New Moto Guzzi Door Mats Available Now
I wore redwings...maybe 20 years ago or so. They are great boots, tough as nails and they'll last forever. In the boots that I owned, the leather stretched a bit, but buy them on the small side. I wore mine in work conditions- wet, wet, wet, then I dunked them in diesel oil to waterproof them. That may have contributed to the stretching a bit ;). Those are good looking boots- I might have to get a pair for myself!
I’ve always broken in my pull on boots by soaking them in hot tap water for 30 minutes then wearing them dry. Immediately put a heavy application of MINK OIL, rubbed in well, when removing them when they dry out. This process molds the boot to your foot for a custom fit.
For a little more than the Redwings you can have a pair of Gasolina boots custom made. I’ve had mine for years and they’re extremely comfortable. Just pull your jeans over them. No need to tuck your pants into boots but pics of Gasolina’s always show a hipster with his jeans tucked in.