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Catching Rae

7 Steps to Finding Comfortable Travel Shoes

Welcome to JULY, my friends. Wow, time flies, and I’m sure many of you are getting set to take wing yourselves this summer. I have been hard at work, getting my clients ready for all sorts of adventures, and this month I’m going to share all of our trip tips and tricks. 

By reader request, I’m kicking off the series with what I feel is one of the most essential elements of a happy and relaxed vacation: choosing comfortable, stylish footwear. No one really wants to be immortalized in picturesque vacay photos wearing Those American Tourist Sneakers, yet the prospect of cramps and blisters sends most of us reaching for them anyhow. And to make matters worse, I can’t tell you how many people have sheepishly admitted that their feet hurt terribly in their sneaks while sightseeing, too. 

The thing is that foot comfort is highly individual and activity-dependent. I’m sure we’ve all been sorely (pun intended) disappointed in supposed Comfort Brands in the past. Still, there are plenty of things we can do to reduce the margin of error and really dial in truly comfortable footwear. 


1.Plan to try on at the END of an active day.

This tip is #1 for a reason. I can’t stress enough how important it is to evaluate all your possibilities when your feet are already swollen, puffy, tender, and tired - otherwise you won’t get a good approximation of how a shoe might bother you, because all you will have to work with are theories about comfort. When I worked in retail, I was horrified to find that I needed to buy all my “work” shoes a half size larger to account for 8 hours worth of swelling. Don’t even set foot in the mall or open your Zappos boxes unless you’ve had a nice hard day of walking/chasing the kids/doing your cardio at the gym/etc. 

Photo by warrengoldswain/iStock / Getty Images

Photo by warrengoldswain/iStock / Getty Images


2. Parse your pain.

If you’ve never experienced ready-to-cry-and-or-eat-an-entire-pie-to-self-soothe foot pain, I’ll tell you: there are so, so many different types of pain out there. Just look at’s nifty chart, and you’ll see how many spots can conceivably catch fire. I will also add that I sometimes get pain at the top of my foot called ankle impingement. The image on the right is from my favorite Foot Pain Identifier tool. This tool, for example, helped me get out of the mental block that says “comfy” shoes must be flat. One of the suggestions for ankle impingement was to wear an elevated heel, cluing me into the fact that, for MY foot, I need heels to be comfortable. Similarly, zoning in on your foot pain will help give you a better idea of what shoe you need - wider toe box? arch support? stability for pronation? And so on. It is also super helpful to show a pic to a shoe pro to get suggestions.

Note that for these purposes, evaluating pain that simply comes at the end of a long day, you can probably rule out stuff like fractures and arthritis as the culprits. 


3. Identify your ideal heel height.

Check out this fab write-up from After I realized that I needed a heel, I figured there had to be something out there about the perfect heel - and there is! The idea is that everyones foot “wants” to sit at a certain pitch, and that preserving this natural pitch puts less stress on you. For me, this works perfectly, and I’m not sure if I would have discovered my love affair with 3” heels otherwise. 

To illustrate, here are pics of my personal Most Comfortable Walking Shoes: (left to right) Report Marks bootie, Dr Martens combat boot, and Tsubo Cellini wedge. I have worn all of these shoes for 12+ hours, for activities like tromping around Italy, retail sales days running up and down stairs, and long days sightseeing in Los Angeles.

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4.List other past irritations to avoid. 

Time to get gross! One last thing to do before selecting your shoe dating pool is to remember what kind of... other shoe problems you may have had in the past - and give a good hard think about what to avoid in the future. For example:

5. Amass candidates

Now that you’ve established what you want and don’t want, use this rubric to collect some options that will fit your travel plans and the dress codes you will encounter. 

If you have a ton of foot issues to work around, you should probably start with brands that make comfort the top priority. While you may very well own a pair of Nine West sneakers that cradles you like a dream, the truth is that the ultimate comfort of a non-comfort brand pretty much all comes down to luck, and you may have to roll the dice a lot before you hit Yahtzee. 

