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3 Pairs of Men's Shoes That Got Me Through 10 Days in Tuscany With Only a Carry-On

Updated: Feb 5, 2023

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With airports still overwhelmed and understaffed, overseas travel can feel a bit like rolling the dice; I’m sure we all know people who have had luggage lost while traveling over the last few months.

When it came to packing my bag for an old friend’s wedding in Tuscany, I couldn’t help but think of another friend who had to wear flip-flops with his suit when his luggage was lost en-route to Greece — and I certainly didn’t want to replicate that look.

My solution: Packing only a carry-on, ensuring I had full control over the whereabouts of my bag. There is something satisfying about traveling without a checked bag, cruising past those long check-in lines straight into security and beating the rush to the taxi line at the other end while everyone else waits for their bags to finally arrive on the carousel (if they arrive).

The biggest dilemma, however, was trying to work out how to squeeze the range of clothing needed for the variety of activities we had planned for our 10 days in Tuscany, from lazy afternoons on the coast, to truffle-hunting in the forest, to the wedding itself.

The biggest (and heaviest) problem was clearly going to be footwear. There was no way I would be able to narrow myself down to “one pair fits all activities”, so I had to be strategic. My main priority was not to have to pair my suit and tie with flip-flops, so the first shoes to make it into my bag were my Tod’s.

Tod’s Gommino Driving Shoe

The Gommino Driving Shoe is a timeless classic that can be dressed up or dressed down — in leather or suede — an ideal partner to my navy suit and a great evening option to wear while exploring the bars and restaurants which line the cobbled streets of Florence. They’re also incredibly soft, lightweight, and easily packed into carry-on luggage.

Reef's Cushion Phantom Flip-flops

My next decision was to select from my vast collection of flip-flops. Having recently purchased Reef’s Cushion Phantom flip-flops after being drawn to their “squeeze me” sticker, I don’t think I could have chosen a more comfortable or versatile flip-flop – perfect for hot summer days at the pool, walking to the beach, or exploring city streets. Feather-light and easily contorted, they’ll almost go unnoticed in your hand luggage.

Nike React Infinity Run Flyknit

Finally, I needed to pack something for our more active days – hunting for truffles at Castelfalfi, hiking through the Tuscan hills, and cycling between the myriad of wonderful vineyards – I needed sneakers. I’ve always been a fan of Nike when it comes to sneakers, and the React Infinity Run Flyknit is a true running shoe that easily doubles as a fashion choice. It’s not the most compact sneaker, but the thick cushioning makes it a great choice to wear when traveling. This meant I didn’t even have to worry about squeezing them into my hand luggage, which left plenty of space to bring home a new set of souvenir espresso cups!


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