Footloose and Fancy Free Travel Style – How to Choose The Right Shoes For Travel

When it comes to travel, the best way to see almost any destination is on foot. Scrabbling over the ruins of Machu Picchu, climbing the steps to Montmartre, ambling down a dusty road on the east side of Angkor Wat, wandering through the cobblestone streets of Florence; these are all experiences everyone should have at least once and they are only possible on foot. But as wonderful as walking is, if you are walking in the wrong shoes it can make a great trip miserable and a challenging trip unbearable. Now I could just tell you, find comfortable shoes and be done with it, but it’s not that easy. At least not for me.

I have an aversion to shoes that look like they were cobbled for Gumby. You know, the kind that don’t really have a discernible shape and come only in black and a pale flesh color? I understand that some people truly need these shoes and if they are out there doing their thing, traveling the world, in those orthopedic foot pillows more power to them. For me, I have to strike a balance between style and comfort especially when I travel. Thankfully with my personal choices, I don’t have to decide between the two! My way may not be your way, but if it is, keep reading.

These days, with the advances of insole materials and thousands of others, like me, who want style and comfort, there are literally hundreds of options for comfortable yet smart shoes. From flats to booties to trainers, chic shoes have hit their stride and we are left to enjoy the spoils. Below are some styles that I fully endorse for travel (and daily) style. But, before we get to photos, here are my top tips to ensure your shoes are right for your travels.

  • Make sure all your choices are broken in BEFORE you go. Don’t buy a pair of shoes a week prior to your trip and expect them to be comfortable. They may be, but if they aren’t you will add a layer of misery to everything you do.
  • Consider what you will be doing. Lots of walking in a metropolitan area is different from hiking around the back of beyond. Your shoes should fit the locale. My trainers may be suitable for a walkabout in the jungle, but if there are snakes, you can bet I will be in my high shaft leather boots! For me, a good rule of thumb is that 3 pairs of shoes should accommodate all I plan to do. If I know I am going on a beach holiday or 3-day business trip that probably comes down to 2 pairs. Again, your mileage may vary, but for the minimalist packer in me, that works.
  • Plan your outfits to ensure each pair of shoes works with a variety of clothing  options. If you’ve packed properly you can go from beachside burger joint to fine dining establishment with a minimal selection of separates and your shoes should be able to flex to those situations, too.
  • Pack lightly but bring at least two pairs to alternate between. Apparently, from a podiatric perspective it is good to rotate your shoes.
  • BONUS TIP: Take a foot care emergency kit which contains a pair of adhesive heel pads, duct tape (great emergency blister cover/bandage), safety pins, antiseptic wipes, and this stuff!

Okay, onto the shoe parade! In no particular order, these are my choices for the most comfortable and stylish shoes for travel. It feels weird to share my shoe photos with the world, but if it helps one person get more from their travels, I am game so here we go.

1. A good oxford/brogue (there is a difference, but it’s a minimal style element). With durable soles and a timeless style a good pair of oxfords will take you from NYC to Paris to Tokyo and many points in between. This striking pair are from Manolo Blahnik at Barney’s and are simply gorgeous, but I am still wearing a pair of grey suede oxfords from 5 years ago (shown below) that cost me $30 and just walked Chicago in them without issue. Expensive is not always better. My grandmother always had ‘sturdy walking shoes’ as she called them and I thought she always looked so smart in her tailored tweed suit and oxfords, so if it was good enough for her, it is good enough for me! I own the old grey suede and a new pair of patent leather black oxfords. Both provide me ample cushioning for a day about town. I style these with cropped skinnies, rolled boyfriend chinos,  slim cut dresses, and perfectly tailored wide leg trousers. Keep in mind, I would take one of these 2 pairs, not both.

