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The Creative Class: Gregory Siff

May 02, 2017


Meet Gregory Siff, Angeleno-by-way-of-Brooklyn.

This contemporary artist captures the raw aesthetic of America’s Gotham and the unstructured prismatic scene of alchemical Angeles in a signature blend of symbolic imagery and minimalist text that speaks incomparably to the living duality of modern pop culture.

DSTLD: Tell us a little bit about yourself – how did you get to where you are today?

Gregory Siff: I got to where I am today by doing what I love every day. The more time I did the happier I got, the more cool people I met along the way and the better the paintings began to look. Create everyday. I am an artist, a feeler, a force in the world that goes through something every day and lives to tell about it in paint.


Gregory in his studio (wearing custom bomber jacket and black skinny jeans)

Siff: In high school I was in love with music and theater and opera and guitar and movies and dressing up like Ninja Turtles… superheros. I was always the youngest in the class and I never really got into the whole boyfriend-girlfriend type of thing. I just really wanted to understand about movies, and I was into acting, and I sang in the New York City Opera, and I did commercials, and I really loved the idea of expressing myself through these kinds of means –– even saxophone and bands.

… and, of course, I played baseball and basketball –– but was really drawn to life in the arts.


Gregory outside his studio in DTLA (wearing custom bomber jacket)

I went off to study Communications and Journalism at NYU, while doing acting and music still. I was making some money doing commercials back then, and I wanted to get a degree in something else. Then there was a humanities class where the teacher gave me a bunch of books that I probably wouldn’t have discovered had I not gone to college. One was a book of Jean-Michel Basquiat’s artwork and I asked myself: ‘Why do I need to go to school when I felt that I loved these guys?’ … like reading Vincent Van Gogh’s, and other artist’s lives, that felt like a Shakespearean play. These were people that lived with their heart.”

So, I wasn’t really into art until I left N.Y. with my family and moved out to L.A. to pursue a little more of the acting world and Hollywood. And, out there when things weren’t 100% anymore –– you’re without your family, your dream isn’t going the way you thought it would, and you start to find this kind of inner turmoil, a kind of struggle inside of you.


Gregory outside his studio in DTLA (wearing custom leather bomber jacket and black skinny jeans)

Siff:  We did a scene for our acting class where I was Jackson Pollock, and I made all of these Pollock-style paintings ahead of time that were in the scene. There was a big fight, between me as Pollock and the actress playing Lee Krasner’s wife, and at the end took the paintings off the wall –– because I made them… these were works that I made. And when I did the scene the acting coach was like, ‘Okay, that’s it; we’re done: you did it in one cut.’ Usually, you take time, and you go back and put it back up again; but it was because I actually, really, cared about the things that I made –– with my hands and my heart –– and I put them on the wall, and I didn’t want anyone to hurt them, and I wanted to defend them.


Gregory outside his studio in DTLA

I felt like there was a bigger amount of reverence and respect for what I was making, instead of who I was trying to be.

And then I met lots of cool artists that do this for a living –– that paint what they want, they print their own books, like Louis Cannizzaro. [He] is this great artist who, I love his work –– and it reminds me of all of my favorite artists. I got to talk to him, and he said: ‘Dream up your biggest and craziest idea and do it.’ And I just went in to The Standard Hotel, back in about 2005, and said: ‘This is my art, and I want to do a show, and I’ll donate it all to charity.’ He gave me the space, I sold out the show, and I was like, ‘Wow!’”


Gregory Siff x DSTLD Womens Leather Jacket

So, the art is there to do things to other people; to do good things for them, and you get to live this kind of life. I mean, it wasn’t regular 9-5 stuff –– these were paintings that I was thinking about at like, 3 and 4 o’clock in the morning. This was like my early-twenties, out in L.A. I guess things didn’t go right, and I moved back home to New York… and it was a low time.

My dad lived until he was 85, but when he passed away, another type of me came around that I had been trying to find that was like another person. I was another person after my dad passed, and I just didn’t want to wait around anymore for this acting dream, or I didn’t want to wait around for this idea of: “You got to be a lawyer,” or a doctor, or whatever. And things weren’t going right.


Gregory in studio working on Art Basel collection

That’s a funny thing: when things aren’t going right, you actually get shook to do something about it –– and that is where some of the most beautiful paintings came out of, the most important decisions come out of.

And I came back out to L.A., and I started putting work on the street, and I was just always thinking about art. Then, I got recognized by a gallery that told me they wanted to put my work in there, and then you just start doing it every day.

