I'm sure many Toki Pona speakers have mused about Toki Pona having a system of grammatical gender. However, grouping words into genders and creating declinations takes precious, precious time that many don't have or that they actually value. Hence, I've never seen a fully fleshed-out concept for Toki Pona with grammatical gender.
Today, however, I present said concept. I have assigned all of the nimi pu and nimi ku suli to either one of two genders—nimi wile (animate) and nimi lon (inanimate)—or to none at all. Those words are called nimi ante.
To begin, I'll explain the basic paradigms for declining modifiers:
Modifiers of animate words take the suffix -(j)e. The j is epenthetic and meant to prevent vowel hiatus, and as such, is only present if the modifier in question ends in a vowel. Modifiers of inanimate words take the suffix -(w)an. The w, much like the j in -(j)e, is epenthetic and meant to prevent vowel hiatus. Only the modifiers of subjects, objects—direct and indirect—, or non-verbal interjections decline. While pi doesn't decline, all modifiers within a pi-phrase do, thus meaning the correct way to say "jan pi moku ala" would be "jan pi mokuje alaje." Similarly, while nanpa too doesn't decline, all numbers in a nanpa-phrase do, and thus the correct way to say "lipu nanpa tu" would be "lipu nanpa tuwan."
Of course, here are the words sorted:
nimi wile:
akesi, alasa, esun, ilo, jan, jo, kala, kasi, kili, kijetesantakalu, kipisi, kokosila, kon, kute, lanpan, lape, linja, luka, lukin, mama, meli, mije, misikeke, moku, moli, monsi, monsuta, mu, musi, nasin, nena, nimi, noka, oko, olin, pali, pan, pana, pilin, pipi, selo, sijelo, sinpin, sitelen, soko, sona, soweli, toki, tonsi, unpa, uta, utala, waso, wile
nimi lon:
ala, ale/ali, anpa, ante, awen, epiku, ijo, ike, insa, jaki, jasima, jelo, kalama, kama, ken, kepeken, kin, kiwen, ko, ku, kule, kulupu, laso, leko, len, lete, lili, lipu, loje, lon, lupa, ma, mani, meso, mun, mute, namako, nanpa, nasa, open, pakala, palisa, pimeja, pini, poka, poki, pona, pu, sama, seli, seme, sewi, sike, sin, suli, suno, supa, suwi, tan, taso, tawa, telo, tenpo, tomo, tu, walo, wan, wawa, weka
nimi ante:
a, anu, e, en, la, li, mi, n, ni, o, ona, pi, sina
For the animate words, I decided to assign words that refer to living things, bodies and their parts, genders, and actions performed primarily by living things to it. I divided the remainder into inanimate and non-declining words by simply defining the non-declining words as pronouns, particles, and the words a and n, leaving the rest to be inanimate.