Picasso, Cary Grant, James Dean – these prominent men may or may not have known their port from their starboard, but they definitely knew a thing or two about the power of nautical style.

Less a trend (as it’s often dubbed by the fashion media), more a summertime perennial, the nautical aesthetic has endured by virtue of its sheer simplicity. Which, funnily enough, is also what sometimes makes it so difficult to get right – tread a little too far into the water and a look that started out as refined rapidly plunges into the cringe-inducing depths of fancy dress.

“It’s so important not to be too literal with this look,” warns Tony Cook, menswear editor at online luxury retailer FarFetch. “Nautical stripes are more than fine, but matching with chinos, boat shoes, a flat cap and anything with anchors will leave you looking like you’re in costume.” A little goes a long way, then.

If this is your maiden voyage with nautical, remember that while the below pieces are all important in their own way, don’t go overboard by piling every single one on together. Anchors away.

The Breton Long- Or Short-Sleeved T-Shirt

An indisputable classic – nothing is more integral to a nautical look than the timeless Breton T-shirt. A short-sleeved style will allow your skin to breathe but a long-sleeved version offers you a little more mileage, lending itself well to both casual and smart-casual getups, year-round.

While the Breton top’s traditional fabrication of wool and cotton was a good fit for fishermen who spent hours toiling at sea, 100 per cent cotton will do fine for your cruise or weekend getaway. As for the stripes, we suggest sticking with the traditional navy and white palette.

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Key Brands & Pieces

Key Brands: Saint James, Sandro, A.P.C., Saint Laurent, Ralph Lauren, Ami, J.Crew, Gucci, ASOS, Reiss.

  • Reclaimed Vintage Military Striped Long Sleeve T-shirt
  • Allsaints Alanim 3/4 Crew Tshirt
  • Topman Slim Fit Navy Stripe T-shirt
  • Derek Rose Alfie Striped Stretch-modal Jersey T-shirt
  • Reiss King Stripe Short Sleeve T-shirt Navy
  • Mki Long Sleeve Stripe Tee Dark Navy
  • Ami Striped Cotton-jersey T-shirt
  • A.p.c. Striped Cotton And Linen-blend T-shirt
  • Saint Laurent Striped Cotton-jersey T-shirt

The Double-Breasted Blazer

First sported by Cambridge rowers in the first half of the 19th century, this trusty piece of tailoring has stood the test of time, looking every bit as sharp now as it did back then.

Easy to button up over a Breton top or just as good thrown over a simple white T-shirt, a double-breasted white, off-white or navy blazer (preferably with gold buttons) will lift your summer looks from unremarkably casual to carefully put-together.

Given you’ll be wearing this as a second layer, take some sweat-prevention measures and find a style that’s made from 100 per cent cotton or a cotton-linen blend, rather than a comparatively heavy wool version.

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Key Brands & Pieces

Key Brands: Suitsupply, Reiss, Tommy Hilfiger, Mango Man, Jaeger, Canali, Boglioli, River Island, Burberry, Banana Republic.

  • Modern Slim Navy Linen Double-breasted Blazer
  • He By Mango Double-breasted Pique Blazer
  • He By Mango Double-breasted Pique Blazer
  • River Island Navy Linen-blend Double Breasted Blazer
  • Suitsupply Madison Blue Plain
  • Jaeger Plain Twill Modern Jacket
  • Burberry London Off-white Double-breasted Linen Blazer
  • Burton Light Grey Double Breasted Blazer
  • Suitsupply Madison Light Brown Plain

Chinos

Although technically a soldier’s staple gone civilian (first invented for British and French military uniforms), chinos are now just as connotative of seamen’s style as stripes. And it’s all in how you wear them.

Whether or not you generally make a point of ‘mankle’-baring during the warmer weather, going sockless and rolling your trouser hems is a necessity for nailing nautical style.

Look for a moderately slim fit; not so skinny as to look like you’re auditioning for a boy band to rival McBusted, but not so baggily cut as to undo any effort you put in entirely.

Colours-wise, stick to the traditional nautical palette of red, white and blue, while bearing in mind other pieces you plan to wear them with.

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Key Brands & Pieces

Key Brands: J.Crew, Ralph Lauren, John Lewis, Tommy Hilfiger, ASOS, Reiss, Mango Man, Uniqlo, Incotex, Club Monaco.

  • John Lewis Linen Slim Fit Trousers White
  • Norse Projects Aros Light Twill Chino
  • J.crew Urban Slim-fit Lightweight Cotton Trousers
  • Club Monaco Connor Slim-fit Cotton-twill Chinos
  • Uniqlo Men Slim Fit Chino Flat Front Trousers
  • Kin By John Lewis Laundered Slim Fit Chinos Deep Red
  • Incotex Slim Garment Dyed Chino
  • Polo Ralph Lauren Newport Slim-fit Pima-cotton Chinos
  • He By Mango Slim-fit Cotton Chinos

Boat Shoes

Invented by Paul A. Sperry in 1935, boat shoes may originally have been devised for traversing a slippery deck, but today they serve just as well as the anchor to your fair-weather looks.

