“Boot Season” is never over when you own a pair of Chelsea boots. There are thousands of variations to choose from, so it’s not hard to find your own. Still, how do you look like you’ve always worn them? The answer is in the quality, shape, and color. You can’t go wrong with one of these pairs. Trust us, we’ve “always” worn Chelseas.
New Republic Man Sand Houston Boot
Nobody makes a better, or more affordable, Chelsea boot than New Republic. The footwear-brainchild of Mark McNairy, the brand is surprisingly tame and expectedly quality-conscious. The boot is comfortable, stylish, sturdy, and lasts forever. Plus, they even look better the older they get. The Sand color will slowly darken and your Chelsea boot will become yours—unique with your own stains and stretch marks. $99
Shoe The Bear Black Chelsea Boot
You need a matte black leather Chelsea boot. No one can wear a pair of shiny Saint Laurent boots around all year. You have got to switch it up. This boot, by Shoe The Bear, is sturdy, affordable, and with time, perfectly matte. $160
Base London Burnished Dalton Boot
This is the right kind of shiny. What does that mean? Burnished Chelsea boots look great with a tux, and a black pair will set you apart from all of the loafers and brogues. A burnished pair of Chelsea boots with jeans or chinos? No. Yet, this pair by Base London is worn in enough to look good with any outfit. $158
New Republic Man Gray Houston Boot
Here’s New Republic on the list again. Their gray Houston boot is just as classic as their sand version mentioned earlier, but with a darker, less standout-ish look. They’re the exact same boot, just a different color. If you could, we’d recommend you get a pair in every color. They’re that good. $99
Common Projects Black Suede Boot
Common Projects is the Ferrari of Chelsea boots. They’re made from the finest materials, emblazoned with their logo, and sold at an outrageously high price. But, if you can afford it, do it; they’re worth every penny. $530
Dr. Martens 101 Gusset Boot
Dr. Martens is famous for their distinct, laced-up silhouette. But, this time they tested their hand at a pair of Chelsea boots. Expectedly, they’re still uniquely DM, but they’re an artful attempt at the Chelsea silhouette. They feature a zipper, eyelets, and the essential, mesh-like material. $145
Good For Nothing Merlot Boot
Have you ever seen a pair of Chelsea boots in such a sultry, silky color? No? Same. But, somehow, Good For Nothing made a Merlot colored boot that works. Keep up with these, though. If you let them get wet, or dirty, that color will not last. Treat this pair like an expensive bottle wine. $81
Selected Homme Leather Boots
Selected Homme has quickly risen up the ranks. Their outerwear is stocked in some of the best stores, but their boots have been relatively unknown. Until now. Their black and brown leather Chelsea boots are of the same quality as their jackets. They’re a fine looking boot with a unique silhouette. A+. $135
Base London Navy Ferdinand Boot
Base London also makes a great suede, dual-colored boot. They call it the “Ferdinand.” It’s outgoing, colorful, and stylishly subdued. These will easily land you the title of “best dressed” in the office or in your friend group. They’re so unique, too, that you could even get away with saying they’re custom. $148
Rag & Bone Spencer Boot
Rag & Bone took the standard Chelsea—suede, high silhouette, rubberish cork outsole—and made it theirs. The “Spencer” features a stylishly high upper, a beautiful gray body, and a high-quality mesh U. This one will cost you, but if we were to recommend any boot—just one that’ll never go out of style—we’d choose this one. $495
