Black & white man sailing

Effortless Sailing Style Nailing the trend on and off the water

Maybe you don’t live by the sea or set off for weekend journeys in your yacht but that doesn’t mean sailing style is inaccessible. Great sailing style looks relaxed and timeless. Think more brunch with friends and less Jack Sparrow in Pirates of the Caribbean. Let’s take a look through its history and how you can pull off this classic trend.



Sailing or nautical style arose in the 1800’s with the prominence of the British Royal Navy. Colors like blue, white and gold came to be hallmarks of the style. These colors often signified the rank of officers with gold and silver trim indicating status. Men of lower rank sported the classic striped shirt.
Beyond the sloops and frigates of eighteenth-century navies, sailors back home had styles as their own. The knit sweater has its origins with these men. Their wives sewed symbols and patterns in their husband’s sweaters to make them identifiable if their bodies were found at sea. These designs encompassed images from the village flag or family quests. The ugly sweater trend that has become so popular during the holidays, owes its origins to this as well.

Many of the traditional pieces of seamen, reflected the need for functionality at sea. The materials were chosen to keep sailors warm on long and damp voyages while the colors worked often as camouflage and signaling. This is carried over to how commercial fishermen dress today. Their yellow windbreakers make them easy to find if thrown overboard while the material protects them from the rough seas.

Nautical style has made its way into men’s fashion in much the same way most timeless trends do. Soldiers and workers returning home sported sturdy, reliable and often fashionable clothes that fit perfectly into their lives off the job. Solidifying this trend are the classic men of old Hollywood who made this look iconic. For these reasons, sailing style is not just another menswear fad but rather a staple style that’ll exist as long as men sail the oceans.

Key Pieces

The Knit Sweater

Knit Sweater

No matter the time of year, days and nights out on the water can get chilly. Nautical knit sweaters keep the wind at bay, while still being breathable. This makes it perfect for transitional weather and won’t leave you baking in the summer sun. Opt for cotton pieces as opposed to wool and you’ll be set for a day by the water.

Our Pick

Stripes Done Right with The Breton Shirt

Breton Shirt
The Rake

Long touted as the epitome of sailing style, the Breton shirt is the most versatile item on this list. Its nautical stripes bring just enough of the sailing look while still downplayed enough for any guy to pull off. An added benefit is the stripes can extend the look of your chest, making up for all those days you skipped at the gym.
There are a lot of takes on the Breton shirt but we recommend the classic blue and white combo.
For materials, linen and wool blends are your best bet.

Our Pick

A Slim Pair of Chinos

Express Mens Extra Slim Buttondown Shirt

Express Men’s Extra Slim Buttondown Shirt

  • 100% Cotton
  • Imported
  • Button closure

Originally invented for the British military, chinos have made the jump to everyday menswear. No nautical look is complete without a great pair of chinos.
Picking the right pair of chinos is important. Too baggy and you’ll be dragging them through the sand and water all summer long. Too skinny however steers you in the 90’s boy band direction. Aim for a slim fit instead.
As far as colors, you can’t go wrong with blue and white. Just make sure to balance them with the rest of your outfit.

Our Pick

Slip on Some Boat Shoes

Boat Shoes

Sperry Men’s Gold Cup Authentic Original 2-Eye Boat Shoe

Sperry Mens Gold Cup Authentic Original 2 Eye Boat Shoe
  • 100% Leather
  • Rubber sole
  • Shaft measures approximately low-top from arch

It’s little surprise that boat shoes are a must for sailing style (boat is literally in the name). Paul Sperry popularized the shoes in the thirties and they’ve been a favorite of menswear ever since. Boat shoes are most popular in leather and canvas. Leather immediately dresses up your look while canvas follows the trend of laid-back and airy.
With boat shoes, brown and tan will never steer you wrong. The neutral color works perfectly with navy and white while giving contrast.

Our Pick


The Classic Fisherman Jacket

Fisherman Jacket
Barbour Mens Sapper Wax Mens Waxed Cotton Jacket M

Barbour Mens Sapper Wax Men’s Waxed Cotton Jacket M

  • Cotton

Summer showers and splashing waves can threaten to derail your nautical look. That’s where the fisherman’s jacket comes in. It’s lightweight and waterproof, giving you some protection from the elements.
While yellow can look seriously good, there’s always the risk of looking like you sell fish sticks for a living. Gravitate more towards dark blues. Like I’ve said, you can rarely go wrong with blue.

Our Pick

Keep it Formal with The Double Breasted Blazer

Double Breasted Blazer

Dressing up nautical style is as easy as throwing on the right layers. The double-breasted blazer hits all the right sartorial notes.
Once again blues and whites are your friends when choosing colors. The added benefit of white is it’ll reflect the sun away from you and keep your temperature down.
Linens and blends are a no-brainer when coming to materials. Stay away from anything else, especially wools unless you like bathing in your own sweat all summer.

Our Pick

Why You Should Choose Sailing Style

Sailing and nautical style is timelessly cool. Easy, well-fitting pieces like the Breton shirt and a good pair of chinos makes this trend plenty doable. Every time you suit up in a sailing style you’re not only choosing an ageless menswear trend but expressing the depth of sailing history. So next time you’re on the water, make sure to look the part.

Tell us about your summer styling moves and how you bring the beachy sailing trend to your wardrobe!

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