense of kinship with the artist Christian Bérard.
Which living person do you most admire? Ian McKellan. Balancing the ordinary and the extraordinary with such grace and passion is inspiring.
What is the trait you most deplore in yourself? I have a very short fuse when confronted with ignorance, intolerance, or injustice.
What is the trait you most deplore in others?
A sense of entitlement. No one is entitled to anything. Even if you're lucky to be a 'have' versus a 'have not' you wake up every morning and must earn it by contributing to the world in some meaningful way.
What is your greatest extravagance?
Building a library. Can't get enough books, films, and music.
What is your favorite journey?
The walk to Starbucks every morning.
What do you consider the most overrated virtue? Talent. Having talent is merely chance, what you do with it is another matter all together.
On what occasion do you lie? To spare someone’s feelings.
What do you dislike most about your appearance? For the most part, I like the guy in the mirror looking back at me as I brush my teeth.
Which living person do you most despise? Once you have witnessed how fragile people are, it’s hard to despise anyone. However, I am deeply disappointed by human beings on a regular basis.
Which words or phrases do you most overuse? Yes.
What is your greatest regret? I would not characterize it as a regret, but I like to think I would have made a good father.
What or who is the greatest love of your life? My husband. Twenty-eight years and counting.
When and where were you happiest? The most unexpected thing just popped into my head as I read that question. Dancing at the Palladium in New York during my early twenties.
What talent would you most like to have? The ability to play an instrument well. Harmonica or ukulele.
What is your current state of mind? Curious.
If you could change one thing about yourself, what would it be? I’d be taller.
If you could change one thing about your family, what would it be? I’ve learned to appreciate my family as they are.
What do you consider your greatest achievement? Building communities.
If you were to die and come back as a person or a thing, what do you think it would be? A priest.
If you could choose what to come back as, what would it be? A red-headed Scotsman.
What is your most treasured possession? My wedding band.
What do you regard as the lowest depth of misery? To be surrounded my inane conversation.
Where would you like to live? I enjoy being based in Boston, but more time in New York, London and Montana would be great.
What is your favorite occupation? Teacher.
What is your most marked characteristic? My work ethic.
What is the quality you like most in a man? Integrity.
What is the quality you like most in a woman? Intelligence.
What do you most value in your friends? Respect for themselves and for me.
Who are your favorite writers? Stephen Fry, Noël Coward and Oscar Wilde.
Who is your favorite hero of fiction? It’s a tie between Howard Roark and Hank Rearden.
Who are your heroes in real life? Mister Rogers. “I feel so strongly that deep and simple is far more essential than complex.”
What are your favorite names? Ava and Zak
What is it that you most dislike? Waiting for people.
How would you like to die? Knowing that I did my best to make the world a better place while I was here.
What is your motto? "¡Síganme los buenos!" ("Good guys, follow my lead!")
Which era of fashion history do you personally romanticize the most?
The 1940’s. The clothes of that time reflect some very admirable human qualities; strength, dignity, ingenuity, resilience, and vulnerability - and the music strikes a chord with me! I'm listening to Glenn Miller's Moonlight Serenade right now. Then of course, there is the plus of having the decade close with the introduction of Dior’s ‘New Look.’
Which three fashion icons, past or present, would you most want to meet?
Christian Bérard, Diana Vreeland, and Cristóbal Balenciaga.
Who do you think has made the greatest contribution to the art fashion in the past 10 years?  There are many great designers and celebrities who are putting the art of fashion first and foremost, but I believe that the curators of museums around the world should be credited with advancing the appreciation of fashion as art, not to mention making it more accessible to a broader audience than every before.
Where did you first experience the power of fashion? I was a distracted teenager in a rush, and the power of fashion hit me head on, literally. I crashed at full speed into Oscar de la Renta as he was coming through a revolving door. 
What is your current go-to fashion accessory?
Sienna's collection of cool designer Band-Aids.
How many pairs of shoes do you own?
Way too many, but more often than not I end up in sneakers.
Which contemporary designer do you believe will stand the test of time?
Ralph Rucci is already considered a designer’s designer and is sure to have a place in history much like Cristóbal Balenciaga.
Which fashion designer do you believe most influences your personal style?
I'm a t-shirt and jeans kind of guy.
How do you weigh in on fashion versus style?
Fashion is schedule. Style is a companion..
What trend do you regret having followed?
Excessive use of shoulder pads in the 1980’s. A shoulder pad in the shirt, one in the jacket, and another in the coat -- by the time I left the house it looked like I was ready to play football.