The Best Chelsea Boots for Men Are Tall, Dark, and Handsome

Ask me what Chelsea boot you should get, regardless of price, and I will tell you to buy the R.M. Williams Gardener boot. The simple reason is that it does so many things right that the competitions simply don’t. Off the bat, it’s a real stunner. The silhouette is sleek and chiseled, timeless and fashion forward. The  leather is perfectly suited for a shine and polish to attend any black tie event, but takes on a handsome ruggedness when worn hard. Plus, the quality is fantastic. The wholecut leather uppers are shaped over the shoe last as a single piece of leather rather than several panels stitched together resulting in a shoe that’s as pretty as it is durable. With Goodyear welted construction for easy peasy resoling, you’ll have these Aussie-born boots for well over a decade.

How does a boot originally built for cowboys down under manage to be the best looking dress boot and hardest-wearing rough-and-tumble boot  at the same time? I don’t know, frankly. But there’s no way it’ll be topped. The one sticking point? They’re gonna cost you a few more bones than you want to pay. Considering the versatility and durability, though, the math still makes sense.

Best Budget Chelsea Boots: Beckett Simonon Preston Chelsea Boots

Material: Full-Grain Leather | Colors Available: 5 | Size Range: 7-14

For the budget conscious/the dude looking for his first pair of “nice” Chelsea boots, my answer is easy: Beckett Simonon. Menswear bros might scoff at a web-only DTC clothing brand, but unlike the other brands with infinite marketing budgets looking to “disrupt the entire industry”, Beckett Simonon seems content with making great shoes at a great price, without all the soulless millennial pandering. The Preston, a slick sleek, true-to-form  Chelsea boot, is just the poster child for the brand’s modus operandi. It uses full-grain Italian calfskin, which is lined with Vachetta leather, stitched by master shoemakers in Columbia using a recraftable Blake stitch construction—all for just a shade under $250.

In other words, it’s a Chelsea boot with A-list looks, Northamptonshire-style pedigree, and a price that’s at least half of the competition. But if there’s one thing that will stop most people from buying a pair immediately is, well, you can’t get them immediately. Each pair is made to order which means you’ll have to wait six to ten weeks to get yours. But you know what they say: patience is a virtue.

Best All-Weather Chelsea Boots: Blundstone 500 Chelsea Boots

Material: Leather | Colors Available: 6 | Size Range: 3-14