Drew Barrymore’s best looks span decades. Since the actress landed in the spotlight at seven in 1982 after her breakout role in E.T., she has continually owned red carpets and showbiz events with her distinctive style.
After making her debut in Steven Spielberg’s iconic movie, the award-winning A-lister has been cast in numerous other big roles. Some of her biggest films include Never Been Kissed, 50 First Dates, Charlie’s Angels and The Wedding Singer, and she has also delved into the world of TV – appearing in the series Santa Clarita Diet and launching her own daytime talk show, The Drew Barrymore Show, in 2020.
Just like her career, Barrymore – who has two daughters with ex-husband Will Kopelman – has had an evolving dress sense. From the more edgy looks of her youth, – complete with denim and leather – through to the sexier ensembles she favoured in her 20s and 30s. By her 40s, she embraced the sweeping gowns and chic tailoring that she has continued to favour in recent years.
In particular, Barrymore has made eveningwear her forte – and if it’s an area of your wardrobe that you really struggle with, then the star is proof that you can rip up the rulebook when it comes to colour, pattern, silhouette and even sleeve length. The key, as she demonstrates, is to feel yourself, and – as you’ll see – you can never go wrong by adding a red lip.
Drew Barrymore’s best looks
From rocking some of the best dresses to owning some of the best red carpet moments of all time, these are the outfits we’ll never forget.
1. The voluminous yellow gown
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Barrymore brightened up the red carpet at the CFDA Fashion Awards in New York in 2021 with her dopamine dressing. Her tiered tulle yellow gown, by Christian Siriano, featured a voluminous skirt and nipped-in waist. She finished off the elegant look with a slicked-back bun and gorgeous blue earrings.
2. The silky red suit
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Proving that relaxed tailoring can very much make for a chic eveningwear look, Barrymore opted for a silky red trouser suit at the Christian Siriano show at New York Fashion Week in 2022. She wore the striking ensemble with tousled waves and some simple gold jewellery.
3. This 90s ‘nice top and jeans’ combo
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Barrymore knows that some well-chosen basics can make a big impact. She looked incredible at the premiere of The Freshman in 1990 in a pair of classic straight-leg blue jeans – essential in any capsule wardrobe – along with a button-through red and white polka dot crop top and black Converse sneakers.
4. The sparkly pink gown and understated updo
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Looking every bit the Hollywood princess, Barrymore stunned on the red carpet at the Emmy Awards in Los Angeles in 2009. Her pink sleeveless gown was by Monique Lhuillier and featured sparkly detailing on top of a voluminous skirt. She finished off the look with her hair in an elegant updo and minimal jewellery.
5. The elegant floral dress
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Barrymore demonstrated that florals needn’t be relegated just to daytime at the premiere of Miss You Already in New York in 2015. Her navy Stella McCartney maxi dress featured a plunging neckline embroidered with intricate flower detailing. She accessorized her look with grey court shoes and tousled waves.
6. The slinky black midi dress
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When the occasion requires, Barrymore certainly knows how to bring a sexy edge to her ensembles. The actress looked incredible in a form-fitting black lacquered tweed midi dress by L’Wren Scott at the Whip It premiere in 2009. She paired the sultry outfit with statement earrings and a pair of red platform heels.
7. Keeping it casual with a statement printed blouse
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Barrymore put her most stylish foot forward at Glamour’s Women Of The Year Awards in New York in 2017. The star wore a long-sleeved embroidered white blouse from her own fashion line Dear Drew, along with a pair of classic black trousers and black platform heels. She finished off the head-turning ensemble with dramatic eye makeup, colourful statement earrings and a baby blue clutch bag. This look feels reminiscent of pieces from her own collection, Dear Drew.
8. The perfect pinstripe suit
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Clearly conscious of the powers of the trouser suit, Barrymore looked like she meant business as she stepped out in a grey pinstripe, tailored number at the CBS studios in New York in 2023. She paired the matching blazer and wide-leg trousers with a silky white blouse, shiny locks and a yellow heart-shaped crossbody bag.
