How The Founder Of Boston Fashion Week Has Been Mobilizing A Community Of Artists For 25 Years

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If you were to summarize the extent of Boston Fashion Week founder, Jay Calderin’s, storied career, it would have to be broken down into at least two parts. First, there’s his New York City upbringing, where he acted on his fashion obsession early, enrolling in The High School of Fashion Industries before going right to work in the city managing designer workrooms. There, Calderin put his pattern-making and sewing skills to use and learned the industry first-hand before moving onto the next phase. Beginning early on his twenties, the creative hit a fashion fatigue that led him to change course and move to the slower-paced city of Boston. Intending to leave fashion and start a new chapter in the New England town, the move was steeped in irony, as Calderin quickly tapped into an under-represented community of creatives and ultimately organized them with a deft vision of what the city’s fashion scene needed.

Decades later, the School of Fashion Design and Museum of Fine Arts instructor has penned books like Fashion Design Essentials and What They Didn’t Teach You In Fashion School, founded  Boston Fashion Week and has served as the organization’s Executive Director since 1995. Ahead of Boston’s the Boston Fashion opening event this September 22nd, I talked to Calderin about what sets the city apart, the people who inspired him and the future of fashion in the education and technology hub.

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Montero: Tell me about your background in fashion?

Calderin: I was born and raised in New York City and my first connection to fashion came when I was in I was applying to high schools and there were all of these different high schools and so I applied to all of these specialized high schools in New York like Art & Design and Performing Arts and also High School of Fashion Industries and I got into all of them but Fashion High had a work study program where you can make a  little money every month by working in an office at the school and we didn’t have a lot of money so that gave me the money for art supplies and sewing supplies. I thought I could always transfer out later if I don’t like it but I fell in love with it because fashion brings all of those interesting together like the performing arts with the shows and presentations, the graphic design and pattern design. I was really strong in math and science so it was like I could also do engineering for the body with patterns so I got hooked right away.

Montero: What made you want to leave New York so shortly after finishing school?

Calderin: Right out of school I worked and then when I was twenty-two or twenty-three I decided I wanted to leave New York because I decided I was done with fashion. I said no more, I’m exhausted. It had already been about ten years of working in the industry and I moved to Boston, where there was all this great local talent like photographers, models, and stylists but there was nothing unifying everybody. The  press wasn’t really paying attention. When I moved here, I didn’t think there was any fashion here and that was kind of the draw.

Montero: What was it about Boston that made you want to move there? 

Calderin: I moved here and I thought it would be a nice fresh start. People had said how beautiful it is up here and how clean. It felt like a little New England town. I moved here in 1989 and part of the reason for moving was that I was just tired. I was working decent jobs and it wasn’t even really about the competition it was more that it takes a lot out of you when you’re in this race. It wasn’t anybody’s fault but that’s just what everybody agreed that it was a race. Everybody signs up for the race when they live in New York. I didn’t know that I could say no and just go at my own pace but here I realized that the same thing happens here but you have to make that conscious decision. People were telling me that everyone was going to be working slower than me so I thought I’d be working at half pace but then I moved here and people were still saying to me, “calm down, don’t rush.” In New York it’s really fast-paced

Montero: What was it like when you first came to Boston? Tell me about your impression of the city at that time? 

Calderin: I really fell in love with it right away because it was just pretty, it was clean. I didn’t feel this pressure to be competitive in the same way that I had been trying in the environment in New York. I didn’t mind being a big fish in a small pond, I just wanted to be a part of a community. Because of my sewing skills and my pattern making I was able to manage a small shop for Pierre Deux. I managed their workroom with all these great French country fabrics that were mostly for home but I thought these would make great clothes. So I got permission to make some shirts and vests for the store and they sold really well and then the following year in 1990, I go the shock of my life and I realized I had to go back into fashion because I got the September issues of Vogue and Elle and in Elle  there was an editorial where a stylist had pulled one of my vests in New York and the same month in the September issue of Vogue and Christian Lacroix was wearing my vest. In a full page editorial about him but they dressed him in my vest that I designed and made with my two hands. He was always a hero of mine and I thought maybe I shouldn’t give up on all of this.

Montero: Then what happened?

Calderin: By then I had been exposed to some of the local talent and was into the swing of things myself so I started on local cable doing a TV show for 5 years on public access television covering all the local fashion shows. Then we had a magazine for 5 years called Maverick magazine and became the local fashion resource so we brought everybody together. It was so much fun. I learned about publishing and producing and we did it all ourselves. The magazine was monthly and the TV show was weekly. It was all about learning all those skills like how do you do something. That led to me going down to New York for the second or third fashion week. We came for the magazine and the tv show because it was all new.