The minute that I chose to do it every day, I would figure out: “Okay, now the rent is covered; what else do you want to do?” So then, every month, it would grow longer. Now, if I stopped, and waited around, and read articles on Google, and looked at what other people were doing… I mean, there was no Instagram at the time to constantly see what people are doing to the left of you—I would have gotten 


Gregory outside his studio in DTLA

My dad always said: ‘When you are running a race, if you look to your side: you’re gonna lose; you just look forward –– just look at what you are doing: keep going.’ So, I kept doing that and doing that and doing that.

And it’s tough –– we’re in Hollywood, and we are in a beauty-conscious type of place. It’s a competition nowadays, you know –– with the “likes” and “the people” –– but you have got to block all that out.

You got to look at the piece: what it means to you, and why you are making it.

So, I just kept doing it and met some of my best friends. You know, it is tough to make friends as you get later in life; but a lot of my best friends are artists, and I get to be honest in them. It’s tough… while it’s beautiful, because everyone is out here on the hustle –– and that’s what you want to be: you want to be around people that are going for it.

But yeah, you got to keep your guard up because with that kind of attitude: you can have someone be your best friend, and then one day they are gone. I’m a very fun guy, and I love everybody; I have a lot of love. And I have a lot of friends, a lot of great people in my life, and there is not enough time sometimes to do all of that –– which I’m trying to balance out;


Gregory working on DSTLD x Gregory Siff Art Basel Collection

I’m trying to be the best I can be, but I can only be the best to so many people; otherwise, I’m useless. I got to create work and that’s where you have to be. If you’re not making art, you’re not an artist.

You can’t just make ten paintings and wait for those to be sold: you have to consistently keep making stuff –– not for anything more, but because it feels good to make it, and you want to do something with it, and share it. My thing is create something every day and share it; and eventually after 2010, 11, 12, 13, 14, 15, 16!”

Sometimes, I look at my bio and look at the things that I have done… you know, I couldn’t have planned any of this; and it’s really like: when you put the effort in, even the mistakes lead to the right things. And that’s with every one of my paintings. 


Gregory outside his studio in DTLA (wearing custom leather bomber jacket and black skinny jeans)

The best paintings that I do have ten paintings behind it, because they add gravitas to the artist and the artwork.

DSTLD: Why did you decide to collaborate with DSTLD?

Siff: “The thing about art, that also works with fashion is: the more I paint, and the more I think about painting, and the more I’m around it –– the more I can do whatever I want, the more the artist can do whatever they want.

To become something called, “There are no mistakes:” where even when you make mistakes, they become something beautiful, and something that you couldn’t even plan. 


Gregory Siff x DSTLD Mens and Womens Leather Jackets

What I love about DSTLD is there are no mistakes; and in art, keeping it simple, and simplicity done right, is one of the hardest things.

A ton of people could look at a simplistic piece of art, and they say: “I could do that;” and then, when they try it, it doesn’t work –– you can’t do it –– only one person can do it that way.

The art of being simple is a hard thing, and what DSTLD does right, is strip down to the marrow of what is essential, and what is beautiful to wear: the classic jeans and a t-shirt, a leather jacket –– and, by the way, when you get a leather jacket: that’s supposed to be the jacket that you keep for the rest of your life, it’s not like you are going to need to get another one.

These are constants that don’t go out of style, and that is why gestural action painting like Jackson Pollock doesn’t go out of style. When you walk into a museum, and see that beast of a painting, it still holds weight as a modern day painting that comes from your heart and comes from something that is done right.


Gregory outside his studio in DTLA

A great artist is someone who can create anything with the materials around them. You don’t need some magic pen or magic brush –– if you only have toothpicks and… motor oil, a good artist can create a strong work of art out of those things, and that is why there no bells and whistles when it comes to DSTLD; the work, in itself, is the perfect blank canvas for an artist and a person.

So, when you want to think about your day, you’re not branded with anything but the way that it fits, the way that it feels, and the way that it makes you feel; so, the logo is your face, the way that that feels.

Given these canvases: the leather jacket, the bomber jackets, the t-shirts… the things that are used every day. So, if I’m going to paint every day, you wear the jeans, you wear the t-shirt, you wear the jacket that stay with you your entire life –– that is what a great work of art is.


Gregory Siff x DSTLD Mens and Womens Leather Jackets

Nothing in this life lasts forever, but art is immortal.

This type of collaboration is not one with a glittery logo. The whole, the piece in itself –– my paint enhances your fabric, the same as your fabric enhances my paint –– that is why it is a special collaboration.

