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.

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.

Equally mesmerizing in its effortlessness is how Corinne fell into the position of rock and roll lead singer of a band that has had its run at number one on the charts. The manager of the band was living in her flat and asked if she would be interested in the job, to which she said a casual yes, abandoning fashion design. Her band partner, the keyboardist and composer, Andy Connell, is someone she describes as the person with whom she then fell in love, life and work. In a traumatic twist of fate, Swing Out Sister lost their first record deal when Corinne was thrown from a horse and cracked her skull. However, the accident led her to a full commitment to living her dreams in music and greater successes with the band.

Like the piles of signature bangles on her arms, some of which are curtain rings, Corinne inspires admiration for how little she tries yet how unique she is. Her magnetism evokes her idols such as Mary Quant, Twiggy, Diana Ross and Dusty Springfield, but in her everyday uniform of Commes black drop crotch pants, a healthy glow from swimming and a love for exploring London on her bicycle, she has a timeless attitude that is very much her own.

If you love Corinne, you may also like Tamara Lowe, Drue Kataoka and Christine de Lassus.

A “tough”exterior uniform of black jeans, tees, and boots are not meant to be a cover up for how devastating it was for Holly to deal with the challenges of losing what seemed to be a once in a lifetime opportunity. She’s honest about the hard lesson of being too cocky and unready for fame, and today she is ecstatic to be on a label that backs her creatively 100%. Holly’s boyish touches, like Costume Nationale’s army green twill blazer on top of something feminine, and the strong impression of her serious wedges , are a testament to her uncompromising attitude concerning one’s ability to overcome adversity with perseverance. Holly’s eighty-four year old grandmother, who has purple hair and a nose ring, rediscovered her inner lesbian when she left Holly’s grandfather, after having five daughters together, for a woman. Clearly role models are important in having the chops to follow your dreams.

If you love Holly, you may also like Liza Thorn, Dana Suchow and Annakim Violette.

When Heather feels like what she’s wearing on the outside mirrors how she feels on the inside she is at her best. Like the notes in the songs she writes, her clothes hold so much imagination that they are like individual characters, each with lives of their own. A merciless wardrobe editor, the discards are like people that she feels she has no idea how she become such good friends with, or how they ended up in her life (and closet). They get dumped. Frequently. This is not the case with her 1940s “Honeymoon suit” that she had to have, whether she was going on a honeymoon or not. Wearing the fitted, cropped jacket with jeans and a better-than-classic pair of ankle boots, Heather confides she feels bad for people who can’t find that kind of joy in their clothes.

Her Dad’s impeccable taste rubbed off on Heather when she was just a kid and in what she calls her “I Am Orphan Annie” daydream. His insistence that she learn a Beatles song once a week every week taught her how to compose pop music and paid her rent in his house and figuring out what she wanted to do. Her dad traveled the world with his rock band, bringing back kimonos, Dries, and Yohji. In better-than-Westwood sturdy, strappy two-toned boots that the cobbler wore, a floor-length Victorian skirt and vintage Tahari striped shirt, Heather is in her “day off from the circus” look, though being a 4th generation musician is far from the hard knock life she led as a kid, “hanging” out with Annie. “When I was twenty, I just started writing songs. It just started coming out of me, really easily, and it felt right. I was just, like, ‘This is what I’m supposed to do.”

If you love Heather, you may also like Elizabeth Spiridakis, Kaelen Haworth and Alia Penner.

At twelve, Brian was hanging out in Cincinnati with giants, men that had shared a stage with legends like Count Basie, like the drummer Jon Von Ohlen and veteran pianist Ed Moss. “I was always around music– I picked up the trumpet at nine years old,” he says, “Because I thought it would be easy. It only had three buttons.” By the time he was fourteen he was making his debut in the Cleveland jazz scene, playing for packed clubs. For Brian, timelessness is everything– Cole Porter, George Gerswhin and the Great American Songbook never age. Neither does the Rat Pack swagger of Frank Sinatra. “Either you’ll see me in jeans and a t-shirt, or a suit… classic man stuff,” Brian says, behind his cool-as-ice black shades. His left arm is a sleeve full of traditional, old-school tattoos; “Sailor Jerry-like,” he says. The most prominent tattoo was also his first, modeled on a lion-head ring with diamond eyes given to him by his father which he wears on his pinky, like one of his mentors might have. In a charcoal handmade pinstripe suit from Against Nature and Swank cufflinks pulled right from the 50s, like his love of storytelling through music, the elegance of the “old guys” lives on in Brian. “On stage,” Brian reflects, “you lose sense of what time it is and what era it is.”

