“I’m often inspired by people with stories of strife, lawmen and criminals, political figures, activists, drafted military men, and people near death. They are the ones that make me understand that it’s important to live for now.”

occupation: menswear designer

Early in Craig’s career, there was a crossroads between music and fashion. He says that he chose fashion, but in a way, he chose theater – “there is a non-reality [about clothes]. You can sew up your own reality.” The amount of imagination and passion that goes into Craig’s customized clothing is more worthy of a screenplay. The ankle-length mohair toggle sweater was designed while envisioning himself as a grumpy older man – he’s sitting by himself in a house where no one comes to visit him, he can’t pay the bills, he’s carrying a shotgun, and blowing holes in the wall. By then, he says, the knit cardigan will have had just the right amount of aging, as it would be if it were in Cold Mountain – “you gotta get the good scrapes, holes, and smell…eventually this sweater will smell like whiskey mixed with mohair.” As a designer, Craig draws upon the good taste of his ancestors, whose roots are deep in authentic Mexican-American “wrangler, rancher” culture (they are real “Spanish-influenced cowboys, with ponchos, hard-pressed clothes, and flat-brimmed hats”). I love his childhood story of hiding his Converse sneakers in the bushes outside of his house (that was in a “windy, dirty town”), because he was expected to dress more formally with suits and bolo ties. Today, the sneakers are long-gone, unless he changes the script to less weighty characters. Craig’s three-piece suits are inspired by criminals like John Dillinger, and his cavalry-twill cape by legends such as Ichabod Crane.

If you like Craig, you might also enjoy Michael Arenella, Thomas Khadafy, or Cator Sparks.

“I often think of when Henry David Thoreau wrote, ‘To affect the quality of the day – that is the highest of arts. Every man is tasked to make his life, even in its details, worthy of the contemplation of his most elevated and critical hour.’ I don’t presume that Thoreau had waistcoats or cufflinks in mind when he wrote this, but it inspires me nonetheless. What one wears truly does have an affect on how he feels about himself, how others treat him.” Thomas Crowley

occupation: wine director of the Bar Veloce empire

Thomas was one of those people that stopped me in my tracks when I saw him in the subway station, with his rich and passionate taste for modern classicism in dressing. Standing still as a monk in his prototypical custom suit: “two-toned shoes, patterned socks, and stingy brimmed fedora” (perfectly shaped for his face). Needless to say, he is not a fan of the “herd mentality” of fashion and prefers to say “style” when talking about his aesthetic. For Thomas, dressing sends a message to oneself and to the world about your place and value. I thought it was notable that he was reading a Zen Buddhist book called Ending the Pursuit of Happiness, that addresses people’s anxious preoccupations with changing – he thinks of his own style as a constant evolution, rather than a trendy, sudden about-face. Everything from his handlebar moustache (that he has been obsessed with having since he was five-years-old) to his peak lapels, niches to place flowers, mother-of-pearl buttons on his suit sleeve to the orange silk lining in the jacket is thoughtful, deliberate, and consistent. Thomas’ icons are the time-honored kind: Steve McQueen in Bullet inspired him to wear turtlenecks, and Cary Grant in To Catch a Thief provoked him to wear an ascot under a pullover. Never without the most perfectly fitted button-down, I felt I had to hide in my hugely oversized, ripped-to-shreds men’s Victorian shirt.

If you like Thomas, you might also enjoy Cator Sparks, John Wellington, or Mister Burton.

occupation: playwright, poet, and tie designer

“Be yourself, take time to get to know yourself and love and embrace everything about you, and always keep your pinky up.” Mister Burton

