I still have a pair of HD engineer round toe boots bought in Tokyo in 2005. They were waterproof until a shoe/boot repair shop re-soled then in late 2010 and didn't use the correct stitch to keep them waterproof (the bastid...)!

I keep them maintained and they still look good, but I use my lace up 8" work boots these days...

The only "real" (sic) boot we get here are called "Johnny Reb" and they are square toe with some stupid looking harness around the ankles-- looks like crap.... and overpriced at nearly $275 as well.

 

I've owned two different pairs of HD boots and I hated both of them. They were uncomfortable and offered little in the way of arch support. They may work well for some, not for me though. Now I wear Vasque hiking boots exclusively. Just my 2 cents.

 

Danner Mountain lite II. Vibram sole, goretex, foldover tongue to keep the wind out. Love em

 

I have a pair of Riddicks from the MoCo and love them. Comfortable for me, they're holding up nicely, and I like having the zipper on the inside for taking them on and off. Before these I had a pair of these:
http://www.harleydavidsonboot.com/hadame9tarib.html

They held up great too and I still have them. They are a little ripped where the fabric meets the leather but considering these are the boots I was wearing when I went down at 50mph on the freeway, they're in GREAT shape. most people can't even tell they were damaged unless I point it out. Hence why I didn't get rid of them. No need too.

 

I don't really like the HD boots, bottoms are really hard, and they scuff up pretty easily. I wear Dr Martens Oily finish, the rubber bottoms squish just like sneakers and they usually last me about 2-5 years depending how much riding i do.

I buy them from zappos, no I don't work there.. here is a link to the pair I'm currently wearing. heaverier than a sneaker but can walk long distances and not have pain from hard soles and the bottoms help to absorb the vibes from pegs or floorboards
http://www.zappos.com/dr-martens-8836-st-black