The Summer Holiday Shoes My Husband Swears By
Men tend to be a little more straightforward when it comes to holiday packing. My husband certainly is. Every pair of shoes he packs has a job to do, and if it doesn’t, it doesn’t make the suitcase.
Once he finds something that works, he keeps it for years. His style has always been pretty timeless, so most of the shoes below are over ten years old and still look just as good today. Quality matters, and when something lasts that long, the cost per wear becomes incredibly easy to justify.
If you’re wondering what shoes men should pack for a summer holiday, these are the styles my husband comes back to year after year.
Beach & Pool
No summer holiday starts without a pair of flip flops.
Over the years, he’s ended up with three favourites: Havaianas, Orlebar Brown and Vilebrequin. Depending on the destination and the length of the trip, he’ll usually pack one pair, occasionally two if we’re away for longer.
Shop the Beach & Pool Edit
Water Shoes
My husband only really wears flip flops when sand is involved. For everything else — pool clubs, marinas, boat trips and luxury resorts — he’ll usually choose a pair of water-friendly shoes instead. They offer the same practicality but with a more elegant look.
Shop the Water Shoe Edit
Boat Shoes
The pair that does it all. Comfortable enough to travel in, smart enough for dinner and versatile enough to wear almost every day of the holiday.
Whether you prefer Sebago, Timberland or a more luxurious pair from Tod’s or Loro Piana, this is probably the hardest-working shoe in his suitcase.
Shop the Boat Shoe Edit
Espadrilles
A summer holiday wouldn’t feel complete without a pair of espadrilles.
His classic Castañers have travelled with us for years and remain a favourite, but the newer loafer-style espadrilles have become a brilliant addition. They’re a little more elegant, making them ideal for long lunches, cocktails and relaxed evenings without losing that effortless Mediterranean feel.
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Proper Shoes
For dinners out, two styles never let him down: Tod’s Gomminos or Loro Piana Summer Walks.
Both have been in his wardrobe for years and are the kind of investment pieces that only seem to get better with age. If you’re building a timeless holiday wardrobe, you really can’t go wrong with either.
Or both!
Shop the Evening Shoe Edit
- Shop Tod’s Gommino
- Shop Tod’s Suede Loafers
- Shop Loro Piana Summer Walk (out of stock currently)
Trainers (If Your Holiday Calls for Them)
He rarely packs trainers for a classic beach holiday, but if we’re combining a city with the coast or know we’ll be doing a lot of walking, a lightweight pair smart trainers earns its place in the suitcase.
Shop the Trainer Edit
- Shop Tod’s Trainers
- Shop Loro Piana’s Trainers
Final Thoughts
A good summer holiday wardrobe isn’t about packing more shoes — it’s about packing the right ones.
Most of these have travelled with us for years, accompanying us everywhere from California and Italy to Greece and Sotogrande. They aren’t the latest arrivals or this season’s trend. They’re simply the pairs that have stood the test of time, proving that buying well almost always costs less in the long run.
Mrs. O
P.S. Building the perfect summer holiday wardrobe doesn’t stop with your shoes. Have a look at what’s in my beach bag and the summer beauty essentials I never travel without—two more articles based entirely on what has genuinely earned a place in our suitcases over the years.
