THE VIRTUOSOS

Jacobs wears his own GUCCI suit, boots, and scarf and Prada shirt; sunglasses by LOEWE; hair products by R+Co; grooming products by Marc Jacobs Beauty.

MARC JACOBS

OCCUPATION: Fashion designer. HOME BASE: New York City. HAPPIEST WEARING: Custom patent leather boots by Alessandro Michele and a suit "designed and cut perfectly by Ralph Fitzgerald," the NYC-based tailor for Savile Row's Huntsman, to "marry my husband, Char, this year." CURRENT OBSESSION: Nail art. Mei Kawajiri "paints each nail by hand—pure talent and passion."

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SERGE IBAKA

OCCUPATION: Toronto Raptors center/forward. HOME BASE: Toronto, Barcelona, NYC. HAPPIEST WEARING: Custom suits during playoffs, "just walking into the arena with confidence." STYLE ICON: "My dad." CURRENT OBSESSION: Nick Fouquet chapeaux. "A nice hat can be very powerful." TREND I DESPISE: Big logos "just to show you wear expensive clothes." FAVORITE DESIGNERS: Valentino, Balmain.

ZOË KRAVITZ

OCCUPATION: Actor. HOME BASE: Brooklyn, HAPPIEST WEARING: Wedding dress, Paris, June 29, 2019. CURRENT OBSESSION: "Not being on my phone." TREND I DESPISE: "The one where everybody looks the same. ITEMS I OVERUSE: White tees, black pants, OVERRATED: Super-high heels. FAVE DESIGNERS: Saint Laurent, Alexander Wang, Maryam Nassir Zadeh. STYLE MOTTO: "No fear."

"Zendaya blows the roof off of how we imagine young stars dress. Her look is evolved, 'mature. You sense she's in complete control of her Image." — KIMBERLY DREW Writer, activist, curator, 2019 Best-Dressed List committee member

DIANE KEATON

OCCUPATION: Actor. HOME BASE: Los Angeles. THE LOOK: Architectural genius. Sharp tailoring, hats, belts in "black and black and white and white and black and white," as one caption goes, SPOTTED: Farmers marketing in Maison Margiela with Nancy Meyers.

PRIYANKA CHOPRA JONAS

OCCUPATION: Actor. HOME BASE: L.A., NYC, Mumbai. CURRENT OBSESSION: Kitten heels, TREND I DESPISE: Super-tight clothes. TREASURED POSSESSION: "My mangalsutra, the necklace a groom ties around the bride's neck." FAVORITE DESIGNERS: Chanel, Dior, The Row, Attico, Peter Do. BURY ME IN: Diamonds.

RAMI MALEK

OCCUPATION: Actor. HOME BASE: L.A. THE LOOK: Mr. Robot's hoodie out; Dior Homme in. ITEM I OVERUSE: Valentino combat boots; "my father's vintage Dior and Lanvin ties." TREND I DESPISE: "Chunky spaceman shoes." SEXY IS: "Ultimately, whatever makes you feel most confident."

JEREMY O. HARRIS

OCCUPATION: Playwright, actor. HOME BASE: New Haven, Connecticut; "soon" Chinatown, NYC. HAPPIEST WEARING: "insane" floor-length tartan skirt for callback to New York Theatre Workshop 2050 Artistic Fellowship. ITEM I OVERUSE: Brown Gucci horse bits, "perfect when you're running through a forest on 'shrooms and need to climb a fence." POWER CENTER: My Telfar bag "holds the keys to my entire universe."

Dion wears her own Ronald van der Kemp gown and hat; hair products by L'Oréal Paris.

CELINE DION

DID YOU INHERIT YOUR SENSE OF STYLE? "I have 13 siblings, and I was the last. I wore all their clothes. At Christmas, what do you think we received?" SOCKS? "Yeah. Clothing. My mom didn't have money to buy it, so she made the clothes. She was very sensitive to the cut of the moment, if the pants were wide or narrow. She was paying attention." SOME SAY YOU HAVE 10,000 PAIRS OF SHOES... "I'm not quite sure. But I'm building a new home in Las Vegas. I treated myself to a playground: two stories of archives for all my clothes, shoes, belts. I kept everything. So I'll be able to count." YOUR CURRENT OBSESSION? "RVDK. Every piece they do is one of a kind. And last time I went to Paris Fashion Week, Valentino blew my mind." FAVORITE PAST FASHION MOMENT? "John Galliano, the backward white pantsuit [Oscars, 1999]. People thought, Is that a joke? What is she trying to say? I wasn't trying to say anything. I'm just having a great time."

