I have the Blaire DM’s and the Voss DM’s. Blaire you really need to try on as I found the middle strap cuts across a certain point of your foot and can be uncomfortable walking long distances or all day. Not because of the sole which is fab and so comfy but just that strap issue for me personally. I’ve never really had the whole breaking them in thing but I think that might be because I wear DM boots year round and my feet are probably hard as old boots themselves.
The Voss I had no issues with whatsoever. Super comfy. But I know what you mean about preferring the look of the Blaire.
Birks. I got Arizonas last year and yes the breaking in was a bit of a pain but yeah they are most definitely the comfiest thing going as I wear them round the house constantly now. But I can’t walk distances in them as I need a strap so I’ve just ordered the big buckle Milano for this summer.
As to which is more ‘in’ my take would be the Blair’s was summer 2021 breakout smash on the sandal circuit and still going for summer 22. I think summer 2023 the birks took over. As to what will be the go to this year, might be something new but both birks and DM’s still in the frame of being ‘in’.