How to break in Pioneer 396s

Some of our customers step into a brand new pair of 396s and wear them all day, from day one, without experiencing any discomfort. However, for some of us, breaking in a new pair of shoes can be a little like a rite of passage. Due to the way Goodyear Welted shoes are constructed, with layers of fine materials, they are stiff and for some, can be uncomfortable, to begin with.

This simple guide guides you through the steps for a painless experience.

Before we begin, a note about fitting. In some cases, the shoe may feel ‘snug.’ This is in part because of the Comfort Bridge and Comfort Forever inner sole. However, it’s also due to the stiff construction.  The leather will stretch in time and ‘snug will become ‘just right.’ Don’t attempt to break in a shoe that is ‘tight.’ Just don’t attempt to break in a shoe that is too tight. If it feels too tight, take out the footbed and try again. Does it fit better now? If so, we can send you a flat footbed with the same PORON memory foam for comfort but takes out a half size. To receive a free pair, email If removing the footbed doesn’t seem to work – although it usually does – return the Pioneers for free and order the next size down.

Step One

Wear the shoes around your home or for periods while sat (in the office). Increase the wearing time a little each day, from minutes to hours. Avoid long distance walks and wear suitable socks. Do this for the first week,

Step Two

The shoe leathers should be beginning to soften. If they have been very stiff and rubbed on the heel or toes (for example), they should do so less.  Increase the time you wear them for the second week.

Step Three

The shoes should be molding to your feet. Any discomfort should be waning. You’re nearly there. You can try to complete the breaking process with softening. Essentially massage the heel cup of the shoe by pushing and squashing it. You might also ‘pack’ the shoe with something like a kitchen ‘tea towel’ to ‘open the toe cavity. Take a break between each day of wearing in week three.

Step Four

Your shoes should fit you and be comfortable. You should remember that the Pioneer is a Goodyear Welted shoe and while it has the heart of sneaker, it’s not one. How it performs – and how comfortable it feels – is always unique to you.