The first time I got fitted for hiking boots, I found out two things about my feet that have forever changed the way I shop for shoes of all kinds. First, I learned that my toes are disproportionately large for my feet. That was something I had guessed, but knowing it led to another discovery: Because of my toes, the flex point in my foot rarely matched up with the natural flex point in many shoes. That meant that with every step, my feet were fighting against my shoes to flex as they naturally would if I were barefoot.

The footwear “guru” at Eastern Mountain Sports that day suggested I try a lightweight pair of Oboz’s Sawtooth Lows, whose laces started closer to the toes and therefore allowed my foot to find its own flex point. It was love at first fit, and I wore them into the ground.

Suffice it to say, I’m a huge fan of getting measured by an expert and having them pick out shoes for you rather than guessing which boots might match the shape of your foot.

To get a better understanding of what goes into the perfect fit, and what hikers should ask when searching for the holy grail of boots, I reached out to Oboz and connected with Dave Dolph, who travels the country training gear shop employees on boot fitting. He explained that part of the reason I found such success with Oboz is that they start with a supportive “O-Fit” insole, and build the rest of the shoe around that. This way, hikers get a better fit right out of the box rather than having to also hunt down after market arch supports.

I asked Dolph what we need to know about our feet and how to shoot for success with the fitting process. Here’s his advice.

How do you find the right boots for you?

Invest the time to go to a specialty outdoor retailer for professional advice where the staff has the training and tools to find you the best match. Don’t rush through the process. Be open to suggestions. They should ask where you’re hiking, how far you’re you going, what kind of load you’ll carry, whether you have any injuries, and what the terrain’s like. This will help determine the best boot for the job.

The whole boot fitting process boils down to finding the internal shape of a shoe that matches the shape of your foot. A boot fitter will measure and evaluate your foot, then pull pairs from their selection that best match the shape of your foot. Then, it’s your job to narrow down which one feels best for you.

How do you know how much support your feet need?

If you have serious foot pain or plantar fasciitis, consult with a medical professional. But for people who aren’t experiencing acute problems, a specialty retailer will have the knowledge to guide how much support you need. They will consider: the terrain you’ll be hiking, the weight you need to carry, your arch height, whether you pronate or supinate, and the type of shoe construction that would best meet those needs.

As you go through the fitting process, pay attention to the insole as well. Adding an aftermarket insole, such as the Oboz O FIT Insole™ Plus, can provide additional support and comfort if the stock insole doesn’t provide the fit you’re looking for. Make sure you consult a sale person to get the proper fitting insole based on your foot.

How do you know the boots fit you?

Once you’ve gone through the fitting process with a sales person, you should walk around the store for 15 to 20 minutes to test the comfort, support and fit. Pay attention and sense if you feel any hot spots and heel lift when you flex into the front of the boot, make sure the boot flex points align with the flex points of your foot.

Fit Tip: make sure there is enough space to accommodate for foot swelling and to prevent toes from hitting the front of the boot during descents. You want about a thumb’s width between the end of your longest toe and the end of your boot, even when you’re walking downhill.

As you’re walking around the store, see if you have any points of irritation or hot spots. Full leather backpacking boots are going to need some break in, so you’re going to have to determine if any irritation or pressure points are coming from areas that will break in. Leather has about a 5 percent stretch. The retailer may be able to modify the boots for you and stretch them a little bit.

What questions should you ask during the fitting process?

Ask to have both feet measured. You want them to measure you seated, standing, overall foot length, arch length, and width. This will give the salesperson the information they need to determine which shoe will fit best. It might be helpful to call in advance to ask if a boot fitter will be in before you go.

You should also ask about the boot construction. The upper, insole, midsole and outsole work together as a system to provide the proper support, comfort and fit for the best performance. Lastly, ask if the shoe comes with a supportive insole. A proper fitting insole maximizes stability and support with goal of placing the foot in a neutral position.

Any final words of wisdom?

Head to a specialty outdoor retailer during off hours, they’re typically not as busy and you’ll get lots of attention. Go in the afternoon, when your feet are swollen, to get the best measurements.

Be willing to be surprised by the answers you get. Your feet might not be the size you thought they were, or they may not be as narrow or as wide.

Footwear is all about tradeoffs. You’re choosing something that’s either really stable and supportive, or something that’s really lightweight. It’s hard to get everything, so it’s important to consider materials and longevity.

And don’t pick shoes to try on based on what they look like. The color and design are irrelevant [to the function]—you’ve got to be willing to detach yourself from aesthetics. 

Oboz footwear is written in light green text on a white background.