Ryan Phillippe has shared a vintage magazine page on his Instagram Story, and it reads like a time capsule. In one frame, he poses beside his ex, Reese Witherspoon. Two other images show him with Breckin Meyer and Salma Hayek. Each look earned a verdict from a reader and the editors of the magazine, and the result is a playful snapshot of Y2K-era style.
Ryan Phillippe and Reese Witherspoon’s vintage photo offers a glimpse of the pair before their eventual split
Ryan Phillippe’s Story lays out three photos side by side, taken from a magazine. Each carries a smiley or frowning face, followed by a comment from a reader named Tess and a verdict from the editors. Placebo’s “Pure Morning” plays over the slides.
The picture of Phillippe and Reese Witherspoon sits in the middle. In it, he is wearing a pale fisherman hat, a navy jacket over a grey tee, light trousers, and sandals. Beside him, Witherspoon sports sunglasses, dark trousers, and a dark top layered over a white shirt.
Tess seemed to be won over by Phillippe in this photo. “Ryan looks white-hot! I love the fisherman hat and sandals, even though I usually don’t like guys in open shoes,” she said. The editors added, “The clothes and hat are great,” and said the “Cruel Intentions” actor made the sandals look good too.
The photo on the left shows him next to Breckin Meyer in a dark jacket, a grey top and baggy jeans. Here, Tess gushed about his smile, “Oh my God, I’m in love!” The editors then awarded him “a perfect 10” for his clothing, hair and face.
The frame on the right brought the only frown. Phillippe stands beside Salma Hayek, who wears a black dress, while he sports a black sheer shirt. Tess wrote, “I don’t think he could ever look bad, but I’m not a huge fan of the sheer shirt.” The editors agreed he is among the best-looking actors they had seen. Even so, they called the see-through piece “just cheesy.”
The post captures how his outfits drew both praise and teasing, and places Phillippe alongside Witherspoon, Meyer, and Hayek in one nostalgic spread. It also shows the actor and his ex-wife together before their eventual split. The couple was married between 1999 and 2007.
