While in his 20′s in London in the 60′s, Duggie went to the underground jazz clubs where a band called The Rolling Stones was playing, he saw the Who before they recorded records, and he roomed with Pink Floyd’s Syd Barrett for years. Duggie would return home from art school in those days to Pink Floyd rehearsing with light shows in his flat, and he would advise them to get more rhythm into their music, actually enlightening them to his soul music. But what is coolest about Duggie is that while Syd and a few other of his close friends (who he feels privileged to have known) destroyed themselves, he learned to withdraw and in his words “be a part of it, but not be a part… open, but cautious.” He recalls painting himself right through the ups and downs of being an artist and encourages the importance of not ever getting too far from one’s creative expression and “keeping the connection.”

I love how timeless Duggie is while never being out of step with the times. His bespoke Ozwald Boateng pink blazer is eternally chic and his Post Modernism paintings harken back to Paint by Numbers from when he was a kid, but are filled with social commentary on culture, from sexuality to pop icons (he makes ties, pins & throw pillows of Michael Jackson, Lady Di and the late Luciana Martinez de la Rosa, an influential artist and friend, among others.) Currently, Duggie works in digital media with his art and is also exploring his voice and musical talents. He says that he loses himself at the end of a paintbrush as much as he does a mouse these days. About his eclectic world and life, Duggie says, ” I make my environment something that sustains me,” intuitively knowing, “This doesn’t work for me and that does”– and that is cool.

If you love Duggie, you may also like Andrew Logan, Edmundo Desnoes and Freddie Leiba.

Myf explained that her parents didn’t let her have toys that were based off of pop culture, in order for her to develop her own imagination. Thus, when she spontaneously runs out to grab coffee in the creative combination of an Ohne Titel multi colored knit cardigan and a patchwork sheepskin coat tied around her waist, with only her tye dyed boys underwear underneath, it looks so good that she ends up staying in the ensemble for the rest of the day and night, while doing her usual meandering around the city. I love how she wears her roommate’s button down shirts as skirts as well and how everything gets her signature written all over it, like her tie-dyed Ksubi jeans.

Interesting conversation is what Myf most admires in another person and it is almost as if she is seamlessly conversing her expression with the world through everything she touches. This can be seen in her artwork, which mostly depicts her friends who she paints because she loves them “to death,” or the morphing of an outfit form one day to the next, deriving from things that her peers have left at her place or traded with her. Buying clothes for Myf is rare, except for the occasional Indian dress from a store where the owner, who has a crush on her, gives her a discount.

Myf gets her independent spirit from her mom who presently lives in Tazmania (Myf is from Australia), in the middle of the forest in a house that is entirely self sufficient, equipped with solar panels, water tanks, dams, a vegetable garden and fruit trees. In the tapestry of a Phillip Lim floral cowboy shirt with fringe, royal blue shorts from Where Romance Was Born, cuffs and a scarf from India and a linen duster, Myf says of her mom, “She does pretty much whatever she wants to… and I am much the same as she, just 30 years later.”

If you love Myf, you may also like Susan Cianciolo, Gerald DeCock and Alia Penner.

Extraordinarily real and low key like her dad, Malia is makeup free and unfussy in Rosebowl vintage finds. Her earthiness (and some of her clothes, like her amber necklace and orange bustier Alaia dress,) also comes from her mom who she describes as a Brazilian “Amazonian goddess.” Having grown up on the beaches of South America and with a dad who painted everything from the washer & dryer to his cadillac in which he picked her up from school, her parents built a world around her that is dedicated to elevating the mundane and infusing the magical. Fruit loop boxes hang on Kenny’s walls (better than cluttering the counters with junk), he swings from a trapeze and covets his 70′s new wave sharkskin suits that came out of garbage cans (like all good things did in those days, he states.) The artist whose art was initially inspired by MC Escher and the psychedelic posters of head shops in the 70′s, is interested in everyone’s story and feels everyone deserves respect, whether it be a janitor or the president. And Malia, who seems refreshingly unaffected by trends in her favorite Lucien Pellat Finet comic-inspired sweater and Moschino tiger knit leggings, feels that the open mindedness of her family has created her to be very accepting and fearless when it comes to people’s differences.

One of Kenny’s first memorable experiences with Keith Haring was when the latter artist painted himself into the corner of a room to the beat of the Devo song he was listening to. Keith, Kenny said, “was one of the most important people in my life.” We ended our shoot in Kenny’s other worldy-hyper trippy, colorful basement of a 3D art explosion with father and daughter dancing in day glo, Kenny in a full on neon painted suit and Malia in a Keith Haring tee shirt that he had given her. Malia knows little else but a world of beautiful things with every surface covered by her dad’s hand as a result of his obsession with the idea, why should any experience be mindless?

If you love Kenny and Malia, you may also like Andrew Logan, Mia Christiana and Glenn O’Brien.

