Drew Barrymore Reflects on Justin Long and Kate Bosworth’s Engagement — and Revisits Her Stylish Gucci Era

Drew Barrymore shared her thoughts on her ex-boyfriend Justin Long’s engagement to actress Kate Bosworth during an episode of The Drew Barrymore Show that aired in 2023.

At the time, the 48-year-old actress expressed her genuine happiness for the couple and praised their connection, noting that she and Bosworth “have a very important person in common.” She was referring to Long, with whom she shared an on-and-off relationship from 2007 to 2010.

Drew Barrymore and Justin Long’s Gucci Era: A Brief but Stylish Love Story

Their romance, though brief, remains one of Drew’s most stylish eras on the red carpet. The pair frequently attended premieres and charity galas in coordinated designer looks, including a memorable appearance at the Gucci Malawi UNICEF Benefit held at the United Nations Plaza in New York.

Drew Barrymore glows in a black-and-yellow floral Gucci mini dress cinched with a gold-buckle belt, paired with black tights, metallic gold heels, and a white clutch beside Justin Long at the Gucci Malawi UNICEF Benefit held at the United Nations Plaza in New York on February 6, 2008 (Credit: Dara Kushner / INFphoto)

She wore a black-and-yellow floral-print Gucci mini dress from the label’s Spring 2008 collection, styled with a wide patent belt featuring a gold buckle that highlighted her waist. The playful yet sophisticated look captured the essence of late-2000s Gucci—feminine, confident, and subtly bohemian.

Completing her outfit, Barrymore added black opaque tights, a white structured clutch, and gold peep-toe heels, injecting just the right amount of metallic glamour.

Long matched her effortlessly in Gucci, wearing a dark, tailored suit—typically black or navy—with a classic shirt and tie. The polished yet relaxed styling echoed the brand’s understated luxury during Frida Giannini’s tenure as creative director.

Together, the couple’s appearance at the event reflected an era when Drew Barrymore’s personal warmth and romantic optimism met her evolving fashion sophistication—an enduring blend of emotional authenticity and Hollywood glamour that continues to define her public image today.

Drew Barrymore’s Gold Heels and Other Celebrity Metallic Moments

Even years after her Gucci Malawi UNICEF Benefit appearance, Drew’s choice of gold metallic heels feels timeless. Gold shoes have remained a Hollywood red-carpet staple — a symbol of glamor that bridges vintage sophistication and modern edge. From subtle shimmer to full-on mirror finish, these metallics continue to dominate runways and premieres alike.

A Candid and Warm Exchange Between Drew Barrymore and Kate Bosworth

Barrymore spoke with genuine affection as she reflected on her past with Long. “My very dear old friend Justin Long — a boyfriend, a dear friend,” she said, smiling. “He and Kate have found each other in this world and become this incredibly joyous, bonded, real deal — the ultimate couple you root for.”

Bosworth, who appeared on The Drew Barrymore Show as a guest, giggled in response. “That’s so sweet,” she replied. “He loves you so much. He just loves you so deeply.”

The Blue Crush actress went on to recall being with Long when he received Barrymore’s invitation to appear on the show. “I remember him getting the ask,” Bosworth said. “He was like, ‘Oh, Drew wants me to go on her show,’ and I told him, ‘You have to do it!’”

Drew Barrymore and Kate Bosworth talking about their shared connection on The Drew Barrymore Show (Credit: YouTube)

Bosworth reflected on the connection between Barrymore and Long with warmth and humor. “I was so excited because I knew there’s so much love between the two of you,” she said. “It was such a fun, wild time in your lives — that kind of tornado energy when you just want to feel everything and live the adventure. He just loves you so much.”

The candid exchange followed the pair’s earlier 2023 reunion on The Drew Barrymore Show, where Barrymore and Long openly reminisced about their relationship. She described it as “chaos” but also “hella fun,” while Long affectionately called it “fun chaos.” Both acknowledged they’d grown significantly since those whirlwind years.

As for Bosworth and Long, their own love story unfolded publicly in 2022. The Wonderland actress and the Tusk actor were first photographed together in Los Angeles, later seen walking hand-in-hand through New York and vacationing in Hawaii.

In early 2023, the couple confirmed their engagement on Long’s Life Is Short podcast — marking a full-circle moment of affection, growth, and enduring connection among all three stars.

Kate Bosworth exudes timeless elegance in a strapless black-velvet gown with a soft blush drape detail, while Justin Long complements her in a classic black tuxedo at the 2023 Vanity Fair Oscar Party (Credit: PA Images / INSTARimages)

Bosworth described the proposal as “the most romantic, honest, and loving.”

Meanwhile, Long said, “It came out in a very organic way,” and “it felt connected to something very deeply, profoundly personal that we were going through a real-life change.”

Drew Barrymore and Kate Bosworth’s Timeless Style and Shoe Evolution

Both Drew Barrymore and Kate Bosworth have carved distinct yet enduring paths in Hollywood fashion—Drew through her playful, bohemian sophistication, and Kate with her minimalist, polished grace. Across red carpets, galas, and off-duty outings, the two have consistently showcased designer footwear that mirrors their personalities and cinematic eras.

Below, explore a curated selection of Your Next Shoes articles celebrating their most memorable shoe and fashion moments.