What happens when as a young boy you are “different” (meaning sensitive), with a strong artistic streak (in James’ case, “a Taurus, ruled by the goddess of love and beauty”), and is a misunderstood and solitary figure in his neighborhood? At fourteen, James found alot of inspiration from a superstar named Cyndi Lauper, who sang a song that said it’s okay to be different (coincidentally, she and James grew up in the same town). As soon as James felt the confidence to step into his imagination, and implulses, instead of caving to the norms, he started ripping up his clothes and painting them. Fast-forward about twenty-five years, and welcome to James’ “wildest dream,” his life, filled with a cast of characters that do get him. There is his god and priest, the poet Oscar Wilde, his favorite lady of drama, Sarah Bernhardt, silent film stars and beauties Rudolph Valentino and Clara Bow, French and American novelists Collette and Edith Wharton, and the dreamy females of a Dante Gabriel’s Rossetti painting, among thousands of other period references that (along with his modern-day friends and treasures) he’s pretty sure were meant to be in his life. If ever there were someone who is single-handedly bringing back glamour, romance, tradition, and an ultra-attunement to the endorphin rush of high aesthetics and its corollary of pride in one’s appearance, it’s James. I thought I loved cuff links, intaglia rings, antique men’s vests, silk ascots, watch fobs, capes, and embroidered hundred-year-old anything, but I don’t hold a candle or a hand-painted tea pot to James. What doesn’t kill you makes you stronger, so when James failed English class because he argued that a poem, like a painting, could have more than just one meaning, maybe it was a blessing in disguise. He decided to prove his teacher and every other person of such limited thinking wrong by showing how someone as talented as himself can create and star in their own silent movie by tuning the followers and sheep out.

If you like Mister Burton, you might also like Michael Arenella and Ludwig Kuttner.

occupation: artist in the medium of clothing

“People are very insecure as far as fashion is concerned. It’s just something they do to look good and not be criticized, so a quick answer for them is to buy for the brand. I am my own brand.” Shail Upadhya

Shail is in the process of becoming “honest with himself” and finally fully discovering the artist within. He was born in Kathmandu to a family of politicians – three of Shail’s uncle’s were Prime Ministers of Nepal. Though he has always loved dressing up, his parents wanted him to have a “respectable” job, so he became a diplomat at the UN rather than following a creative pursuit. Despite working in politics, Shail’s inner “Lord Gaga” has gotton lots of attention, including meeting Andy Warhol at Studio 54 in the ’80s and numerous features in Bill Cunninghan’s style section of The New York Times. He has always been driven to put his own personality into his wardrobe, as you can see in the witty layers of argyles with sweater upon sweater (I love this look with the knee socks!) and in his whimsical but chic interpretation of a white evening suit covered in polka dots. Shail is taking his self-expression to new heights by designing his own collection of clothes that are hand-painted, based on the designs of the grand masters like Miro, Kandinsky, and Picasso. He says that his ruffled shirt with gold embroidered jacket is his Beau Brummel version of the classic tuxedo, and that he wouldn’t wear it to the UN, but he would wear it to a party given by the Fame Monster herself.

If you like Shail, you might also enjoy Ms. Fitz and Cody Ross.

“[London] is such an amazing place. Period. I’ll never forget riding the subway one day when I saw a man in a bowler, a bow tie, a cane, and a wax mustache. He just looked at me and winked. And I just [thought], ‘This is it kids. This is what I want to do.’” Cator Sparks

occupation: writer, blogger, and dandy

Cator loves the Auntie Mame quote, “Life is a banquet, and most poor suckers are starving to death,” because for him, you have to live it and breath it all in. And he does – this man is all passion. We recently emailed him to let him know that his post was coming up, and we received an automatic response saying, “Greetings! I am away for a wedding in the depths of Africa, therefore I have no internet access, only tribal drums and smoke signals.” Cator was inspired to become a writer on a trip to India in his late 20′s, but not a “yogacentric nirvana trip. It was a boozed out wild party with a bunch of English people,” where he met a renowned British journalist that recognized his vivid imagination, well-bred sophistication, and ability to put “pen to paper” or “fingers to keyboard.” Today, Cator is a leading authority on men’s fashion, an interest that stems from his aesthetically Anglo-infused childhood in Atlanta, surrounded by people like his grandfather (who was “a bit of a dandy”), his great-grandfather (who wore only “white suits in the summer and wool tweeds in the winter”), and his mother (who let him set the table with lavish place settings every year for Christmas dinner). It’s all about visuals for Cator, and you can see it from his red room (an ode to taste icon Diana Vreeland) to his impeccable three-piece Brooks Brothers suit with every detail intact down to the Etro shirt, Vivienne Westwood tie, and antique watch fob. (It’s absolutely wild to think of Cator in his rave days, with stickers on his face and glitter everywere.) Appearance is so imperative that Cator writes in an Egyptian dress and Turkish slippers in order for his genius to flow.

