STYLE EVOLUTION

Reese Witherspoon’s Style Evolution, From Election to Big Little Lies


Following her role as the unstoppable and irresistible Elle Woods in the Legally Blonde films, Reese Witherspoon, who had previously starred as slightly more sinister characters in Election and Pleasantville, was quickly appointed as America’s newest sweetheart. Since then, Witherspoon has come even more into her own, showing unpredictable ambition through a diversity of roles. which includes her pinnacle, Oscar-winning work as June Carter in Walk the Line, the self-destructive Cheryl Strayed in Wild, and, most recently, the gleefully short-tempered Madeline Mackenzie on HBO’s Big Little Lies. Off-screen, Witherspoon has garnered even more attention for her powerhouse-producing streak and recent venture, Hello Sunshine, which aims to project female-driven stories across multiple digital platforms. She has also branched out and incorporated her timeless style into a contemporary women’s clothing line, Draper James. Witherspoon’s brand offers pieces reminiscent of her Southern roots; knee-grazing frocks, off-the shoulder tops, scalloped dresses, printed tunics, all with vibrant color. Witherspoon is the company’s best advertisement, frequently pairing her own designs with the likes of Saint Laurent, Christian Louboutin, and Tom Ford for a prim yet modern street style moment. In honor of her 41st birthday, click through for a look back on her best looks, on and off the red carpet.

1
1991

Witherspoon attended the 1991 premiere of her debut movie, The Man In The Moon, sporting an adorable daisy top, black skirt, and cowboy boots.

2
1997

Witherspoon embraced true 90’s fashion at the Nowhere West Hollywood Premiere in clogs, choker, and an eclectic hairstyle in May1997.

3
1998

The actress opted for a sheer, silver ensemble for a 1998 film premiere with complimenting bag and peep-toe pumps.

4
1999

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.

5
2001

In true Elle Woods fashion, the actress attended the Legally Blonde premiere in a pink dress with tulle accents.

6
2002

The actress stunned in a strapless, navy dress with gold accents at The Importance of Being Honest premiere in New York City.

7
2002

Witherspoon toughens up a feathery, grey number with a velvet belt at the world premiere of Sweet Home Alabama in New York City.

8
2004

A brunette Witherspoon opted for a pale blue Carolina Herrera number for the Venice Film Festival’s Vanity Fair premiere in 2004.

9
2005

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.

10
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.

11
2006

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.

12
2006

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.

13
2007

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.

14
2009

Witherspoon dazzled with a futuristic, ruffled Rodarte frock with green accents– perfect for the Los Angeles premiere of Monsters vs. Aliens.

15
2012

The actress wowed viewers in Zac Posen’s pre-fall 2012 peony taffeta bustier gown at the 69th Annual Golden Globe Awards in 2012.

16
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.

17
2014

Witherspoon posed with designer Stella McCartney, wearing her designs, at the Costume Institute Gala at the Metropolitan Museum of Art in May 2014.

18
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.

19
2014

The actress wore a Balenciaga frock (in pink, of course) with nude pumps at the premiere of Inherent Vice in December 2014.

20
2015

Witherspoon channeled old-Hollywood glamour in a strapless, sparkling Calvin Klein gown at the 72nd Annual Golden Globes in January 2015.

21
2015

The actress went glam in a sleek, black and white, off-the-shoulder Tom Ford gown at the 87th Annual Academy Awards.

22
2015

The actress sparkled in a silver embellished dress by David Koma to the 50th Academy of Country Music Awards in 2015.

23
2015

The actress stunned in a strapless, red Jason Wu gown at Metropolitan Museum of Art’s Costume Institute Gala in 2015.

24
2015

Witherspoon attended the opening of Draper James’ Nashville store opening in a lace dress by the brand.

25
2016

Witherspoon wore a floral, J. Mendel dress with Tiffany & Co. jewelry to one of the brand’s Blue Book parties in 2016.

26
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.

27
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.

28
2016

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.

29
2017

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.

30
2017

Witherspoon stunned at the Vanity Fair Oscar Party in a black, embellished, long-sleeved Michael Kors number with simple black pumps.