a men’s guide to cruise ship style

Man on deck cruise ship

Gents, get shipshape with old-fashioned style at sea – you might even enjoy it, says fashion blogger Lee Osborne

Wind the clock back 100 years and every man boarding a cruise ship would have strolled up the gangplank stylishly adorned, from his trilby-bedecked head to his Goodyear-welted toes. Dressing smartly was a given and that odious term “smart casual” had yet to be coined.

So where did it all go wrong? Why do most men nowadays cringe at the prospect of dressing up?

For a start we’ve got out of the habit of doing it. It’s hard to go from nine-to-five business attire to sun-kissed Instagram man overnight, but turning up dressed like a banker on a cruise will immediately set the wrong tone. The only suit you’ll need on board is the “dinner” variety.

Before I go any further there are some “nevers”. Never go sockless at dinner. Avoid anything slim-fit (this includes narrow lapels and slim ties – unless you’re a teenager) and bear in mind that cheap footwear can kill a smart outfit (invest in well-made timeless classics such as leather or suede tassel loafers or monk straps).

But embracing style at sea is about more than avoiding cheap footwear. In the halcyon days of cruising, the theatrical descent from the upper decks of the vessel into the dining room was the highlight of the day for guests of both sexes. It gave them the opportunity to see and be seen in their dazzling evening best.

Comfortable shoes are a must on a cruise holiday


If we want a lesson in how to dress stylishly on the high seas then we need look no further than our American cousins. Bing Crosby and Clark Gable both favoured Cunard on their transatlantic crossings but film star Cary Grant (more of a Holland America man) was the one who brought the romance of the waves to the big screen, taking the immaculately groomed lead in films including An Affair to Remember – where he and Deborah Kerr met and fell in love on an ocean liner. Indeed, the film is often cited as bringing cruising to the masses.

My personal under-the-radar favourite, though, was the American diplomat Anthony J Drexel Biddle Jr. Oft-recipient of best-dressed man accolades, his style was simply legendary. In fact, his sartorial mastery was highlighted in the Ocean Liners: Speed and Style exhibition at London’s V&A museum last year. His role as ambassador to exiled governments in London in the Forties meant he regularly crossed the pond and was the epitome of refined elegance whenever he did.

Indeed his double-breasted, pinstriped, wide-lapelled blazer, paired with cream slacks would not look out of place at Pitti Uomo today (the doyen of menswear shows is held biannually in Florence). He cleverly forgoes wearing a shirt in favour of an immaculately positioned scarf – nonchalant perhaps, but being smart doesn’t always have to involve wearing a tie.

Stylish European cities are the perfect place to show off your cruise outfits


While style seemed to pass my father’s generation by, I have my grandfather to thank for passing on the sartorial baton, instilling in me a penchant for knitted ties and brushed cotton button-downs. He would always look smart, even donning a tie to prepare dinner at home. Although a lot of men cannot wait to dispense with theirs (the association with work is too much to bear), there’s a growing, albeit steady, appreciation for classic menswear once again.

Just like their grandfathers did (and Italians have pretty much always done), a new generation of 35-plus-year-old men are now beginning to embrace made-to-measure tailoring for the intrinsic benefits it can bestow upon their silhouette (Instagram bears testament to this). And even if they don’t have the budget for bespoke, they have their tailor nip and tuck their off-the-peg purchases.

Wide lapels are making a comeback and there’s definitely been an upsurge in higher waisted trousers with deep turn-ups, either worn Hollywood style with a slim belt or with traditional braces.

If you focus on fit above all else and never go too snug or too loose you’ll be on the right track. Don’t wear belts with suits or separates, instead opt for side fasteners (reserve the belt for denim and chinos). Knitwear is hugely underrated, but it’s something that can work really well with tailoring if executed correctly. Cary Grant would pair a simple red polka dot bandanna with a crew-neck jumper, for instance – similarly to the way Drexel Biddle Jr employed the neck scarf, no shirt required.

It’s often just having the confidence to break from the norm – but once you’ve done it, people will really take note… and you’ll get the sartorial bug.

Lee Osborne can be found blogging about men’s fashion at Sartorialee.

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