Gooped & Gorgeous! Gwyneth Paltrow's 25 Most Iconic Fashion Moments

At the 71st Academy Awards ceremony, the blonde beauty took home the Best Actress Oscar for her role in ‘Shakespeare in Love’ while wearing her now-iconic pink Ralph Lauren ball gown.

At the Rei Kawakubo/Comme des Garçons Art of the In-Between 2017 Met Costume Institute Gala, the ‘Shallow Hal’ star  kept her look ultra simple, wearing a Calvin Klein Collection pink sequin midi dress with a side-split detail, styled with black pumps.

On May 6, 2017, the actress hit the grey carpet at the 5th Annual Kaleidoscope Ball, benefiting the UCLA Children's Discovery and Innovation Institute at the Mattel Children's Hospital, wearing a white sleeveless sequin crop and matching center front split skirt by Prada. Black sandals finished up her look.

Paltrow oozed elegance in a blush pink Prada gown featuring an organza T-back bow detail, styled with yellow gold and diamond Bulgari earrings. She completed the look with a light pink Prada hard-case clutch and matching patent leather Prada peep-toe platforms.

The cookbook author attended the 2013 Tiffany & Co. Blue Book Ball, held at the Rockefeller Center, wearing a Ralph Lauren steel-blue silk-mousseline cold-shoulder gown, which she, of course, styled with Tiffany & Co. diamonds.

At the Netflix premiere of 'The Politician,' co-created by her husband Brad Falchuk, the proud supporter (and show's star!) wore a green strapless, floor-length wrap jumpsuit from her own G. Label collection. David Webb jewelry completed the simple look.

On October 25, 1999, at the Los Angeles premiere of ‘The Talented Mr. Ripley,’ the actress showed off her unexpected brunette tresses with a dark blue, graphic mid-length jersey dress by Gucci.

The ‘Se7en’ actress rocked a Tom Ford Fall 1996 red velvet pantsuit paired with blue shirt at the 1996 MTV Movie Awards.

At the 2016 LACMA Art + Film Gala at the Los Angeles County Museum of Art in L.A., the California native showed off her gorgeous gams in a Gucci Spring 2017 black silk crêpe cocktail dress with embellished multicolored sequin embroidery, a black clutch with a cat head closure and gold sandals.

The Goop founder walked the red carpet on April 24, 2013, at the El Capitan Theatre in Hollywood for the 'Iron Man 3' premiere wearing an Antonio Berardi Fall 2013 gown, which featured the navy, teal and iridescent silver panels top with sheer kimono sleeves, and a black-and-white maxi skirt with sheer panels on the side.

At the premiere of the film ‘Hard Eight’ on February 23, 1997, a pixie-haired Paltrow was the epitome of trendy '90s style wearing a carpet-print chiffon coat with matching slip dress and furry collar and chunky sandals.

At the 11th Annual God’s Love We Deliver Golden Heart Awards in New York City, the actress received the Michael Kors Award for Outstanding Community Service wearing a sparkly silvery sequin frock from the designer’s Spring 2018 collection.

At the 2015 EMA Awards, hosted by the Environmental Media Association at the Warner Bros. Studios in Burbank, California, the ’Proof’ star looked totally fresh in a mint-colored Cushnie et Ochs Spring 2016 cutout cocktail dress styled with rose-gold Jimmy Choo sandals.

At the premiere of 'Country Strong' on December 15, 2010, Paltrow looked white hot in a column Emilio Pucci Spring 2011 gown with a sexy back cut-out.

On April 23, 2018, the Estée Lauder spokeswoman rocked an orange Retrofête Fall 2018 orange beaded long sleeve mini dress with a tie waist detail to the 'Avengers: Infinity War' premiere. Center part straight tresses and gold sandals finished up her look.

While pregnant with her second child, Moses, the daughter of actress Blythe Danner attended the 78th Academy Awards in a romantic creamy Balenciaga dress featuring capped sleeves and a lacy front.

At the 2017 Baby2Baby Gala that took place at 3Labs in L.A., the mom-of-two suited up in a Tom Ford two-piece look with satin lapels, which was teamed with silver sparkly pumps.

At the 77th Annual Golden Globe Awards, Paltrow showed off her toned tummy in a Fendi Pre-Fall 2020 sheer brown, tulle gown which she dressed up with Bulgari jewelry.

At the 2019 amfAR Inspiration Gala in New York City, Paltrow walked the purple carpet in an Adam Lippes Spring 2020 white-and-red sequin panel dress, which she accessorized with Bulgari jewelry and Jimmy Choo sandals.

At the 2013 Met Gala, Paltrow was pretty in hot pink wearing a custom Valentino Couture ball gown featuring a nude insert in the shoulders, styled with Wilfredo Rosado earrings.

‘The Royal Tenenbaums’ star topped numerous best-dressed lists when she wore a Tom Ford Fall 2012 winter white-caped gown to the 84th Academy Awards.

At the 44th Country Music Association Awards in Nashville, the ‘Country Strong’ actress worked her fabulous figure in an Atelier Versace one-shoulder beaded ombre gown featuring a sexy thigh-high split and a cut-out detail on the side.

At the 79th Academy Awards, the ‘Sliding Doors’ actress brought old Hollywood glamour to the red carpet wearing a vintage-inspired, dusty rose-colored Zac Posen mermaid gown.

At the premiere of ‘Great Expectations’ on January 18, 1998, the film’s leading lady slayed the minimalist look wearing a simple and sophisticated semi-sheer charcoal Donna Karan dress with spaghetti straps, styled with a black pashmina, strappy low-heel sandals and blunt platinum bob.

At 74th Academy Awards, the ‘Emma’ star went goth wearing a revealing Alexander McQueen Oscars creation and dark makeup, which landed her on many worst-dressed lists. Despite the negative reviews, the actress still thinks fondly of the frock.

“I still love the dress itself but I should have worn a bra and I should have just had simple beachy hair and less makeup,” she admitted in a Goop Q&A back in 2013. "Then, it would have worked as I wanted it to – a little bit of punk at the Oscars."