Yes, that’s 69 pairs of my shoes. This is even after donating a lot, lot, lot before moving abroad. But don’t tell my hubs because if he actually knew how many I had, he wouldn’t let me buy more. And I do need more! I thought I had more than enough from my working career to last me a very long time but may I introduce a new shoe challenge: cobblestones.
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Cobblestones & 69 Shoes: Which wore best?
If you live in an old city in the USA or anywhere in Europe, then you can relate to my shoe problem. My main drag to the city center, heck my driveway, can’t be navigated without stepping on cobblestones. The only way to avoid it is to walk in the street but that’s just suicide. Have you seen how narrow my street is?
Just enough room for one car to go up and down at the same time.
And then there was that time in Rome when we went out to dinner. I wanted to dress up so chose a nice pair of Saks black pumps to go with my Italian leather jacket. When in Rome, right?
I got the calf workout of my life! Not to mention I probably looked incredibly stupid slowly maneuvering each stone in a zig-zag. People likely immediately knew I was a tourist for not walking gracefully like the Italian women that live there or that I had a little too much vino. Likely a bit of both.
Though I found myself wearing Nike gym trainers every time we went to St Albans city center or to London to save me from the annoyance of another Italy repeat, I was tired of wearing the same shoes all day every day. And feeling frumpy. Not exactly my best first 🇺🇸impression when meeting new people.
Sure, my Nike gym trainers are by far my most comfortable shoe of choice but they are not cute. And a girl needs versatility.
I love a sporty look but there needs to be a bit of separation from going to the gym to having lunch with the girls.
Just because I don’t go to a corporate office anymore doesn’t mean I shouldn’t look and feel my best, right? (Rationalizing more shoe purchases.) 👠
What’s in my closet.
I have a variety of shoes from simplistic J.Crew to sparkly Jimmy Choo. Some have seen the ground far more than others, like my Sam Edelman and Cole Haans, and some have never left the box. 🤫
Why? Quite frankly some are just not that comfortable.
I love the idea of Tory Burch but honestly, they aren’t the most comfortable. Zero chance they are going to be great shoes for cobblestones if the carpet is a killer. That brand might never see the light of Europe.
So, what are the best shoes for cobblestones?
Since cobblestone streets are new territory for me, I observe what the locals are wearing to travel to/from the train, shopping, running around with kids, and even work. If anyone is going to know, it’ll be what the locals wear to navigate the cobblestone streets of London and beyond.
London women predominantly wear these top 4 brands.
How do they walk to work, shop and float over those uneven surfaces? What I noticed is that most women wear white fashionable trainers with everything, from trousers to dresses, and then transfer to heels if headed to work or going out for an evening.
The most notably worn shoes are trainers from these 4 brands:
- Veja – British Traditional
Ash – trendy- Golden Goose – super high end
- Nike Air Max 97 – a stylish fitness trainer
The Nike Air Max is reportedly what everyone in London is wearing these days.
But there’s more.
Before you buy new shoes, consider trying everything you own in your closet.
You’ll be surprised what you find if those lids haven’t been removed in a while! And I did have success.
The downfall is that the best shoes for cobblestones, the ones I could walk Europe in, are fairly worn and ready to be replaced. 👇🏻
Best flats for cobblestones…
Pairs in both black and brown.
I purchased mine 9 years ago at Nordstrom’s in Portland, Oregon. Yes, 9 years ago! So yes, I have lots of shoes but if they can last this long, who wouldn’t have 69 pairs of shoes. 😂
Born shoes are classic and go with everything. Born is by far the most comfortable shoe I’ve ever owned. More than just for driving from here to there. I’ve been wearing them everywhere in England, all cobblestones included, and sometimes for a couple of miles at a time.
Best trainers for cobblestones…
Although I considered Veja which is a super popular British choice, I bought 2 other brands to test in slightly different colors: Ash Jordy Python and Nike Blazer. 
Both have been tried and tested on Fishpool Street and a full walking day out in London…over and over again. 👟
The trainer winner: Nike Blazer Low Essential Sneaker
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The Ash is more stylish and trendy with a thicker heel but better for a cool day. And there is a bit of a squeeze between the bridge of my left foot after wearing for a while, so they are not as comfortable.
The Nike Blazer is comfortable on hot and cold days. The only downfall is the slight squeak you can hear which is annoying. However, the squeak does go away after breaking the trainers in. The comfort and look outweigh the noise nuisance (it’s not that loud). I wear them with nearly everything.
Best boots for cobblestones…
After wearing Cole Haan black boots to the point of no repair, I replaced them with the Fairfax & Favor Regina Flat. And I must say, I did a 4.4-mile walk around London’s Mayfair and they were amazing. Pricey but worth it.
And what I love about Fairfax & Favor is the interchangeable tassel. Perfect to wear to support a cause, like breast cancer awareness month.
Cobblestone Winners
Whether traveling to Europe or trying to sort out the best shoes for walking on cobblestones, two things are for sure: Choose Born for classic flats and Nike for a white trainer. You will not be disappointed.
71 and counting. 🥿
UPDATE Jan 2020: Born still ranks as my most comfortable flat.
Looking for more resources about life in the UK? Try these.
- Popular American Shops and Brands In The UK
- 5 Must-Have Kitchen Gadgets For Expats
- Get my FREE guide to help with the SAHM transition 👉here
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