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THE CLASSICS

MAHERSHALA ALI

OCCUPATION: Actor. HOME BASE: L.A. THE LOOK: Uber-elegant with a hint of rebellion. Stand-collar shirts; unexpected-hued suits; subtle, personal hints of jewelry. THE TWIST: Who can pull off wearing a black beanie—and winning two for two—at the Academy Awards? The new Blade, that's who.

PAMELA JOYNER

OCCUPATION: Cultural philanthropist, collector. HOME BASE: San Francisco; Sonoma, California, TREND I DESPISE: "Casual that devolves to sloppy." STYLE ICONS: Dorothy Dandridge, Katharine Hepburn, Madame de Pompadour: "women ahead of their time." TREASURED POSSESSION: "My art collection," by talents who "would not be denied despite incalculable obstacles." STYLE MOTTO: "Classic with a curated edge."

"Somethings should never be messed with. Tuxedos are one. Brad Pitt is another. He should just make this his uniform, like the Rat Packers: Pure movie star." — LISA EISNER, Jewelry designer, 2019 Best-Dressed List committee member

GEMMA CHAN

OCCUPATION: Actor. HOME BASE: London. HAPPIEST WEARING: "Cotton sundress, jelly shoes, and a bucketful of hermit crabs" as a child in Mallorca. CURRENT OBSESSION: Bum bags [Brit for fanny pack]. "I have eight on rotation." ITEMS I OVERUSE: Oversized denim jacket, vintage tees. TREASURED POSSESSION: Grandma's super-delicate cardigan: "I'm too scared to wear it." STYLE ICON: Cher from Clueless. BURY ME IN: "The fuchsia Valentino [right] I wore to the Oscars."

ELLE FANNING

OCCUPATION: Actor. HOME BASE: L.A. HAPPIEST WEARING: A ribbon-covered '80s prom dress from L.A. vintage store Playclothes at her ballet-themed 21st-birthday party. "I was beaming all night sipping Champagne!" CURRENT OBSESSION: Monochrome looks. "Love a twinset!" TREND I DESPISE: Peplums. ITEM I OVERUSE: White dresses. STYLE ICON: "Samantha Stephens from Bewitched!" TREASURED POSSESSION: Plaid jacket from London's Brick Lane market "magically turns every outfit into a winner." OVERRATED: Skinny jeans. WORST-DRESSED MOMENT: Bedtime. "My sister thinks my pajamas are hideous." LUCKY CHARM: "For years I kept chicken wishbones in my purse." ON MEN'S STYLE: Persol shades; crewneck sweatshirts. "I want to see him before I see his clothes." FAVORITE DESIGNERS: "DON'T MAKE ME CHOOSE!" BURY ME IN: "Pink! A flower headdress would be nice."

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"Since that plunging Versace in 2000, Jennifer Lopez has proven that sex appeal is not the enemy of chic. She's simply iconic." — KIMBERLY DREW

KEANU REEVES

OCCUPATION: Actor. HOME BASE: L.A. SIGNATURE LOOK: Polished with a hint of grunge. Streamlined suits, rock tees, Merrell boots, and black. So much black, TIMELESS MOVE: Best hair toss in the business. SPOTTED: Roaring down the streets of L.A. on a KRGT-1 by Arch, his own brand of motorcycle.

CICELY TYSON

OCCUPATION: Actor. HOME BASE: NYC. TREND I DESPISE: "Anything overdone." CURRENT OBSESSION: Sleep. STYLE ICON: Audrey Hepburn, WORST-DRESSED MOMENT: "Any given day when I'm running around. My agent, early in my career, declared I 'clean up well.' " TREASURED POSSESSION: Presidential Medal of Freedom "placed around my neck by President Obama." BURY ME IN: "My wedding dress, worn when I married Miles Davis [in 1981]."

FRANK OCEAN

OCCUPATION: Musician, enigma. HOME BASE: NYC, L.A. THE LOOK: Discreet high-end (Prada bucket hats, Balenciaga boots) meets utility (Mammut puffers). SPOTTED: Front row at Raf Simons's fall 2019 menswear; defying "camp" at the Met Gala in a sleek black hoodie (selfie caption: "The valet wears Prada"). STYLE BEYOND SELF: Decor. A Michel Majerus painting hangs above his bed; a modular teal sofa by '70s designer Pierre Paulin dominates the living room.

