I think this is definitely the HHOF. Being a "Hall of Famer" transcends hockey and is recognized more widely in the sports world. Sure there are a few players in the Hall who weren't all-time superstars (i.e. Lowe, Andreychuk) but the quality in the HHOF is higher, IMO. Even though there are a lot of HHOFers who didn't get their number retired, that is more due to team context. If you don't play enough years for a certain organization and potentially win a Cup with them or go to the Finals, etc. it can be tough to make the case for lifting their jersey into the rafters.
I just feel that the bar for retired jerseys is much lower than that of being inducted into the Hall. As a Canucks fan, I look at our rafters. Outside of the obvious Bure and the Sedins, you have Naslund, Linden and Smyl up there. The latter 3 will never be up for consideration for the HHOF and even the Sedins would come in under the wire. And look at some of the other guys from around the league: Yvon Labre, Adam Graves, Wendel Clark, Bob Plager, Al Hamilton, Glen Wesley, or even someone as great as Bourque after playing one full season with the Avs. And we all know about the Minnesota Wild #1.
Getting your jersey retired is a little more about the warm and fuzzys (unless we're talking about the Habs), while the more prestigious honor is the Hall.