From left: Marcus Cohen, Ceacy Shakoor, Ken Fulk, and Joyce Hu

THE PURIST: Marcus Anthony Shelby

46, Composer (Mission)

"I started wearing a hat 25 years ago because Ellington and Basie wore them. I also own a pair of cuff links engraved with Duke Ellington's face."

Marcus's BDF: "Marcus is an uber-metrosexual. Everything he wears looks good; he's my only male friend who can pull off open-toe sandals."

Marcus Cohen

32, Musician (Mission)

"I'm a sucker for vests and cardigans--my favorite piece is a slate gray cashmere cardigan by Marc Jacobs. I wore it so much that it became holey, so I added some suede elbow patches."

Marcus's BDF: "Joyce's global style reminds me of London Town, with a hint of Asian flair."

Joyce Hu

35, Creative Director (Lower Pac Heights)

"I strive for a visual balance in color, shape, and accessories."

Joyce's BDF: "Yugala reappropriates pieces like no one else. She once turned a pair of harem pants into a blouse."

Yugala Priti

38, Fashion Designer (Daly City)

"My favorite outfit is an asymmetric cocktail dress, a brocade evening coat, and a fedora. It makes me feel like a spy in a James Bond movie."

Yugala's BDF: "Ceacy reminds me of the elegant women on the streets of Paris."

Ceacy Shakoor

38, Visual Merchandiser (Mission)

"I'm elegantly louche. I love wool shorts worn with a Viktor & Rolf tuxedo jacket--formal but whimsical."

Ceacy's BDF: "In a sea of black, Zoe will be the one wearing refreshing whites and nudes."

Zoe Magee

40, Swimwear Designer (Mission)

"I have to be comfortable at all times; I love to layer up. My favorite look is a loose-fitting sweater, leggings, flat boots, and a scarf--always a scarf."

Zoe's BDF: "Estrella's look is 70's with a twist."

Estrella Tadeo

39, Fashion Designer (Mission)

"My go-to is a feminine dress and a trench. I make it mine with accessories, like an obscenely large necklace and colorful bracelets."

Estrella's BDF: "Adrian can look like a businessman without putting you to sleep. Rugged and refined, no matter what the occasion."

Adrian Jenkins

44, Writer (Nob Hill)

"I call it 'old Italian man elegance.' I love the look of beat-up boat shoes with a wickedly cut formal suit."

Adrian's BDF: "Thierry's look is very 'West Coast-French': intricately patterned ties, plaid shirts, and loafers."

Thierry Buisson

44, Stylist (Union Square)

"I recently purchased a cobalt blue silk dinner jacket by Tom Ford. It transcends all styles."

Thierry's BDF: "Though Ken is tailored to perfection, he exudes a debonair, nonchalant attitude."

Ken Fulk

46, Interior Designer (Clarendon Heights)

"My style was shaped by my southern upbringing. I hope to someday be that little old man who still makes the effort to dress the part. My favorite piece is a Thom Browne overcoat: a bit of Dr. Zhivago on the high sea."