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It’s just about time for us to hit the road (skies) again, which always has me mentally preparing for what will fit our carry-on only travel style before it’s actually time to pack. The most frequent question I get about packing for an extended trip into a small roller bag and backpack only is: How do you fit all your shoes? I’ve been thinking about what shoes I’ll need for the UK in May lately, so let’s size this up, shall we?

Gordon tartan women's flat shoes and traditional black lace-up men's shoes are not great for the UK in May
Shoes from our Vow Renewal in Scotland – Photo by LJF Photography
The struggle is real, friends.

As a self-proclaimed sometimes fashionista (I do own a women’s clothing boutique after all, but also a farm, thus the “sometimes”), this is something I have struggled immensely with for YEARS. So often shoes make the outfit you’re wearing better, and who doesn’t want to just knock it out of the park!? *Jason raises his hand* However, I’ve realized that when you travel, you’re there for the experience, or at least we are. If you’re forcing your feet into shoes that are even the tiniest bit uncomfortable, or trying to shove another pair into your bag that will only go with ONE outfit you’ve packed, you’re taking away from the joy of that experience. No one wants to lug around a bag of shoes, and no one wants blisters. Which reminds me, pack big Band-Aids, because you never know. So, this really is a situation where function and comfort are more important than fashion.

An example situation.

Since we are first headed to the UK, let’s talk about how to get your feet from the soggy cobblestones of Edinburgh to the unpaved, swampy, and rugged Highlands of Scotland and then finally landing yourself on the fashionable streets of London in May – aka rainy season. Somehow, we’re going to manage it without tracking in mud from the highlands to London. That’s the goal, anyway.

The plan.

I’m planning three pairs of shoes for this trip – waterproof sneakers for city walking and tours, waterproof boots for highlands hiking, and flats for dinners & shows (not waterproof, so there’s a good chance I’ll have soggy feet for a few hours). I’ll be skipping sandals for now since the forecast looks like rain every day and it’s still a bit chilly in May. Here’s my line-up:

Jason’s line-up looks slightly different. He’s only planning on two pairs of shoes and forgoing the hiking boots. Looks like I’ll be hiking alone or he’s going to be borrowing some Wellies from the hotel. His lineup looks like this:

There’s a good chance our lineup could change a bit once we start packing, but this is generally the plan. I may substitute a pair of waterproof ankle boots instead of flats as my dress shoes if I end up taking all pants instead of dresses, which is likely. I’m waiting for a closer inspection of the weather forecast. If that’s the case I’ll be taking these instead in a waterproof (discontinued) version – Born McKenzie Booties.

Our Recommendations

If your trip to the UK has you sticking to the cities, you can skip the hiking boots. However, if you plan any adventures into the wild, especially during the rainy season, we highly recommend them.

We also recommend never trying to do a trip with only one pair of shoes. This is one place you shouldn’t try to be an overachiever. Always have a backup in case one pair breaks, is sopping wet, or is just rubbing your feet wrong. Your second pair will almost definitely feel different from the first and give your feet a break from any places that are bothering you.

It also helps to figure out what you’re planning to wear in conjunction with your shoe selection. For example, you probably don’t need to take both brown and black shoes. Instead, pick one and then find clothes that go with them. Traveling with one color family of styles makes packing so much easier – it’s all mix and match! Unless you like mixing black and brown like I do, go for it!

Whatever you choose depends largely upon your style, but always keep in mind comfort. If you’re anything like us, travel generally involves a TON of walking. If you end up with blisters on your first day, it’s going to be a long trip. Trust me, I know. Also, heels and cobblestones aren’t exactly a perfect pairing. Just leave them at home.

Packing it all in.

And now, packing. Always wear your biggest and heaviest pair of shoes on your big travel days. Whenever we bring hiking boots, this often means I’m wearing them on the plane. I consider this a huge bonus because my hiking boots are the most comfortable shoes I own. They even run through the airport quite well. This usually means the weight of those shoes is, well, at your feet and not on your back. Having TSA Pre-Check makes this easier as well, because you don’t need to remove your shoes when going through security.

This leaves you with only two pairs of shoes to pack on this trip (or one if you’re the overachieving husband) – fit them in how you best see fit. One of the reasons I try to take flats is they pack down very small and weigh almost nothing. This is also the reason I chose very lightweight sneakers. You can also pack socks (merino wool – trust me) into your shoes or anything that needs a little extra protection to avoid a dead space in your bag. Use every possible inch! There are also clips you can use to hang your shoes off the outside of your backpack; we’ve seen people using them but haven’t explored them ourselves…yet.

That’s it! Have a great trip, and maybe we’ll see you over there. It is our favorite place after all!

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PLUS - We'll send your our Essential Carry-On Packing List for less stuff and more adventure!

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