2. A low-heeled bootie. These may be the most versatile travel shoe, because with the right outfit you could dine in an upscale establishment and still meander through the Louvre without any discomfort. I own (and wear the hell out of) both colors of the Basel style of Lucky Brand booties. They are solid, yet flexible making them incredibly comfortable. I got my usual size so there is not a lot of extra room to accommodate thick socks, but I wouldn’t wear these in that kind of cold. I style these with skinny jeans and with tights and skirts/dresses.


3. For rough and tumble travel, I swear by my Timberlands (below) with an 8″ shaft (please move past the oh-so easy innuendo). They have held up to desert temperatures, jungle humidity, and manage to look cute (after a polish) with skinny jeans and a coat for the city. Mine are several years old and I can’t find the same model online but the Frye Carson boots look somewhat similar. These are the heaviest of all my recommendations and typically I’d tell you to wear these during travel to save weight in your bag, but since I am a light packer (and wear a 6) I can get these laid in the bottom of my bag making it faster for those rare occasions when TSA PreCheck is closed or I am in another country where I still have to take off my shoes for the security line. I style these with skinny jeans, hiking pants and tights/leggings under a skirt.


4. A pretty flat. I love my ballet slippers but have yet to find a pair that travels well. There are some that are touted as travel-friendly but lack the sleek profile I want, having instead a thick sole. Those with thin soles don’t work well as every pebble on which you step sends ricochets through your foot. When I want to take a lighter shoe it is usually one of the two pictured below. The black patent leather loafer is the Vama from Anne Klein and it has something called iFlex in the insole. SUPER cushiony on your feet! They are not real leather making them a good choice for warm-ish wet climates. They will smush strangely in your bag, so be sure to stuff them with undies or camisoles. The leopard pair are from Target, probably the Sam & Libby line and I loved them so much I bough all 3 pairs of size 6 in the store and put 2 away. That may be the only non-minimal clothing purchase I’ve made in the past 10 years! I style these with skinny cropped pants/jeans, boyfriend cut chinos, and slim skirts/dresses.


5. Trainers. I have not, and likely will not, jumped on the athleisure bandwagon. I envy the tall who can pull off track pants and Supergas with a continental insouciance but that’s not me. I am much more comfortable in a structured blazer and skinny jeans. That being noted, I have come to love my Converse for their laid back appeal and seeming style fluidity. Not just for the gymnasium, these went mainstream some years ago. There are those who would say these are “basic” in a bad way or no longer de rigueur, but as long as mine remain white I will wear them when appropriate. I style these with skinny jeans cuffed at the ankle and a blazer, short skirts and tees, and beach side apparel.


*Not shown, but ALWAYS packed are a simple pair of  black flat sandals. Used for the beach, dodgy hotel room floors or flooded streets, my sandals are cheap and can easily be replaced when they give up the ghost. They take up less than 1/2 ” in height and about 8″ in length in an exterior pocket of my bag.

I have other shoes that I will pack depending on the trip that are not listed. I may pack riding boots for an autumnal visit back east or pack my espadrille wedges to attend a tropical destination wedding but the theme is still the same – all my shoes are comfortable and proven to stay that way no matter how much walking I may do. For business trip, I will take my black 3″ heels to wear with my suit and will do my best to stay in them only as long as I need to do so (hint: always book a hotel close to the client) and rely on liberal applications of this for those times when I have to hoof it across town.

Remember, I will only ever pack 3 pairs of shoes (plus the sandals) for any one trip based on plans, landscape, and season. If the trip is short, I only pack 2. Another important thing I should note is that ALL of the shoes (except the Lucky Brand Basel booties) have either had heel pads or inner sole cushions (or both) added. I have bony feet and every shoe needs a bit of help so as not to rub somewhere or to give me more cushioning. When you are making your shoe selections, don’t forget that it may take a bit of ‘after market’ tweaking to get them where you need them. While this list is not complete, I hope it helps get you started.

Oh, and gentlemen, most of this list can be adapted to your needs as well. Leave off the pretty flats (unless your like them, no judgement) and the list is the same.

What do you think? Do you agree with my choices? Did I miss any go-to styles? Let me know in the comments!

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