HALL OF FAME

Dress by Miu Miu; sandals by Roger Vivier; jewelry by Chopard.

CHLOË SEVIGNY

OCCUPATION: Actor. HOME BASE: NYC. HAPPIEST WEARING: Black Alber Elbaz for YSL gown, Oscars 2000. TREND I DESPISE: Xenophobia ITEM I OVERUSE: Mascara. LUCKY CHARM: Deco onyx and diamond cross ring from Kentshire. OVERRATED: Underwear. STYLE ICONS: Catherine the Great, Joan of Arc, Therese of Lisieux, the Virgin Mary, Poison Ivy, Bette Davis, Greta Garbo, Marlene Dietrich, Thumbelina.

THE ORIGINALS

Gown by Christian Siriano; parka by Craig Green; blazer [worn as turban] by Dries Van Noten; hair products by R+Co; grooming products by La Prairie.

BILLY PORTER

OCCUPATION: "I'm a Renaissance bitch!" HOME BASE: NYC. HAPPIEST WEARING: Christian Siriano tuxedo gown at the 2019 Oscars. TREND I DESPISE: "The constant need for our culture to drag folks." CURRENT OBSESSION: London. ITEM I OVERUSE: Hats. STYLE ICONS: Diana Ross, André Leon Talley. TREASURED POSSESSION: "My wedding ring." OVERRATED: "The sneaker situation." WORST-DRESSED MOMENT: "Taking out the trash." BEST QUALITY IN A PERSON'S STYLE: "Proper fit and giving zero F's." MOST POWERFUL THING ONE CAN WEAR: "Highheels!" SEXIEST THING ONE CAN WEAR: "High heels!" BURY ME IN: "Something that sets my soul free."

"Wear what the F you want," says Billy Porter. "Ain't no rules." — BILLY PORTER

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KEHINDE WILEY

OCCUPATION: Artist. HOME BASE: NYC, Beijing; Dakar, Senegal. HAPPIEST WEARING: A chalk-line-print custom suit for the unveiling of his portrait of Barack Obama, TREND I DESPISE: Fast fashion "shows a disrespect for the ceremony surrounding clothing." ITEM I OVERUSE: "Simple white Converse go with everything." FAVORITE DESIGNERS: Amine Bendriouich, Sarah Diouf, Adebayo Oke-Lawal.

LENA WAITHE

OCCUPATION: Creator, producer, writer, actor. HOME BASE: L.A. THE LOOK: Off duty: flawlessly cozy. On duty: bold statements spotlighting queer designers DVMN PIGEON, Stuzo Clothing, Pyer Moss. OBSESSION: For a sneakerhead raised in Michael Jordan-era Chicago? Air Jordans. LUCKY CHARM: Her "engagement sneakers." SPOTTED: Scouring vintage rails for non-rock tees: Jodeci, SWV, Luther Vandross.

B. AKERLUND

OCCUPATION: Fashion activist, costume designer; co-owner, The Residency Experience. HOME BASE: L.A., Stockholm. TREND I DESPISE: "Overdone plastic surgery of 2019." ITEM I OVERUSE: YSL platforms. OVERRATED: "The Birkin bag." BURY ME IN: "One million Swarovski crystals and a fabulous hat." STYLE MOTTO: "More is more, and go with your gut."

JEANNE GREENBERG ROHATYN

OCCUPATION: Gallerist, Salon 94. HOME BASE: NYC. CURRENT OBSESSION: Black wool-lined Birkenstocks. ITEM I OVERUSE: Nike Air VaporMax X Off-White sneakers. "I'm into uniforms. Overused is good—buy two next time!" TREASURED POSSESSION: Karl Fritsch rings that "read as miniature sculptures." OVERRATED: It bags. Her canvas tote bears "Sylvie Fleury's missive, 'Yes to All.'"

"Solange Knowles is an artist whose medium is song, but also style—which she understands and explores as a radical art of presentation." — DURO OLOWU, Fashion designer, 2019 Best-Dressed List committee member

TYLER, THE CREATOR

OCCUPATION: Musician, designer. HOME BASE: L.A. AKA: Tyler Gregory Okonma. THE LOOK: Kaleidoscopic preppy on acid. STAPLES: Marni, Sunnei; tomato-print button-downs from his label, Golf Wang. SPOTTED: Facetiming with Solange at the French Open in a cotton-candy-pink sweater vest. CATCH HIM NEXT: At Dodger Stadium, hosting his eighth annual Camp Flog Gnaw Carnival this November.

