He often makes a wry face after he says something ironic.
He always frowns when he hears something he doesn't like.
ーHe often makes a wry face after he says something ironic.
「彼はよく皮肉を言った後、しかめ面をする」
to make a wry face で「しかめ面をする」
ーHe always frowns when he hears something he doesn't like.
「彼は嫌なことを聞くといつもしかめ面をする」
to frown を使っても「しかめ面をする」ことを言えます。
ご参考まで!