HIking boots are nice to have. Properly breaking in hiking boots is critical for comfort on the trail.

Look at their feet.

Long ago, in another place early in my career, a co-worker relayed that piece of advice. Her father passed it on to her previously.

What he meant was, if you want to know how someone is faring, check out their shoes. A person trying to make a good impression might get a fresh haircut, press their suit or put on a sharp dress.

But they’re less likely to think of their shoes, at least as a top priority.

If they are new or shiny or well kept or all of the above, chances are they’re doing pretty well, he suggested. If their shoes are worn, well, they’re probably looking to move up financially and otherwise from a place lower on the totem pole.

That might be true, I suppose. I’ve never really worked at testing his theory.

I do know one thing, though.

Feet – or more specifically, shoes – tell the tale at the trailhead.

Look at what your hiking neighbor is wearing. If he or she sports hiking boots that look comfortably broken in, they’re going to be fine.

But the person with stiff, straight from the shelf, never been dirtied by grass or dirt boots? They’ll suffer in short order.

The start of a hike is not the first time to put those boots through their – or your – paces.

But how to break boots in? There are several ways to accomplish that.

Wear them often. And do it long before ever getting to the trail. Start by wearing your boots to work, to go shopping, even around the house. What you’re doing is shaping your boots to move and flex like your feet do.

Wear them together. Together with what exactly? The socks you’ll wear when hiking. You’ll learn what’s comfortable and, potentially, what’s not. If you feel hot spots, for example, tweak your setup or, if worse comes to worse, get different boots.

Decide on insoles. Some people don’t need these. But for others, a good insole – something that can make your foot fit the boot a bit better, and maybe keep it from slipping around – make a huge difference. Experiment to see what help, if any, you need in this way.

Treat the boot. If you’re boots are leather, the uppers will need some tender care. Work a good waterproofer or conditioner into the boots to make them water resistant. That will also soften the leather a bit.

Finally, hit the trail. But even here, don’t go too far too fast. Do a day hike in a local park, carrying a light pack with you. The next time, add a little more weight to what’s on your back. Then, when you head off into the woods in a multi-day trip, carrying your life on your back, your boots will be ready.

More from Everybody Adventures

See also: Backpacking a pathway to outdoor adventure