Out Ranked the 15 Hottest Male Singer Underwear Ads. Calvin Klein Still Owns the Brief.
Bad Bunny's Calvin Klein campaign generated $8.4 million in media value in 48 hours. Usher's SKIMS drop landed six days before his Super Bowl halftime show. Out Magazine just put together the receipts.
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Out Magazine this week ranked the 15 hottest nearly nude underwear campaigns by male singers, and the list doubles as a brand strategy case study. Calvin Klein accounts for at least eight of the 15 entries. SKIMS, Kim Kardashian's brand, has two. Everyone else split the remaining five.
The ranking includes Mark Wahlberg's 1990s Calvin Klein campaign (the original), Justin Bieber's 2016 CK shoot, Lil Nas X, Shawn Mendes, Dominic Fike, A$AP Rocky for Savage X Fenty, Calvin Harris for Armani, Troye Sivan for Calvin Klein's Pride campaign, Bad Bunny, Maluma, Nick Jonas (who explicitly recreated Wahlberg's original pose), Moses Sumney, Joe Jonas for Guess, and the two SKIMS entries: Usher and Post Malone.
Calvin Klein's Thirty-Year Conversion Rate
The brand has been running this play since Marky Mark and the Funky Bunch was still charting. What started as a single campaign in the early 1990s is now a genre. Calvin Klein occupies more than half of Out's ranking not because the brand is the most aggressive buyer of celebrity talent, but because it created the cultural expectation that a male pop star in his prime does this, and that doing it means something.
Nick Jonas recreating the Wahlberg pose was the clearest signal of how deep that expectation runs. The joke was the point: Jonas knew the original well enough to pay it back, and the audience knew it too.
The numbers from Bad Bunny's Spring 2025 campaign are the most concrete measure of what CK gets for its money. The Puerto Rico shoot, photographed by Mario Sorrenti, generated $8.4 million in media impact value in under 48 hours, according to a Launchmetrics analysis cited by NSS Magazine. The 46-second campaign video reached 20.3 million TikTok views and 30 million Instagram views within a week.
SKIMS Is Buying the Moment, Not the Legacy
SKIMS entered menswear in October 2023 with NBA athletes: Neymar Jr., Patrick Mahomes. The leap into music came at the highest possible volume. Usher's SKIMS campaign went public February 5-6, 2024, six days before he headlined the Apple Music Super Bowl LVIII halftime show at Allegiant Stadium in Las Vegas.
The campaign, shot by photographer Donna Trope, showed Usher in SKIMS Men Stretch boxer briefs in Midnight Blue, Stone, Military, and Oxblood. The brand tied the drop to his album *Coming Home*, offering a limited digital edition with a bonus track titled "Naked" exclusively on the SKIMS site starting February 9. The collection itself went on sale February 12, the day after the performance.
Post Malone's 2025 SKIMS campaign extended the challenger strategy: a Western-themed shoot in camouflage undies, casting an artist who is not an obvious underwear model, which is now the point.
What the Underwear Ad Actually Does
The celebrity underwear campaign is not a fashion play. It is a proximity-to-the-body play. A red carpet look involves a stylist, a designer loan, and a publicist's veto. An underwear campaign involves the celebrity in almost nothing, alone in a frame, for a mass audience.
For Calvin Klein, the format works because it offered something beyond the fee: cultural translation. Justin Bieber went in as a tabloid fixture and came out coded as an adult. Bad Bunny, already the most-streamed artist in the world by 2024, got an $8.4 million media valuation applied to a 46-second video in 48 hours.
SKIMS' answer is timing. It does not compete with Calvin Klein on legacy. It picks the performer who is about to own the biggest live audience in American television, and it drops the campaign six days before the show.
The brief is, at this point, the fastest-liquidating asset in celebrity endorsement. Calvin Klein owns the rite of passage. SKIMS is renting the moment.
Ad Watch News is an independent commentary site. We have no affiliation with Out Magazine, Calvin Klein, SKIMS, or any artist mentioned here. This piece draws on published sources listed below.
Sources & further reading
- Out Magazine: Ranking the 15 hottest nearly nude underwear ads of male singers (2026)
- NSS Magazine: Bad Bunny's Calvin Klein campaign broke the internet, $8.4M media value (2025)
- Revolt TV: Usher and SKIMS team up for mens underwear drop (Feb 5, 2024)
- Breaking News IE: Usher strips down for SKIMS campaign ahead of Super Bowl halftime show (2024)
- Wikimedia Commons: Bad Bunny 2019 by Glenn Francis, CC BY-SA 4.0
