What shoes to wear when travelling?

Personally, the toughest piece of attire to pack for a trip tend to be the shoes. I have to choose a pair that would match everything I’m planning on bringing, be comfortable enough to walk the distance, yet chic enough for my liking. After all my travels, I realize the magic number for me tends to be three pairs (unless of course you’re going for hikes or any other additional activity that would require special attire). And so, I bring you my choices of the best things to put on your feet.

1. Flip flops… but nice dressy flip flops

Let’s not pretend. You’re going to need flip flops when you head into the bathroom or to walk around your hotel/ hostel room. Even if you’re a hardcore Asian who tends to take your shoes off in a house, do not put that much faith in the hygiene factor of your b&b. You should pack a pair that you truly don’t mind getting wet (because you may have to wear these while you take a shower itself), a pair that you can still use when you’re walking around outside and a pair that you could use on the beach as well (assuming you are going to the beach). I find the Havaianas sandals are my best travel friends when it comes to meeting all these criteria. Their soft padding ideal for long walking trips and also molds to the shape of your feet the longer you wear them. The fact that they’re true flip flops means you can get them wet without worrying about things like leather fraying. They’ve upgraded their product even more now making dressy gladiator-like sandals that I can’t wait to get my feet into. Otherwise I would recommend the one’s with back straps to make it easier for when you’re walking around.

Havaianas2(Awesome Havaianas options)

2. Walking shoes

This is an absolute essential, and can make or break your trip. I tend to walk around a lot when travelling. On a vacation, I’ll most likely be on my feet anywhere from 10:00 a.m. until ~8-9:00 p.m. non-stop. I rarely (pretty much never) head back to my hotel again once I’ve stepped out, so I find it essential to have a good pair of flats with me.

There are a variety of good walking shoes out there, but I’ve found the pair that passes the test of time are my Tod’s ballet flats. When buying a pair of walking shoes (even Tod’s) make sure to get one’s with a padded insole. This makes a world of difference. There are a number of cute ballet shoes out there that may seem comfortable without the padded insole. But that decision will come and bite you in the feet on hour tend of your trip. If you insist on bringing a pair that you find cute, you may want to think about getting individual set of padded insoles that you can slip into your shoes.

Be mindful when travelling in these that you may have to take off your shoes and leave them outside when visiting temples or sacred areas. Unless there’s a man that you trust watching your shoes (and perhaps tip accordingly if you’re bringing an expensive pair) you may want to bring a dust bag with you so that you can stuff your shoes into your handbag to bring it around the temple. You should also be cautious as not all locations would actually allow you to bring your shoes inside (even hidden in a dust bag).

Tods2(Tod’s walking shoes)

3. Dressy shoes

When travelling, at most, I would bring one pair of dressy shoes. I prefer wedges that are lightweight and not too high (i.e. nothing more than 2 inches). The same rule applies as walking shoes. Imagine walking in these for 10 hours a day, every other day. Again, because if you’re going to lug these babies with you, you need to make sure you use them enough. Otherwise they’re just dead space in your luggage. Make sure to get one’s with straps that won’t cut into your feet after an hour or so. I personally have loved having my Uggs wedges (I know, Uggs does wedges???) but they have to be the most comfortable pair of wedges I have that still make my legs look a million meters longer.


(Wedge options – R: Ugg wedges, you would imagine that they’re not comfy, but they really are)

So there you have it, depending on my travels I tend to do a pair of each – 3 total. With wedges worn on the plane since they take up the most space. Or one pair of flip flops and two pairs of walking shoes (but making sure they look dressed up enough).

We are living in a fashion era where designers are heading back to flats and low heels. So embrace this fashion period as your best travel friend. I’ve selected a few options here (high end and high street) that I would wear to travel anytime. I actually own the first and third pair of Topshop shoes, and they’re cute AND comfy!


What shoes and how many pairs do you tend to pack? Sound off below!