I'd argue there are different types of pennies.
There are the trad American style, rounder lasts.
Some of the Europeans like Carmina (Simpson last), Crockett and Jones, and Ralph Lauren's made in Italy are pretty sleek. My pennies skew in this direction, and it is hard to imagine me wearing shorts with them.
Some makers have models that skew casual - Epaulet in NY carries a Carmina handsewn moc penny - these are far less sleek than the Carmina Simpson last...