9. Her zig-zag slip from the 90s
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Barrymore, sporting a sweet pixie cut, exuded confidence arriving at the premiere of Scream in London in 1997. The Hollywood star, then just 22 years old, let her printed zig-zag slip with spaghetti straps – one of the most failsafe types of party dress – do the talking. She finished off her head-turning outfit with a bold lip look – a very 90s berry-red shade.
10. The simple white dress
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An 18-year-old Barrymore channelled classic Hollywood glamour when she stepped out for an evening event in 1993. The teen elevated her plain silky white dress with an elegant pearl choker and styled her locks curly.
11. The perfect prom dress
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Barrymore emanated serious star power at the Golden Globe Awards in Beverly Hills in 2007. Her pink Christian Dior sleeveless gown featured draped detailing at the waist and a small train. She finished off the look with diamond earrings, silver heels and an elegant up-do.
12. The statement pink cape
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Barrymore is certainly a fan of bold shades. The A-lister looked incredible as she attended the Harper’s Bazaar ICONS & Bloomingdale’s 150th Anniversary in New York in 2022. She opted for a striking pink Christopher John Rogers cape with a ruffled-neck Ralph Lauren white blouse and black trousers. She accessorised with pink heels and a black clutch – which makes one of the best evening bags for versatility.
13. The perennially on-trend black bootcut trousers
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A tailored black trouser is one of the cornerstones of smart office attire. Barrymore looked understated but classy in a bootcut-style pair with a printed black blouse while heading out to an evening event. For a smart casual look, she accessorised with a skinny sparkly belt and a tan-brown clutch bag.
14. The off-shoulder blue gown
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There are few people who look quite as at home on the Hollywood red carpet as Barrymore. She looked every bit the leading lady at the Golden Globe Awards in Beverly Hills in 2009, wearing a blue gown from Christian Dior along with statement silver jewellery and a bouncy blow-dry.
15. The classic black biker jacket
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Barrymore was already carving out her own sense of style as a teen. To attend the premiere of Longtime Companion in Los Angeles in 1990, the 15-year-old stepped out in a black leather biker jacket, which she paired with a white top, black shorts and a bold red lip which would go on to become her go-to look.
16. The long-sleeved mini dress and sky-high courts
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There are few things more fun to wear on a night out than a mini dress. Barrymore impressed in a long-sleeved khaki green frock from Alexander McQueen, with a black and gold Balmain belt and nude platform heels from YSL at the Going The Distance premiere in London in 2010. She finished off the sexy look with a natural-looking wave and berry-red lip.
17. The ruffled green gown
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Barrymore is partial to a classic silhouette – but always with a twist. The star wore a sleeveless floor-length gown by Christian Dior to the premiere of Lucky You at the Tribeca Film Festival in 2007. The lime green shade and ruffles made this is a truly showstopping piece.
18. The statement orange frock
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There are few people who can pull off a citrus hue quite like Barrymore. The star stepped out in a Jil Sander orange strapless dress for Covergirl Cosmetic’s 50th Anniversary in West Holywood in 2011. She kept the rest of her look simple with sleek straight locks and a black clutch bag.
19. The ultimate ‘cardigan and jeans’ combo
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There’s nothing like a good pair of artfully ripped jeans to bring a stylish edge to an outfit. Barrymore, at the time just a teen, stepped out in a distressed pair with a cosy cream cardigan and brown boots at a red carpet event in Westwood, California in 1991. She finished off the look by styling her blonde hair into relaxed waves.
20. Her 2006 Met Gala LBD
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Barrymore knows that less is more when it comes to the best eveningwear looks. The star stunned in a strapless black Oscar de la Renta gown, featuring a plunging neckline and lacy detailing, at the Meta Gala in New York in 2006. She kept the rest of her look simple, with understated black heels as well as a silver clutch and minimal jewellery.
