Uploaded November 2025 | Updated September 2026, 1 week ago
* Get @VaerWatches' Black Friday sale while you can! vaer-watches.sjv.io/XmBqvM
* Full article with links to products + extra entries: stridewise.com/most-comfortable-boots
↓ Here are the other videos I mention ↓
* Bootmaker talks leather vs crepe vs rubber soles: youtube.com/watch?v=g0ZEomtYUUY
* Boots vs barefoot shoes: youtube.com/watch?v=vC8tpj6nNX4
* Visiting Rancourt, Maine's moccasin maker youtube.com/watch?v=I970DXNqGPk
Since day one I've been asked to list the most comfortable boots I've worn, but unfortunately, reviewing a ton of boots means I know there are actually many, many different KINDS of comfort. Softness or stability? Groundfeel or grip? No midsole or three? Fortunately, I've been doing this long enough that I think I'm finally able to do a 'most comfortable boots' video by explaining all the different kinds of comfort and giving suggestions for each of them.
00:00 What is a comfortable boot?
01:28 boots with no break in and soft insoles
03:28 sponsorship!
04:37 boots with soft soles
05:27 boots with roomy toe box
06:33 chelsea boots with roomy toe box
06:54 barefoot boots
07:47 boots with leather soles
08:46 genuine handsewn moccasin construction
09:51 boots with lots of widths
10:54 boots with lots of lasts
11:58 boots with custom lasts
12:45 bespoke boots
13:44 what I missed
* Get @VaerWatches' Black Friday sale while you can! vaer-watches.sjv.io/XmBqvM
* Full article with links to products + extra entries: stridewise.com/most-comfortable-boots
↓ Here are the other videos I mention ↓
* Bootmaker talks leather vs crepe vs rubber soles: youtube.com/watch?v=g0ZEomtYUUY
* Boots vs barefoot shoes: youtube.com/watch?v=vC8tpj6nNX4
* Visiting Rancourt, Maine's moccasin maker youtube.com/watch?v=I970DXNqGPk
Since day one I've been asked to list the most comfortable boots I've worn, but unfortunately, reviewing a ton of boots means I know there are actually many, many different KINDS of comfort. Softness or stability? Groundfeel or grip? No midsole or three? Fortunately, I've been doing this long enough that I think I'm finally able to do a 'most comfortable boots' video by explaining all the different kinds of comfort and giving suggestions for each of them.
00:00 What is a comfortable boot?
01:28 boots with no break in and soft insoles
03:28 sponsorship!
04:37 boots with soft soles
05:27 boots with roomy toe box
06:33 chelsea boots with roomy toe box
06:54 barefoot boots
07:47 boots with leather soles
08:46 genuine handsewn moccasin construction
09:51 boots with lots of widths
10:54 boots with lots of lasts
11:58 boots with custom lasts
12:45 bespoke boots
13:44 what I missed
