The Best Shoes for Flying

Travel has suddenly become a larger part of my life.

It’s a fun challenge to learn how to eat right, work out, maximize mileage, and do a million other things you road warriors are already good at.

One of the unique challenges for me is dressing well while traveling. Since most of my trips are related to the world of menswear, my game has to be on point. And that can be a bit more difficult when it’s all done out of a suitcase and a duffel bag.

Not only do I have to look great, but I want to keep my packing as minimal as possible. It makes the actual act of traveling much easier and mitigates my potential damage if a bag gets lost.

Like many of you, I’ve found that the outfit I wear while I’m on a plane or in a car is often the most important of the trip. It needs to be functional, comfortable, and stylish – three concepts that can often be in opposition to each other.

Which is even more the case with shoes. So today I’m going to give you my new favorite travel shoes and show you how well they do in the previously mentioned key areas.

Click Here to watch the YouTube video: The Best Shoes for Flying

Click Here to watch the YouTube video: The Best Shoes for Flying



The post 9/11 world of flying is trickier and more frustrating to navigate than the world before. We have to go through a lot of hoops to be able to board a plane – one of which is the removal of shoes.

Shoes that are easy to remove can be seen all over the airport. And it makes sense because no one wants to unlace and redo a pair of boots each time they go through security. This little requirement has led to the prominence of flip-flops, slippers, loafers, and sneakers.

At the same time, a pair of shoes needs to be functional. Even in my limited travel, I’ve seen my fair share of hurried traveler who has to double back to grab a rogue sandal which went flying while he was running to make a flight. Shoes do us no good if they don’t stay on our feet.

The maximal functionality is a shoe that is easy to take on and off, while still offering the security and support needed for more than a brisk walk.

This need should knock out most flip-flops, driving loafers, moccasins, and other loose-fitting shoes.


A self-explanatory need – because anyone who as spent 13 hours on a flight with uncomfortable shoes will never make that mistake again.

Thankfully most men don’t have to deal with the same frustrations a woman does. A pair of heels may be easy to slip on and off, but it sure won’t be comfortable while moving around.

While we don’t have to deal with it to the same extreme, we still see some discomfort in overly structured, heavy dress shoes. That goodyear welt is great for durability and longevity, but it sure sucks when a shoe doesn’t flex with the steps of its wearer.

The comfort requirement will remove a lot of dress shoes and anything else that leans too heavy.


Whether you are a casual dresser or fly in a suit, a man who falls on the Rakish side or more Refined, a pair of shoes needs to look good.

You never know who you’ll bump into while traveling and the last thing you want to do is have them distracted by how awful your shoes look.

At the same time, no one wants to pack a pair of shoes for the sole purpose of flying. If you’re like me and travel for business, you already have (at least) one pair of dress shoes, a casual pair, and some sneakers for the gym. Having flight shoes just adds to the stress, weight, and even the cost of flying.

The ideal shoe is something that can dress down as well as dressing up. If it can eliminate one or two of your other required pair, then it’s done its job.

As much as I like a pair of vintage Nike’s or New Balance’s, they’ll never look good with a business suit – which means a traveller needs to find something that works just as well with jeans as it does with a three-piece – no small order.

The Solution

In the past I’ve had to compromise on one of these areas. I’ve worn dress shoes that weren’t easy to remove and weren’t the most comfortable, but they worked great with the aesthetic of a suit.

I’ve worn sneakers and insisted on dressing casually and comfortably while I fly, but changing into a suit in the airport bathroom is worse than flying uncomfortably.

I’ve tried loafers, sneakers, boat shoes, and other slip-ons but never really loved any of them.

Screen Shot 2016-03-17 at 12.09.56 PMFor me, the best solution is a pair of Chelseas

These are so ideal because they hit all the key points. They’re easy to put on and take off, they won’t slip or fall off while running, they’re comfortable all day long, and they look as great with a pair of jeans as they do with a pinstripe suit.

My recommendation is to go with a pair in a brown suede. Suede dresses up as easily as it does down, whereas calfskin can look too dressed up for many casual outfits. Brown is also more versatile than black.

I continue to wear a pair I got from Cobbler Union more than a year ago, but there are a huge number of brands who make some great Chelseas.

They strike the balance between Refined and Rakish very well and cover all my other needs.

So if you haven’t given them a go yet, I strongly recommend you do so.

Don’t know what I mean by Rugged, Refined, and Rakish? Well go check these out.

The Three Masculine Style Archetypes

Rugged Man

Refined Man

Rakish Man


Want to know where you fall into the Three Masculine Style Archetypes?

Take this quick quiz and I’ll tell you. CLICK HERE

Want more?

Your shoes contribute to the story you tell with your style.

Learn the how men throughout time and across all cultures have use their clothing to communicate specific, masculine virtues and tell stories that lead to more success, happiness, and fulfillment.