1. Best Boots
    #1

    Red Wing Iron Ranger

    The Red Wing Iron Ranger is a boot with enough mythology to be dangerous, but the object itself earns most of it. The leather is substantial, the cap toe gives it identity and the sole can handle actual weather rather than just a coffee-shop floor. It takes time to soften, as good boots often do. Once it does, the Iron Ranger becomes less a fashion choice than a seasonal habit: denim, wool socks, coat, out the door.

  2. #2

    Blundstone Classic 550 Chelsea Boot

    Blundstone’s 550 is the boot for men who want one thing by the door that can manage errands, travel, rain, mud and a restaurant that will forgive them. The shape is plain, the pull tabs are useful and the comfort arrives much faster than with heritage work boots. It is not elegant, exactly, but elegance is not always the brief. Sometimes the best boot is the one that keeps being worn because it makes the fewest demands.

  3. #3

    Clarks Desert Boot

    The Clarks Desert Boot has survived because it is simple enough to be reinterpreted by almost everyone who wears it. The crepe sole, suede upper and ankle height create a shoe that is neither sneaker nor dress boot, which is why it keeps finding work. It suits denim, chinos and light tailoring, especially in sand suede. The charm is informal but not sloppy: a boot for men who prefer ease with a little mid-century intelligence.

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