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I have the HD covers and think they're great. 300 miles of rain to Sturgis last year and my feet stayed dry. The wife was a little skeptical but by Rapid City she was a believer.
I have some rain boot covers from Tourmaster that I use on my Heritage in the rain. On my Limited, if I keep my feet behind the lowers, they rarely get wet at all.
When I wear them I stay dry. If it is only a passing cloud sometimes I won't wear them. It's the sometimes when I don't wear them, I sometimes get wet. I like dry, the real pain in the *** is getting wet and trying to dry out.
I also use the Harley boot gators. If I put my rain gear on, they go on too. I used them today. I set out in a down pour for about 30 mins, then light rain. I figure not only will they keep my boots dry, they will prevent the heavy rain from blowing or wicking up my legs. Hey I stay 100% dry so why not?