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Classic look for tropical holiday?

JJ Katz

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Jeans and Chelsea boots, to me, are more mid-season than tropical.
Have you considered trousers in a lighter weight and colour?
Unlined loafers? Espadrilles?
 

Thin White Duke

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He’s right ^^ that’s too much.
We go almost every year to Cozumel, Mexico where it’s hot and humid all year round.
During the day I’m in t shirt, shorts and flip flops around the beach or the pool.
In the evenings there may be some entertainment on at the hotel or a theme in the restaurant otherwise we stroll into town for a wander round and pick out somewhere to eat. I’ll either be in a polo shirt, khaki cutoff shorts and classic trainers or maybe a linen or madras shirt, linen strides and driving moc loafers.

I may have taken white jeans in the past but that wouldn’t be normal. The only time I need a second layer is for the drafty aeroplane flight. If I take a light jacket it’s not worn at the destination, only for the commute. I have yet to ever see anyone wearing a blazer or Chelsea boots in this environment and as much as I like any excuse to put some effort into my dress, for tropical holidays the cross section of comfort and style is light weight and light/bright colours.
 

comrade

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He’s right ^^ that’s too much.
We go almost every year to Cozumel, Mexico where it’s hot and humid all year round.
During the day I’m in t shirt, shorts and flip flops around the beach or the pool.
In the evenings there may be some entertainment on at the hotel or a theme in the restaurant otherwise we stroll into town for a wander round and pick out somewhere to eat. I’ll either be in a polo shirt, khaki cutoff shorts and classic trainers or maybe a linen or madras shirt, linen strides and driving moc loafers.

I may have taken white jeans in the past but that wouldn’t be normal. The only time I need a second layer is for the drafty aeroplane flight. If I take a light jacket it’s not worn at the destination, only for the commute. I have yet to ever see anyone wearing a blazer or Chelsea boots in this environment and as much as I like any excuse to put some effort into my dress, for tropical holidays the cross section of comfort and style is light weight and light/bright colours.
Let Klaus be your guide:

unnamed.jpg
 

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JJ Katz

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Though, to be fair, old Klaus looks a bit overwrought, there... :-D
You could use some of the old AA-Esquire images for inspiration...

b01.jpg

b02.jpg

b03.jpg
 

JJ Katz

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Now, those are from the 1930s.
For today's much more informal take, I think some of the ideas from the 1950s might feel more easily adaptable. I think that quite a few years ago "Die Workwear" once posted on his website some B&W pics of various artists, etc. on Riviera in the summer which looked good.
Lots of white, ltos of linen. Very lightweight "frescolana" wool can work well for trousers and even and unlined jacket as long as it's not too hot.
 

comrade

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