The Best Chelsea Boots for Winter

Hippie style is making a comeback. At least the shoes look good.

London stopped swinging a long time ago, but Carnaby Street style has survived. Though the mods (except Bradley Wiggins) have modified their look, Chelsea boots have the same rock star cachet they’ve always had. And, this season, they represent a practical solution and sound sartorial thinking. We’ve said it before, and we’ll say it again ad nauseum: Chelsea boots look good with everything, and will take you anywhere, from gala to game. 

Fortunately, labels are refocusing on the sixties classic, creating a modern look that’s as easy to pull off as it is to pull on.

Cole Haan Lenox Hill Chelsea

As all-black makes the transition from popular to de rigeur, having a spot of brightness at one’s base separates an outfit and an individual. The Lenox Hill is fully welted and fully leather lined for a near-impervious boot. [$248,]

Frye Phillip Leather Chelsea

Frye has historically produced boots that might charitably be described as “chunky.” This boot, though, has all of Frye’s solidity, the wooden heel and full-leather outsole, in a sleeker silhouette. [$288,]

Prada Spazzolato Chelsea

This is the dress boot of the bunch: high sheen, tab-free back panel, and a Euro-sharp pointed toe. We’d hesitate to chop wood in these slip-ons, but they should appropriately dress up pretty much every other thing you find yourself wearing. [$760,]

John Lobb Misty Leather Chelsea

With respect to all other boots on this list, John Lobb is the cobbler we trust above all. These boots are flawless, with solid construction, grippy rubber soles, and anywhere/anytime looks.  At six weeks per pair, these boots have plenty of time to age and mellow, arriving in your hands perfectly cured. [$1,295,]

Prada Linea Rossa Chelsea

These are the sportiest of the assembled shoes. Prada sewed on a textured, 1-inch midsole that underpins a contoured and rounded toe—much more plimsole than workboot. While American style is enjoying a renaissance, you’ll never make a misstep in Italian boots. [$690,]

Marsell Leather Chelsea

These are no less than old friends, even bought new. Marsell is known for its subtle distortion of classic menswear shapes, and these boots bear that reputation. The leather around the pull is distressed, and the toes bulge ever-so-slightly, as if from years of wear. Our favorite part, though, is the color: a dark, is-it-black blue that looks incredibly rich, even royal. [$950,]

Dries Van Noten Wool-Insert Chelsea

Dries Van Noten holds up the utilitarian end of this round-up with its wool-lined, rubber crepe-soled work boot. Though rugged, this is a handsome beast with just enough detailing (the boiled wool paneling, the contrasting-color sole top) to keep things from getting too agricultural. [$915,]

Lanvin Panelled Leather Chelsea

Lanvin peddles elegance reliably and with unparalleled quality. These boots seem organic, of a single skin, with the only visual contrast coming with a rear panel of pebbled leather. [$790,]