You can picture rakish as a man who is not tidy and looks all the better for it: the collar open, the hair not combed flat, the hat pushed to one side, and no sign at all that he minds. Under that picture sits an older one — the man who really does live loosely — and the word still carries a little of it.
rakish 可以想成一個不整齊、卻因此更好看的男人：領子敞著、頭髮沒梳平、帽子往旁邊一推，而且看得出他一點也不在意。這個畫面底下還壓著一個比較舊的畫面——一個生活真的放浪的男人。所以就算今天只是誇一個人有型，這個字多半還帶著一絲「他不太守規矩」的味道。
From the word’s history
Wiktionary gives rakish as rake plus -ish, where rake means a man habituated to immoral conduct. So the word began as 'having something of the rake about him', which explains why the stylish sense still carries a faint edge of disrepute.
Wiktionary 記的是 rake 加 -ish，而這裡的 rake 指「習於放浪行徑的男人」。所以這個字一開始就是「帶著那個浪子味」，也就解釋了為什麼今天用來誇人有型時，還隱隱有一點不安分的邊。
Wiktionary, "rakish"
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