Witherspoon attended the 1991 premiere of her debut movie, The Man In The Moon, sporting an adorable daisy top, black skirt, and cowboy boots.
Witherspoon embraced true 90’s fashion at the Nowhere West Hollywood Premiere in clogs, choker, and an eclectic hairstyle in May1997.
The actress opted for a sheer, silver ensemble for a 1998 film premiere with complimenting bag and peep-toe pumps.
The actress tied together a pink maxi skirt and white top with a gold belt for the Cruel Intentions premiere in Los Angeles in 1999.
In true Elle Woods fashion, the actress attended the Legally Blonde premiere in a pink dress with tulle accents.
The actress stunned in a strapless, navy dress with gold accents at The Importance of Being Honest premiere in New York City.
Witherspoon toughens up a feathery, grey number with a velvet belt at the world premiere of Sweet Home Alabama in New York City.
A brunette Witherspoon opted for a pale blue Carolina Herrera number for the Venice Film Festival’s Vanity Fair premiere in 2004.
Back to blonde, the actress went for an embellished, tea-length Monique Lhuillier dress for the Just Like Heaven premiere in Los Angeles in 2005.
The actress opted for a bright red Caroline Herrera frock with an oversized black bow belt for the NYC premiere of Walk the Line in November 2005.
The actress shined in a Chanel dress at the 63rd Annual Golden Globe Awards, where she won Best Performance by an Actress in a Motion Picture – Musical or Comedy for Walk the Line.
Witherspoon arrived at the 78th Annual Academy Awards in an embellished Christian Dior, later taking home her first Oscar that night for Walk the Line.
The actress opted for a yellow, strapless Nina Ricci dress with a contrasting red open-toed shoe for the 64th Annual Golden Globe Awards in January 2007.
Witherspoon dazzled with a futuristic, ruffled Rodarte frock with green accents-- perfect for the Los Angeles premiere of Monsters vs. Aliens.
The actress wowed viewers in Zac Posen’s pre-fall 2012 peony taffeta bustier gown at the 69th Annual Golden Globe Awards in 2012.
Witherspoon sparkled in a green and black sequin Louis Vuitton mini dress and Christian Louboutin pumps at the This Means War premiere in 2012.
Witherspoon posed with designer Stella McCartney, wearing her designs, at the Costume Institute Gala at the Metropolitan Museum of Art in May 2014.
The actress picked out a classic LBD with a twist at The May Fair Hotel Gala Screening of Wild during the 58th BFI London Film Festival.
The actress wore a Balenciaga frock (in pink, of course) with nude pumps at the premiere of Inherent Vice in December 2014.
Witherspoon channeled old-Hollywood glamour in a strapless, sparkling Calvin Klein gown at the 72nd Annual Golden Globes in January 2015.
The actress went glam in a sleek, black and white, off-the-shoulder Tom Ford gown at the 87th Annual Academy Awards.
The actress sparkled in a silver embellished dress by David Koma to the 50th Academy of Country Music Awards in 2015.
The actress stunned in a strapless, red Jason Wu gown at Metropolitan Museum of Art’s Costume Institute Gala in 2015.
Witherspoon attended the opening of Draper James' Nashville store opening in a lace dress by the brand.
Witherspoon wore a floral, J. Mendel dress with Tiffany & Co. jewelry to one of the brand's Blue Book parties in 2016.
The actress was seen out and about in Los Angeles pairing a Draper James a-line skirt with pops of yellow and dainty jewelry in March 2016.
Witherspoon opted for a pink and silver off-the-shoulder dress with nude pumps to the Sing premiere at the 2016 Toronto International Film Festival.
The actress let this black, embellished Elie Saab number steal the show with simple black pumps and minimal accessories at the Los Angeles Sing premiere.
The actress-turned-producer optde for a silver sparkling Elie Saab number for the premiere of her most recent venture, HBO’s Big Little Lies.
Witherspoon stunned at the Vanity Fair Oscar Party in a black, embellished, long-sleeved Michael Kors number with simple black pumps.