Yeah, as someone who's spent time around Harvard, and more time in "Boston proper," I don't see any market there for Ivy clothing at all. Those who want to wear traditional clothing in Boston already have everything they need and have for decades... And if they need to replace a shirt or tie here and there, with the rise of the internet, no one needs a local Ivy store anymore.

I lived in Boston for two years and never saw anyone dressed in Ivy clothes, or in much resembling traditional men's clothing. As opposed to NYC, where I've seen quite a few men on the street wearing Ivy or at least elements of the look...

Really sad news. 

For me, that shop has been such a fixture in the landscape of Harvard Square and its environs.  I used to pass it every day during student summers working in Cambridge in the 1980s, and the place seemed to exude that aura of effortless Ivy confidence, not least because I couldn't afford to shop there then. (Though truth be told, at that time I was more excited by the easy availability of white Levis, so elusive back home then.)

But whenever I was in Cambridge in recent years, I always looked forward to dropping into the J Press shop.  I loved the atmosphere, as well as the sight of OCBDs piled high on the shelves and the racks of tweed. Sacrilege though it may be, I much preferred going there than to the Andover Shop.

And as Woof says, it's very sad for the staff, who I found to be very old school, in the best sense of the word: courteous and helpful, with just the right amount of off-hand briskness.  But there was also an air of fatalism when I asked the staff how things were going there the last time I was there, during the J Press Blue era, with dark mutterings about the wisdom of trying to sell such contemporary cut clothes to college professors.

It's true though that the writing has probably been on the wall for some time: there was precious little Ivy clobber in evidence around Harvard Yard in recent times.

Still, a real shame.

P.S.  I'm sure Stan has some great memories on the subject, if he'd care to share...

Hear, hear in the lack of Ivy Style in Cambridge.  Downtown Boston is almost as bad with the skin-tight sharkskin suits, ugly, pointy shoes, and wacky socks exposed.  It’s like a peacock fashion nightmare. 
The few well-dressed fellows are of the old guard, or the ultra-rare young college student having a go at it(which I applaud even if it DOES sometimes look like cosplay).
  All-in-all though, it's mostly rich kids dressing down and hoping they’re passing as the great unwashed segment of society.   

Re: Boston Bobby’s.  Good call.  Aside from their shop in the South End, they have a giant warehouse north of the city with tens of thousands of items.  An acquaintance works there, though I’ve never been.  Fashion designers and period movie clothiers can get in by appointment only, though I have an in I haven’t yet used.
  And speaking of the shop in the South Emd— it’s ridiculous that I haven’t been there in 10-15 years since I’m in South Boston, just adjacent to the South End.