Figured I'd chime in being a boot wearer.

Despite the aforementioned "hipster lumbersexual" connotations, I think you 
can get one hell of a good boot from them that is honestly still a fair 
deal. Yes they have "boutique" and limited run models that command silly 
prices (wait...is this the Rivendell forum...) but if you stick to the 
basic line you can get a US made boot that can easily last 25 years with 
resoles for @ 200-300 depending on style. As with every RW boot I've had, 
sizing and break in are key. They all seem to fit a bit different. I wear 
from 8-9.5 depending on style. And yes, they do seem good at fitting at a 
RW store. Here are my impressions and advice on a couple styles.

Moc toe boots. Started with a pair of Irish Setter moc-toes back in the 
80's when I worked for the family firewood/tree service. Wore them for 
years, in every condition Colorado could throw at them, never took ANY care 
of them, and would still be wearing them had they not been stolen. Now I 
have essentially the same boot, but in a 6" high version. Classic moc 875. 
Fine for walking, but maybe overkill. However, I can and often do spend all 
day in them. Hiking (though poor traction), mechanic on foot all day, on a 
motorbike across the country, a summer of carpet installing, and, gasp, 
even to the coffee shop. I have even ridden the bike with them, but they 
are heavy and clunky. As with every RW boot I've had, sizing and break in 
are key. They all seem to fit a bit different. I wear from 8-9.5 depending 
on style. And yes, they do seem good at fitting at a RW store.

Chukka (work version) Style 3140. These are probably my favorite RW boot. 
Still US made, resoleable, treatable leather, but less chunky and lighter 
weight. Still no lightweight by any means, but I've done many all day bike 
rides in them. These used to pop up on the feet of many Riv riders not too 
long ago. I don't follow as close anymore, maybe they still do? There is an 
even lighter version called the weekender I think, but I have no experience 
with them.

I also have a pair of blundstone's but find them a little odd fitting and 
don't wear them often. I love the vastly lighter weight, and slip on 
aspects, but they fit my foot really sloppy so I end up with a lot of 
rubbing. I'm sure foot volume is the culprit. I messed with inserts to some 
success, but they mainly sit by my back door if I need to run out to the 
garage for something. And I'll agree with the above, no options for 
re-sole, and the leather finish does not come back with proofing.

Now, if you're willing to go outside the "boot" and US made parameter, I am 
a huge fan of Clarks. Specifically the heavier beeswax leather / crepe 
soled versions of both the Chukka Desert Boot, and it's low top counterpart 
Desert Trek. Both can be resoled, both can be re-treated at home, and are @ 
$100 cheaper than redwing. I have done 3 trips to Europe in my life, and 
these were my shoe of choice each time. Our last one was 8 days straight of 
walking tours, from 7am to often past midnight. I LOVE my Desert Treks for 
walking. The one mark against them is water intrusion. The soles and 
leather uppers are fine, but where they meet seem to let water in if you're 
in standing water. Now it's never been a big enough issue for me to 
address, but a simple treatment of that edge could fix it? I used to ride 
bikes in my suede desert boots almost exclusively, but the elements quickly 
took their toll on the suede uppers while the pedal pins quickly ate away 
at the crepe soles. Grippy as all get out though!

Aside from motorcycling, I don't specifically swap footwear for differing 
activities. Whatever shoes get call in the morning, often stay on till I 
hit the sack, no matter what the day saw.

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