What to wear to a sailing regatta

“A man should learn to sail in all winds” (Italian proverb)
Image: De Visu

So you’re off to Cowes Week, Falmouth, or Fowey. Summer sailing regattas are a fun time but you’ll need impeccable dress sense to fit in with your fellow yachties! Here’s our guide to help you look the part.

On Board

deck shoes

Image source: Samuel Windsor Deck Shoes
Deck shoes are de rigueur on board

If you’re sailing, or even if you’re just a social guest on board a yacht, it’s vital to wear boatshoes. Deck shoes aren’t just fashion accessories. Their non-slip soles will stop you taking a tumble into the dock, and even more importantly, won’t mark decks. Beware turning up in anything with black soles, your skipper probably won’t have you aboard.

For racing, you need your oilskins ready for when the weather turns nasty, and of course you must wear a lifejacket at all times. On warmer days, unless otherwise stated, a practical but stylish casual outfit is the way to go.


Model 2 wearing White Short Sleeve Pique Polo Shirt From Samuel Windsor

For hot days, invest in a breathable cotton polo shirt
Image: White Short Sleeve Pique Polo Shirt From Samuel Windsor

A cotton polo shirt is perfect for baking hot days on the water, but never take to the sea without adequate clothing. The weather can change very quickly and even on the brightest days the sea breeze is very cooling, especially on those upwind legs. With this in mind, it’s a good idea to pack a fleece or a rugged fishermans jumper.

A pair of tailored shorts are a great choice for yachtsmen on the water and they’re perfect wear for the yacht club tea that often follows the racing. A pair of lightweight trousers might also come in handy because the inevitable splashes of water will dry quickly without leaving you chilled to the bone.

Take a cap with you if you’re going sailing, especially if you’re follically challenged. A baseball cap is fine, but the protruding brim means it’s easy to lose overboard in a gust of wind. A well fitting linen flat cap will probably do the job better, but if in doubt, secure it to your top with a lanyard.

Last but not least, do remember to pack your sun lotion, or the glare reflected off the water will leave you very red faced indeed.

Solve your ‘what to wear’ woes with Samuel Windsor
Men’s Deck Shoes Men’s Panama Hat


Apres race functions

Most yacht clubs have changing facilities and will be more than happy for you to make use of them. Bring your evening wear in your kit bag so you can change in time for dinner.


Model 4 wearing Cambridge Summer Blazer from Samuel Windsor

Let your blazer do the talking
Image: Cambridge Summer Blazer from Samuel Windsor

A single or double breasted navy blue blazer is perfect attire for an evening at the yacht club. A cream coloured number is also fine for summer wear, or alternatively, you might like to consider the sophisticated look you’ll get from a tasteful moleskin jacket. And of course if you really feel like pushing the boat out, a boating blazer makes for a bold and eminently stylish statement.

Twin your smart jacket with a pair of moleskin trousers or chinos in a complementary colour and finish off your boaty look with a silk tie.


Model 1 wearing Cornflower Long Sleeved Cotton Twill Shirt

Find style and comfort with a cotton twill shirt
Image: Cornflower Long Sleeved Cotton Twill Shirt from Samuel Windsor

For functions that demand a smarter appearance, go with a white shirt or a subtle pastel shade. Stripes and checks are also fine but keep them muted. Dress codes vary from club to club so it’s always wise to check beforehand and choose your outfit accordingly.

For more casual afternoon and evening events wear a cotton tattersall check shirt with chinos. A cotton twill shirt also makes a fine choice with the added benefit of being slightly thicker than a standard shirt – ideal for insulating you against the chilly sea breeze.

No Need to be Dull

Remember a sailing regatta is meant to be an enjoyable summer event. Don’t get bogged down by agonising over your attire. As long as you respect the more formal gatherings and dress accordingly, the majority of occasions give you a pretty free choice. Have fun!

Posted in What to wear guides.