21. Channelling Barbiecore in a pink caped gown
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Was there any A-lister not rocking Valentino pink in 2022? There are few people who can pull off a cape, but the style superwoman that is Barrymore sure can. Her fuschia pink Valentino look turned heads at the Emmy Awards in Pasadena, California in 2022. She kept her hair sleek but accessorised with chunky statement jewellery for a wonderfully bold result.
22. The chic navy suit
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Barrymore regularly turns to a classic understated suit – and she always demonstrates easy ways to jazz up what otherwise might be rather unexciting tailoring. For this off-duty look she sported in New York in 2023, she added a red and white ribbed silk scarf to her all-navy look.
23. The pleated pink dress
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Barrymore is partial to an elegant, loose silhouette – and we can see why. The star wore a flowing pink Brandon Maxwell gown to a Paramount event in New York in 2022. With billowing sleeves pleated detailing, and a cinched waist, she let the dress do the talking, accessorising with a simple red lip and minimal jewellery.
24. The sparkly one-shouldered nude gown
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On the night she took home a Golden Globe Award for her role in the 2009 series Grey Gardens, Barrymore hit the red carpet in a winning ensemble. Her one-shouldered champagne-hued gown from Versace featured sparkly detailing at the shoulder and waist. She wore her hair in a sleek updo and carried a metallic clutch.
25. The bold blue eyeshadow look
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On occasion, Barrymore will have a bit more fun with her makeup. The actress wowed in blue eyeshadow and a nude lip at a beauty event in New York in 2016. She kept the rest of her outfit suitably colourful too, wearing a pink printed BCBG Max Azria maxidress along with a statement cuff bracelet.
26. The yellow A-line midi dress
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Barrymore proves black needn’t be your only go-to shade for the evening. She was a ray of sunshine at a make-up event in Los Angeles in 2007 in this striking, structured yellow dress. The bright yellow Carolina Herrera midi dress featured a scoop neckline and A-line skirt, which she accessorised with green pointed court shoes by Christian Louboutin and poker-straight hair.
27. The tweed blazer jacket
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There are few things quite as chic as tweed. Barrymore looked stylish in a blazer jacket covered in the iconic pattern while in New York in 2022. She paired it with a brown shirt and beige wide-legged trousers, along with her reddish locks styled into a bouncy tousled blow-dry.
28. The green thigh-split dress
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Barrymore wowed in a Versace look at a Beverly Hills event to honour the Italian designer brand in 2007. Her form-fitting green dress featured a carefully placed thigh slit and special detailing around the neckline. She accessorized with a silver clutch bag and matching silver heels, along with a smoky eye.
29. The sophisticated maternity look
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While pregnant at the Golden Globe Awards in 2014, Barrymore demonstrated that you needn’t compromise on style if you’re expecting. She glowed in a floral pink and ivory Monique Lhuillier short-sleeved dress at the Beverly Hills event. It featured a waterfall hemline, all the better to show off her red heels, and she accessorised with a cream clutch bag.
30. The cream midi dress and statement red lippy
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During her decades in the spotlight, Barrymore has been a dedicated fan of a bright red lip. The star opted for the striking make-up look while promoting her make-up line FLOWER Beauty at the Beautycon Festival LA in 2018. Her outfit comprised of a cream floral midi dress by Jil Sander and gold platform heels.
31. The off-shoulder striped frock
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Barrymore was already giving early indications she was going to be quite the fashionista during red-carpet appearances in her years as a child actress. At the Children’s AIDS Foundation Benefit in West Hollywood in 1989, when she was a mere 14 years old, the rising star stepped out in an off-shoulder monochrome stripey dress with black boots.
32. The long-sleeved floral gown
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While much eveningwear is of the sleeveless or off-shoulder variety, Barrymore has long stepped out in an array of chic long-sleeved dresses. This includes the green, floral Giambattista Valli number that she wore to Variety’s 2022 Power Of Women event in New York in 2022. She styled her hair up at the sides, which highlighted her statement drop-down earrings.