Sartoria Lab


How to dress on holiday when you're over 40

What to wear on holiday? It’s traditionally thought that British men are terrible at dressing on holiday – think white legs with a blue tinge, knotted hankies and socks with sandals. Yep that was my grandad at Winchelsea beach – occasionally he’d go crazy and take his socks and sandals off and roll up his trousers to sit in his deckchair. If only I could find that photo to show you.

Thankfully, the majority of men have moved way beyond this, what with travel becoming so much easier and global warming hotting up the UK summers.

But it can still be a little tricky to dress for holidays as you get older – I don’t know but you but I prefer to show a little less flesh and find things that are closer fitting but not tight are the most flattering.

I’ve put together a little holiday guide with some suggested items for holiday looks:


Derek Rose polo shirt holiday dressing for the over 40s

Derek Rose pique polo shirt

 Hamilton and Hare polo shirt - how to dress for your holiday when youre over 40

Hamilton & Hare polo shirt

I tend to find most of my older clients prefer to wear some sort of collar so a polo shirt is preferable to a t-shirt. This could be because the neck becomes a little less taught and a little more lined as we age or perhaps it’s because it gives a focus to take away from a less than trim waistline – either way a polo shirt is the most popular choice.

You can’t go far wrong with a white polo which will go with everything and the striped navy and white one from Hamilton & Hare is like your go to blue and white striped shirt for work – failsafe and the narrow stripes add some texture if you don’t want to go for completely plain.


Realm and Empire camp collar shirt - personal shopping advice for men

Realm & Empire

 Budd linen shirt - dressing for your holiday middle aged men

Budd casual linen shirt

Currently I love the camp (or Cuban) collar shirts around. This style is usually a boxy cut so flattering for those of a stocky build and great if you have a short or wide neck as it opens up this area with the v shape and the lower collar. Designed to be worn outside your trousers or shorts they have a straight hem and are a little shorter. Perfect for summer and if it gets a little cooler in the evening they look great layered over a short sleeved white t-shirt too.

Alternatively, if you don’t mind the crumples the linen shirt is a favourite of Grey Fox and a classic for summer style. Either go for long sleeves and roll them up or short sleeves though I’d suggest if wearing short sleeves and you’re a slim build that you go for something a little more fitted so the sleeves aren’t flapping around on you. As an alternative to the classic white or light blue, try navy and contrast it with lighter coloured shorts or trousers.

Shorts and trousers

Universal Works shorts Holiday and warm weather dressing personal styling advice for men

Universal Works

Timothy Everest washed linen trousers - Holiday dressing for middle aged men  

Timothy Everest washed linen trousers

If you have slim legs then wear your shorts in a slimmer cut so you don’t look like you’ve escaped from dad’s army! Or for a wider cut to fit chunky thighs try Universal Works (see above) or Drakes. Just above the knee is the best length to go for regardless of height.

For trousers and shorts try lightweight cotton, linen or if you prefer a crisper style then seersucker. Navy and khaki are default colours to go with everything or if you fancy trying something a bit more out there, like an ice cream shade then a washed in muted tone will be easier to wear than a bright pastel. The brick colour of the Timothy Everest ones above will be great to break up all your blues and whites.


Hemingsworth swim shorts - personal shopping and styling for men

Hemingsworth swim shorts

After a conversation with my friend and her husband, where she was begging him to get some new swim shorts so he didn’t embarrass her and their teenage daughter on the beach, I’d say it’s pretty essential not to drag the same old faded swim shorts out again year after year! I really like the more tailored styles that are appearing and this is the ideal time to add some colour to your wardrobe as you don’t have to think what it’ll match with other than your skin tone. Choose from a small range of British made tailored fit swim shorts at Hemingsworth.


Clarks boat shoes - What shoes to wear on holiday with shorts


Anderson Shepherd espadrilles - what to wear on holiday when youre over forty

Anderson & Shepherd

Swims loafers - holiday dressing for the over 40s

Swims loafers

This is where many of my clients struggle. Many aren’t keen on wearing open toes so here are my suggestions of alternatives.

Espadrilles – you could go for cotton for but if you fancy something a bit more plush to wear for evening then these suede Anderson and Shepherd ones certainly fit the bill. I’d advise spraying the suede with a protector first and then if you need to freshen them up, steam them over the kettle and brush with your hand or a soft suede brush.

Deck shoes – a great summer staple to have, go for classic tan, brown or navy. Choose a slimmer sole to flatter skinny legs or something more substantial if you’re a large guy.

Swims – If only my grandad had known about these, he could have gone for a paddle without taking his shoes off, as they’re made of neoprene and are very lightweight and quick drying!

Tusting holdall - holiday dressing and advice for men

Tusting wheeled holdall

And of course, you’ll need a fabulous bag to put it all in like this one from Tusting.

Would you like to go shopping for a holiday wardrobe? I'm offering a 20% discount for the month of August! If you’d like to do a Half Day personal shopping trip in August, the price will be just £272 instead of the normal £340. It must be booked in before the end of August. To take up this offer please contact me making sure to also subscribe to the newsletter to be eligible.

This article first appeared on Grey Fox blog.

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