We just had a Vineyard Vines store open in Pittsburgh. It's definitely gaining popularity as a brand, and it happens to be one of my personal favorite brands, right up there with Polo Ralph Lauren.
I have noticed a few more younger people (teenagers) wearing it, but there are also a lot of adults who like the brand. Most of them are the kind who buy Polo, Lacoste, etc.
I got a bit of a laugh from the OP's description of "stuffy country club attire for older people"...yes, some of the purchasers are the country club type, but it does have some traction among those who aren't members of any club. I wear Vineyard Vines a lot, and have set foot inside a country club once...to install a projector. The brand does seem to have a certain appeal to those who like to sail. <<Raises hand>>
The quality is good, definitely on par with Polo. All of the shirts I have are of high quality. They have some great pieces in their collection. Most recently, I bought a belt with American flags on it. I'm thinking of getting a few of the ties now that we have a store and I don't have to either hunt the clothes down at Nordstrom or pay shipping for online orders!
In terms of price, be sure to look at their website or subscribe to their emails if you want to save some money. If you wait until things go on sale, you can get pretty good deals and save over half the price. Since preppy clothing never goes out of style, it's always a safe bet. (Seriously, Macy's puts all the summer Ralph Lauren shirts on sale in the fall, then brings the same ones out again six months later...and they still look every bit as good in terms of being current).
If you want any incentive to buy directly from the store or website, you get a FREE whale sticker with every purchase!!
Last year, I actually say some Vineyard Vines shirts at Fittings and Fairings, the shop at Yacht Club at WDW. (I was tempted but got a nice Nike golf shirt instead...funny since I don't even golf...I just liked the shirt!)