Well I admit that the title is a little bit pretentious, JW wasn't really the outfitter to the gentry in the same way Gieves and Hawke or Barbour are. However, for a little while, they were the outfitter for the gentry's children. Of cours, we don't really have much of an upper class left so the very few of them that are still making money from estates and polo (think, Prince Harry) don't really constitute the "Gentry" nowadays. Instead, one has to factor in bankers and lawyers to the "upper class" grouping.
Also, it seems that much of the country perceives anyone that attends a public school (for our american cousins, that is a Private School) to be "Upper Class". Anyways, sociological musings aside, bankers children suddenly seemed to be taking notice of this new brand back in about 2007: Jack Wills. I think this is partly because of there being a store in Salcombe, in Devon. Salcolmbe is one of those places where every banker who has a country retreat seems to migrate to in the summer. So it was possibly the most business savvy move the brand could have made hitting the epicentre of their potential clientele's world. Everyone was now coming back with one or two pieces of Jack Wills and a teen fashion revolution was taking place.
Of course, Jack Wills now has a far greater spread of customers' backgrounds. This has, in my opinion, been massively detrimental to the brand's credibility. "Outfitters to the Gentry" now had people who certainly weren't the gentry clamouring for a piece of the pie. And so they made more tee-shirts, scrapped the velvet smoking jackets and hunting tails and replaced them with items that had JW all over them rather than the original peacock. No longer did this brand cater only to the rich (or those who saved for that one item they loved) and the refined.
While Ralph Lauren has always stayed on the same course as the original polo clothing, one can see people walking down the high street or in Primark wearing a loud RL polo or a jumper. However, RL keeps up the Black Label and Purple label and still is popular with the 5th Avenue children and teens and still embodies the stereotypical WASP image in much of its clothing. However, Jack Wills seems to be in between the new naff items and the old traditional public schoolboy clothes.
It seems to have done the impossible, made chavs want to wear tweed and chinos. I know this because on my last visit to the Brighton store, I heard five different people muttering, "S'Too expensive, lets get some socks and get summin' next time." Now I don't want to be classist, far from it, but if the majority of the brand's loyal customers are the complete opposite of the original followers then of course the whole brand will change. And by it changing, the original JW wearers move on, deeming it to be "Chav clothes".
Fortunately, I still have loads of the original clothes they made and so do others however I don't think I will ever purchase anything other than their chinos and their accesories (even the socks aren't as good as they used to be, no more 40 pound hunting socks!) because the whole brand image has become tarred. In the same way Abercrombie doesn't come across as being the All American clothing of choice because everyone out there seems to have some of it or have pictures of them posing next to the topless guy outside (how much is he payed?!).
I guess what I'm trying to say is that brands have to watch out for a seismic shift in their customers' backgrounds and to try to stay true to their original ethos (in this case "Outfitters to the Gentry") or risk losing the people they originally relied on. Beware!!!