Sabrina Carpenter is in the running for song of the summer. Her stylist shares what it's like to dress a pop star on the rise.

The singer goes retro beach chic in her "Espresso" music video, then pivots to loud luxury in "Please Please Please."

Sabrina Carpenter on set of the "Please Please Please" music video. (Photo: Alfredo Flores)

If it feels like Sabrina Carpenter is everywhere this summer, that’s because she is. Releasing back-to-back Billboard Hot 100 hits “Espresso” and “Please Please Please” just two months apart — and dethroning herself on the global Spotify songs chart in the process — Carpenter has established herself as a bona fide pop princess.

But her catchy, retro pop and country-tinged tracks aren’t the only reason she stands out from the crowd. In a sea of up-and-coming pop stars, Carpenter’s fashion choices help to set her apart. From sparkly corsets to dresses with heart-shaped cutouts, her flirty, feminine and chicly coquette looks are in a league of their own.

For her “Espresso” and “Please Please Please” music videos, Carpenter looked to stylist Ron Hartleben to curate a series of outfits to help visually usher in her Short n’ Sweet era, ahead of her Aug. 23 album release.

Sabrina Carpenter.
Sabrina Carpenter poses on the set of the "Espresso" music video. (Sarah Carpenter)

Hartleben is a New York-based stylist whose roster of clients includes Anitta, Willow Smith, Pamela Anderson and Megan Fox. He began working with Carpenter in 2022 and has since styled her for a handful of music videos including “Because I Liked a Boy” and “Feather.”

“With Sabrina specifically, she usually has a really strong point of view and there’s a really strong narrative with each music video or project we do,” he told Yahoo Entertainment. “We’re trying to build characters and make identifiable silhouettes or wardrobe staples that make this character [she’s playing] more structured... It really starts with, ‘Who is the girl that she is playing in the role?’”

Hartleben’s collaboration with Carpenter is built on trust. The stylist and fashion editor is grateful that clients like Carpenter give him complete control.

“There’s not necessarily [conversations], like, ‘Oh, I love this dress’ or ‘Oh, I love this designer,’” he said of working with the singer. “It’s more so [Carpenter] trusting me to know what’s going to make [her] look the best and feel the most confident.”

He added, “You want the person to feel comfortable. No matter if it’s a string bikini or a burlap sack. If they feel comfortable and if they feel confident in it, then that will exude in the video or the photo.”

Carpenter’s music videos seem like a stylist’s ultimate playground. The “Espresso” video, released April 12, had a retro, beachy summer vibe. Carpenter, dressed in pinup-style one-piece swimsuits, vibrant headscarves and oval-shaped sunglasses, looked as if she were plucked directly from an Old Hollywood-era vacation.

“We wanted to [reference] the ’50s and ’60s, that era of old-school swimming suits and Marilyn Monroe, but also modernize it and make it a little more contemporary and still young and fresh for today,” Hartleben explained.

Hartleben cites Carpenter’s black mesh halter swimsuit by Norma Kamali as a “great staple piece” that effortlessly blends the past with the present. Carpenter is also seen in a textured two-piece by Viktor & Rolf, which Hartleben describes as a more modern and fashion-forward take on a vintage bathing suit.

Sabrina Carpenter, in a bathing suit near a body of water, poses on a surfboard held aloft by a half dozen people wearing swimming trunks and sunglasses.
Sabrina Carpenter poses on a surfboard in a Norma Kamali swimsuit. (Sarah Carpenter)

“We made a few custom things that were a bit more old-school but had a new kind of flair to them. Maybe the colors were updated or we accessorized it in a way that was still Old Hollywood but believable for today,” he explained.

Carpenter’s video for “Please Please Please,” released June 6, can best be described as the visually gaudy, edgier counterpart of “Espresso.” While “Espresso” sees a laid-back Carpenter lounging on the beach and taking in the summer heat in the sweetest vintage-inspired swimwear, “Please Please Please” shows a visibly distressed Carpenter in all of her loud luxury — think fur coats, bold pops of color and sexy silhouettes — as she deals with the criminal tendencies of her onscreen boyfriend (played by her offscreen love, actor Barry Keoghan) .

Carpenter and Keoghan on the set of
Carpenter and Keoghan on the set of "Please Please Please." (Sarah Carpenter)

While he’s hesitant to label Carpenter’s aesthetic in the video as taking cues from ‘mob wife’ glamour, Hartleben explained that the looks were largely inspired by Quentin Tarantino films and Scarface femme fatale Elvira Hancock (Michelle Pfeiffer).

Hartleben worked closely with the music video’s director, Bardia Zeinali, to ensure that each outfit served a narrative purpose.

“There [are] two scenes where [Carpenter] is picking Barry [Keoghan] up from prison and it was intentional for the faux fur jackets to be the same but just [in] opposite colors,” Hartleben explained. “So it’s like, things are the same, he’s not changing, and she’s always picking him up… It’s just a different day [and] different time of year.”

Sabrina Carpenter.
Sabrina Carpenter films the "Please Please Please" music video. (Sarah Carpenter)

But for Hartleben, there’s one look from the music video that stands out above the rest: Carpenter’s cherry red corseted dress by Dilara.

“I think that’s going to be a timeless image that lasts in her career,” he said. “I think that look, specifically, was the right place, right time. I’ve been working with her for two years now, and I think two years ago, it was something she would have wanted to wear, but wasn’t necessarily ready to wear for where she was at.”

When Hartleben showed Carpenter the piece ahead of the shoot, she was “in love” with it.

“It’s the outfit that has the most screen time. I think [it] makes the most sense for where she is in her career now,” he said.