Like everyone else said, wear them. I went to europe over the summer and i only wore sperrys. Now they are extremely comfortable. It might feel better to wear them a litttle loose to make it easier to slip on and off.
Wear them around the house with socks. You may look ridiculous, but you'll save your feet from the blisters. Believe me, Sperry blisters are not fun.
Let's be honest...you don't break-in Sperry's, they break you in! All I wear is Sperry's and now I have callused feet. Blisters - tough it out, where a band-aid if you must, and don't resort to socks (except for around your bedroom, maybe).
Sperry blisters are not fun but who said being a man was always fun? I bought some last month and then walked all over Manhattan for a full weekend. Needless to say they shredded my feet but if you grin and bear it then you'll be fine after a few days. It builds character, and now I just need to give my Sperry's a sideways glance and they immediately know who's boss.
Patrick is right, they def break you in. You could honestly wear socks with them every where if you're worried about blisters or your heels being worn down. Journeys makes a pair of socks that are cut to be unnoticeable when worn with Sperrys. http://kl.am/1s9I
use one of those cedar shoe stretch contraptions that you use to break in wingtips and loafers. wear them as much as possible, use bandaids or vaseline on your ankle to keep the friction down, and throw them in the stretcher at night is how i've done my last 2-3 pair and its idiot proof.
...the hard part is dealing with the stink once you DO break them in.
wear them in the water(beach,shower,pool) and let them get fully submerged, then let them dry inside for a couple days. if you let them dry outside, the sun will make the leather coarse and rough but inside softens the leather.
Like everyone else said, wear them. I went to europe over the summer and i only wore sperrys. Now they are extremely comfortable. It might feel better to wear them a litttle loose to make it easier to slip on and off.
The best way is to walk around in some saltwater, completely submerge them, and then walk around again until they are dry. This is the easiest way if you have access to a beach or port. Another way is to fill a container with water and sea salt, leave your shoes leather-side down in their for 24 hours, then walk around in them until they dry.
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Wear them, wear them, wear them. You might get a blister so take a day or two off and within a few weeks they'll be good. If you go for walks or live in the city, wear them out for a day of errands, that way you'll be walking and stopping to take care of business to give your feet a break.