HARRY STYLES

OCCUPATION: Musician. HOME BASE: London. THE LOOK: Lounge-act louche. Touchable suits with low-cut tanks; Austin Powers prints; elaborate blouses; manly heels; significant hair mousse. THE VIBE: A little bit Mick, a little bit Elton. GO-TO DESIGNERS: Gucci, Saint Laurent. SPOTTED: At 6:15 a.m., wearing pink trousers, posing for selfies with 300-odd screaming fans at Tokyo's Haneda airport.

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THE PROS

HAIDER ACKERMANN

OCCUPATION: Fashion designer. HOME BASE: Paris; Antwerp, Belgium. THE LOOK: Fashion nomad. The Bogota, Colombia-born Frenchman, son of a globe-trotting cartographer, loves silk scarves, drop-crotch trousers, and wire-rimmed glasses. SPOTTED: Zhuzhing muse Tilda Swinton's silvery armor at Cannes; posting up at Rome's La Posta Vecchia with old pals actor-designer Waris Ahluwalia and stylist Robert Rabensteiner.

RENI FOLAWIYO

OCCUPATION: Founder/CEO, Alara boutique. HOME BASE: Lagos, Nigeria. CURRENT OBSESSION: Magical '70 swatches that "close up and become beautiful bracelets." STYLE ICON: Josephine Baker. FAVORITE DESIGNERS: Duro Olowu, Phoebe Philo, Kenneth Ize, J.W. Anderson. BURY ME IN: "Clothes are for living. Ask me to drinks after I just got a Valentino gown, I could turn up in that."

HÉRIARD DUBREUIL

OCCUPATION: Founder/creative director, The Webster, LHD. HOME BASE: L.A. TREASURED POSSESSION: Wedding ring designed by husband Aaron Young. LUCKY CHARM: Aurelie Bidermann necklace with son's lucky number. BURY ME IN: "My husband's silk pajama shirt."

ANASTASIA BARBIERI

OCCUPATION: Fashion director, Vogue Hommes International; contributing editor, Vogue Paris. HOME BASE: Paris. HAPPIEST WEARING: "The elegance and sharpness of menswear." TREND I DESPISE: Bermuda shorts. TREASURED POSSESSION: YSL couture black safari tunic. SEXIEST OF ALL: A white tux. FAVORITE DESIGNERS: Dries Van Noten, The Row, Sartoria Giuliva.

BRUNELLO CUCINELLI

OCCUPATION: Chairman and CEO, Brunello Cucinelli SpA. HOME BASE: Solomeo, Umbria, Italy. TREND I DESPISE: "What I like least is the color green." STYLE ICON: Gianni Agnelli, "icon of the Italian lifestyle." TREASURED POSSESSION: "My jackets." GREAT STYLE IS: "Bearing, poise, courtesy." FAVORITE DESIGNER: "There are many. I'll choose my master, Ralph Lauren." BURY ME IN: "A navy cashmere tuxedo."

"Few celebs look as chic in rolled-out-of-bed sweats as they do in red-carpet gowns. Clothes simply Become cool when they're on Rihanna." — LISA EISNER

HALL OF FAME

REI KAWAKUBO

OCCUPATION: Founder/creative director, Comme des Garçons. HOME BASE: Tokyo. THE LOOK: New World Order. Dark glasses, triangular bob, architectural all-black uniform. SHE ALSO WEARS: Azzedine Alaïa, Paul Harnden, Celine, Lewis Leathers, Nike. SPOTTED: Rarely, outside of work. (Her day runs 7:30 a.m. till "late.") REVERED BY: Junya, Marc, Miuccia.

THE ENSEMBLES

Wade's tuxedo by DZOJCHEN; necklace by Jason of Beverly Hills; necklace [worn as anklet] by Monisha Melwani Jewelry; grooming products by Koh Gen Do. Union's dress and sandals by Bottega Veneta; earrings by BULGARI; hair products by FLAWLESS by Gabrielle Union; makeup products by PAT McGRATH LABS.

