Fine and fare (paying) in matching purse and shoes, CAROLINE KENNEDY SCHLOSSBERG, the ultimate Uptown Girl, zipped around Manhattan last October like an average citizen. "Very clean, very cosmopolitan," says PEOPLE's Steven Cojocaru. "Jackie would be proud."

DEBRA MESSING showed off at L.A.'s TV Guide Awards in February in a sparkly T-shirt, tailored trousers and high-heeled boots. To TV's Grace, our panel says amen.

JADA PINKETT SMITH, who gave birth to daughter Willow last October and will next appear in Ali with husband Will Smith, was a monochromatic knockout at the L.A. premiere of Kingdom Come in April.

Turning heads in a striking red-and-white cheongsam, NICOLE KIDMAN, at a Cannes press event in May, was both daring and delicate. Says PEOPLE's approving panel: East meets best.

In New York City last October to honor Sopranos star and pal James Gandolfini at the GQ awards, JULIA ROBERTS gave her sophisticated black Calvin Klein dress an extra kick with a pair of the designer's biker boots.

May's London premiere of Pearl Harbor was the perfect place for costar KATE BECKINSALE to launch Givenchy's inspired take on WW II-era fashion. "Kate loved this outfit," says her stylist Jessica Paster.

For a magazine awards bash in Manhattan in April, DIANE SAWYER edited down her wardrobe to better show off her svelter-than-ever shape. The result? A newsworthy look. "She defines New York style," says Cojocaru.

Bringing a breath of spring to an October charity event in Manhattan, UMA THURMAN picked this floral frock from among several sent to her by Prada, says the actress's rep. We're awarding a second bouquet for the matching pumps.

In New York City for an April party celebrating the first anniversary of her magazine O, OPRAH WINFREY confirms to us that she's a master at reading current fashion trends, particularly when they're right there in black and white.

At L.A.'s Golden Laurel Awards in March, MICHELLE PFEIFFER looked fit and fab in Armani. "A simple drawstring dress is a silhouette one would expect to see at the beach," says the designer. "But made in silk and on Michelle Pfeiffer, the dress is perfectly at home in a ballroom."