Fashion-Forward Takes on the Classic Chelsea Boot

“None of us got where we are solely by pulling ourselves up by our bootstraps. We got here because somebody—a parent, a teacher, an Ivy League crony or a few nuns—bent down and helped us pick up our boots,” the late Supreme Court Justice Thurgood Marshall once said.

Marshall, the first African-American to serve on the high court, was not talking literally about your beloved Chelsea boots when he offered this observation, the same point that Hillary Clinton made when she said that to realize our full magnificent potential, “it takes a village.” (Oh, Hillary, we are thinking of you and what might have been.)

There is, if you will, a line that can be drawn between your own boots and Marshall’s metaphorical boots, the ones with bootstraps. (Hello, what are bootstraps? Does anyone know?) First off, your chunky-heeled Chelsea boots, poised to take to the streets, must be comfortable! (“You do what you think is right and let the law catch up,” Marshall also said.)

And of course, your footwear should also be fun—ready to withstand an icy holiday night, ready to take on the sad slushy streets, but still looking chic and even, in an offhand way, glamorous. Your Chelsea boots must be right at home sticking out from the bottom of a Batsheva dress as they do accompanying your artfully shredded Levi’s. You can’t go wrong with a classic Frye, beloved for generations, but you might also consider the winter white version from Tretorn, at first blush not so practical perhaps, but it turns out they are waterproof! Or why not a pair of classic black platform numbers from Burberry (thank you, Ricardo!) or seriously-soled Pradas (thanks, Miuccia!) or beige babies from Proenza Schouler (thanks, Jack and Lazaro!)

Whatever you choose, you can stomp into 2020 knowing that even if your head is in the clouds—things may seem dark, but you can dream!—your perfectly-shod feet will remain firmly on the ground.