holiday clothes for men

The winter sun style guide: Chic holiday clothes for men

30 Nov 2023 | |By Annie Lewis

Heading for tropical climes this winter? That calls for an updated holiday wardrobe

All products are chosen independently by our editors. Luxury London may earn commission on items purchased.

With the winter chill settling in fast, it’s time to escape the motherland’s gloomy winter weather for sun-drenched destinations. While you may be looking forward to basking in the Bahamas or cruising around the Caribbean (and, quite frankly, we don’t blame you), we recommend you pause for a moment to survey the state of your holiday wardrobe. Digging out those worn-out shirts and wrinkled linen shorts from the back of your cupboard simply won’t do for your sunny winter holiday. Allow us to point you in the direction of this season’s chicest winter holiday clothes for men, so you can dress to impress wherever you’re headed. 

What to wear to fly

Those nine-hour flights to sunnier surrounds aren’t always the most comfortable, even if you’re in business class. But as the old adage goes, no pain, no gain. From resting in the airport lounge to strapping into your seat in the sky, the savvy frequent flyer knows to look for comfort that doesn’t sacrifice on style. Our top tip: look for loose, unstructured shapes in supreme quality fabrics.

Dries Van Noten pleated track trousers

Smart but comfortable, these casual bottoms feature pleats and that all-important elasticated waistband so you feel relaxed when sitting down all day (and can take advantage of the airline’s snack bar).

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Brunello Cucinelli Cotton Jersey T-shirt

Made in Italy from soft cotton-jersey, this breathable T-shirt has a classic crew neckline and regular fit. Layer beneath a jumper or coat which you can remove once you’ve landed in paradise.

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John Lewis Cashmere Half-Zip Jumper

Luxuriously soft, this half-zip will work perfectly over a T-shirt and under a lightweight coat. It’s versatile too, and can easily be paired with joggers or jeans. That’s what we call a bargain.

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Polo Ralph Lauren Longwood leather trainers

A pair of white trainers is a staple in every man’s wardrobe. These have been crafted in soft white leather with logo detailing, and can be worn throughout your holiday with shorts and trousers.


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In the bar

Whether it’s a beach bar or a hotel lobby, evening drinks call for a chic dress code. While you don’t have to dress up to the nines in a dinner jacket or tuxedo, opt for something that looks a little more put together than your average T-shirt and shorts combo.

Brunello Cucinelli striped linen and wool suit

This striped beige suit features a single-breasted blazer, allowing for a more relaxed fit, and mid-rise straight leg linen trousers. Wear it with a white tee or smarten it up with a crisp shirt.

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John Lewis Non-Iron Slim Fit Shirt

A wrinkled shirt looks good on no man. Banish creases in this casual non-iron shirt that will be a staple in your wardrobe throughout your holiday (and when you get home).

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Brunello Cucinelli Woven Leather Belt

Even the most perfectly fitted trousers require a belt, and this Brunello Cucinelli design provides a great opportunity to jazz up an outfit. This classic woven belt ties well into the striped suit, too.

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Saint Laurent Culver sandals

Many men are hesitant about sandals but, trust us, once you’ve tried them you’ll never look back. Our pick of the season are these Saint Laurent Culver sandals featuring crisscross leather straps and supple hide footbeds that you’ll be sure to wear all through the holiday.

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On the beach

When you're looking forward to your winter sun holiday, there’s probably one thing that immediately springs to mind: the beach. Whether you’re treading the Australian sands of Whitehaven or sunbathing on Harbour Island in the Bahamas, a brand-new pair of trunks will make your time in paradise that much better. 

Love Brand & Co Staniel Swimming Trunks

You really can’t go wrong with a classic 1950s pattern like navy stripes. Plus, these trunks are made from 100 per cent recycled materials and will dry super quickly, so you can wear them morning, noon and night (if you really want to).

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Love Brand & Co Arawak Linen Shirt

Sticking with the navy theme, opt for a timeless linen shirt to pop on with your trunks before you leave for the beach. This design by Love Brand & Co also features a collar, so perfect for those who are trying to protect their neck from the sun.

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Taylor Morris Ladbroke Sunglasses

Featuring a vintage-inspired square frame and finished in timeless deep tortoiseshell hue, these sunglasses make a serious statement.

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Birkenstock Arizona oiled-leather sandals

The classic Birkenstock sandal is now available in a leather edition. The anatomically-formed cork footbed and shock-absorbing EVA sole will keep your feet comfortable and supported.

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Out to dinner

While you may get away with dressing down for drinks at the bar, if you're holidaying somewhere particularly glitzy, there may be no escaping a suit at dinner. Fear not, the men’s market is now saturated with lightweight suits that are fit for any occasion (and, importantly, humidity).

Richard James Double-Breasted Linen Blazer

Expertly made in London’s tailoring heartland, just like its accompanying trousers, this blazer comes with neat lapels and a double-breasted vent for a comfortable fit. Wear buttoned up or undone, and as it’s meant to be worn slightly crinkled, it won’t need a press before you head out for cocktails.

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Richard James Straight Leg Linen Suit Trousers

Made by Savile Row tailor Richard James, keep your cool in these pleated linen trousers. Pair with your favourite white T-shirt and the matching jacket for evening soirées.

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Tom Ford suede loafers

These classic loafers are crafted with Italian leather and have durable double soles, so are a safe bet. Plus, the chocolate tone is endlessly flattering with a tan – after all, if you can’t flash a little ankle on holiday, when can you?

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Taylor Morris Bonchurch Sunglasses

A great all-rounder (excuse the pun), these glasses feature a delicate Windsor Rim finished with antique-gold stainless steel frame.



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