I never eat downtown Oakville because of the pretentiousness. I have found Paradiso to be bearable but never tried other restaurants.Any and all venues around Lakeshore and Trafalgar, trust me, I live there.
Except one, Southside Cottage Grill - very cool interior, reasonable prices, pretty good food, nice venue, great hangout.
But a few of the clientele can be pretentious fucks, but I ignore them as much as possible.
Then got introduced to 7 Pizzeria.. amazing food and great crowd of employees there. I was expecting them to be snooty, overpriced, with average food.
Probably the best pizza joint I've been to, not overpriced ($20/person for pizza plus appetizers/drinks/etc... a bargain for a 'high end' restaurant as much as it is one). Staff is friendly although you can tell they're trying to please the snooty people too so they're a little bit abrupt. But they do it in a nice way.
Won't eat anywhere else downtown Oakville but 7 is a winner. It's absolutely packed on Fri/Sat nights unlike some of the other restaurants... so obviously others agree with me.
No way am I setting foot into Olivers, Mye or Jonathans ever again by the way. And I got pissed off with the attitudes of all 3 restaurants over 10 years ago and never went back. I can only imagine how bad it is now!