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As I noted, that’s where the OMW boot comes in (along with 45NRTH, Lake, etc). Bontrager is based in Wisconsin so I’d say the folks there know a few things about riding bikes in cold.
I’ve also ridden the river valley on a cold November day and I think there’s a strong argument to be made that it’s harder to dress for a winters day on the Shore.
For one, the need for dexterity for braking prevents the use of really heavy gloves here.
With the largely adjustable volume the JFW is also quite variable based on what socks I wear although I haven’t had an opportunity to ride them below -1/-2.
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