If you love Brian, you may also like Michael Arenella, Dandy Wellington and Justin Dean Thomas.

The reappropriating of divergent vintage clothing that Jean does with ease – like the Nantucket picnic basket bag he wears around his neck over a polka dot button-down with an ebony and gold medallion necklace, couture tribal jeans, Nike sneakers and an handmade American Indian wooden pouch with feathers slung around his torso – speaks to his refusal to cop to the usual divisions between people. He is the leader of an artistic collective in his hometown called the “Jersey Klan” aka “NJ Street Klan,” that was inspired in part by a collaborative called A.L.I.E.N NYC, which stands for A Legion In Every Nation, and expresses themselves so freely with music and style that Jean vividly recalls their exciting intermingling of streetwear like ninja pants and shoes meets skater punk. The Jersey Klan is a collective that promotes artists of all kinds, from concerts to art exhibits. Jean is an artist himself who raps and writes his own music, but the coordinating of his events is driven by a passion to give a platform to others, espcially young kids who would otherwise not have a chance to be exposed to the public.

The attendance at NJ Street Klan affairs are as diverse a tapestry as Jean’s genres of dress. He laces his Air Classic Kicks with zebra laces, mixes a camouflage top with a multicolored patchwork jacket and a Davy Crockett hat, and wears a Hawaiin print shirt with DIY studded Eskimo boots. “Punks, college kids, street kids…come together for the music… if you’re white, black, Asian, whatever color you are, it’s for everybody. It’s not about where you’re from and what race you are, it’s about the music, the culture, the word, the energy, the vibe.” He is so intense about the ability to express oneself though music that he produced a project called “No Faces,” that is a freestyle mix without any visuals in an effort to promote the importance of pure music, free of the pervasive hype of celebrity and “faces” over substance. Of his music and “No Faces,” Jean says, “You don’t have to know who I am… listen to my words… it doesn’t have a color…it’s something that I love to do…we are surrounded by too many people who just want to be celebrities and not leaders.”

If you love Jean, you may also like Matt Parrotti, Erica Yarbrough and Ian Bradley.

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.

Annakim grew up traveling and, as a result, does not consider herself part of one world. To her, every person is so unique and connected at the same time that whether you’re part of a cult, in a family or married, there is the potential to have a twin or soulmate in any part of the world, no matter their seeming disparaties. As she puts it, “You can take people that are in diifferent places in the world, [who] have never met, and have a collective that could be so similar that it’s terrifying, yet their experiences are completely distinct from the people around them.” Dressing up every day is a meaningful ritual for Annakim, even if she is just an ornament in her own house. “Music is like liquid, and I feel like clothing should be more like music. It’s like a song that you love. It shouldn’t be about something that’s trying to fit in or out of the world. It should be something that’s bringing people closer to the world… it’s one of those things where it makes me not take life so seriously. I feel like clothing should be the opposite of anxiety.” We live in a society that is very addictive, she continues, “I feel like the only way I can really relate to people is to get past all of the labels. Is this person college-educated or not, sober or not, do they know fashion or not?” Instead, Annakim concerns herself with figuring out why we’re illuminated here when people are being bombed all over the world. “Every person has earned the right by being born onto this planet to be a part of it. So if you can start from that cave level, then I can hold a conversation with somebody,” she says, “We’ve all come from a whole place of viewing people on a level that has always been deeper than our current surroundings.”

Annakim has a room dedicated to her closet, filled with clothes and beautiful things that reveal her passionate world. Passion itself is her inspiration. Her friends’ closets make her heart skip a beat and she is fascinated by how people view their strengths and their weaknesses in their sartorial armor, as well as the memories that their belongings conjure up. She pulled out a printed multi-colored Alexander McQueen dress from the bottom of a mound of eclectically patterned fabrics, not because it’s a known brand, but in an effort to explain her zeal for rainbows. The colorful rainbow apparition is fascinatingly vivid, but also a manifestation of storm clouds and clashes. Annakim explains that from one’s macabre side comes rebirth: “It’s like Day of the Dead or one of these festivals where they celebrate that actual death brings on this huge rainbow of rebirth. The looping reminds me that I can’t take myself too seriously or the world too seriously…I can’t be afraid of change.” Similarly, her cobweb dress reminds her of all the things that she loves about living in Los Angeles and the insane pieces that you know had to have belonged to somebody that you would have loved to hang out with, but you’re never going to meet. “So it’s not vintage in the sense of like retrolicious, it’s vintage in the sense that I feel like it’s reborn.”

