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.

In what Maad refers to as her James Dean meets Madonna look, she wears black leather shorts with over the knee socks, a fringe shirt and one of her many black leather studded jackets. Like one of her tattoo’s that is an ode to the Maya Angelou poem, The Caged Bird, Maad finds her ultimate freedom in her voice as a singer/songwriter. Her song Glitter is a reference to Maad’s fashion icons and the spirit of NYC of the 80′s. However, one cannot see her pitch black “Queen Nefertitti” bob and not recognize the monumental influence of Diana Ross on Maad’s style. Maad’s long silk vintage dresses with cinched waistes and lots of leg, have glamour high priestess written all over them. But diva is all the more refreshing on Maad Moiselle for her humble aesthetics as well, which are exemplified in her classic Ernest Sewn jeans and Reformation colorful silk blouses that are accented with her signature MAC red lips and of course, monster Fendi wedges.

If you love Maad, you may also like Fatima Robinson, Mia Christiana and Jean Lebrun.

Liliane says that she was “born a star,” with her feet turned out and “one foot above her head,” ready to become a prima ballerina (which she later did). Her mother, a milliner and dressmaker for Balenciaga who dressed with extraordinary care (Liliane reflects that she never saw her without her make-up until the day she died), got them arrested in Spain in the ’50s for how short Liliane’s dress was. “She wanted everyone to see her daughter’s legs.” During the war, when they barely had enough to eat, Liliane’s mother made her coats out of blankets, dresses out of drapes, and wooden shoes wrapped in the same material to match– a dress a day, so she never had to wear the same thing twice. So, when Liliane later saw feathers in a shop she loved, naturally she had them made into a dress by her favorite designer, Mark Bouwer (whom she intentionally supported for being, at the time, a total unknown). “You do not have to have money to be chic,” she says, wearing a fringe suede jacket that she bought in a Texas thrift shop.

It’s that “I-can-do-anything” attitude that found Liliane in Hollywood with a seven-year studio contract in the ’50s, despite not speaking a word of English. When the producer John Houseman saw her dancing with her ballet company in NYC, he had to have her audition. She read a part from For Whom The Bell Tolls phonetically, but added that she “must have looked cute.” During her seminal years learning how to sing, tap dance, and fence, Marlon Brando took her aside during the filming of Young Lions and tutored her. “He made me think of the part I was playing… from the inside.” Montgomery Clift took her to the Actor’s Studio, where she met and roomed with Marilyn Monroe. She hunted ducks with Clark Gable in Oregon. Her diamond rings, given to her by “the man she adores, but does not see enough,” didn’t command attention until he gave her twenty-five of them, one for each year of their relationship, that she now stacks on her fingers, just as the movies never fully satisfied Liliane’s passion for the thrill of the moment on stage. In the theater, she says, “You are with the public. You don’t cheat. If they don’t like you, they don’t like you. If they love you, they love you.” When asked what her most memorable role is, she says, “None. It’s yet to come.”

If you love Liliane, you may also like Barbara Flood, Lucie Porges and Jake Oliver.

Ironically, Selima feels that kids can be more judgmental than their parents. When Zoe says that her mom’s Dolce and Gabbana dresses are too super-sexy, Selima’s response is: “Why not?” Pretty much her response to everything she wants to do. When avant-garde French eyeglass designer Alain Mikli hired Selima to work for him in NYC in 1990, she went. When Selima fell in love with a space at the corner of Mercer and Broome, she opened her own eyewear store. When celebrities want her glasses for free, she says no, but then gives them to the people who don’t have the money to buy them. When I asked her to get into the bathtub to shoot her in her red top hat, veil, and Balenciaga blazer, she jumped right in. With Pierre Hardy heels.

Equally her own, but leaning towards a more classic understatement in the Breton stripes and eyelet that her Mom sometimes refers to as her “grandma clothes”, Zoe is not disinclined towards the Balenciaga dress that her Mom bought for her. She has been brought up not to care about what others think when it comes to dressing, including her Mom. However, Selima does admit that her daughter’s style often ends up in the windows of American Apparel, years later. Classic red bermudas and Madewell lace-up boots express Zoe’s unassuming mindfulness. She is concerned with the present state of the world, and her responsibility to it as someone of privilege. “Since I’m surrounded by everything that’s good, I think I should focus on the bad, so I can make it better for everyone. Like with the oil spill– No one went to jail for it. How?!” she says. Clearly her mother’s daughter, Selima lives by thanking God for everything that she has and trying, always, to be as good as possible despite the fact that she is not (yet, anyway) wearing vintage Claude Montana like her Mom.

