How to Plan Your Shoes for Travel

If I could give you just one packing tip, it would be this:  Plan around your shoes.  You will see more, do more, enjoy more, burn off more of the delicious cuisine you’re sampling, and get more for your money if your feet don’t hurt.  Here’s my tried-and-true method:

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Day of Travel Shoes:  1 pair 

I live in sandals as much as possible, and they’re my first choice for shoes when I’m on the move.

My go-to brand is Munro; their shoes are moderately priced and downright cushy.

If I need a closed shoe, I’ll likely go with a flat like Tommy Bahama‘s super-soft “Relaxology” slip-ons.

If snow is likely, I’ll put on sturdy boots like Stuart Weitzman‘s low-heeled “Britain Suede”.

I try to stick with black because it won’t show any scuffs that might happen while travelling, and will always go with the Tory Burch tote and ECBC backpack that are my go-to carry-ons.

Carry-On Shoes:  1 pair  

I didn’t learn my lesson in my 20s when USAir lost my luggage on the way to my then-boyfriend’s law-school graduation, to which I wore the jeans I’d flown in and one of his pull-overs.  He spent the day introducing me as “my girlfriend Leslie, whose luggage the airline lost”.  (I didn’t marry him.)  But in my 30s, after United lost my suitcase on the way to a job interview, to which I wore the cotton pants and turtleneck I’d flown in, I learned my lesson:  Always bring spare clothes and shoes in your carry-on.  (I did get the job.)  If I’ll need dress shoes, I rely on medium-heeled pumps; Tory Burch‘s are surprisingly comfortable.

If the trip is super-casual, I’ll go with something like reasonably priced Coach slip-on sneakers that can keep me active while the airline searches for my bags.

I veer toward keeping these black as well for simplicity’s sake.

Day-to-Day Shoes:  1 or 2 pair  

I do a lot of walking when I travel.  Depending on the length of the trip, I pack one or two pair of shoes I could wear from breakfast till cocktail hour.

My go-tos are Munro sandals or booties, Cole Haan penny loafers, or lace-up sneakers like cute Kate Spade‘s, depending on the expected weather and my plans and what’s already slated for my carry-on.

I try to keep to black and only one other color, so that I only need to pack one additional coordinating shoulder-bag.

Specific-Need Shoes:  1 or 2 pair 

These are shoes called for by specific activities.  I won’t wear them all day, but I’ll miss them if I don’t have them.

For fitness, I bring my Skechers cross-trainers, which have a removable foam insole for extra cushioning.

And if I’m going to a beach, I’ll tuck in a pair of flip-flops, like my grey Gurus.

On the other foot, plans might be on the itinerary that put me in the mood for something ultra-impractical, like 4-inch heels by Calvin Klein.

Once your shoes are planned, you just have to coordinate your clothes and accessories with them, and you’ll always have something appropriately comfortable on the road.  And you’ll have a much better time.