Shoes To Travel By
- Brian Robinson
- Jan 3
- 4 min read
Traveling Overseas? What Shoes to Take?!
The holiday season is, hands down, the biggest travel period of the year for many people. I have several trips planned between December and February, and I’m getting excited.
My most significant trip is a two-week visit to Portugal in January, and I’m already thinking about what shoes to pack.
A confession: despite having visited 40 countries across 5 continents, I’m a habitual over-packer. I get really excited before trips to Europe or Asia. About a month before departure, I start envisioning all the posh hotels and fancy restaurants I’ll be visiting. However, reality rarely meets my lofty expectations, and I inevitably pack shoes and clothes I never wear. This wastes precious space and adds unnecessary weight to my checked bag. Yet, somehow, it keeps happening.
So, let this be a classic “do as I say, not as I do” situation. Learn from my mistakes!
I’m also a big shoe lover. I have about 75 pairs in my collection: formal shoes, dress shoes, slippers, athletic shoes, beach shoes, boat shoes, snow boots, Chelsea boots, loafers, cowboy boots, Wellington boots, hunting boots—you get the picture. Deciding what shoes to take is always a dilemma.
Let’s Talk Shoes for Travel
Your choice of footwear should always be tailored to your needs and preferences. Everyone is different. What follows is what works for me, based on my travel experience and lifestyle.
Start with the Basics
I typically take at least one pair of casual leather loafers and a pair of Oxford/Derby shoes.
Pro Tip 1: Whatever shoes you take, make sure they fit. There is no substitute for a proper fit, and few things are as uncomfortable as wearing poorly fitting shoes on a trip. And never break in new shoes while traveling—it’s never a good idea.
Once you’ve selected your best-fitting shoes, consider your itinerary and environment.
Will you be dining out at nice restaurants or attending social events?
If yes, plan to pack at least one pair of nice leather shoes. A quality pair of loafers works for me in most instances. Bonus: loafers are ideal for airport security—slip on, slip off, no hassle. For those who prefer the no-socks-with-loafers look, I’d suggest socks for air travel. Walking barefoot on airport carpets or airplane floors? No bueno. Nobody needs to see that.
I also pack a pair of brogue type shoes as a backup for more dressy occasions. This pair often goes unworn, but if I need to elevate my look for an evening in a tweed jacket and tie, I’m ready. This loafers-and-brogues combo works well for performances, informal social gatherings, and visits to places of worship where dress codes may apply. It gets the job done.
Will you be doing a lot of walking?
I’m fortunate to have healthy, pain-free feet and can wear leather shoes for almost any activity short of a 5K run. Well-made leather shoes should be comfortable for extended wear. Ill-fitting ones? You’ll feel the discomfort before you leave your hotel. For example, during a recent trip to Geneva, I walked several kilometers a day in second-hand Edward Green single monk straps, and they felt fantastic.
On another trip to Kyrgyzstan in 2016, my wife recruited me for an unscheduled hike to a national park outside Bishkek. The only shoes I had were English-made Brooks Brothers Peal & Co. Oxford Brogues. I ended up hiking for three hours, much of it crawling up steep grades.
In the Peale & Co. shoes below…
Amazingly, the “wrong” shoes held up, and I escaped injury.Still, this isn’t a choice I’d recommend if you know a hike is in your plans!
What about sports shoes?
While sports shoes are comfortable, I avoid wearing American athletic wear while touring overseas. It’s a personal choice, mainly for security reasons. A pair of On Running Shoes paired with a Minnesota Vikings T-shirt is like wearing a neon sign that says “American.” It draws attention I don’t want.
What’s the weather or climate like?
Shoes that fit perfectly with thin summer dress socks, or no socks, in Florida might not fit as well with heavier winter wool socks in Scotland. Plan accordingly.
For rainy destinations, prepare for wet shoes. It’s no fun putting on damp leather shoes the morning after a downpour. A backup pair is essential. Treat your leather shoes with a good conditioner before a trip to help repel water.
If traveling to cold snowy locations, winter boots are a must. Wear them on the flight to save suitcase space.
Pro Tip 2: When packing shoes, leave the shoe trees at home. Instead, stuff your shoes with socks, undershirts, or underwear to maximize space. Packing an empty shoe wastes valuable room.
I hope this helps you start thinking about what shoes might work best for you on your next journey. Pack well, pack light (unlike me!), and enjoy!
Travel well!
Brian Robinson
IG: @cwoodcockandco
Over 35 years, working in industry and government, I’ve curated my experience in a way that brings a singular perspective to my pursuits.
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