I have works on canvas that go for thousands of dollars, and it’s a chance for people who might not be able to –– or are traveling, and might not want to hang a painting on the wall –– they might want to get this jacket, and wear it a bunch, and then eventually hang it on the wall; or they might want to stretch the t-shirt onto a canvas, and hang it on the wall because it is a piece of art… or they might want to paint in these clothes, and work in these clothes, and feel the inspiration that both of the artists –– and I call DSTLD an artist too: because you are building your art, and I’ve seen how you’ve evolved with your art. While you don’t completely change it, but you get there, and that is why this is a good collaboration; and we are going to do 20 leather jackets, because that is enough to make the work great.


Gregory Siff x DSTLD Mens and Womens Leather Jackets

We’re not trying to oversaturate –– this is not something we are trying to make a million dollars at –– we’re trying to make a great work of art. My fam and following, my friends who support and love my art, without a doubt, are in the same crew as people who share love for the bare, simplistic clothes. Hey, the more successful I am, the less I wear a suit; if I don’t have paint on my hands, and I’m not comfortable, then I am not doing what I am doing. Of course, there is a time and place for that, but most of the time, I’m throwing on a bomber and going to my meetings. The t-shirts you gave me two years ago still have paint on them, and it doesn’t even matter –– they get better with time and experience.


Gregory working on DSTLD x Gregory Siff Art Basel Collection

As an artist, you want to make quality paintings: it’s not quantity –– you got to make solid work. If I could be constant, and have my clothing represent how I paint –– and a lot of my palette has been in the black and whites‚ and we are going to go off the page and do some color and different things, which is cool that I get a chance to do it on your clothes –– but, I think that where it works is that: it is stuff that I wear, and it’s stuff that my friends that love my work would want to wear. At the end of the day, when I make a painting, it has got to be something that I would want to hang on my wall.

If it isn’t that good, and I don’t really care about it, then I didn’t make a good painting, and it is just filling the ‘job,’ or the ‘role’ of the artist.


Gregory Siff x DSTLD Womens Leather Jacket

When you are doing dope work: you care about it, and you are proud of it, and it hurts to give it away when it sells, because it’s like –– ‘Damn, that’s a good one.’ And I already feel that way about the jackets.”

Beyond the Brush: A rapid-fire riff, and the whole nine with Gregory Siff:

DSTLD: Who are your idols?

Siff: “As far as idols, I respect those who are authentic and made their path by sticking to it: Jean-Michel Basquiat, for taking his pain and turning it into beauty; my father, for showing me you never get old if you love what you do and dance like it’s New Year’s Eve everyday; my mom, for getting up everyday and making kids smile in school, and having a laugh every Friday with friends, and a drink after a long week. I just want to continue making real sh*t and having the life worth waking up for. Those who help those who really need it impress me. I try to live in that.

DSTLD: What is your favorite work that you have created?

Siff: “Right at this moment,

[I]t is a painting called ‘Prayer,’ which I created this year for my show Portrait of an American Ice Cream Man. It is an abstract collision of ink and pencil that makes me feel good. It’s ferocious.


“Prayer” Gregory Siff

I’m making a series of scarves out of it that will be unveiled in Miami, during Art Basel, this year.”

DSTLD: How has your work / creative process evolved over the years – is there any specific event that acted as a turning point for you?

Siff: I’ve been painting every day since 2010. It evolves quickly when the hours stack up. I like that what I do may seem like a simple form of painting, but what is embedded in it is meaning that lines each line.


Gregory Siff x DSTLD Womens Leather Jackets

DSTLD: When do you feel most creative / inspired / driven to create?

Siff: When I am angry with my day. When I love my night. When I go through something new. And when I smell the past. All of those ignite. Sex is a great jump off too.

DSTLD: Besides your work, what are other creative outlets for you?

Siff: At this current time, it’s all painting and making art.

DSTLD: Does technology play a role in your creativity?

Siff: Yes. It’s a megaphone with the work. More see it because the computer screen.

DSTLD: What is your favorite book?

Siff: Letters to a Young Poet by [Ranier Marie] Rilke.

DSTLD: What type of music do you work to? Favorite artist right now?

Siff: Miles Davis, Radiohead, Kanye. Francis and the Lights.

DSTLD: Who should we cover next?

Siff: Brittney Palmer. She’s hot on many levels.


Gregory in his studio (wearing custom bomber jacket and black skinny jeans)

Photos by Corey Epstein