Jolie and Brad Pitt looked very much the part of the red carpet's golden couple at the Kodak Theatre in classic, almost retro, styles. She wore a black sweetheart-neck strapless gown by Elie Saab, accessorized with green drop earrings, and he wore a classic bow tie.
Winslet also went with dark and sophisticated in a gray satin and black tulle dress by Atelier Yves Saint Laurent by Stefano Pilati. She looked "flawless," said stylist Mary Alice Stephenson. "Everything is right!"
But Jolie, Stephenson added, was disappointing. "Angelina Jolie is always beautiful but boring and ho-hum in that black dress. It is just too drab, dour and depressing for the Oscars. I really hoped she would step it up and have some fun with color and take a chance with wearing something unexpected."
Leading the charge of light colors was Mickey Rourke in his Jean Paul Gaultier suit without a tie.
Anne Hathaway sparkled in a strapless champagne-colored Armani Prive gown covered in crystals and circular pailettes with a jeweled dragon brooch on the back. Evan Rachel Wood was in a strapless ivory-tone number by Saab, and Jessica Biel was in a sleek Prada strapless column gown in shiny white satin with a bow detail on the front.
Penelope Cruz wore a white 1950s Balmain gown, with a strapless neckline and hand-embroidery with gold treads, she got from top vintage curator Rita Watnick's Lily et Cie. Miley Cyrus' beaded Zuhair Murad dress was mostly white but had tiers of midnight-blue beaded petals.
"She looked old Hollywood," observed Suze Yalof Schwartz, executive fashion editor at large for Glamour magazine. "It looked like something from the '40s - and it was on the youngest person there."
"I couldn't believe how much white there was," added designer Pamella Roland. "Most times we're told that actresses want color ... but I also was amazed how glamorous everyone was."
Alberta Ferretti put Meryl Streep in a light gray empire-waisted gown for one of Streep's most stylish turns at the Oscars - which she so often frequents.
Marisa Tomei's one-shoulder, dove-gray gown by Versace was covered with dramatic fan pleats.
Taraji P. Henson made her big style statement with an oversized 19th-century diamond flower necklace by Fred Leighton, paired with a cream-colored strapless dress with uneven tiers of fabric and a train by Roberto Cavalli.
"Taraji Henson knocked it out of the park," said Lisa Rinna, fashion commentator for TV Guide Network. "She and all the other nominees really looked like nominees."
Rinna noted, however, that from her perch she saw fewer stars than she had expected. It was a tactic to keep some stars off the red carpet so they'd be a surprise during the ceremony. Jennifer Aniston and Tina Fey were among those kept under wraps until the telecast.
Amy Adams stood out thanks to her chunky Leighton necklace - a colored gemstone and diamond bib from the 1950s - complementing a crimson bustier dress with black spider web-piping by Carolina Herrera.
"Even though we're in a recession, I've never seen as many luxurious fabrics on the red carpet, and the jewelry - the bling - is bigger than ever," Schwartz said.
Heidi Klum designed the ruby red-dress charm on one of her funky bracelets that fit the vibe of her fashion-forward asymmetrical Roland Mouret gown with a high slit that showed off her model figure. The charm aims to raise awareness about heart disease.
Fashion star Sarah Jessica Parker wore a light green strapless gown by Dior Couture with gold waves decorating the bodice, and Natalie Portman had flashes of gold beading on her orchid strapless gown by Rodarte.
Beyonce's body-hugging black gown was also jazzed up with gold floral embroidery, and Queen Latifah's navy one-shoulder gown by Georges Chakra was dotted with crystals.
In full-on gold lame was Viola Davis in a Reem Acra gown with a plunging V-neck. Melissa Leo wore a copper-colored chiffon gown with ruching and beading by Badgley Mischka.
Freida Pinto provided a pop of electricity in a beaded blue John Galliano gown with one bejeweled lace sleeve.
Her pint-sized "Slumdog Millionaire" co-stars wore custom-made outfits by Brooks Brothers.
By Samantha Critchell