Yes, gilets are dumb-looking.
Ankle boots are wonderful in my opinion, although maybe because I lived in Chuck Taylor's and Doctor Martens since the age of 13 I just got a huge boot habit.
Speaking of habits, I'm not a big fan of the monk strap shoe. I'm not sure why - perhaps I've seen too many Aldo-style townie variations in my time. No, I'm not tempted to buy monkstrap shoes, even the nice ones.