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The Best Mens Summer Holiday Shoes

The Best Mens Summer Holiday Shoes

Posted on May 7, 2025 By rehan.rafique No Comments on The Best Mens Summer Holiday Shoes

What shoes should men wear on holiday?

My timeless Summer sandal edit is always popular each year, as is my espadrille selection, which I try and update annually. I was quite surprised when more than a handful of readers (first male and then female) asked me to do an edit of our favourite men’s summer holiday shoes, but as always, happy to oblige.

Without further ado, here are some of our favourite summer holiday shoes for men (and believe me, my husband has more than a few).

Here are some of my husband’s favourite Summer holiday shoes for men

The men’s flip flop

Orlebar Brown, from £45 

Get it from Orlebar Brown

My husband was never fond of Havaianas (just because they were always the same) and has loved the flip flops he got from Orlebar Brown (one of the most recent Chanel purchases). These ones are great and he also really likes the cork ones.

A foot peel is highly recommended!

ORLEBAR-BROWN-HASTON-NAVY-SIGNAL-BLUE_270767_FRONT

 

The men’s swim shoes

Swims, from £165 

Get it from Amazon Europe, Zappos, Saks

Mr. O loves loves loves his Swims – he has a few pairs and they come with us on every trip. You can just take them to the beach if you don’t like to wear flip-flops, or they became perfect swimming shoes when beaches or the seashore isn’t sandy. And they are perfect to take for lunch or sundowners afterwards. Highly recommend this model or the more traditional penny loafer.

mens summer holiday shoes swims

The men’s classic espadrilles

Castaner from £80

Get it from Matches Fashion, Mr. Porter

A classic that never ever goes out of style – and Simon likes Castaner’s classic cut in canvas (not suede), which fold in the back if and when necessary. He has them in navy (of course and green). They will also last you for years.

castaner pablo canvas espadrilles for men navy best summer shoes for men

 

Perfect for everything loafers

Costs £225 from Frescobol Carioca

Get it from Matches Fashion, Mr Porter, 24S.com

 

Perfect for everything loafers in brown (and other colours)

Costs £750 from Loro Piana

Get it from Mr Porter, Nordstrom 

 

 

The men’s classic boat shoes

Timberland, from £110

Get it from Timberland (UK), Timberland (USA)

The staple shoes any man needs 2 pairs of (navy with white soles and brown/burgundy with brown soles). They blend in with every environment – you can travel in them, you can go for a decent walk (not hiking!), to the beach, for lunch and even dinner if they aren’t dirty. Simon buys a pair of each a year and gets his steps from them. Cheap and cheerful.

best summer holiday shoes for men timberland navy boat shoes

 

The men’s penny loafers

Tod’s from £340

Get it from Harrods, Mr Porter (see variation). Also available in navy.

My husband’s absolute favourite shoes and they don’t do his exact type at the moment (his are dark brown leather and currently you can only find full grain or suede, which are still great of course). He looks after them like a baby – and year after year, this part of Gommino driving shoes are absolutely perfect.

They are as comfortable as slippers and he loves them. Every man should have a pair.

mens holiday summer shoes tods Gommino driving shoes

 

 

I hope you enjoyed our list of men’s summer holiday shoes and they come in handy for your next trip.

xo

Mr. & Mrs. O

 

Pin for later

6 Perfect Summer Shoe Options for Men

 

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