Following the release of the song "Post to Be", a collaboration with Omarion, the line "I might let your boy chauffeur me, but he gotta eat the booty like groceries" was described as a standout lyric and "the lyric of the summer, or the lyric of the year," by Rob Markman, editor for MTV News.
In March 2016, Aiko announced a collaboration album with rapper Big Sean, under the name Twenty88, their self-titled debut album was made available to stream exclusively on TIDAL for four days, and was made available for download on April 1.
Described by Erin Lowers a reviewer from XXL magazine, Aiko's music is alternative R&B, which the reviewer described as being created with the use of heavily used synthesizers and "wooly drum loops," the reviewer continued to say that her genre is caught in a "revolutionized limbo." Bradley Stern of Time, compared the Aiko's musical style to the work of Sade, calling the album's genre "future R&B", Stern continued to compare her music to the work of The Weeknd, Tinashe and FKA twigs.
Aiko writes music everyday, often writing lines or a poem, and begins to add them to melodies.
A 23-minute autobiographical film titled after the album was also released a day before Trip on September 21, 2017, co-directed by Aiko.
D.'s record label ARTium, distributed through Def Jam Recordings.Adam Fleischer of MTV described Aiko's lyrical content as being "catchy and emotive," continuing to note Aiko's lyrics as having no boundaries; which mix "moments of sensitivity and love, but also moments of confusion and aggression."Aiko’s newfound style lies somewhere between the soothing sounds of Sade and what can be nebulously described as “future R&B,” a broad spectrum of pioneering music-makers making tunes best served in the midnight hour, including The Weeknd, Tinashe and FKA twigs.Aiko has described herself as being part of this movement, she noted her own musical style as being "alternative" and a "new-generation R&B", which she compared herself to the style of Frank Ocean, Miguel and Drake.In 2013, Aiko appeared on Big Sean's single "Beware", also featuring Lil Wayne, which became her first top 40 single on the US Billboard Hot 100 chart.In November 2013, she released her first project for Artium and Def Jam, an extended play (EP), titled Sail Out.For the most part, I like to not have second thoughts." Aiko revealed that whilst writing music she enjoys being high in order to use the feeling as inspiration and that for the entire writing and recording process of her debut mixtape Sailing Soul(s), she was under the influence of cannabis.When writing for her debut studio album, she did the same, but recorded while sober.In this meeting, I was innocently told, to 'sell' myself when walking into these meetings."That's when I decided I would 'sail' myself rather than sell myself." In 2011, she also began working closely with artists from Carson-based independent record label Top Dawg Entertainment such as Schoolboy Q and Ab-Soul who was featured on her EP released November 12, 2013 titled "Sail Out".The EP was supported by the singles "AM", "Bed Peace" and "The Worst", the latter of which went on to become certified platinum by the Recording Industry Association of America (RIAA).Aiko released her major-label debut album, Souled Out, on September 9, 2014. E" (re-recorded from Tha' Rayne version in 2002), which debuted on BET's 106 & Park when she was 15 years old.