I think I can speak for everyone when I say that packing shoes for a trip goes one of two ways:
You do it first because shoes take up the most room, and you’ll know exactly how much space to work with once that piece is covered.
Or…
Formulating an adequate selection is itinerary is stressful, so you wait until the Uber is two minutes away to address it.
This is a non-issue if you operate on a minimalist shoe lineup, but if you’re like me, someone who frequently wears everything from flip flops to cowboy boots, narrowing it down to a select few feels like taking one kid to Disney World and leaving the rest at home to scrub the grout.
I don’t take my ink-soaked passport pages for granted. It took a lot of deep examination of my footwear choices to make them so colorful, though.
With that, allow me to share what I consider to be the most efficient shoe trifecta whether you’re heading one city over for the weekend or fleeing the country altogether.
A Comfortable Athletic Sneaker
Saving the best for last is overrated, so let’s get right to the most important: a comfortable pair of sneakers.
A “sneaker” doesn’t mean much these days unlike a horsebit loafer or rain boot. Jordan 11s and Vans are both described as such despite very different use cases.
My criteria for any travel-worthy shoe follows three main components: style, soles, and upper material. With enough mileage, you (and your feet) will quickly realize that even if one attribute isn’t up to par, you’ll be so fixated on getting back to the hotel room that the beautiful views around you go completely unnoticed.
Style
Believe it or not, a vacay-worthy sneaker is only as versatile as its style.
A good-looking shoe that happens to be comfortable will get you into a snazzy Athens nightclub and hit all the Greek ruins during the day. I wouldn’t count on hiking boots, no matter how supportive, to do both.
I always start with a clean color palette—a white or gray base with one or two accent colors that aren’t neon. I particularly like navy, forest green, or even deep purple are a “blanker” canvas than royal blue, red, or acid green.
Some sneakers have a busy look to them. Pull tabs, reflective material, and a heavy dose of branding can bring an otherwise clean shoe into “hype territory.”
On Cloud is a culprit of this. They used to be my go-to travel sneakers, but like any brand that suddenly became the public’s obsession, the logos got bigger and the designs crazier.
Wolf & Shepherd’s Crossover Victory Trainer encompasses my idea. They follow a traditional sneaker silhouette, but leather accents and mature colorways give them enough character to not need a big logo on the side.
You officially don't need to bring separate gym shoes to work anymore. I think Wolf & Shepherd has recognized that much of business is conducted outside the office these days, and the Crossover trainers are perfect for these more casual environments.
Soles
Smart casual sneakers are one thing, but for traveling, it’s all-day comfort or bust.
The sole is going to be the main stakeholder in that equation, so knowing what to look out for is essential.
If a shoe looks too close to the ground, it probably is. I wouldn’t bank on an overseas pharmacy having a Dr. Scholls kiosk if you’re hobbling around in a pair of vintage tennis trainers with soles no thicker than a White Castle beef patty.
A sneaker with enough cushioning for plenty of sightseeing should have a thick, wedge-shaped outsole made out of one or a combination of cork, EVA (ethylene vinyl acetate), rubber, or TPU (Thermoplastic polyurethane). Both the shape and material will soften the impact of each step while promoting a natural stride.
Custom insoles are another bonus to look out for. I see a lot of shoe brands promoting their in-house designs, but anything above a flimsy piece of foam or fabric is a plus.
Upper Material
I studied abroad in Spain my junior year of college. One of the “walking shoes” I packed were Doc Martens boots.
A treated sole with durable leather should be great, right? No amount of bandages could stop my ankles from bleeding, and my feet stank all the time. They weren’t sneakers, but the message here is the same. Don’t look down on the upper. You’re at the mercy of it.
There are simply too many upper materials, not to mention how the upper itself is constructed, to tell you exactly what to go for. This is the thought exercise I use when I’m scoping the market for new sneakers:
If the upper features leather panels, what kind of leather is it? Top grain is the best money can buy, but it’s stiff at first. Bonded and vegan leather are more forgiving out of the box, but they don’t typically last as long.
For fabric uppers, pay attention to the overall composition—material and the amount of panels used. Other than the heel and side panels, most of a Vans Slip-On’s upper is a single piece of fabric. It lacks breathability and support—perhaps dangerously so if you’re sporting them on the cobbled streets of Rome.
Again, I can’t help but use the Wolf & Shepherd Crossover Victory Trainers as an example. Italian calfskin trim and mesh panels deliver the style, durability, and airflow I’m talking about.
A Dress Shoe
Someone soon to embark on a month-long expedition scaling the Andes won’t need a pair of dress shoes.
Destinations such as Mexico City, Bern, or Cape Town offer metropolitan and wilderness experiences in close proximity to each other. For a place like that, upscale dining or gallery visits call for a proper dress shoe.
Style
Dress shoe silhouettes are diverse, and not all should be treated equally just because they fall under formal attire.
At the same time, dress shoes can blend into most environments unless you’re going with something ultra-formal like a monk strap shoe that doesn’t go with much besides a full suit.
On ski trips where dress boots would stave off snow better than a low-top, my recommendation would be a derby or loafer.
Let’s get more specific. My pick for a true, do-it-all dress shoe would be a light-brown loafer.
Take the Wolf & Shepherd Crossover Loafer in the honey colorway, for example. This shade of brown looks natural with dark and light jeans, whereas black loafers aren’t my first choice for deep-blue denim. Brown leather isn’t held to spring and summer, and neither is black, but anything black can get hot quickly if you’re visiting somewhere warm.
They’re made from soft Italian leather and have a memory foam footbed that’s super comfy. The lining keeps your feet dry, and the durable sole has good grip. What part about any of that doesn't sound exceptionally travel-oriented?