If you love Selima and Zoe, you may also like Valerie and Jean, Marcelina Kieskiewicz and Karen Robinovitz.

Hats and hatmaking are the ultimate enchantment for Heidi, as they can be made with your own hands, spark a conversation and carry a certain mystique. One of her happiest childhood memories took place at the Queens Botanical Gardens, while wearing her favorite white beach hat with a rose – her golden Kodak moment. As if the illusion of being naked is not chic enough in her chainmail dress that she likens to string theory or how the galaxies net together, Heidi wears it with her melting clock hat, a reference to Salvador Dali and her own attunement to vivid dreams. Heidi’s mom, whom she looks up to for her effortless ability to be gung-ho about everything, remains both a role model and a provocateur for Heidi to push for her own excellence. Heidi describes a dream about herself and her mom, explaining, “There are two beds…both of them identical. One side is me, the other side is my mom, and we would have these joint competitions with each other where we’d both have to make our beds. Every time, my mom would be able to beat me, a split second better.” A haute hat made up of strange plastic flowers and ferns is a creation spawned by Heidi’s interest in how fungi grow out of ants’ heads, worn with a Search and Destroy leopard and lace slip that she describes as Philistine with an old Roman feel to it.

In an iridescent, ecto-plasmic “kind of jelly fish shirt” that Heidi finds playful for its contours, shapes and a voyeuristic peek at the body, she wears her umbrella hat inspired by Issey Miyake, math and architecture. “There’s an alchemy that’s happening that’s interesting. And I go with it and then it’s a whole new concoction. A lot of times, it’s exploratory… but I am always happiest when I am wearing a hat,” Heidi says.

If you love Heidi, you may also like Goldie Rush, Ran Q Huang and Kristine Barilli.

Experiencing a place like Cuba at an impressionable age left Gabriel indelibly instilled with the idea that you don’t need a lot to be happy and even when you are told that you can’t be yourself, you can still find a way. He recently quit modeling after one of his first jobs with Bruce Weber for French Vogue because he couldn’t deal with other people trying to dress him. Gabriel is very particular about going for the real McCoy when it comes to his uniform of cowboy boots, vintage bandanas, wife beaters and Levi’s, all of which reflect his zeal for engaging authentically in this world. Once back in his Washington state hometown after living at sea, while most others during pre-adolescence were “finding” themselves on Facebook (he still doesn’t have one), Gabriel started taking part in Native American ceremonies like sweat lodges (which is about going back into the womb, cleansing yourself and being reborn), pipe smoking and pow wows. At twelve, Gabriel was adopted by ceremony into the Omaha tribe through the Making of Relatives, where, if you love someone as family and they love you as family, you can publicly name them as such. Essentially, Gabriel has the good fortune of having acquired another set of parents of Native American descent, whose crests are tattooed prominently on his left ankle, along with the moon and stars of his adopted deer clan and a wolf for his wolf family.

The UT tattoo on Gabriel’s left forearm stands for urban tribe and commemorates a portion of Gabriel’s adolescence in which he was involved with putting on hip hop shows, rapping and playing with GZA from the Wu-Tang Clan, Hieroglyphics, AC Alone and Abstract Rude. Fast forward to Gabriel’s time spent in New York City, and possibly the definitive kinship for him to date is that of his band Dog Soldier Society, which was formed when he was part of Collective Hardware, an artist colony on The Bowery. The band’s first song, “Fire on the Bowery,” which was not about a physical fire but the passion and dedication to making something outstanding and beautiful, eerily foretold the burning down of The Collective and all of Gabriel’s belongings along with it. He was left homeless once again with just the clothes on his back, including all of his traditional pow wow dancer regalia, eagle feathers, hooves, a bustle, a staff, a wing fan and art.

The actual Dog Soldiers are a Cheyenne warrior society that went into battle with a sash of rope tied around their waist and three arrows, which are tattooed on Gabriel’s right forearm. They’d pin the rope into the ground and when the battle started they could only fight as far as the rope would let them go, like a dog tied to a leash. The symbolism of the ritual was that there was no surrender, simply victory or death. You weren’t able to retreat and that was your chunk of land. “That’s the way we try to live with this band – no retreat, no surrender, victory or death,” Gabriel says. “I prefer to make my connections with a smile and a handshake and a hug or through my music.” Of his new leather jacket, Gabriel explains that he bought it along with a whole new vintage wardrobe so that he could hold his new nephew, Ira Joaquin Friedman, whose birthday – the eighth of the third month, in the eleventh year – is represented in a tattoo in honor of his bloodline: “He’s the first of the new generation.”

If you love Gabriel, you may also like Chris Ford, Ludget Delcy and Naomi Melati Bishop.