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Toughest shoes you had to break in?

post #1 of 21
Thread Starter 
Just got some Sebago Docksides and my gosh are these stiff. I wore them days ago for around 5 hours and they were just killing my feet especially around under my ankle. Its like the shoes opening it just digging into it even though my left shoe doesnt have this problem (though they are still killing me)

Fantastic shoes but when I put them back on the pain just comes back again which has been dissuading me but I really want to wear them.

They honestly feel even stiffer than what I remember my Red Wings ever being.
post #2 of 21
gosh
post #3 of 21
Quote:
Originally Posted by kookydooky View Post
Just got some Sebago Docksides and my gosh are these stiff. I wore them days ago for around 5 hours and they were just killing my feet especially around under my ankle. Its like the shoes opening it just digging into it even though my left shoe doesnt have this problem (though they are still killing me) Fantastic shoes but when I put them back on the pain just comes back again which has been dissuading me but I really want to wear them. They honestly feel even stiffer than what I remember my Red Wings ever being.
I have those same shoes and you're right about the stiffness of the leather: first time I wore them I was bloody around the back of my heel. I used some boot cream to soften them up, and wore them around my apartment with thick socks for a little while. Super comfortable now, and the strong leather has kept them looking almost brand new with a little Obenauf's. A lot of guys complained about the stiffness of their Katahdin's around the ankle. I haven't had any problems. My Indys were tougher.
post #4 of 21
My redwing 1908's were a bitch to break in. I think my ankles had blisters for like 3 weeks straight after just wearing them for a few days. Once broken in its not too bad. I think its because they are unlined.
post #5 of 21
Corcoran combat boots... ouch.
post #6 of 21
awaiting aeglus rw story
post #7 of 21
Worst pair I have ever broken in of anything were a pair of Rainbows haha feet bled for days
post #8 of 21
Stingray cowboy boots. Way stiffer than anything else, including elephant or shark.
post #9 of 21
my wife
post #10 of 21
RW875's. everything is easy, comparatively.
post #11 of 21
Hiking boots usually. I like trainers more but some outings call for the shoe-tanks.
post #12 of 21
Banana Republic driving mocs - the leather at the back of the heel was as stiff as plastic, couldn't do anything but drive rental cars in them.
post #13 of 21
Quote:
Originally Posted by Humperdink View Post
Banana Republic driving mocs - the leather at the back of the heel was as stiff as plastic, couldn't do anything but drive rental cars in them.

it probably was plastic
post #14 of 21
Quote:
Originally Posted by Uncontrol View Post
it probably was plastic

Nah, then you wouldn't even be able to drive rental cars...gotta ride the bus.
post #15 of 21
What's it like driving a rental car with Banana Republic driving mocs, despair?
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