Soles
Men have never been so lucky to live in a time when dress shoes aren’t held to thin, dense leather soles.
Some soles sacrifice comfort for the sake of tradition while others forego “how it’s always been done” for extra mileage. For the sake of travel, I’ll always side with the latter over the former.
This can be a touchy subject among menswear enthusiasts, but even for a leather-sole dress shoe with an orthopedic insert, nothing comes close to a cushioned outsole for maintenance-free comfort.
I’ll use the Wolf & Shepherd Crossover Loafer as an example particularly for travel. First, it has a memory foam footbed and EVA sole—way more comfortable than a leather sole with minimal traction.
Yes, it has a white outsole. However, the edges only consist of straight horizontal lines, whereas other dress shoes I’ve seen with a cushioned outsole so sporty that it looks like a cobbler swapped it from the latest running shoe.
Don’t be afraid to side with comfort over rigid design norms for dress shoes. I tend to over-dress for air travel. If anything, you’ll have a pair of good-looking shoes that can stand up to long lines at TSA or the only edible food counter that’s still open.
Upper Material
Put simply, preserving the handsome charm of a dress shoe is nearly impossible if it isn’t leather. It’s just the way it is.
Velvet loafers, even ones adorned with graphic embroidery, have enjoyed the spotlight in recent years, but an outfit has to be built around them when it should be the other way around.
A dress shoe’s upper material follows the same point I made about sneakers: go for something that balances comfort and longevity. Full-grain leather or similar bonded with a non-irritating lining is good for years of wear without a long break-in period that takes the fun out of seeing a new place.
G.H. Bass Weejun loafers are the starter loafer according to every style page on Instagram and Reddit. My pair look great, but the rigid leather has hardly budged after six months of wear. Unless I’m going from taxiing to and from an event, my feet are in for a bruised, bumpy ride. Certainly a no-go for any trip with even a small amount of footwork.
A Do-It-All Low Top
The “do-it-all” low top has looked a lot different throughout my journey of style self-discovery.
They used to be Nike Air Force 1s for every college party and the fried feast to recover the next day. To seem “with it,” I graduated to a pair of Acne Studios Lace-Up Sneakers once I moved to NYC.
Go for what you’re truly in love with, but less logos and avant-garde motifs better serve my overseas and domestic affairs.
Style
The white leather sneaker is the poster child of this entry. Every brand makes one, and they all look pretty good.
That should say something. I’m not a contrarian, but I wouldn’t deviate from white leather as it’s truly the easiest to work with. Grey is decent, but it looks bland and doesn’t contrast nicely with the outsole.
Put simply, this shoe should be the glue and the grease of your globetrotting. If I wasn’t traversing forested paths or pairing hand-rolled cigarettes with ham croquettes in Madrid’s best tapas restaurant, I needed a dapper generalist to support everything else.
You won’t find much silhouette diversity. That isn’t a bad thing. Options can quickly hinder a quick decision.
Most options on the market draw inspiration from vintage court sneakers—upper material, outsoles, and laces that all share the same color.
I still look for some degree of creativity that isn’t an enormous logo. I’ve always thought that the Cruise Lo from Wolf & Shepherd, with its sleek crease along the outsole edge and a subtle hint of color near the heel, is the right amount of visual appeal to stand out among the commoners.
The Cruise Lo's leather lining is super smooth, and the TPU sole is built for a high step count. They’re made from super soft Italian leather and have a memory foam footbed that handles the gate, hotel, scenic overlook, and back again with ease.
Without this designer-esque approach, a pair of low-tops easily blend in with the Stan Smith, Veja, and Golden Goose models that commodify this style.
Soles
Most options with this silhouette will have a flat outsole beneath them. Anything else loses the minimalist aesthetic that gives them the “do-it-all” factor in the first place.
Anything above the cheapest options will have more than just a rubber slab, though.
Going off of the same example as before, Wolf & Shepherd’s Cruise Lo has a removable memory foam footbed on top of an already premium TPU outsole.
So many low-top shoes have supported my travels through the years, and even if they didn’t possess a double-whammy of foot comfort, the ones with arch support were noticeably better for long walks than those that were truly flat through the sole.
This is definitely something to consider if you have high arches like me, but the main takeaway here is that it’s worth spending a few extra bucks for more comfort tech in the sole.
Upper Material
I might be speaking out of both sides of my mouth on this one, but white leather isn’t the end-all be-all for a low-top sneaker despite it being the industry standard.
Leather is my first choice as I value its durability and easy maintenance, but most fabric options will be more breathable, flexible, and less expensive in most cases.
With all of my criteria in mind, I only recommend going the fabric upper route if the overall shoe looks good enough for a smart casual outfit and has an agreeable sole comfort.
Even for the most in-the-know style summoners, packing always seems to turn the concept of “calm before the storm” on its head. Gone are the days of free checked luggage, so some of us have to get creative with a carry-on and personal item.
This isn’t a hard-and-fast guide, but I’d venture to say that this trio will cover the majority of men’s jet setting and whatever they have planned on the other side.
For intermediate trekking and a solid eight hours of foot travel, a stylish pair of sneakers will be the front line of support with a dash of style for any social moments that should (and probably will) arise.
Dress shoes should be on standby for anything planned that requires your sharpest appearance—the Louvre, a special date with the lady, or a photo shoot she’s planning to have framed. And while they should emphasize class, spring for a pair with a modern sole in the name of comfort.
Finally, a minimalist low-top for everything in between. There’s no shortage of stylish sneakers out there, but I’d veer towards something elevated like Wolf & Shepherd’s Cruise Lo that has an edge over the mass-market options.
Oh, and even if three pairs sounded like a lot, don’t forget you have to wear one on the plane.
