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After a whole lot of research, here’s what ended up helping him not just survive a walk circumnavigating the entire island of Manhattan — but thrive.

In preparation, we did a ton of research on the most comfortable walking shoes, the best athletic underwear for men and more. Matt walked for over 12 hours and covered 35 miles by the end of the day. Miraculously, he only got one blister and kept all his toenails! Keep reading to see the essential items that helped him survive walking further than a marathon.

After a challenging training walk in a pair of standard boxer briefs, finding a good pair of compression shorts became level one critical. We found an Under Armour pair that was at the top of every list. He wore them for the entire 32 miles and experienced minimal chafing and discomfort. 

The Under Armour HeatGear Shorts are designed for intense activity with integrated mesh panels for ventilation and flat seams that are cleverly positioned away from delicate areas.

Promising review: "I love these, they are perfect for running, I have an iPhone 16 pro max and they hold my phone in the thigh pocket perfectly and it doesn't bounce around at all. They are very durable, as expected after a few years they start to tear, but I trained for 3 half marathons, 1 marathon, an ran about 40-50 miles per week for 2 years before the first pair I bought became unusable, so I’d say it’s easily worth the price and a high quality product as always from underarmor." —Nick McCarty 

Get it from Amazon for $24.99+ (available in men's sizes XS–4X, in tall fits, and 11 colors).

The most important decision was choosing a pair of sneakers that could support Matt's bad knees and flat feet. We went to a running store in Brooklyn and were steered towards the cushiony and high-support Brooks Adrenaline GTS 25s. Matt wore these shoes every day for two weeks before the big day so they would be fully molded to his feet. The best review we can give is that after 35 miles of walking, he had only one blister!

There's no sneaker that prevents soreness after 32 miles, but this Brooks pair prevent significant damage. Plus, he had almost zero pain after practice walks up to 12 miles.

Get them from Amazon for $133.73+ (available in men's sizes 7–16, with wide, narrow, and x-wide options, and 17 colors).

Between his AirPods, phone and Apple watch, Matt had a lot tech to keep charged over the course of walking for 12 hours. That's why we set him up with this lightweight power bank that has built-in micro, USB-C and lightning cables. It is so convenient to charge it by just plugging it into the wall. By the end of the walk day, the bank miraculously still had some juice. The power bank is about the size of an iPhone, so it didn't add unnecessary weight to his bag. 

Get it from Amazon for $26.99+ (available in five colors).

Long distance runners told us that socks are almost as important as shoes. The right socks can limit blisters, manage moisture and provide another cushion against impact. Matt chose the Feetures High rerformance socks and immediately felt the difference from his regular socks. We're calling these game changers because of the lightly compressive band around your arch and the blessedly seamless toe. 

Promising review: "These are my favorite socks OF ALL TIME. I wear them anytime I am going to do any amount of real walking - they hold up to tens of thousands of steps at Disney World. They are reinforced in all the right places, especially the TOE. For me, have shoes pinch my toes after lots of walking is the worst - this goes a LONG way to prevent that entirely. They are pricy but so worth it." —Caitlin Jeansonne

Get a three-pack from Amazon for $45.60+ (available in sizes S–XL).

We didn't want to spend $90 on a CamelBak, so we chose this 2-liter model on Amazon and it was perfect. The straps comfortably fit across his chest, so the pack hardly shifted during the entire walk. Plus, the extra pockets meant he didn't have to carry any other bag. His 32-ounce water bottle (filled with ice) fit in the side pouch.

Promising review: "Great backpack, highly recommend! I got it to hike Arches and Canyonlands National Parks, hiked 11 miles in each and this backpack worked great. Size perfect to carry enough stuff (sunscreen, water, etc) but lightweight. No leakage. Water flow system worked well." —Danny Brambilia

Get it from Amazon for $28.99+ (available in 11 colors).

When a Great Saunter alum told us to buy "moleskins," we weren't so sure a chic notebook would be helpful. Turns out that the premium blister prevention strips are made by Promifun. These are recommended by Shorewalkers, the group that sponsors The Great Saunter, to relieve hot spots on your feet and ankles during the walk. The latex-free strips come in four shapes that are easy to contour on your skin.

Matt used one on a painful blister that popped up around mile 20; it cushioned the tender area and never fell off.

Get 24 sheets from Amazon for $9.99 (also available in black and in packs of 48).

Chafing is an unfortunate reality of any intense physical activity. The thought of that kind of raw discomfort at mile 18 of 32 was unbearable, so Matt got Squirrel's Nut Butter. It's an anti-chafing salve that is made with coconut oil, cocoa butter, beeswax, and vitamin E. You apply it like stick deodorant wherever on your skin you're prone to hot spots.

After some practice walks in less than ideal clothes, Matt used this to soothe irritated skin.

Promising review: "This stuff is the smoothest and the best for avoiding chafing. Love how all natural this is too — no major smells and non-greasy too!" —L. Ziobro

Get it from Amazon for $9.99+ (available in four sizes).

We originally bought these Lululemon pants after a particularly sweaty summer going to work. One of his friends recommended these for golfing because they're breathable, offer full range of motion and look business casual. My boyfriend now owns three pairs and exclusively wears them to the office, which is why he was in them for a 12 mile training walk that he did after work one day.

Obviously, he preferred athletic shorts, but the Lulu pants were remarkably comfortable for three hours of walking. 

Get them from Lululemon for $138 (available in men's sizes 28–46, five lengths, and 13 colors).