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I prefer trousers over boots, but my TCX S-Speed (waterproof) have big shin protection which means a lot of trousers need to be tucked in. I used to be able to get my leathers over my old basic boots.
I had an awesome fun testing their waterproof abilities my first time in the rain.... all the water just ran down my leg into the top!
Boots over trousers or trousers over boots? Assuming good weather...