Chelsea boots are only hard to pull off if they don't suit your lifestyle. What kind of lifestyle is germane to wearing twelve hundred dollar Junya Chelsea boots, you ask? The kind that involves reflecting over coffee at your favorite coffee shop. And by "reflecting," I mean aggressive chain smoking and eating a small charcuterie plate at noon right before you meet up with your friends to sit on a bench and aggressively chain smoke some more in front of a bar that also happens to serve really good french fries. So, basically if you're a rich degenerate that spends money exclusively on frivolous things like Belgian mayonnaise-based dipping sauces for pommes frites and exotic hair pomades, you can pull of Chelsea boots.