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@ds3000
Hi,
I would recommend clipless (I have used Shimano m520 on all my bikes for years now, they're ultra reliable and cheap) with MTB shoes, i.e. something you can put your foot down in and not be slipping all over the place/occasional walking. You could also benefit from some waterproof overshoes for the wet days, and if you're feeling really keen - gaiters.
Just some ideas anyway.
Your spiffing condor shoes would need road cleats specific to the type of clipless pedals you were using. New pedals come with the appropriate cleats included.
Obviously this would mean investing in new/ 'new old' stuff, but we all like that, don't we?