Season Three, the Boot Brand That Snapped My Sneaker Addiction, Is Over

Editor’s Note (12/14/22): Season Three broke onto the season a few years ago with a sneaker-like hiking boot with no break-in period. As of this week, it seems it’s shutting down. (There will be no Season Four, as my editor joked.) But it doesn’t read like the brand is fully closing. Instead, as an email read, “We’re clearing out our inventory to make room for some new projects.” For now, the boots are only $100, while supplies last, of course.

I must confess. I’m not really a boot guy. I know a lot about boots and shoe construction and have rapped lengthily about which boots are worth your time and money. My favorite TV show category is cobbler voyeurism. But day in and day out, my go-to shoes are sneakers. They’re comfortable, they’re stylish and they’re less expensive. Though, if I have a few dozen sneakers, the price disparity evens out, if not totally throws my logic out the window.

Season Three changed that. Founded by Jared Ray Johnson and Adam Klein, the brand’s first shoe (and first-ever product) was debuted on the Paris runway in Reese Cooper’s FW20 show. The nouveau outdoors/heritage aesthetic of the young designer was an ideal pairing for Johnson and Klein whose own brand takes challenges and respects traditional menswear.

Its flagship boot, The Ansel, is made in Northern Italy in a region known for its traditional shoemaking. The two were lucky enough to find a factory that was willing to step outside of its shoebox and take on a young brand with new ideas.

At first, the boots don’t look much different than most other hiking boots — which is the point. The design is classic, if more minimal. Though, not without sounding off a few bells and whistles.

Gerald Ortiz

Maybe the most notable difference is the lining. “We had to push our factory to try new things and they’d say ‘that’s not how we do things,’ but we’d said ‘let’s just try,'” Klein said. The lining is made from 100 percent wool from New Zealand. A wool-lined hiking boot sounds like a shoe you’d only pull out for deep winter excursions, but Season Three uses it because it actually makes it a better year-round shoe. That’s because wool is a great temperature-regulator in the cold and in the heat. It has the ability to insulate, but can also wick away moisture and allow sweat to evaporate more easily which makes the shoes breathable.

Gerald Ortiz

Breathability was also a key factor in deciding upon the lining. Tech-forward hiking shoes like those from Salomon and even heritage brands like Danner often use Gore-tex to line their boots in order to make them waterproof and less breathable. That’s where the merino wool comes in. “One of the issues I had with my Gore-tex boots was that they would get too hot as soon as I came indoors,” Klein says. You might not be the kind of person to leave your shoes on as soon as you get home, but I found myself keeping the Ansels on even if my furthest journey was to the kitchen.

The shoes are waterproof up to a certain point. Though I didn’t test out their 45-minute rainproof claim even though we recently had several straight days of downpour, I inadvertently did exactly what Season Three had intended. “We wanted to make a shoe for the 95 percent of days,” Klein says. “For the days when it’s torrential, most people will just put on their serious boots.” He was right. When sheets of rain were dumping outside, I opted for proper rubber rain boots instead.

Gerald Ortiz

Concerning break-in, the Ansel has none. In every respect, they’re incredibly comfortable straight out of the box. The leather is sturdy without being stiff, so breaking in the toe and ankle was a non-issue. The Vibram Morflex Christy sole is super spongey, lightweight and flexible. Plus, the included ortholite insoles (which are removable, should you need to insert your own) are bouncy and supportive in all the right places. “With every decision we had to make, it came down to ‘is this going to make it more comfortable?'” Johnson says.

Quality, resolable Goodyear-welted boots have a several barriers to entry. Aside from price, comfort and a break-in period are major turn-offs. I’ve parted ways with some shoes because the pain just wasn’t worth it. Season Three has broken down that barrier and made one of the most comfortable pairs of shoes in my closet, sneakers included.

Gerald Ortiz

They’re easier to put on than my Converse high top sneakers. Why? One of the little innovations that makes the Ansel great is a surreptitious one. Hidden at the back of the ankle is a cutout that splits the ankle in two, making it easy to don and doff the boots. That cutout won’t turn these hiking boots into slip-ons, though. You’ll still have to lace them up. But in combination with the easily adjustable D-ring lacing and speed hooks, the cutout takes the Ansel’s ease-of-use to another level, eliminating another boot barrier to entry.

“We wanted to make a shoe for everybody,” Klein says. For the majority of the year, for the largest swathe of people, Season Three’s boot has achieved its goal. For all the same reasons I’ve chosen sneakers over boots time and again, I chose to lace up the Ansel over other boots. If you weren’t a boot person, Season Three’s Ansel Boot will make you one — so, give it a proper sendoff: cop one for old time’s sake.

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