DWAYNE WADE

OCCUPATION: Entrepreneur, former NBA All-Star. HOME BASE: Miami, L.A. HAPPIEST WEARING: Double-breasted red Givenchy suit, no shirt, Way of Wade gold glitter sneakers "after my last game, my One Last Dance in Miami." CURRENT OBSESSION: Retirement. TREND I DESPISE: Logomania. "Says a lot about a person's confidence." ITEM I OVERUSE: Lanny packs. "When we travel, I'm responsible for the travel documents." STYLE ICON: James Bond could "stand out and blend in at the same time." LUCKY CHARM: "Most recently, matching hearts chains I bought with my son Zion in Cannes." FAVORITE DESIGNERS: Adrien Sauvage, Dsquared2, Tom ford, Ralph Lauren, Pyer Moss, OVERRATED: Belts. "If your clothes fit, you do not need them."

GABRIELLE UNION

OCCUPATION: Actor,producer, HOME BASE: Miami, L.A. TREND I DESPISE: Super-tiny purses. "Our phones are getting bigger, and no one's leaving home without their Fenty lip gloss. We have stuff." STYLE ICON: Justice in Poetic Justice—"forever."TREASURED POSSESSION: Robes, slippers. "When Dwyane and I are wearing them and the kids are asleep." WORST-DRESSED MOMENT: "When Kaavia James [11 months] has projectile vomited on me." FAVORITE DESIGNERS: Miuccia Prada, Patrick Kelly, Pierpaolo Piccioli, Christopher John Rogers, BURY ME IN: "For starters, a full-bottom brief..." STYLE MOTTO: "But can I wear sneakers?"

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BTS

V: CURRENT OBSESSION: "The British vintage look." JUNGKOOK: GREAT STYLE IS: "Wearing anything you like, regardless of gender." RM: ITEMS I OVERUSE: "Hats, bangles, and watches." SUGA: CURRENT OBSESSION: "Accessories. SO I designed a couple." JIN: ITEM I OVERUSE: "My handsome face." JIMIN: LUCKY CHARM: "A two-dollar bill from my mother." J-HOPE: STYLE ICONS: "A$AP Rocky, Pharrell Williams, Travis Scott."

JASON MOMOA & LISA BONET

OCCUPATION: Artists. HOME BASE: L.A. CURRENT OBSESSION: LB: "Protecting my children's innocence." JM: "Ending plastic pollution, cleaning up our oceans." ITEM I OVERUSE: LB: Maggie's Organics wool socks. JM: Carhartts. OVERRATED: LB: High heels. JM:Ties. STYLE ICONS: LB: Frida Kahlo, Marchesa Casati. JM: Toshiro Mifune, Geronimo. ON MEN'S STYLE: LB: "Does it get any better than old ripped jeans and a white tee?" STYLE MOTTO: LB: "Always a bit of a rebel yell." JM: "Let it reflect your soul."

RICK OWENS & MICHELE LAMY

OCCUPATIONAL: Cofounder, Rick Owens label. HOME BASE: "The dance floor." HAPPIEST WEARING: Comme des Garçons at Kawakubo-themed Met Gala, SIGNATURE MOVE: Eyeliner stripe on her forehead to "keep my brain balanced." ITEM I OVERUSE: "Rick's super-thin tees in the color dust." GOOD LUCK CHARMS: "Gold teeth, rings on every finger, heavy bracelets."

BELLA & GIGI HADID

OCCUPATION: Supermodels. HOME BASE: 35,000 feet, THE LOOK: BH: Carla Bruni, circa 1992. Mini purses, biker shorts, crop tops, slit-up-to-there gowns. GH: Bombshell sportif. Slip dresses, Doc Martens, inventive suits (here: artist Robert Nava for Heron Preston). SPOTTED: Fashion Week after-parties; bikini-clad girls trips.

THE BECKHAMS

HOME BASE: L.A. FEED FRENZY: InStagram offers five blue-checked views of la vie Beckham: David and Victoria's feeds, plus those of Brooklyn, 20; Romeo, 17; and Cruz, 14. COMBINED FOLLOWERS: 99.3 million, SPOT THEM: Mugging with #HarperSeven (age 8); front row at Mum's show; biking the Puglian countryside on family vacation.

AMAL & GEORGE CLOONEY

OCCUPATION: AC: Human rights lawyer. GC: Actor, producer. HOME BASE: Como, Italy. THE LOOK: AC: Power siren. Stop-sign-red Zac Posen day suits; Hollywood royalty Stella McCartney and Ralph & Russo gowns; that hair. GC: Mogul off duty. Moto jackets, regulation scruff, Armani tuxedos. SPOTTED: Be-caped at Buckingham Palace in vintage Jean-Louis Scherrer (below); dining with Barack and Michelle at Hotel Villa d'Este.