My sketchbook is full of experiments where I bend and break the 'rules' until a face reads as it should, so here are the guidelines I actually lean on when drawing stylized characters.
I usually start with the head as a simple circle and a vertical centerline — that centerline is my friend because even wildly stylized faces need believable symmetry and perspective. For vertical placement, the classic halfway eye line is useful as a default, but for cuter, more youthful characters I drop the eyes lower (
Closer to the bottom third) to give a larger forehead and a rounder, softer silhouette. For mature or sharper characters I push the eyes up slightly and tighten the jaw.
Eye spacing tends to stay consistent even in stylization: roughly one eye-width between the eyes keeps things readable, while enlarging or shrinking each eye relative to the face controls personality. Noses and mouths often compress: small, simple noses and mouths sit closer together than in realistic proportions — a tiny nose halfway between the eye line and chin, and a mouth about a third of the way down from the nose usually reads well. Ears align roughly between the eye line and the bottom of the nose unless you’re going for a heavily stylized silhouette.
I also think in shapes — triangles, ovals, and blocks — to decide whether a face feels soft, angular, cute, or gritty. Studying different works helps: the round, expressive faces in 'Sailor Moon' convey dreamy innocence through low-set, large eyes, while 'One Piece' shows how exaggerating jawlines or eye shapes creates instant character identity. Ultimately, I tweak proportions, silhouette, and feature placement until the personality reads — it’s part measurement, part intuition, and I love that messy mix.