Ha - Hipster and Yuppie ... funny.
I think that both brands are around for a long, long time and their classic styles to me are more timeless that hippster. Agree that the classic styles go with a lot of casual stuff so you can't go wrong but you also are not wearing anything that draws attention - They are a pretty safe and versatile choice.
I have to admit that I do like some of the collaborations (e.g. Cabourn with Converse, Diemme, EG with Vans) that are so trendy right now with all sneaker makers, but they can be hit and miss and they have to cater to your own tastes. Those are probably more towards hipster land but then again, this is styleforum, correct? Bring it on, hipsters