Obvious answer is: Go try out a few pairs for yourself, we all have different heads. Commercial Electronics on Burrard and Drake has a great selection of headphones and the staff is friendly. The staffer in the headphone section was awesome. I spent 2+ hours in there just sitting and listening to different pairs and I didn't even buy anything from the store.
That being said, IME the most comfy headphones I've worn are (no particular order, all are extremely comfy):
Sennheiser HD555/595 - friend has the 555s, demoed both sets at Tom Lee. Bass isn't super loud, but I haven't spent too much time on them outside a loud store environment, so I can't speak too much about the SQ.
Sennheiser HD650 - spent an 1hr+ sesh with these at Commercial Electronics; It's my dream headphone but it costs $400+
Beyerdynamic DT440/770/880/990 - I currently own the DT990s and have spent many consecutive hours on them. Bought for $240 online, so maybe a bit out of your price range. The 440/770/880 have the same shape/earpads. 880 has the least bass of all three, 770 the most bass, 990 has a lot of bass but has increased clarity (can be sibilant, though), 440 is cheaper than the other three, had a lot of bass, but was definitely less "clear" than the higher models.
I'm pretty sure none of the sets I listed sound anything like Alessandros/Grados, though. From the headphones I've listened to, based on your budget and criteria, I will suggest you give the DT440 a listen. And from what I've read, I think you should also give the Creative Aurvana Live!/Denon D1001 (they are the same headphone, rebranded) a try.