Be sure to check out Cator’s website and blog.

If you like Cator, you might also enjoy John Wellington, Andrew D’Angelo, or Michael Arenella.

occupation: bandleader, musician, singer, composer, arranger, and events producer

” Style is a celebration of individuality while also a gesture of decorum and humility unto others.” Michael Arenella

So precisely fine-tuned to dressing as the consummate gentleman from decades long gone, it is an ironic twist on generations that Michael’s dad was a hippie and prefers rock and roll, while his son has dedicated his life to the performance and lifestyle of ’20s, ’30s, and ’40s jazz and swing eras. Michael only wears jeans to work on his car and would never go out in them. He is indignant about what the present day mania for casual attire has done to formality, respect for romance, and pride and to the celebration of life. For him, the idea of going out in the evening in jeans or athletic clothes is depressing. When I was shooting him, we got into the conversation of the dummying down of style. And it made me think of standing at Thomas Jefferson’s home, the monumental, Monticello, and thinking how important it was for the third President to create this kind of noble aesthetic for the world and then looking at the sad juxtaposition of everyone there taking it all in wearing the ubiquitous Crocs and track suits. It seemed like a total unconscious disconnect.

Michael grew up in Georgia, where the woods, streams, and rivers he played in are now strip malls. His nostalgia for the past permeates not only his music and clothes, but his way of life. It was a first for me to meet someone who finds his refuge from urban New York by canoeing the Gowanus canal from his home in Brooklyn to Staten Island (where he has found a bird sanctuary) and walking the old railroad tracks where he has discovered many hidden treasures including forests. His most casual attire while doing this is typically WWI boots, WWII jodhpurs, a pre-WWII British army vest, a Russian military striped shirt, an original Woolrich jacket, and ’30s German motorcycle gloves. And of course, he’s ecstatic about the 1945 Hagstrom map which enables him to uncover forgotten areas (the new ones don’t have the old train routes). When listening to Michael’s excitement over the bend of a railroad track (and its historical context) or the tailoring and quality of a ’40s suit inspires him to be and feel his highest self, it makes one wonder what the generation of comfort first (at all costs to design and craftsmanship) will inspire for future decades – a “banana republic”?

Check out Michael Arenella & His Dreamland Orchestra here.

If you like Michael, you might also enjoy John Wellington-Simon, Ebeneezer Nii-Sowah, Dylan Trevelen, or Raymond Chu.

occupation: Creative Director of MyUberLife, a consulting firm that offers marketing strategies and creative direction to fashion, music, and art-related companies

“A human being feels fulfilled when you’re creating and you’re adding, not just consuming. There’s nothing wrong with consuming, but what are you adding? That’s the question I ask myself and that keeps my integrity higher every single day. When I can’t give myself an honest answer, I know my ego is going to do its dance. I think that’s what ego does – it allows us to lie to ourselves when we don’t want the truth.” Jey Van-Sharp

If I had to post a video that expressed the most definitive message of this site, it would be Jey’s. Not just living outside of the box, but smashing it, is what he consults his clients to do if they are going to be relevant in the twenty-first century. He goes on to say that if we don’t, we are heading for the dark ages and if we do, a cultural Renaissance. Like that period of rebirth in the sixteenth century, Jey feels that the internet has manifested the possibility of a comparable period in time of enlightenment with the connectivity of knowledge, language, culture and productivity in a matter of nano seconds. Among the many rigid and pretentious notions that the proliferation of information has suddenly made seem passe are the ideas in certain magazines that things are only wearable by the age of your decade, or need to be a designer head to toe, or that a jacket needs to be right side up or that men’s clothes are for men and women’s for women. Jey walks the walk and talks the talk. Self-confident and politically incorrect, he sees “clothes as dynamic art” and values how they reveal the way your mind works, how you are perceived, how they allow you to be creative, and how important the “feminine” side is to a one’s artistic vision (he is unabashed to the “gender” label of his clothes). He believes in a fine-tuned wardrobe, where you can wear a jacket five days in a row different ways and he is fluid with ideas like pairing loafers with sweatpants. Jey sent us a quote by Norman Mailer, which I think relates to something I have been wondering while doing this site: why are the innovators and creators considered “crazy” or “not normal” in society and why isn’t it the other way around? “Hip is the sophistication of the wise primitive in the jungle, and so it’s appeal is still beyond civilized man.”

