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Special Occasion Late 2000s clothing

March 12, 2023

Late 2000s clothing was quite subdued. Catwalk collections showed both quirkiness and sophistication, but it was the sophistication that stars chose. Restraint was the order of the day. Even at the Oscars. Women wore ballgowns, but in plain colours. The jewellery was fine diamonds, but quite discreet. 

Late 2000s clothing – On the catwalk

For Spring/Summer 2009, Marc Jacobs dared to put a little Afro-Chic into his womenswear collection for Louis Vuitton. Beaded collars and stacks of bangles were one thing, but the strange puff of afro-textured wig attached to each model’s forehead like a fake-hair fascinator was probably going a bit too far. At first glance the outfits looked like the lovechild of Vivienne Westwood and John Galliano in their 90s heydays.


Autumn/Winter 2009 saw Dior Men show only black, white, or black-and-white on the catwalk. The sole exception was three grey-on-grey striped shirts. However, the silhouettes were far more adventurous. The theme was “Angles” and designer Kris Van Assche played with structure a lot accordingly. His skinny close cut menswear suits were perfectly tailored. But he also added oversized printed t-shirts, and spangled jumpers. Also baggy harem trousers and particularly ugly pin-striped, zippered and hooded waistcoats.

Thom Browne

The same season, Thom Browne showed. He has always done excellent tailoring with accessories that add a little spice. One of the looks from this designer was perhaps the oddest in the whole season from anyone. We can call it “All-Seasons Schoolboy With Carpet”. The model wore a tailored long-line grey wool blazer with bracelet length sleeves. It was like an outgrown uniform for a boy’s school. His white shirt and dove-grey tie were fine and reasonable. But his long striped shorts, long striped socks, black boots a, knitted cardigan, only partly buttoned up, added to the oddity. He also wore a furry grey hat and fingerless gloves – striped, of course. And to finish? The model clutched a striped grey carpet. It all matched exquisitely.

Late 2000s Clothing at the Award Ceremonies

But this kind of craziness did not show up at the award ceremonies. The Oscars in particular was Extremely Tasteful all round. Though we’re only talking just over a decade ago, this was before the high heels protest(s), where women without sky-high footwear were banned from the red carpet, and in response took them off deliberately, the Time’s Up protest, where actors turned up all in black to protest sexism in the industry, which blossomed into the MeToo movement.


Women wore restrained colours, and did not have slogans embroidered on their gowns and men mostly were in tuxedos, with not a colourful brooch, cape or high heel in sight.

And the Oscar goes to…

Late 2000s clothing. Kate Winslet outside the Oscars in 2009. Image via Wikipedia.

Kate Winslet outside the Oscars in 2009. Image via Wikipedia – Chrisa Hickey

Kate Winslet, Sean Penn, Heath Ledger and Penélope Cruz who won best actress, best actor, best supporting actor and best supporting actress respectively in 2009. For the ceremony this year, the committee had decided that each of these awards would be presented by five of their peers, who made a speech to each nominee.


Kate Winslet, who won for The Reader turned up to the ceremony wearing a black satin one-shoulder dress, her hair swept back. She had large diamond earrings, but no necklace. The dress was very structured, with a full skirt and a sequinned chiffon overlay like a cape at the back.


Marion Cotillard, who presented the award along with five others wore a strapless back dress with a sequinned bodice and full tulle skirt. Nicole Kidman was in strapless white, sequinned all over and with a feather-like trim waving at the bodice with a fishtail skirt. Halle Berry, strapless black chiffon with gold stripes and a fishtail skirt. Shirley MacLaine wore a sophisticated black tuxedo suit, with a knotted silver necklace.  Sophia Loren’s dress was amazingly structured, a corseted and cleavaged froth of full length light gold silk which set off her deep tan. Ever glamorous, she wore a diamond choker and diamond drop earrings.

Late 2000s clothing – The Men Wore Penguin Suits

Late 2000s clothing. Sean Penn at the 2009 Oscars. Image via Wikipedia.

Sean Penn at the 2009 Oscars. Image via Wikipedia – Chrisa Hickey

Sean Penn’s award for Milk was presented by Robert De Niro, Adrien Brody, Anthony Hopkins, Michael Douglas and Ben Kingsley, all former winners of the award themselves, who turned up in matching black and white penguin suits. Penn bucked the trend a little by being all in black, including his shirt.


Penélope Cruz’s award for Vicky Christina Barcelona was presented by five actresses who had previously won the award themselves: Eva Marie Saint in a stunning white satin trouser suit with a Nehru collar and matching white shift top, with a bold silver necklace as jewellery. Tilda Swinton in an interesting draped and knotted stone-coloured top with black trousers, along with immaculate short hair and a red lipstick, and matching gold bangles. Goldie Hawn in a simple beige dress with plenty of cleavage, yet no necklace to highlight it only a stunning gold bangle for shine.


Angelica Huston was a little more glitzy in a plum-coloured full length wrap gown with silver beaded embroidery, again no necklace but large gold earrings and a matching plum lipstick, and dramatic eye makeup. And Whoopi Goldberg a in a swirling leopard print chiffon gown and her trademark dark glasses perched low on her nose.


Cruz herself wore a beautiful simple graduated diamond necklace and matching huge diamond solitaires as earrings, and a white strapless ballgown with a satin top and huge chiffon skirt. She looked radiant.

Late 2000s clothing overall…

What mostly stood out about all of these red carpet outfits was the restrained colour palette. There was no gold lamé, no scarlet, turquoise or fuchsia. White, grey, beige or black was the choice of most presenters and nominees. Even Whoopi Goldberg’s leopard print was wasn’t bold. People wore huge borrowed jewels, but it was EITHER a necklace OR earrings, and if they wore both they were, though still priceless diamonds, relatively modest looking. The men wore black suits and ties or bowties. There was no colour, no jewellery for them at all.

Quite a difference from the clothing on the street at the time. You’d see high waisted mini denim skirts, Ugg boots, tank tops, cargo pants, crop tops, Juicy Couture tracksuits, skinny jeans,  low rise jeans, leather jackets, studded belts, and flip flops in the early aughts, courtesy of pop stars like Britney Spears. Early 2000s popular accessories were not low key or restrained either. 

A Tragedy

Heath Ledger didn’t have any special outfit either, but that’s because he was dead. The award for best supporting actor on The Dark Knight, playing the Joker, was made posthumously. Ledger died a year before, just after the Batman film had completed. He also won an Academy Award that year for the same role. His death was from an accidental overdose of a vast amount of different prescription drugs, probably combined with a chest infection from filming long hours in damp conditions.


It was quite a scandal, of course, and affected the publicity of The Dark Knight. Maybe it was embodying the manic energy of a character like that. But he complained he couldn’t sleep and that thoughts kept whirling around his head. He just added sedatives to sleeping pills, and he was also taking cold medicine. Perhaps he had addictions, perhaps it was pressure, perhaps he already had mental health issues. But he was only 28, and it was a shock for everyone.