OK, couldn't help but chime in with my own thoughts re: appropriate dress for fine dining. I certainly appreciate Blair's sartorial sense, and believe that it's better to be overdressed than underdressed for an occasion. I've also felt embarassed by some of my fellow dudes that I've seen dining, like the guy chowing down at Biba's while wearing shorts, a Tommy Bahama shirt and flip-flops. Definitely not appropos ...
As for wearing jeans to a destination restaurant, I say it depends on the kind of jeans. If you're wearing some old Levi 501s with patches in the knees, it's best to leave those for gardening or cleaning the garage. But if your jeans cost more than, say, dinner for two at Grange Restaurant, then you're probably OK. No matter the price, I'd stay away from jeans that were too distressed or have holes anywhere. And if you do opt for jeans, it's best to dress them up with a blazer and collared shirt (i.e. leave the t-shirts at home, bros). Quality shoes are also a must.
On the flipside, I've seen men in some very nice three-piece suits act like complete jerks to servers and pulling the "don't you know who I am?" routine. To me, that's uglier than a leisure suit circa the 1970s. So in my book, it's not so much what you wear, but how you carry yourself.
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