A Love Letter to the Shoes That Never Let Me Down

Astorflex Greenflex suede leather chukkas

A Love Letter
to the Shoes
That Never
Let Me Down

These Italian-made chukkas are
extremely comfortable and wildly versatile

Like any good love affair, it began with an introduction by a trusted friend. A few years ago, I was visiting the Huckberry headquarters in San Francisco when the topic of shoes came up. The buying team had just returned from Italy and Ben O'Meara, who heads up the brands team, was telling me about this great footwear brand they were bringing to the States. "I think you're really going to like them," he said. "They're right up your alley."

It turns out, Ben was right. Because he was talking about Astorflex, the family-owned business that's been making classically handsome footwear in Italy from healthy, eco-friendly leather and natural rubber for six generations. Not only did they boast the kind of high-end quality construction that's synonymous with Italian shoemaking, they were also incredibly comfortable right out of the box.

A closer look at the brand's signature Greenflex chukka reveals even more reasons to love them. The suede is made from premium European leather that's aged for 30 days in an all-natural mixture of water, oak bark and powdered mimosa. It's then softened with all-natural ingredients (no toxic chemicals or solvents) to produce a suede that is as supple as it is sustainable. The smooth leather lining is undyed and the footbed is expertly crafted for ergonomic comfort, molding to your foot over time. Even the classic crepe soles are made from natural Hevea brasiliensis rubber, responsibly harvested from Brazil.

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How Astorflex men's footwear is made

The boots being crafted at Astorflex's family-owned factory in northern Italy.

All this care and ethical craftsmanship would, I'd assume, add to the cost. And you could feel good about investing in that kind of mission and quality. But surprisingly, these chukkas cost a little less than half of what I was willing to shell out for them. I picked up my first pair and wore them ... All. The. Time. Not everyday, but most days. And whenever I didn't know which shoes to wear, they were my go-to. That's because they tick all the right boxes for a shoe that scientifically works in any situation.

Honestly, they've never let me down. I've worn them everywhere. And I mean everywhere. To a posh garden party in London and through the dusty fields of Coachella. They've served me well trekking through the agave highlands of Jalisco and later pounding back tequila in a tony Miami nightclub. They never look out of place. You can wear them with jeans and chinos, with dress pants and even with the right kind of suits.

Getting a new pair of Astorflex Greenflex chukkas

The author, wearing his old pair as his new pair arrives.

Getting a new pair of Astorflex Greenflex chukkas

The author, wearing his old pair
as his new pair arrives.

As an ankle boot, you might think these have a more cool weather sensibility. But desert boots were designed for British soldiers stationed in Egypt during World War II, so the lightweight boot actually works well in the summertime. I've worn them with shorts, and they look pretty damn good. That's because they're classic and timeless, yet when you're wearing them with the latest gear, they somehow suddenly look more current.

I wear these so often, it borders on the verge of pathological. The crazy thing is, I'm only on my second pair. The first pair got me pretty far, but recently I decided it was time to trade them in—same style, same color. Ironically, the new shoes arrived while I was wearing the originals (see above). After a quick, but dignified "changing of the guard" ceremony in my living room, I retired the old pair and am ready for all the places my tried-and-true chukkas will take me.

Greenflex chukka, $150 by Astorflex

Astorflex Greenflex chukkas

Take Care of Them

Suede's soft, textured finish means you don't treat it like other leathers. It's not difficult to maintain, you simply need to know what works best. Here's how to spot clean, waterproof and refresh your suede.

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