[1] Rob Kenner of Vibe gave praise to Shaggy's dynamic vocal delivery and his taste for old-school dancehall in romantic dance tracks and depth-filled social tunes, saying that "Clothesdrop seamlessly blends Shaggy's sharpest pop sensibilities with his (much slept-on) roughneck pedigree.

"[8] Rolling Stone's Christian Hoard felt the album carried an amalgam of tracks ranging from hip-hop-styled and club-oriented to mind-numbingly generic and a bit preachy, saying that "[T]he entire album has a mixed-bag feel, but "Would You Be" shows that his gift for winsome melody and R&B clarity is mostly intact.

"[7] Dorian Lynskey of The Guardian said that "Clothes Drop is a typically canny and diverse selection: bona fide dancehall cuts interspersed with hooky pop.

"[6] Entertainment Weekly's David Browne said that despite tracks like "Repent" that better display his talents, he found Shaggy trying to regain his hit-making glory days with middling results, concluding that "Maybe he should lose the monotonous, low-rent beats and banal-hook girls (and boys).

"[5] Writing for Blender, Jon Caramanica heavily criticized Shaggy for attempting to showcase his dancehall credentials with a grating voice and without a featured artist to work lyrics off like Rikrok, saying that "Instead, there’s a Black Eyed Pea (“Shut Up and Dance”), a Pussycat Doll (“Supa Hypnotic”) and the palpable sweat of a man trying to figure out what he’s good at, a decade too late.