Whether in her rastafarian vampire cape and an astounding pair of psychedelic glam ’70s boots, both made by the artist Summer Harrison, or her Snow White and the Seven Dwarfs bedsheet dress with a butterfly necklace that has the gravitas of something science-fi and delicate simultaneously, Annakim has been both lauded for her “outlandish” dress and denounced for her androgyny. What she takes from these various assumptions is the craziness of it all – there’s an entire society of women who aren’t allowed to show their faces without incurring violence, yet people choose to discuss her clothing choices. For Annakim, androgyny is not about driving a wedge between people, but rather about shedding light on duality and bringing people together. Vaguely resembling Ziggy Stardust in both her handsome and fragile beauty with sparkles scattered across her face, Annakim sees the turmoil of Bowie’s fantastically beautiful character as a beacon of hope for humanity, calling people to attempt to understand those that might seem falsely foreign to us. Annakim is interested in a certain detachment that stems from beauty – to her, it’s more than just lighting and retouching.

Annakim feels that hatred comes from the same place as love, just as a treasured, cheerful hot pink ’80s Betsey Johnson gun-print dress makes you consider the fact that we live in a gun-permissive country. Furthermore, darkness and humor are not negative energy for her. She adores Rodarte’s blood dresses for their politically incorrect and intricately classical yet futuristic beauty. Lewis Carroll’s Alice in Wonderland was given to Annakim as a child, and she’s adapted the story as a template for her life. “People are always trying to go by this very rational harsh thinking, but it’s so detached and it’s not pragmatic eventually. It doesn’t ever lead to the circumstances that we’re seeing next.” So open your eyes and put on an embroidered ’20s tulle dress with Grecian Prada sandals, like Annakim does to get coffee and join in on her rant, or what she refers to as her creepy automatic poetry. “Aaaahh, to be a kid again and honor everything as a verb,” Annakim says. “Keep moving like a shark so that you won’t get eaten, you can actually make what you want in the world… we are jaded to think there is nothing original anymore… there’s so much that hasn’t been done, and that doesn’t mean regret, that just means you can start anywhere.”

If you love Annakim, you may also like Mary Lee, Natalie Gibson and Kay Goldberg.

Next to his grandmother, music is Elijah’s love. His signature high top hairdo is influenced by the hip hop duo Kid-N-Play and his passion for basketball attire reflects the style of R&B trio Bell Biv DeVoe, along with a devout respect for Michael Jordan, reflected in the legend’s jersey that he wears with a Chicago Bulls jacket. People like Slick Rick – for his storytelling about adventures and chance encounters alike and Bruno Mars – for writing about whatever comes to his mind, like the song Talking to the Moon – have given Elijah license to emote freely, but none more than Tupac Shakur’s book “The Rose that Grew from Concrete,” which motivated Elijah to write poetry. “There’s a line that is my favorite: ‘If our love is really true, I would gladly die and watch over you.’” When asked about his favorite places to travel, Elijah said sitting under the Brooklyn Bridge and writing his spoken word rhymes.

Kid Love is the name of Elijah’s alter ego which hangs from his chunky gold rope chain necklace. Elijah says his friends gave him the moniker in homage to the status symbol of the rappers of the late ’80s and early ’90s. However, he feels that “Kid Love” stands more for his young, yet mature demeanor. “I’m all over funny and outgoing. I don’t say no, like if everybody said: ‘Oh let’s go skydiving,’ I’d be like, “I’m going to jump first…[I'm] the outgoing one, the dancer, the funny guy, everybody’s friend…” His favorite person on StyleLikeU is Liz Baca not only for her ’80s schoolteacher style, but for her old soul spirit: “I get told that [I am an old soul] everyday because people don’t understand dressing is not just style. To me, it’s who I am.”

If you love Elijah, you may also like Matt Parrotti, Hiroto and Quinn Aston.