Footwear For Frequent Flyers

There are two schools of thought when it comes to choosing the shoes you wear to the airport. The first school says you put on comfortable shoes that are easy to take off, so you don’t look like an oaf fumbling with laces at security. The second says that you wear your heaviest shoes, the ones that would add a ton of weight and take up too much space in your bag. Generally, I fall into the second camp. I’d rather spend an extra five minutes tying laces than lug around boots, or go without and chance spending the weekend inadequately prepared for that random hike, storm, or spilled ice cream (it’s a serious problem). This is especially a concern during the holidays, when the weather is often unfriendly to your favorite suede slip-ons.

Fortunately, we live in a time when you can both be comfortable and prepared. There are plenty of shoes that can take a beating, but be removed quickly enough stave off a steely glare from the business-traveler-in-loafers standing behind you. From Chelsea boots to shoes that untie in a flash, here are a few tough shoes to get you from your gate to where you’re going without any headaches.

Chelsea Boots

Chelsea boots have enjoyed unique popularity in recent years, but they’ve always been a timeless shoe. The chelsea’s initial popularity was propelled by its streamlined shape, but the trend for bulky shoes has led round-toed, thick-soled chelsea boots to thrive. This is good news for anyone looking for something durable but stylish. Blundstone, the Tasmanian footwear brand best associated with a hippie fan base, has found a foothold among an urban subset. RM Williams, another Australian brand, offers a sort of luxe-cowboy look, and Dr. Martens also makes a chelsea that’s at once sleek and tough-looking. All three feature convenient pull tabs.

Desert and Chukka Boots

Shoelaces don’t have to be your enemy, as long as they’re easily undone. Desert boots are especially convenient, as they typically only feature two or three eyelets. This means they can be easily untied and slipped off. The original desert boot, invented by Clarks, is still a great bet. The suede styles come with a super comfortable crepe sole, meaning that last minute gate change isn’t as inconvenient as it could be. There are also leather styles for more unforgiving weather. Aquatalia makes an offbeat moc-toe version, and Red Wing brings a rugged American sensibility to a British silhouette. 

Zippered Boots

Boots with side zippers or buckles are great options for people tired of chelsea boots, but who still want something convenient. Plus, zippers are often more sturdy than the elastic on chelsea boots, which is prone to losing its shape over time. Frye makes several zippered boots, including their sleek Wright style which features an unconventional but stylish back zipper. Del Toro and Wolverine make models with discrete side zips. All three will go as well with cuffed blue jeans as they will a tailored outfit.    

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For more footwear, check out our guide to keeping your sneakers and shoes looking fresh.