Both leather and canvas styles have their virtues; the former being a little more polished in its appearance, the latter often offering unbeatable comfort and breathability – so, opt for the style that suits your requirements best.

Keep in mind the pieces you’ll be teaming your boat shoes with before committing to a particular colourway. Navy might be an obvious choice given the theme here, but they’re only really wearable with white, red or off-white chinos, so tan or chestnut brown might be a better bet.

And we know it’s the done thing to wear these sockless in the truest sense of the word, but slipping on a pair of invisible socks will save your feet as well as your shoes – not to mention contain smells.

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Key Brands & Pieces

Key Brands: Sperry, Timberland, Lacoste, River Island, ASOS, Quoddy, Tommy Hilfiger, Mango Man, ALDO.

  • Tommy Hilfiger Suede Boat Shoes
  • Damasus
  • He By Mango Leather Boat Shoes
  • River Island Tan Brown Leather Boat Shoes
  • River Island Brown Leather Boat Shoes
  • Kg By Kurt Geiger Sorrento Boat Shoes Navy
  • Quoddy Downeast Nubuck Boat Shoes
  • Quoddy Downeast Leather Boat Shoes
  • Sperry Top-sider Authentic Original Leather Boat Shoes

Leather & Canvas Accessories

If you’re a bit of detail obsessive, swapping your usual accessories for styles a little more maritime adds the perfect, not to mention subtle, finishing touch.

Choose from woven leather or canvas belts worn around chinos or shorts, leather or rope bracelets to complete casual takes on nautical, or anchor tie clips and cufflinks for something a little more tongue in cheek.

Remember, less is more: “It’s about capturing the effortless style of seafaring life,” says Tony Cook. “So, simple styling is key.”

It’s advice seconded by Sarah Gilfillan, founder of men’s personal shopping service Sartoria Lab: “Don’t go too mad with a matching look complete with nautical accessories, unless you want some ‘Hello sailor!’ comments as you walk down the street.”

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Key Brands & Pieces

Key Brands: Anderson’s, Miansai, Trashness, Ted Baker, Seven London, Simon Carter, Paul Smith, River Island, Tommy Hilfiger, Austin Reed

  • Andersons Tubular Tri Colour Belt
  • Blue Harbour Stretch Web Striped Belt
  • Gap Striped Webbing Belt
  • Andersons Woven Leather Belt
  • Andersons Woven Elasticated Belt
  • Austin Reed Stone Woven Elastic Belt
  • Ted Baker Wrapped Leather Bracelet
  • Miansai Hooked Silver-tone Cufflinks
  • Seven London Leather Wrap Bracelet
  • Miansai Rope And Gold-plated Anchor Bracelet
  • H&m Miansai Anchor Tie Bar
  • Miansai Brass Rope Hook Bracelet

Nautical Styling Tips

Mind Your Stripes

As much as a Breton top is a universal classic, it’s worth taking some time to ensure your stripes are suited to your body shape before buying.

“Do wear a T-shirt or sweater with stripes at the chest and shoulder area if you want to make yourself look broader,” says Gilfillan. If your frame is on the slimmer side, your torso can take all kinds of stripe.

But we’d suggest you hang back if you’re built like a battlecruiser. Men with broader shoulders and more muscular body types should look to finer horizontal stripes to slim down, rather than emphasise, their above average size.

Image: River Island Summer 2015

Keep The Breeze At Bay

A firm favourite of fisherman for years, the heavy-gauge cable knit jumper is another enduring nautical piece – but in summer they’re only good as sweat rags if you don’t opt for the right type.

Swerve traditional heavy gauge wool versions and instead opt for 100 per cent cotton or cotton-linen blend designs that are both breathable and lightweight – ideal for throwing on over your Breton tee when the temperature drops in the evening.

Image: Gant Rugger Spring/Summer 2015

Go Fish

Still, a lightweight knit isn’t much use in the rain. So if you’re looking to cover up from a heavy summer shower, throw on a fisherman’s jacket instead.

Lightweight and waterproof, one of these seafaring staples will keep you dry and see that the nautical theme stays intact – worth considering if your summer’s more Rotherham than Riviera.

Image: Matalan Spring/Summer 2015

Don’t Forget The Details

Nautical needn’t always mean Breton stripes and heaps of blue.

Try a subtler approach by incorporating marine-inspired details like – as Gilfillan suggests – anchor motifs, brass or contrasting white buttons, epaulettes, rope and toggle fastenings, and boat necklines.

Image: Trashness.com

Final Word

Masculine and perfectly suited to most, nautical style is one way of dressing we suggest you get down pat sooner rather than later – hopefully now you feel slightly less at sea.

What way do you wear nautical? Are there any tips or go-to brands you’d like to share?

Let us know in the comments section.