Okay, hey fellow tomboys, don’t look at me like that. If your feet aren’t happy, then your hike is GOING TO BE MISERABLE, guaranteed. Out of sheer stubbornness I wore my Vibram Five Fingers on a backpacking trip one November. We had to do some stream crossings (because OF COURSE we did, there is always a secret stream crossing that you didn’t expect) and after that moment they NEVER dried out. My feet were wet the whole trip. I brought two pairs of socks, but because it was generally misty the whole time those NEVER dried out, and my feet were wet the whole trip. I legit don’t remember much of that trip except that my feet were wet the entire time. It makes THAT MUCH of a difference.

So, I’ll wear my Five Fingers on future day hikes, but maybe not backpacking trips where you want to limit what you’re carrying. For backpacking trips, I wear my Ahnu boots. I got them so long ago I can’t remember if they’re the Sugarpine or Montara model. Whatever they are, they are genuinely waterproof and breathable.

As a section-hiker, here are my key tips for how to pick the best pair of shoes for your hiking/backpacking trip:

1. DON’T BE STUBBORN. Don’t pick a pair of shoes just because you like how they look or a friend told you they LOOOOOVE their pair of Kangaroo Tree Hopper Bullfrog-Skin Skyboots. Okay? Don’t do it. I did it, and all I remember of that trip (reminisced above) is that my feet were wet the whole time.
2. CHOOSE COMFORT. You want your feet to be comfortable. If the pair you tried on is too snug in the toe box, try a different pair. Sure, they MIGHT stretch out, but you’re not going to spend the right amount of effort breaking them in before the trip, ARE YOU? So try pairs on until you find something that makes both feet stretch out and relax.
3. TRY SHIT ON. I feel like this goes with the above tip, but seriously, don’t just order shit online. Go to a store and try shit on. And preferably buy from the store at which you tried shit on, instead of then going online to buy the same shit. Support local businesses.
4. BREAK THEM IN. Spend a mile or two at home, BEFORE YOUR TRIP, wearing your new shoes in as many different environments as you can. This will tell you via blisters whether the shit you bought is going to be comfortable on the trail. Blisters suck at home. THEY ARE TEN TIMES WORSE ON THE TRAIL. Especially when the shoes that caused them are the only things you have to wear.
5. MEASURE TO YOUR ARCH LENGTH. This is a thing that surprisingly most folks have zero clues about. At a proper store, they will have a device called the Brannock device which rather looks like a torture implement but is not. In the right, educated hands (SUPPORT LOCAL BUSINESSES!!) this device can be used to measure 1) your arch length, 2) your toe length, and 3) your foot’s width. There are Mens and Womens Brannock devices. If you are buying a pair of Mens shoes, use the Mens Brannock device for sizing. Likewise with Womens. I don’t give a fuck if you’re a woman buying a pair of Mens shoes because the toe box is always wider or the colors are better, use the Mens Brannock device if you’re buying Mens shoes. Gender is stupid. Hiking shoes are designed to bend where your foot naturally bends, and this region is called your arch. If you measure to your toe length and your arch length is DIFFERENT (which it generally is) then your shoe will be bending at your toe and that’s going to result in painful, unhappy feet at the end (or, indeed, middle) of a hike. If the store you’re at doesn’t know how to use the Brannock device, fucking pull out your phone and Google/Youtube that shit. It’s not hard.
6. HIGH-TOPS DO NOT GUARANTEE ANKLE SUPPORT. In most cases, they don’t provide it at all. Think about it. If the bit that comes up around your ankle is SOFT MATERIAL THAT IS PLIABLE AND BENDS, it is NOT going to prevent you from rolling an ankle. If it’s thick, sturdy leather, then okay maybe there will be some support but you ABSOLUTELY have to make sure that the lacing is done correctly so that the upper wraps around your ankle with COMPLETE CONTACT IN THE BACK AND SIDES. If there is room between your leg and the upper material for air to move around, let alone a finger to get in there, it’s not a good fit and will NOT prevent you from rolling an ankle. Worse, it’ll make you THINK it’ll prevent you from rolling an ankle, which will make you take risks, which will INCREASE your risk of rolling an ankle. True story.
7. WEAR WOOL SOCKS. Wool socks help to regulate your body temperature, they wick away sweat which helps prevent blisters, and they are less prone to getting an odor. Wool is great. If you’re about to comment that wool is itchy, fuck you, that’s what Merino wool is for. (If you genuinely have an allergy to wool, consult your doctor.)

Enjoy your hike!