Reese Witherspoon Had A Stunning Post-Divorce Style Transformation (Both Times)

Reese Witherspoon has one of the most enviable styles in Hollywood, with her classic yet playful take on fashion. Sure, there were a few instances where her outfits missed the mark, but we can all agree that she's definitely had a glow-up since her split from Ryan Phillippe in 2006. When Witherspoon arrived at the Golden Globes wearing the ultimate revenge dress and a darling new hairdo just months after filing for divorce, fans everywhere gasped. Before that, the "Legally Blonde" star gravitated toward more boho pieces, but post-divorce, she seemingly upped her fashion game to a more glam, sophisticated aesthetic.

Witherspoon continued to rule the best-dressed list as she moved on with Jim Toth, whom she married in 2011. Unfortunately, their relationship wasn't forever, and the two divorced in 2023. "It's a vulnerable time for me," the Hello Sunshine founder told Harper's Bazaar in July of that year. If Witherspoon was experiencing heartbreak, she sure didn't let it show, and she's proven time and time again that divorce will never bring down her unflappable fashion game.

After divorcing Ryan Phillippe, Reese Witherspoon made her first red-carpet appearance at the 2007 Golden Globes and knew exactly how to make a splash. The "Your Place or Mine" star appeared in a bright yellow Nina Ricci knee-length dress with contrasting red sandals and a bejeweled bracelet. As for her hair, Witherspoon debuted choppy side-swept bangs and super-sharp long layers surrounding her perfectly made-up face. While the look was simple, it remains iconic to this day, particularly due to the canary shade of her dress, which can be a challenge to pull off. However, Witherspoon wore it beautifully, and everything about her that night oozed with confidence.

Reese Witherspoon didn't let her divorce from Ryan Phillippe stop her from making hits in theaters and on the red carpet. In 2008, she channeled Grace Kelly at the "Four Christmases" premiere with her glamorous side-parted hair curled in voluminous waves, instantly giving her a faux bob. Witherspoon knocked it out of the park with her 'fit yet again with another Nina Ricci creation — this time, a strapless knee-length satin dress in deep navy with gold detailing on the bustier, with her gold collar necklace adding just the right touch of sparkle.

Reese Witherspoon proved that she's the queen of the black dress at the 2010 premiere of "How Do You Know." Her strapless Zac Posen garment featured dark pink swirls throughout the bodice and waistline that mimicked spray paint in the shape of bows, giving the dress a nice splash of color. Witherspoon chose to go sans jewelry, except for a pair of subtle earrings, making the focus on her gorgeous look and smoky eyes. "I wanted Reese's makeup to reflect the symbiotic contrast of elegance and rock 'n' roll," her makeup artist Molly Stern told Us Weekly. While the dramatic makeup was a far cry from Witherspoon's usually natural look, it went perfectly with her LBD.

Reese Witherspoon's character, Elle Woods, in "Legally Blonde" was one of her most iconic roles, and she looked every bit the chipper law school student during the 2024 Amazon Upfronts, complete with a mini chihuahua standing in as Bruiser. No one would have guessed that she was on the heels of her divorce from Jim Toth as she strode onto the stage in a bright pink jacket and skirt set. Witherspoon then demonstrated the "bend and snap" from the film before announcing the prequel series to "Legally Blonde," titled "Elle," per The Hollywood Reporter. While she was channeling Woods at the upfront, we could totally see Witherspoon wearing the bubblegum-colored outfit on any other given day.

As a Southern gal, Reese Witherspoon's style is very demure, with lots of florals and pastels, but after her divorce from Jim Toth, the "Home Again" star pulled out all the stops at the 2025 Screen Actors Guild Awards. Witherspoon's bright red strapless gown with a thigh-high slit was one of her best red carpet outfits to date, and she stood out as she posed with confidence and ease in front of cameras. The couture Elie Saab dress needed no other accessory other than a simple gold necklace and a couple of rings. Witherspoon also kept her hair and makeup simple, letting her revenge dress speak for itself.

Reese Witherspoon took power dressing to the next level while making an appearance on "Good Morning America" in January. She managed to combine the feminine and masculine aesthetic with a light blue jacket and trousers, and a matching button-down shirt. Draped over her shoulders was a camel-colored coat styled completely effortlessly. With her rust-colored handbag and fresh makeup, Witherspoon looked like she could have led a board meeting easily, which she undoubtedly does on a regular basis.