Shopping for Travel Shoes

The dreary weather has me longing for sunshine, spring, and bright colors. I feel like I’ve got a case of the blahs, and my accessories aren’t exactly doing it for me lately. One thing that I bet would help (because let’s be honest, it always helps) is new shoes. Not to mention that my feet have grown a bit from pregnancy (thanks a lot Mini Warrior!) and only a few pairs of shoes fit comfortably. Sooooo I have to suck it up and go shoe shopping! No fun at all, right?

For any shoes I buy (and really most clothing too) I look for options that will work for travel, work, and play. Here are my main considerations when looking for shoes:

Comfort comes first! If a shoe is too small, comes up too high on your heel, rubs the wrong way, or feels wrong in any form or fashion I won’t get it, and please, please don’t buy it for travel. If you have to have them, buy them for a time when you’ll be sitting. Even if you don’t think you’ll be wearing them on a travel day, I just don’t recommend it. (True story—I had a pair of adorable shoes that I took on a trip to wear at the office. My meetings ran so late on my departure day that I didn’t have time to change, and in order to make my flight had to run/hobble through the airport—alongside my vice-president—in painful shoes. Not my finest moment!)

Not a paper thin sole. I’ll admit—I don’t always buy shoes with the best support. But one thing I always look out for is the sole. If it is super thin, or if I even think I will be able to feel tiny pebbles on a sidewalk through it I won’t get the shoes. Of course, you can always add a gel sole insert to increase your comfort level. Just don’t try it out for the first time on a trip!

Durability. Take a pass on anything that looks or feels like it won’t last. The cutest shoe in the world can turn ugly if it starts falling apart on a long trip!

Grip. Slippery shoes are not your friend in an airport (or anywhere, really). If a pair of shoes is perfect otherwise, you can have a cobbler add grippy soles to the bottom. Another true story—I have the cutest pair of black quilted ballet flats. They are super comfy and I love them. Their soles are very slippery though, and once while leaving a hotel I slipped and fell. In front of a whole bunch of people. Again, not my finest moment. However, now that my cobbler has added rubber soles they are perfect!!

Heels or flats? You guys know I will always choose flats, but if you can comfortably wear heels I say go for it. Again, just don’t wear a pair of shoes for the first time on a trip.

I typically go for colorful flats, either pointy toe or ballet flats. There are several brands of shoe designed to be comfortable and durable. Dansko, Born, and Clarks are often worn by flight attendants and frequent travelers. Many pairs are very cute, like these blue Marnee ballet flats from Born.

I also love these less expensive options: Mix No. 6 Emely cutout flats and French Follies Addy Flat  (pictured above) in a cheerful yellow and white stripe, both from DSW.

Readers, what is most important to you in travel shoes? Any crazy or embarrassing  shoe-related travel moments?


  1. I was just out shoe shopping today! Looking specifically for Me Too shoes, which I’ve found to be both stylish and comfortable for walking, which we do for long periods of time on often- cobbled streets on our tours and travels. Didn’t find what I needed – the hunt will continue!

  2. Spike heels and sidewalk grates do not like each other! My shoe’s heel got stuck in the grate and didn’t easily come loose. Removing my foot from the shoe, bending down to try to yank it free and not get stampeded by the hoards running to the train station at 5pm was a scary moment. Never again have I walked over a grate with heels on.

  3. I have really enjoyed the Dr. Scholls brand shoes lately. They have an amazing style and are super comfy!

  4. I love my Dansko Clogs. However, I will warn you if you are a prefered traveler with the TSA you will have to take them off. They have a metal shank in them. I also love SAS shoes. Those of you that live in Texas if you are near San Antonio go to the outlets. My favorite Shoe from there is $135 dollars in my local shoe store. But only 80 or 85 in the outlets. I’m planning a 2 day trip to San Antonio just to go shoe shopping. I have expiring FF miles to use so its going to be quick trip to restock my SAS shoes.

  5. I travel mostly for pleasure, not business, these days, and I have finally realized that I need special shoes for travel — the comfiest possible, that allow for walking long distances. Rockport and Ecco are current favorites.

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