Drew Barrymore Rides Oscar Mayer Wienermobile in Pastel Jenny Packham Dress and Marc Jacobs Kiki Boots for Her 49th Birthday

In February 2024, as she celebrated her 49th birthday, Drew Barrymore once again proved that joy — and fearless style — are her signature accessories.

For the special occasion, The Drew Barrymore Show host paired her pastel Jenny Packham gown with Marc Jacobs’ now-iconic “Kiki” platform boots. This bold footwear choice perfectly embodied her whimsical, free-spirited energy.

Ross Mathews and Drew Barrymore beam with joy as they step out of the Oscar Mayer Wienermobile in New York City during her 49th birthday celebration on February 20, 2024 (Credit: Roger Wong / INSTARimages)

Marc Jacobs’ “Kiki” Boots: The Sky-High Platform Design That Became a Celebrity Cult Favorite

Initially introduced in Marc Jacobs’ Fall/Winter 2016 collection, the “Kiki” boots have achieved cult status for their exaggerated proportions, multiple buckle straps, and unapologetically theatrical silhouette.

Favored by stars like Lady Gaga, Dua Lipa, and Kim Kardashian, they’ve become a symbol of empowerment through eccentricity — a fitting statement for Barrymore, whose fashion choices often mirror her unfiltered authenticity and love of self-expression.

Drew Barrymore’s Joyful Birthday Ride in the Oscar Mayer Wienermobile

In a clip shared on The Drew Barrymore Show’s Instagram, the 50 First Dates star was led outside the studio wearing a blindfold.

When Ross Mathews began his countdown, Barrymore lifted it—and instantly erupted into gleeful laughter at the sight of the iconic hot-dog-shaped Oscar Mayer Wienermobile.

The Drew Barrymore Show crew surprises Drew Barrymore with a ride in an Oscar Mayer Wienermobile for her 49th birthday (Credit: Roger Wong / INSTARimages)

Drew Barrymore’s Childhood Dream Comes True with the Wienermobile Surprise

Revealing she had a hunch that it was the Wienermobile, Barrymore said, “I was gonna say, this is so crazy, I was like, ‘Don’t tell me it’s the Oscar Mayer Wienermobile!'” Startled, she fell to her knees and attempted to crawl towards the 27-foot-long vehicle, but she had to quickly get back up since her airy pastel rainbow dress was in the way.

“My whole life, I’ve been waiting for this,” Drew said after Ross asked if she was ready to get inside the Wienermobile.

Barrymore happily hopped into the vehicle, carrying a hot dog. Upon seeing the interior, she screamed, then sat down and put on her meatbelts.

Jimmy Fallon Surprises Drew Barrymore With a Madame Tussauds Wax Figure

Following their Wienermobile tour of New York City, Barrymore and Ross returned to the studio, where she was greeted with yet another surprise.

When asked, “What is 5 feet four inches and will have you seeing double?” Barrymore answered, “Me?” Jimmy Fallon was then shown on screen, wishing the actress a Happy Birthday and informing her that she would get a wax figure at Madame Tussauds.

Inside Drew Barrymore’s Birthday Look: Jenny Packham’s Ethereal Rainbow Gown

For her birthday episode, Drew Barrymore dressed to impress in a flowing rainbow-colored ensemble by Jenny Packham, a British fashion designer known for her opulent evening gowns and elaborately embroidered wedding dresses.

Drew Barrymore Shines in Jenny Packham’s Pastel “Sunbird” Gown from the SS23 Collection

The enchanting “Sunbird” dress was semi-sheer, cut from delicate silk, with a pleated design that extended from the bodice to the floor-length skirt. It skimmed over Barrymore’s body, giving her an ethereal appearance.

The Spring/Summer 2023 dress, $6,540 at Farfetch, featured sweeping cape sleeves that added a regal touch to the ensemble, along with a plunging V-neckline and V-back that exposed some skin. It also featured an empire waist, highlighted by a metallic silver braided belt that Barrymore opted not to wear.

Drew Barrymore is ethereal in an airy pastel rainbow dress by Jenny Packham with a plunging neckline and cape sleeves (Credit: Roger Wong / INSTARimages)

Styling Drew Barrymore’s Pastel Look with Marc Jacobs’ Towering “Kiki” Platforms

Lee Harris styled Barrymore’s captivating look with jewelry from Irene Neuwirth. She wore a few gemstone rings and dangling earrings with colorful tourmalines.

Her gorgeous features were enhanced with delicate pink makeup to complement her pastel outfit, and her hair was pulled back into a loose, messy ponytail.

Elevating the look by several inches, Barrymore wore a pair of the Marc Jacobs “Kiki” boots in pink silk satin. Originally part of the fall/winter 2016 collection, these boots boast 4-inch sky-high platforms and towering block heels measuring around 6.75 inches. Along with a 15-inch-tall strappy shaft with decorative buckles, they also have side zips for easy on and off.

Drew Barrymore pairs her colorful, flowy maxi dress with the pink satin Kiki strappy platform boots by Marc Jacobs (Credit: Roger Wong / INSTARimages)

Drew Barrymore’s Timeless Influence on Red-Carpet Fashion and Footwear

From bohemian glam to playful modern elegance, Drew Barrymore’s fashion journey reflects the same authenticity and warmth that have defined her decades-long career. Whether embracing romantic florals, bold color, or sky-high heels, she continues to inspire with looks that balance individuality and confidence.

Below, explore some of her most memorable shoe and fashion moments featured on Your Next Shoes.