Unique is what you have to be to break in the music business today, as “it is no longer this kid is good and get him dressed by a stylist… You have to wake up in the morning and have your own agenda,” Theophilus says. He stops at nothing when it comes to sartorial details– he is a designer as much as a musical artist and alters everything to his exact fit and refined liking, even admitting that as a kid, he would take his pair of Jordan’s over a million dollars. An example of his keen eye for detail can be seen in Theophilus’ custom navy blazer that has gold buttons going up the sleeve, green felt under the collar and touches of royal patches from English flea markets on the pocket. He complements the jacket with DIY Ksubi’s, that have crocodile on the back pocket and monogrammed velvet slipper that he designed.

On the shoot, we got a hint of Theophilus’ taste for the finer things in life, like one of his latest songs that includes a sample from the seminal “Dance Hall Days,” as well as his Prada suede argyle jacket that he wears with handmade camo leather pants. However, despite his success, Theophilus clearly remembers his days of couch surfing and making his first record on 12 dollars a day eating wings and fries. I am inspired to pray for money to fall from the sky like Theophilus does, but his overriding desire to make music that will stick with his generation is his true source of wealth, studded Louboutins and all.

If you love Theophilus, you may also like Jean Lebrun, Chris Benz and Fatima Robinson.

Video edited by John Mattia.

Hannah has chosen to set herself free of a self-imposed stigma that as a black female, animal prints are tacky, as she stands tall in her python Rag and Bone print jeans with a Herve Leger banded knit top and Camilla Skovgaard heels. She is also eager to release herself and the world from some of the antiquated hangovers of our educational institutions. Though fond of her high schools, she is upfront about being one of three African American girls at The Spence School in Manhattan where she was singled out and suspended for smoking pot, which ultimately found her in another, more diverse, prep school, but where she couldn’t identify enough with one group in order to fit in. The trauma ultimately led to Hannah’s redemption. Today, she is taking the dark and forbidden world of pot into the light, by developing a lifestyle brand with her brother called Green Owl. It is a sustainable record label that, among many other things, will have a retail marijuana dispensary to help bring the weed culture of LA out of the 70′s and into the 21st century.

For Hannah, the importance of family, taking care of herself, and in particular a love of food has grown out of the experience of having witnessed her grandmother’s lifetime struggle with anorexia. When we shot Hannah this summer she told us that she was having a “fruit moment” in her 40′s printed shirt of apples and colorful fruit inspired nails, explaining how the particular yellow of her first Vuitton bag was inspired by her passion for mustard. You can also see Hannah’s sense of irony in her attraction to Kurt Vonnegut and her wax sculptures that are inspired by the TV series Alex Mack, where people turned into goo while still having a mind. Her art piece of a woman upside down with her head in a plant is both playful and satirical, and like Hannah, portrays her message that honesty is what makes change happen, whether laughing or crying.

If you love Hannah, you may also like Sophie Conti, Angel Clouthier and Bernd Naber.

A little Joan Crawford meets punk, with her tattoos as accents to peplum jackets and vintage cocktail dresses, Princess Julia is a legendary DJ who enjoys fads, but does not follow them. Suspenders with a red pencil skirt and suede lace ASOS pumps are as trendy as she gets. Unphased by standing out in her Westwood pirate patent mary janes, she considers herself a pioneer in lifestyle as well– between her love for music and writing, and her immersion into the cultural eclecticism of London. “My grandmother was stagey and flamboyant,” says Princess Julia, who feels that old ladies have the best style of all.

If you love Princess Julia you may also like Diane Naegel, Sorcha O’Raghallaigh and Paisley Dalton.

For Fritz and Christina there are no boundaries between life, style, and their zeal to help people heighten their own self-awareness. Life is their stage. Fritz’s criteria for an interesting outfit is whether or not it can be recognized while he is a blur running in it, often over the Williamsburg Bridge. This is why he never wears jeans. Instead, you might see him in his red “filmmaker’s” ensemble, or a gold jacket and unisex leggings — kind of signature for him, as is his mustache, the “international passport to being male,” Fritz says. Once, leaving a play in the metallic piece, a member of the audience was certain that Fritz had been in the cast. By making a “difference” in the world, he feels, maybe somebody will be a little more of themselves. “I think the interplay of our similarities and our differences can take us to a new place in terms of social progress and personal satisfaction.” Christina, in a vintage Pucci dress, toile Dr. Marten’s, torn stockings over crocheted ones, and a Victorian jacket worn backwards, explains that, for her, being “in style” can make you afraid to have fun with how you dress, not to mention what you miss when you get that feeling of finding an unexpected treasure.

When Fritz first met Christina, he put her in his phone as “Christina Punk”. It takes guts to add an exaggerated Mozart wig to a white lace dress while walking down the street, but going against the grain is what creates change; the truest definition of punk. It’s not just dressing up in leather and studs. Punk is what Fritz’s father was living when, as a Roman Catholic priest in New Zealand, he tried to introduce Planned Parenthood and suffered the consequences: getting excommunicated from the priesthood. And Christina’s sewing together a shirt out of his father’s old ones for Fritz is another form of punk; making a conscious and original choice, no matter how small, matters. In his new book, How To Live The Good Life, Fritz explains its main character, who is trying to make other people happy by making his own life happy; someone who is doing something a little bit beyond himself.

