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I ran into Tippie rocking so FiveTen hightop winter shoes - maybe two years ago? - and he was full-Tippied on them. I’d say they’d be worth checking out.
I find all my flat pedal shoes expand enough to accommodate a medium weight wool sock and my Showers Pass waterproof socks so I don’t have any need for a winter flat shoe. On the other hand my clip-in shoes tend to have uppers too stiff to comfortably stretch around the waterproof sock.
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