Ultimate Packing Guide, Part 1: Cute-But-Rugged Footwear
How to optimize the bulkiest items in your bag, for the weekend or the long haul. Plus: the surprising shoes you have to leave behind.
I’m obsessed with making sure I understand what job each piece of clothing accomplishes for me, and doubly so when I’m packing for a trip.
Most critical of all are your shoes. They generally take up the most space of any clothing in your bag, and you have to wear something on your feet every day. So when it comes to packing, start from the soles.
Whether you’re moving to a walking city or just planning to see the sights on your upcoming vacation, here’s the foolproof formula.
MUST-HAVES:
TWO (2) pairs of cute, comfortable sneakers that look good with everything in your wardrobe, and that you can wear on rotation.
That’s it. I’m serious.
You can live with just these two pairs of shoes for any amount of time, as long as you choose wisely. Here are a few criteria to help with that:
Go with two different personalities. For example, one could be a chic white leather and the other, a dark athletic mesh. One could be low-profile and the other, chunky-soled or even a low, comfortable platform.
Do not!! I repeat, do not buy the same pair of shoes in two different colors. Even the world’s most comfortable, broken-in shoe starts to rub a little after twenty thousand steps . So make sure these are two different styles of shoes that fit you in different ways. This way, any budding blisters from Monday can heal while you’re walking around on Tuesday.
Break these puppies in. Don’t wait. They’re going to get dirty anyway, I promise.
I’m under no illusions that everyone is as stingy with the packing as I sometimes am. So once you’ve selected, tested, and broken in your two pairs of sneakers with adorably complementary personalities, you can move on to the next round…
NICE-TO-HAVES:
If you have extra room in your luggage, reach for the following, in this order:
Activity-specific shoes. If you’re ballroom dancing, hiking, snowshoeing, rock climbing, etc., and you can’t rent safe footwear on site… arrive prepared!
Plastic slides. Multipurpose for the shower, the beach, and running to the corner store. They can even stand in as slippers if your room is cold or doesn’t feel quite squeaky-clean.
Water-resistant flat boots. Cheap, combat-style boots that can handle getting wet are the gold standard. If it rains, these will save your sneakers. If you just can’t bear to wear sneakers for one more day, these could save your sanity.
Neutral booties with manageable heels. These are a great confidence booster if you’re taking work meetings on your trip, or going out for a nice meal. They should not pinch your toes, and you should be able to balance in them on a cobblestone sidewalk after three drinks. We’re talking real ride-or-dies, here, not something that will have you calling a cab instead of taking in the sights.
If you have room for all of these, you’re living large. Resist the urge to peek in your closet and see if there’s anything else you can squish into your bag. Leave room for Jesus, or at least some souvenirs.
In a typical fashion publication, this would be the place for affiliate links that send me a kickback when you buy.
I want you to shop your closet first, and your local secondhand store second, so you can be ready for anything without being wasteful. Not only that, I want you to be able to trust me. That’s why I will never include affiliate links.
If you want to support me, I’d love it if you’d subscribe. It’s free!
FORGET-ABOUT-ITS:
What you leave behind is just as important as what you choose to bring.
We all know I have big feelings about shoes, but if they’re not in my top two, three, five… well, then, they have to wait patiently to welcome me home. Sigh. (Shout out to my nude patent ankle boots that didn’t make the cut for Italy. I’ll be back for you!)
Trust me, and leave behind…
Ballet flats. It is so tempting to throw in a pair of ballet flats because they *seem* like great just-in-case shoes. I blame companies that sold folding flats for your purse in the 2010’s, forever cementing them in the millennial consciousness as necessary items. But guess what? This is not even a shoe. It’s actually just a sock that bites. Somehow these provide no protection whatsoever from the hard ground, they’re sweaty when it’s hot, they’re thin when it’s cold, and they give the mother of all friction blisters. They’re a waste of what little space they take up and, honestly, we should probably just burn them.
Anything extremely specific that only goes with one outfit. Your closet in your house is your business. But everything in your travel bag needs to be a Swiss army knife of possibilities. Otherwise, it’s wasted space.
Shoes for your fantasy persona. You know the ones… they were on sale… and they’re just so fun/sexy/sporty/whatever adjective you want to be but feels just out of reach. Anything you’ve never worn in your daily life? Do not pack it. You’re not a different person when you’re traveling. If anything, you’re as ‘you’ as you’re going to be. Trust your past self, and leave the fantasy persona behind.
The final piece is this: When it’s time to pack, keep the biggest, heaviest pair out to wear while you travel. This saves you space and weight for other stuff. So if you made it all the way to water-resistant boots, congrats: chances are you’re wearing those to the airport.
(And if you’re looking at them like, ‘Ugh, too annoying for airport security,’ just put them back in the closet. If you won’t wear them to get to your destination, you’re not going to put them on after you arrive.)
I hope this guide is a useful starting point for your packing. Take it from someone who’s hauled many a pair of unnecessary shoes, and had to buy many a pair at her destination: don’t be afraid to overthink your shoe choices. Nothing will come between you and a great trip like nasty blisters.
Next week: my ultimate guide to packing light and looking insanely hot while doing it. Tested in every season, on three different continents, my one-bag formula is guaranteed to make you feel superior to everyone paying for checked luggage.
Paid subscribers will also get a printable packing list, so if you’re thinking you might want to support this publication… now’s the time ;) Besides, this Substack is a lot cheaper than a checked bag, am I right?