It's that time again! The one where some of the biggest names in Hollywood come together to honour what the Academy considers the biggest achievements in film (and, in the process, summon some of the biggest names in fashion, hair, and makeup to ensure they look their best for the occasion). With each Oscars season [1] comes a new crop of perfectly-coiffed, lined and powdered celebrities walking the red carpet (see some of our favourite looks from 2018 [2], 2017 [3] and 2016 [4]), but some have managed to stand the test of time.
From Gwyneth Paltrow [5]'s ballerina princess makeup and bun to Angelina Jolie [6]'s half-updo and emerald earrings pairing (and who could forget Julia Roberts [7]' glamorous chignon and Valentino moment?), click through for some of our favourite beauty looks dating back to the '90s, and don't forget to tune in for the 91st Academy Awards this Sunday, Feb. 24.
Gwyneth Paltrow, 1999
Gwyneth Paltrow [8] was the epitome of innocence, complementing her baby pink Ralph Lauren gown with an equally rosy cheek and lip, along with silvery eye makeup and a sleek bun parted to one side at the 1999 Oscars, where she won best actress for Shakespeare in Love.
Julia Roberts, 2001
Julia Roberts [9] did her iconic black and white Valentino gown justice with a glamorous chignon, subtle smoky eye and natural lip at the 2001 Oscars, accessorising her look with a best actress award for Erin Brockovich.
Halle Berry, 2002
Halle Berry [10] accented her Ellie Saab gown with a softer, crimson take on the smoky eye, complete with shadow along the lower lash line for greater effect, a shimmery lip and her signature pixie at the 2002 Oscars, where she won best actress for Monster's Ball.
Jennifer Lopez, 2003
Jennifer Lopez [11] had her mint-green moment at the 2003 Oscars, where she amplified her beautifully-embroidered, one-shouldered Valentino gown with a sweep of matching eye shadow along the lid and bottom lash line, finishing off her look with a nude lip, a pop of blush, and a side-parted bun.
Charlize Theron, 2004
Charlize Theron [12] gave new meaning to understated elegance in 2004, topping off her sparkly Dior gown with retro finger waves parted to one side and a dewy. The Monster star look home best actress that year.
Penelope Cruz, 2005
Penelope Cruz [13] brought on the heat at the 2005 Oscars, where she rocked a voluminous pompadour bun with loose strands of hair framing a sexy smoky eye. She kept her lip and jewellery simple as to not distract from the rest of her look.
Natalie Portman, 2005
Natalie Portman [14] looked like a real-life princess in a swept-back bun and jeweled headband at the 2005 Oscars, playing up the sparkle with silver-swept lids.
Michelle Williams, 2006
Michelle Williams [15] accented her canary yellow, ruffled Vera Wang gown with an equally-bold red lip and low bun parted to one side at the 2006 Oscars. A few soft, face-framing waves completed her retro, yet still modern and fresh, ensemble.
Reese Witherspoon, 2007
Reese Witherspoon [16] forewent her usual coiled and coiffed 'dos for sleeker-than-sleek strands and bangs at the 2007 Oscars. She topped off her look with a charcoal-smudged eye and peachy-nude lip.
Angelina Jolie, 2009
Angelina Jolie [17] pumped up the volume with a loosely-coiled, pompadour half-pony and winged eye at the 2009 Oscars, keeping the rest of her palette natural in order to let her Lorraine Schwartz Colombian emerald drop earrings shine.
Beyonce, 2009
Beyonce struck the perfect balance between sassy and classy with a low, slicked-back and waved pony and cat eye-lip gloss combo at the 2009 Oscars. Her perfectly-groomed brows completed the look.
Jennifer Aniston, 2009
As usual, Jennifer Aniston [18] looked effortlessly-chic at the 2009 Oscars, where she donned an ethereal side crown braid that created the effect of a headband to help separate her long, loosely-flowing waves.
Kate Winslet, 2009
Kate Winslet [19] was polished to perfection with a wavy, pinned-back coif, shimmer-swept lids and a rosy lip at the 2009 Oscars, where she took home the Best Actress award for her role in The Reader.
Zoe Saldana, 2010
Zoe Saldana played up the purple tones in her ombre, ruffled Givenchy gown at the 2010 Oscars with a subtle pop of lavender along her smoky eye and light shimmer on her lips and cheek bones, rounding out her look with a messy ballerina bun.
Anne Hathaway, 2011
Anne Hathaway [20] oozed romance at the 2011 Oscars in a red Valentino gown, which was made complete with a scarlet lip, classic-lined eye and old Hollywood chignon. A few loose, face-framing pieces in front added a playful touch.
Mila Kunis, 2011
From the carefully side-swept bang to her meticulously-coiffed, pinned and tucked hair, Mila Kunis [21]'s 2011 Oscars look appeared to be straight out of a fairytale. Her shimmery smoky eye and lip were just icing on the cake.
Emma Stone, 2012
When you have a gown that commands as much presence as Emma Stone's [22] red Giambattista Valli number at the 2012 Oscars, the last thing you want to do is distract from it with your hair and makeup. That's why we were so impressed with her radiant, yet understated winged eye and pink lip duo, which was framed with side-swept bangs and a classic braided bun.
Jennifer Lawrence, 2013
Jennifer Lawrence [23] dazzled at the 2013 Oscars in a loosely-swept back bun, silver-lined eye and glossy-pink lip, creating the perfect stage for her Chopard diamond drop earrings.
Lupita Nyong'o, 2014
Lupita Nyong'o [24]'s old Hollywood makeup look (by Nick Barose) was created using a soft grey shadow and a pop of rose eyeliner along the lower lash for an added brightening effect. She topped it off with a diamond headband (and an Oscar for best supporting actress).
Margot Robbie, 2015
Margot Robbie stole the show with a bright orange-red power pout at the 2015 Oscars, rounding out her look with a warm smoky eye and a lightly-tousled lob parted to one side (more on how to achieve her classic-cool aesthetic here [25]).
Zendaya, 2015
Zendaya [26] dazzled at the 2015 Oscars with long dreadlocks assembled into a half-updo and rose-tinted eye and lip. Highlighter along the inner corners of the actress's eyes and bold brows really made her brown peepers pop.
Kerry Washington, 2016
Kerry Washington [27] made heads turn at the 2016 Oscars with a messy (make that sexy) pompadour pony with a tousled tail, meticulously-lined eye and shimmery almond lips (get the look here [28]) — perfect for a red carpet or a night out with the girls!
Chrissy Teigen, 2016
A pregnant Chrissy Teigen played up her budding Marchesa gown at the 2016 Oscars with an ethereal compilation of braids created by Christian Wood [29] and a head-to-toe bronze glow.
Janelle Monae, 2017
Janelle Monae paired her beaded Elie Saab gown at the 2017 Oscars with a gold bejeweled headband, opting for a champagne take on the traditional smoky eye [30] to complete, but not compete with, her gilded ambiance.
Jennifer Garner, 2018
Jennifer Garner let her hair down [31] at the 2018 Oscars, tucking her loose, glamorous waves behind one ear to allow one of her long, diamond tassel earrings to shine through. A subdued smoky eye and powder-pink lip completed her look.