If you love Fritz & Christina, you may also like Max Vernon, Lizzie Brandt and Hannah & Landon.

Christian is known for designing stage costumes for Karen O of the Yeah Yeah Yeahs, beginning with the deconstructed prom dresses she was making when first she started out as a designer. Their collaboration evolved and persists; Christian recalls a seminal moment for herself as an artist on the band’s tour for 2003′s Fever To Tell. Karen wore a colorful hand-made skeleton suit — “Kind of Day of the Dead,” Christian says — with lots of embroidery, a three-dimensional heart, and arteries. But what excited the designer most was the thirty feet of intestines that could be pulled out by the audience. Christian never stops creating. “I constantly think about it. I dream about it.” Everything in her apartment is silk-screened, from the pillows to her linens. 

Christian’s clean, slicked-back hair and classic red lips make her feel as though she can go a little further out on a limb with her clothing, and reveals the conscious detail with which she approaches everything. A white jumpsuit looks “Bohemian chic” with a burgundy scarf tied like an ascot, matching socks, and shoes covered in her abstract Sharpie patterns — and one of her own silk-screened, floor length skirts with a black tank, and a vintage necklace with bold, “unusual combination of colors.” But most poignant to me is how Christian’s sense of peace in creating manifests in how cool she makes a simple breton shirt from Lands’ End, Ralph Lauren pants and an Ann Taylor belt with her splash-of-paint-on-the-oxfords look.

If you love Christian, you may also like Susi Kenna, Jessica Repetto and Shail Upadhya.

A dedicated yogi, comfort with his age is an understatement for Andrew, who is as timeless as the clothes that he has made by his tailor in a little place called Vrindavan. It’s a small Medieval city dedicated to Krishna, where his tailor has a little room near an open sewer where cows wander by. “You step back three hundred years,” he says. In an ensemble of rich marigold yellow silk, Andrew speaks of his love for crowns, orbs, scepters, and robes. They evoke a sense of ritual he feels man has lost. “Ritual is such an important thing because it denotes your passage through life. I’m fascinated by India because they still have these rituals.” Andrew started designing rings when he saw a traditional Indian wedding that he found magical: The groom arrives on horseback to meet his covered bride, and the first he sees of her is her reflection in a mirrored ring she wears.

Once rejected from entering the Ritz in one of this vibrant suits for not having a tie on – instead he wore one of his breathtaking jewels on his neck – Andrew claims that he is “kind of crafts” and “kind of performance.” As art should do, it challenges the norms and makes you wonder why someone would be rejected for wearing something as magnificent as Andrew’s cosmic egg necklace instead of some piece of fabric. It is meant to convey, with its opulent mirrored glass, where we have come from – and where we are going. “You can see in it eternity,” he says. He is a humble as the materials he uses – mirrors, he points out, are made from sand, or from the Earth, a material of the universe that extends light and is meant to be a window into the next world. Unfazed by the cracks in his pieces, Andrew sees those lines, like the ones in his face, as nothing more than graceful maturation. Of them, he says, “It’s a bit like life.” Fashion, for him, provides us with a means to transcend. “I’m very interested in taking something that’s in the gutter, like a rusty old bit of tin and making it look like a million dollars.

If you love Andrew, you may also like Terence Koh, Natalie Gibson and Virginie Sommet.

Growing up neither from “here nor there” during a time when xenophobia was high freed Rajive from life in the monoculture of suburban American life. That state of non-belonging instilled in him a voracious, life-long wanderlust and identification with Bardo, the Tibetan state of becoming between one thing and the next. Not one to stand in front of a monument and take a photo, when Rajive travels, he says, “I try to associate myself with the parts of that culture that I identify with… then, I create images to bring the experience back with me.” Everything from folkloric Tibetan boots, beaded vests, loafers, and Shetland sweaters fill his closet. He speaks Spanish, French, Hindi, Urdu, Thai, and a smattering of German, Khmer, Finnish, Vietnamese and Dzongkha, switching as easily between them as he fuses Leonardo’s Vitruvian Man with Shiva, the deity of destruction in one of his paintings. Rajive renders Western superheroes in the ancient Thai style of Khon mask-making, re-imagining the American demi-god Batman as a demon out of the Ramayana.

Putting well-known archetypes in a foreign context is Rajive’s way of re-inventing the status quo, which includes himself, teaching high school art in the New York City public schools in vintage army jackets covered with jewels, the newest Doc Martens or a Tibetan rosary made of human bones. In American blue jeans, crocodile-skin cowboy boys and a red silk shirt from Thailand, the kind you get on any street corner in Bangkok for 100 baht (about 4 dolllars), tattoos that recall everything from his mother’s Catholicism to Eastern ritual daggers, a silver Nepelese medallion with turquoise and coral as his go-to necklace and his grandfather’s signet engagement ring from 1939, Rajive is a potent reminder of the liberation that can be found in the space between cultures. “I wasn’t bound by anyone’s rules,” he concludes.

If you love Rajive, you may also like Virginie Sommet, RZA and Mitch Alfus.