IMO Vespas would be something neat and fun to zip around in and who cares what others think about it... but if your question is to help decide whether zipping around in a Vespa will be cool in terms of stylish...
It's kinda cool if someone is zipping around with a IDGAF type of attitude and I've seen people like this with Vespas on the roads (even saw a couple with one each). IMO, it might seem kinda lame if you're zipping around trying to garner attention being all like, "I'm on a Vespa!".
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