LAUREN HUTTON, 80

When not working in front of the lens, model Lauren Hutton has always had a cool, casual sense of style, and she likes to include some boyish elements in the mix. Today her go-to look consists of a blazer and pants with comfortable footwear. Some bold color combinations enliven the formula. Her unfussy updos keep up the easygoing vibe.

TAKEAWAY

A tailored jacket adds panache to almost any outfit.

VIOLA DAVIS, 58

Known for portraying strong female characters, award-winning actress Viola Davis demonstrates her vibrant color sense in the way she dresses for both day and night. She clearly knows how to command attention, whether she’s sporting monochromatic tailoring or a vivid, floor-length gown. By alternating her natural curls with soft waves or even a blunt-cut pageboy, she likes to change up her appearance and accessorizes primarily with earrings and not-too-high heels or flats.

TAKEAWAY

Don’t be afraid to stand out from the crowd.

IMAN, 68

The long-necked, Somalia-born supermodel has an innate elegance that has only increased with the years. Her regal, statuesque bearing allows her to pull off some daring choices (a giraffe-print gown, see-through cutouts, vibrant colors) seemingly effortlessly. She likes structure in her clothes, especially a strong shoulder—and goes light on the accessories. No need to gild the lily when you have her kind of grace and confidence.

TAKEAWAY

Posture and poise are as important as anything you wear.

DIANE VON FURSTENBERG, 76

She may be known for introducing the universally flattering wrap dress to the wardrobes of countless American women, but Diane von Furstenberg rarely wears them herself. Instead, she gravitates toward midi skirts and tunic dresses in her snazzy, colorful prints offset by black separates and knee-high boots. Her flowing, wavy tresses and dark shades are also elements of her signature style.

TAKEAWAY

Introduce prints and patterns to enliven your wardrobe basics.

DIANE KEATON, 77

The star of many a Nancy Meyers movie—and, of course, Annie Hall—Diane Keaton is almost never seen without a brimmed hat (usually a bowler) over her shoulder-length, stick-straight hair and big, black-rimmed glasses. She often accessorizes an eccentric mix of masculine/feminine clothing (tailored suits, full-skirted dresses) with waist-cinching chunky belts and quirky footwear for a look that is uniquely her own.

TAKEAWAY

Feel free to mix some menswear elements with more feminine pieces.

NICOLE ARI PARKER, 53

Actress/model Nicole Ari Parker of And Just Like That... knows how to put the spotlight on her well-toned legs, whether it’s with a short hemline, or a dramatically slit dress. Her accessory of choice? Sexy strappy heels and pumps, natch. She clearly has fun getting dressed and has an “I’ll try anything once” playful attitude.

TAKEAWAY

Highlight your favorite feature.

SARAH JESSICA PARKER, 58

Like her alter ego Carrie Bradshaw, Sarah Jessica Parker is really into shoes, especially her sky-high stiletto pumps! Her clothing choices alternate between super-feminine going-out clothes—full-skirted dresses, shades of lavender and purple, rich fabric mixes—and super laid-back off-duty outfits, like jeans worn with cross-body bags. Wearing a ton of jewelry isn’t her thing.

TAKEAWAY

Indulge in your favorite accessory.

NAOMI CAMPBELL, 53

Another age-defying supermodel, Naomi Campbell likes to make an entrance. She can pull off virtually any trend. Oversized printed pajamas? Check. A sharply tailored white jumpsuit with a plunging neckline? Check. A voluminous cropped bolero over an untucked white shirt and black leggings? Check. She is very good at playing with tricky proportions. Her jewelry choices are discreet: a delicate pendant necklace, layered bracelets, rings worn on her pointer finger. Sexy heels and oversized shades often complete her look.

TAKEAWAY

Fine-looking jewelry can tone down trendiness.

GWYNETH PALTROW, 51

Never one to shy away from controversy, the actress turned lifestyle guru is a bit of a chameleon in her wardrobe choices. Sometimes flamboyant (showing off her well-toned abs and more), sometimes demure (remember her recent courtroom appearances as a wrongly accused reckless skier?), the fresh-faced beauty likes to shake up expectations. Love her or hate her, she always looks great.

TAKEAWAY

Know when to embrace a classic look—and when to kick up your heels!

ANNA WINTOUR, 74

Fashion icon Anna Wintour is instantly recognizable because of her signature bob and oversize dark sunglasses, but she has a few other tricks up her (long) sleeves. She loves a statement multistrand necklace that sits above her collarbone, splashy prints and long dresses with a defined waist. At one point, she wore nude Manolo Blahnik sandals and pumps with almost everything, but she seems to have added boots to her repertoire—an unexpected pairing with her dramatic maxi dresses.

TAKEAWAY

Don’t be afraid to wear a “uniform” if it’s what you like.

Cindy Weber-Cleary is a freelance writer, consultant and on-air fashion expert who has appeared on Oprah, The View, Good Morning America and Today. She began her career as a fashion editor at Vogue and was fashion director at InStyle.