There are so many online guides for what you should buy, but nothing substitutes for experience. Every fall, for instance, I go into the season thinking I should wear my jodhpur boots more often, and every winter, they remain barely touched. I bought a chestnut tan pair from Ralph Lauren four or five years ago, and haven’t worn them more than a handful of times. I blamed their lack of versatility on the color, as I find lighter colored shoes to be harder to wear than dark ones, so I foolishly bought another pair in dark brown (luckily, I didn’t pay anywhere near Ralph Lauren’s retail price). Remarkably, those have been worn even less. The problem is that they can look too distracting when worn with tweeds, and too costumey with waxed or quilted jackets. The only time I’ve seen them look good is in various streetwear ensembles, which I don’t have a good wardrobe for.
So, I’ve been thinking about trading in these jodhpurs for some new Chelseas, which may or may not be as equally useless. On the upside, Mark from The Armoury (pictured above) always looks great in his, and I know a few men who swear by their boots. I can see how a dark brown pair in either suede or calf could look great underneath some jeans, and how a black pair can smarten up some grey flannel trousers. And although I dislike sport coats with jeans, I have to admit Michael J. Fox looks pretty good in his jacket, jeans, and Chelsea boots in the opening to his new TV show.
The best Chelseas I’ve seen are John Lobb’s Chesland and Edward Green’s Newmarket, but I’m reluctant to spend that kind of money on something I’m not sure I’d wear all too often. A bit more affordable are Carmina, Sid Mashburn, and Crockett and Jones, with the last having three versions (model 3 being the sleekest, 5 being the roundest, and 8 being a nice compromise between two). Foster & Son also has a really nice version in their ready-to-wear line. Those still clock in at around $500, which is a lot to spent on something you might not wear that often, but it’s also hard to know until you own them.
(Photos via The Armoury, Esquire UK, AlexHold, Mr. Porter, Sid Mashburn, and Skoaktiebolaget)
