Island Style for Men

William Strachan

Island living demands a certain fashion style. One might call it “island style”. It’s all about being classic with a little bit of flash and a lot of practicality. Here’s why: You’re on an island. You might get up to epic stuff. Wait – you will get up to epic stuff, so you should dress appropriately. You also want to look cool, cause let’s face it – you are cool. You’re (a) on and island, and (b) doing epic stuff. To come full circle, then, classic + flash + practicality = island style. These characteristics should be thought of when compiling the four basic components of island style: sunglasses, t-shirts, shorts, and sandals.


They say a lot, and when you only have few items to work with every one counts for style points. Given our three components of island style, these metal-framed aviators fit the bill:

Personally, I like to up the flash and originality, which is why these are on my wish list:


T-shirts cover a lot of real estate, so make sure they’re awesome. You can do this by keeping three things in mind: colour, imagery, and fit.

For colour, go for either classic (plain dark or light colours) or electric (bold and eye-catching) but remember to balance this off your shorts, which will take on the opposite characteristic. For example, if you’re rockin’ a savage teal t-shirt, it’s best to tone it down with some dark, perhaps pinstripe, shorts and vice versa.

For imagery, it’s going to be pattern, image or text but no combinations thereof. If it’s a brand, make sure it’s legit. No schmuckish apparel allowed (e.g. Ripcurl).

For fit, go for fit. In other words, wear clothes that actually form to your body. Don’t go to extremes, though. The tight “Gino” look doesn’t fly, and neither does looking like a pole in a wizard sleeve.


I’m going to split this category into two: those for wet purposes and those for dry purposes.

For wet purposes, always reach for board shorts. This gets back to the practicality thing. You’re a daring man of action and the materials, cuts, and designs of non-board shorts just don’t flow with that image. In other words, you can’t go cliff jumping or skim boarding in a pair of swimmers from Lacoste and demand respect. Enough said. Just remember that shorts for wet purposes are usually worn by themselves, so there is an opportunity to funnel all your style into this one item. Make them count.

For dry purposes, classic is best but remember to counter-balance these with your t-shirt. Also, don’t go crazy with pockets. Keep it simple, you’re not Rambo.

I actually own a pair of these Volcoms and they are probably the best shorts I’ve ever had:


One hyphenated word: flip-flops. When you’re on an island you should always be ready to kick off your shoes and jump in the water. Flip-flops allow for this while also showing that you are a genuine islander. After all is said and done, flip-flops are the true mark of legitimacy when it comes to island style.


I’ve mentioned the ins and outs of the four basic components of island style threads. If you’ve got those covered, you might want to add some extra shwag to demand the “ooo” in your look.

Hats: Woven fedoras and mesh truckers. Don’t shy away from a well-folded bandana either.

Jewelry: All natural. Coconut beads and hemp. If it ain’t raw, it ain’t right.

Shoes: Sadly, flip-flops don’t mesh with all occasions. If you find yourself in such a setting, roll with some barefoot kicks. This subject deserves a post of it’s own but for now it suffices to know that a pair of slip on canvas shoes a la Toms or some classic leather top siders are boss.

The Last Word

Island style isn’t just for islands. In any case, make sure you give the air of being on one. These style tips will help.