If you like Jey, you might also enjoy Milton Puzy, James Fils-Aime, or James Ott.

occupation: producer, stylist, choreographer, and dandy

“I’m very classic. I call myself a dandy. I live my life as a dandy. I don’t ever leave the house in jeans and a t-shirt or sweatpants.” John Wellington-Simon

John refers to himself as a dandy and he takes it very seriously. Charles Baudelaire defined the dandy as “one who elevates æsthetics to a living religion.” For John, being “impeccably clean” (always with his shirt tucked in) is heaven on earth, and he lifts off the ground into a mean hip-hop, jazz routine when referring to Fred Astaire and Gene Kelly as his “fellas” because of how they wore a suit and tie. Back to Baudelaire: “For the perfect dandy, these things are no more than the symbol of the aristocratic superiority of his mind.” How you dress does create a certain state-of-mind, and for John, “it’s a language that he is speaking to the world in the best possible way he can.” I love the language that he speaks and can only guess that seeing him in his top hat with plume on the subway would send me into a trance. His family is originally from Jamaica, once a colony of England, and thus, where English culture and the traditions of being “the gentleman” were handed down. His mom became a doctor when she and her family came to NYC in the ’70s, but the “the rounds” that John does are in the East Village at Metropolis, Union Square at Rags-A-GoGo, and Brooklyn at Beacon’s Closet. And there is definitely a sense of euphoria when he points to the corduroy detail on his shoe, how he scored the Bentley pants with the feathered pattern, or how a bow tie and pocket square can transform the day.

Check out John’s blog and styling portfolio.

If you like John, you might also enjoy Raymond Chu, Ebeneezer Nii-Sowah, or Carlyle Hanson.

occupation: actor

“I aspire to the times when men tried to be gentlemen and dressed a certain way.” Ebeneezer Nii-Sowah

Wow. The whole time I was shooting Ebenezeer, I was thinking of Sidney Poitier, whom I worshipped growing up (beyond memorable in “To Sir With Love” ) or Denzel Washington – it depended on Eb’s angle. What’s not in the video is my foot-in-mouth moment when I asked him if he would ever wear a skirt or dress. He was visibly floored, but always his courteous and refined self, answered with a thoughtful, “No, not really.” I was looking to bring up some kind of out-of-the-ordinary conversation, and it did when he proceeded to tell me about how the men in his family, Ghanaian royalty, did wear gorgeous and distinguished robes for certain traditional ceremonies (I am dying to see them). Based on the incredible attention to the accuracy of his greatest style inspirations – Sidney Poitier in “In The Heat of The Night”, Alain Delon in “Le Samourai,” Humphrey Bogart in “The Maltese Falcon”, the poet Langston Hughes (who wrote the poem that inspired “A Raisin in the Sun”), and Duke Ellington, it is not a big surprise that he has the depth and sensitivity of an actor. Ebeneezer has already been in two Off-Broadway shows and is as elegant and graceful as they come.

Check out the trailer for Ebeneezer’s short film, “6:8.”

Thomas, in his hoodies and polos in high school, found a way to let his inner Etro come through. His clothing is like a collage of patterns, colors and textures. He grew up in Brooklyn with his dad who painted portraits of artists as iconic as Jimi Hendrix and his rock and roll roots are evident in his signature piles of chunky silver which offset his 3 piece customized suits, ascots and pocket squares. We love how cool his style is and he loves that his cool style makes old ladies smile on the subway.