Fashion week as we  know it now started in New York with 7th on 6th and Fern Mallis who began to show people who were doing great stuff here. They knew that we needed a unified voice. Of course, the production quality was amazing and it was glamorous but the main thing was why they were doing it and I realized that Boston was in the same place. I realized that we are regional and not a fashion hub but there was all this great local talent and I realized that we could help Bostonians know that they have this resource. I knew that this idea of bringing people together was a good idea. New York 1 had a huge camera set-up for the shows and I remember asking the guy if I could just sit under his tripod and watch the shows and I would shoot the shows and all that but I could also watch Fern Mallis and everyone else in action because they were like heroes to me and this force that was working and I observed everything that I could and I would say how can we do this in Boston? What needs to change? What can we figure out that needs to be done?

Montero: How was the Boston fashion scene different from New York at the time?  

Calderin: In Boston, it wasn’t like it was in New York where it was about exclusivity where you couldn’t get in unless you were invited. Here it was just the opposite. Here it had to be about the access. If we had acted like that and told people that they couldn’t get in, nobody would care and they would just do something else. The Bostonians don’t really put up with that kind of stuff. Also on the flip side, it wasn’t about excluding people it was about getting them involved with these local designers and fashion professionals.

Montero: What was it like when you got serious about applying this knowledge to Boston Fashion Week? 

Calderin: The first year, we tried to get everybody on board and have these meetings hosted in a photo studio because it was the only place big enough for a bunch of people to hang out and we would have these meetings and say, “what are we gonna do?” then we started realizing that nobody had any money so we were doing this and we really weren’t in a position where we could charge each other what we were worth. I was never going to be able to make any money off of local designers because they were struggling and they were trying to make their living so I realized right away that we would have to depend on leaders in the community for venues and sponsors and the people who would make it possible for these designers to show without them spending exorbitant amounts of money on lighting and staging and venues and all that kind of stuff. It was a civic initiative. It was basically me saying I want to build this community and I want to know which leaders in the community are willing to step up and provide either funding or their resources so it became this incredible collaborative thing where everybody came to play.

Montero: How is Boston Fashion Week different from other fashion weeks?

Calderin: It reflects what Boston is about and what it wants. I’ve studied all these different fashion weeks everywhere and they’re all different in terms of the fact that some of them are all about the socialites in the social scene. They get together and have these great shows and get to dress up and others are about retail and others are about new designers and incubators and everybody does their own thing but over the years I’ve come to understand how Boston is different but it changes every year depending on who wants to play but it’s always holding up a mirror to Boston and saying “this is your fashion community right now.” And the next season will be a whole other thing. That was our mission to not try and make it be something that it wasn’t going to be. Every city has its identity. You think of New York and it’s American Sportswear, London is more rebellious and Paris is known for haute couture and when you ask what Boston is known for, all the things we used to fight against, they called it a college town, it’s academic, it’s business, it’s in technology, all those things now are things that we embrace. There is business here and science and tech are the new frontiers of fashion now so now we’re home and we’ve found our niche so it really says who we are. It’s not always perfect or glamorous but it’s always smart.

Montero: How are you incorporating technology into the fashion week programming this year?

Calderin: This year on opening night we’re doing this incredible immersive photo installation with four monitors and we have pulled more than one hundred plus images featuring fifty-five designers and then we’re doing a live presentation with twenty-five designers calling it “IRL” and having it come off the screens and be in the room then we’re looking at the future. We’re also going to do a virtual reality presentation so we realized it can be used as a teaching tool to do live sketches in three dimensions.

Montero: What are some of the biggest business lessons you’ve learned over the years of doing this?

Calderin: The biggest change is not something specific that I’ve done but more of a result of the things that I’ve done like after a certain amount of years, I would say half way through this experience it’s been more about listening to what people want to do and letting them do their own thing. Although we do some programming, the whole thing is about activating the communities and that’s what we realized right away. I realized pretty quickly that it had to be self-sufficient in that designers had to step up and do their own thing so we can act as facilitators. Overall, it had to end up sustaining itself because one person can’t be driving it. I can help facilitate and curate and add in what’s missing but in order for it to be a reflection of the scene .

Montero: What does 25 Years of Boston Fashion Week mean to you?

Calderin: In celebrating 25 years, we really want to reflect the past, the present and the future. In terms of the past it’s really about our legacy . We’re exploring technology with virtual reality but we’re also going to represent in a way that we acknowledge that virtual reality is both entertaining and a great vehicle for commerce. As an educator, one of the ways that I don’t think it’s being explored right now is in terms of learning how to learn how to be a creator in that space as a fashion designer. One of my courses I teach is sketching so I want to explore how it changes your perspective when you draw in three dimensions. That’s a personal exploration that I’m sharing. At the end of the week we have an event that features twelve students and the idea is that we are doing an installation where each student has a space and the public walks into these little spaces and sees the entire creation process from start to finish.

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