Dressy Comfort Brands
Paul Green, Anyi Lu, Me Too, Aquatalia, Stuart Weitzman, Oh! Shoes, Gentle Souls, Ara, Rockport, Cole Haan, AGL

Fashion/Artsy Comfort Brands
Fly London, Bernie Mev, Tsubo, Clarks, Arche, Miz Mooz, Trippen 

Casual Comfort Brands
Crocs, Softspots, Eric Michael, Dansko, Mephisto, Munro, Fitflop, Dr. Martens, Dr. Scholl’s, Helle Comfort, Jambu, OTBT, Sanita

Gear-ish Comfort Brands
ECCO, Keen, New Balance, Kamik, Nike, Beautifeel, Camper, Merrell


6. Finally try the shoes on.

Once you have your options laid out, get your feet in there! Here are a few tips to assess fit. 

Measure both your feet. 
Since you have been standing and punishing your feet before shopping, re-measure those boats. You may be surprised by what you find, and this will save you time in size-swapping. Don’t forget to look at the width. Wear your ideal socks (or lack thereof). Your toes should not touch the end of the toe box, yet there should not be so much room that your foot will slide and wiggle (slide-wiggling causes blisters).

Stand still and walk. 
Foot flesh squishes around when you walk, so it’s impossible to check fit while sitting. Try to reach a good clip when you walk, and try different surfaces if possible. If the salespeople look queasy when you aim toward the hard aisle, see if they might be willing to tape the bottoms to protect the shoes. You need to make sure you can do what you need to do in these shoes, because you can’t bring your entire shoe closet on vacation. Bend your knees and do an almost-hop, trying to drive pressure directly downward. If you plan to stand still for long periods (e.g. museum and gallery viewing) the pressure will fall on different parts of your foot. 

Make sure the footbed touches your entire sole. 
Take a peek at the perimeter of your foot with the shoe on. Have a friend or salesperson take pics with your phone if necessary. If your sole hangs off the edge of the footbed, then the shoe does not fit. Many of my clients make this mistake in heels and sandals, because the shoes don’t feel tight in the arch. But a footbed that doesn’t touch your entire foot cannot support your entire foot. You will eventually feel fatigue and even cramping in your arch/sole. Pay special attention to the arch of the shoe, as your foot may slide forward while standing, placing your arch out of alignment with the arch of the shoe, effectively giving you zero support.

Consider inserts. 
This one is a bit tricky because, just like the footbeds in shoes, not all inserts are created equal. Just like a footbed, inserts also might have arches that sit incorrectly, provide too much or too little cushion, irritate your skin, et al. Instant Arches, created by Santa Monica podiatrist Dr. Steven L. Rosenberg, are a favorite here since there are options that even work with the most skimpy sandals and can be placed exactly in the right spot for your arch. They also have options for sports footwear. 

Confer with Salespeople Wisely
I used to work on commission, so trust me when I say that you have to keep control of a shoe fitting session. Be directive, ask the questions that matter to you, and stay on track with your needs. I don’t care how faaaaabulous he says shoes ABC would look on your feet in Paris; be firm about your hard-won criteria. If the store doesn’t have what you’re looking for, then thank the sales associate and move on - there’s no point in looking at thousands of options once you’ve established that nothing fits the bill.


7. Choose at least two winners. 

Yep, I’m officially giving you permission - if not a mandate! - to buy. more. shoes.

For a walking vacation, even if your general activities don’t vary at all, one of the best things you can do for your feet is to alternate between two completely different pairs of shoes (no cheating by buying two of the same style in different colors). Your battered pressure points will need a rest while other spots on your foot bear the load for a day. 

Whew. That may seem like a lot of work for shoes, but... hey, it’s less steps than 12! I’ve honed in on the process after years and years of buying and returning shoes online in a frustrating process of elimination, wasting tons of money on The Wrong Shoes, assaulting my feet with The Wrong Shoes, and limping around in sneakers all vacation long. 

I promise: it will be worth it. :)