You likely have one pair for when it’s real nasty, real shitty. But, you probably can’t wear them to your desk job, nor could you wear them on a particularly nice date. For that, you need a specialist.
We love a Chelsea boot year-round, and there are nice waterproof (or...waterproof-ish) versions for when the weather takes a turn. Made of supple leather and meant to develop a nice patina over time, Chelsea boots toe (pun intended) that line between stylish enough to wear in more polished settings but also far more functional than your average dress shoe—and there’s that bit of rock-and-roll lineage. They make for great commuter shoes on especially rainy days—good cushioning, good shock absorption, great coverage.
The secret to a weatherproof Chelsea boot is two-fold: First, go for rubber soles, not leather. Leather, though the more formal and fashionable choice, is a porous material. It’s fine to walk through a rain storm in a leather jacket, but on the sole of your foot it’ll soak up water, become soft, and get ripped at by concrete.
And once they start spreading salt in winter, keep leather-soled shoes far away. The second key is to care for your leather shoes. You don’t need to shine them weekly, but keep them clean and apply the occasional bit of shine, mink oil, or beeswax-based seal.
After that, most of these boots will go the same places your rubber duck hunting boots go. For any guys who spent their high school years stomping around in a pair of Dr. Martens, do we have some good news for you.
While that OG pair you saved up to buy from Hot Topic might not totally fly in all offices, the brand’s Embury Chelsea boot certainly well. The shoe keeps things pretty nondescript—save for that trademark yellow stitching between shoe and sole—making it a familiar shoe to graduate into. Williams Craftsman boots earlier this year.
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