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How To Dress For Success On Your Next Hike

Two girls standing in front of a lush valley on a cliff

Dress for success 101: Layering & The 3 W’s

The Hawaiian Islands boast 10 of the world’s 14 climate zones! Weather patterns are localized and quickly changing. The system of dressing described below, known as “layering”, will help keep you safe and comfortable on your next hike.

The core principles of layering apply to activities in all outdoor climates, as mentioned in my last blog post How To Master Outdoor Layers (this post is geared more towards the colder climates you may be visiting from). Our bodies are happiest when warm & dry. Weather and subpar trail conditions can challenge this “happy place” in a variety of ways, layering is our best defense.

The idea behind layering is to have maximum versatility to maintain an optimal body temperature despite what the weather is dishing out. As long as you have a small day pack, you can put on and take of these layers according to changes in the weather combined with changes in your level of activity (which will produce heat and sweat).

The easiest way to explain layering is the classic, “The Three W’s” – Wicking, Warmth, Weather – or, as I like to say, “3 W’s Squared”: Wicking, Warmth, Weather x (Wind & Water).

Finally, a dressing situation where function trumps fashion, how refreshing!


The “Wicking Layer” is your first line of defense, choose a material such as silk or Capilene that is designed to pull moisture away from your skin, and dry quickly. When it’s really hot out this may be the only layer you need. In this case the old adage, “cotton kills”, does not apply. Having a wet t-shirt may be no big deal, the cooling effects from your sweat will be doing exactly what they were designed to do. You may want to just wear a bathing suit and/or board shorts – something breathable and quick drying. On a side note, excess sweating can also lead to dehydration – so let it breath!

Where sweat becomes an issue is when you are exercising in a cold climate or a warm climate that suddenly drops in temperature. As soon as you stop exercising the excess heat your body has created will begin to quickly dissipate. For this reason, you will want to wear as little as possible while exercising and have a warmth and/or weather layer to throw on shortly after stopping to take a break. Things get tricky when exercising hard in inclement weather. In colder climates a thin wicking layer with a thin weather layer should work great. In warmer climates like Kauaʻi, on days when it is raining heavily and a bit humid, you will likely get wet no matter what – but hey, you’re on Kauaʻi, the sun is never far away and a rainbow is probably just around the corner!


I know what you’re thinking – why should I worry about warmth on Kauaʻi? Believe it or not day time temperatures can drop to the low 50’s on Kauaʻi. That combined with hard driving rain can be enough to make even the heartiest northerner have a shiver or two. Now I don’t mean to scare you, it rarely gets that cold and the localized weather changes often, so it likely won’t be too long before the sun shows it’s face again! Even so, you’ll want to be prepared with at least one insulating warmth layer just in case – chose a lightweight packable material such as fleece or wool that will keep you warm even when wet and dry quickly.

​We are often questioned about the warmth layer by folks already “on island” preparing for their hike with us. Something to keep in mind is that many of our hikes are in Kōkeʻe & Waimea Canyon State Park(s) at elevations of over 4,000 feet. The temperature up there is usually 10 – 15 degrees colder up there than on the coast, where all of the hotels are. That, combined with the localized weather, is why we ask our guests to come prepared for anything. For a frame of reference, the three pictures above were taken within a couple hours of each other in the same general areas of Kōkeʻe & Waimea Canyon State Park(s).

Weather (Wind, Rain, and Sun)

The “Weather Layer” is perhaps the most important, choose a material such a Gore-Tex which is wind and water resistant but also somewhat “breathable” (has features such as “pit zips” and a breathable membrane that allow excess heat and moisture from your core to escape). Plastic ponchos will work in a pinch, but keep in mind they are the exact opposite of “breathable” – if you wear them while hiking you may end up more wet from your own sweat than you would’ve been from the rain. On the other hand, if you are stopped for lunch on a colder wet day a plastic poncho may prove to be the perfect layer.

As far as keeping your bottom half dry, we find that rain pants are not necessary except in the most extreme cases of cold/rain/wind. Much like the poncho, they can lead to excess sweating and be difficult to remove quickly. It’s much more important to keep your core (upper body) warm and dry than your legs which is why we recommend boardshorts or similar shorts made from a quick drying material. But by all means, if you have a nice pair of rain pants that zip up at the ankles for easy on & off, bring them along!   ​

Finally, weather can also mean intense sun with temperature in the high 80’s – low 90’s and no wind (thankfully this is not usually the case on Kauaʻi). You can protect yourself against the sun with a sunhat, sunscreen, and even long sleeve tops and bottoms made from breathable quick dry material. Long sleeves will also help protect you from scratchy brush if we happen to be on a particularly overgrown trail. Yoga pants seem to be all the rage these days – most are made from breathable material and will protect your legs against sun & scrapes..just try not to get too mad if your favorite pair of Lulu Lemon pants get a small rip or forever stained with infamous Kauaʻi Red Dirt (free souvenir)


In most cases breathable low-cut hiking shoes with good tread that dry quick and withstand water is what you’re going for. Boots will provide the most support and protection for your feet and ankles. They are especially useful when carrying a heavy pack and/or traveling over jagged, rocky terrain. In most cases we recommend folks wear trail running shoes or plain old sneakers instead of boots. The reason for this is that boots can be heavy, clunky and make it easier to slip & trip on certain trails. This is especially true for trails that are steeply graded.

Kauaʻi soil has a high clay content that can make these trails particularly slippery when very wet, or when very dry (hard pack surface with hard round granules laying loosely – like little marbles – on top). Having a thinner sole allows your feet to feel subtle changes in the surface underfoot and adjust how you step accordingly, to prevent slipping – the human body can be amazing at calculating subtleties like this! If the conditions are particularly challenging, we will provide trekking poles and traction devices that fit over your shoes to help keep you safe.

To Gore-Tex, or not to Gore-Tex?

The downside of Gore-Tex, or “waterproof” shoes & boots is that they are more expensive, aren’t very breathable, and usually don’t dry as quick as non-gore-tex shoes. There are some exceptions to this rule – Montrail comes to mind – but mostly it will depend on what’s available near you and what fits your foot best (best to try on footwear in person, rather than order “blindly” online).

The biggest negative to waterproof shoes on Kauaʻi is that on a really hot day you’re feet will likely bake in them, and actually be wet from sweat. That being said, if it’s a cool and/or wet day your feet will most likely be happier in them. Since we are usually just doing short day hikes, non-waterproof trail running-style hiking shoe will work best. I look for ones with good tread that fit snugly & securely around my foot. My personal favorite brand of trail running shoe is Hoka One One – this is due to the amazing amount of support and cushioning their shoes provide. My other favorites are BrooksMontrail, and Inov-8.

Finding the perfect fit

Everyone’s feet are shaped a little different. Well known boot and hiking shoe companies are usually known for having a certain “overall fit”. For example, some people swear by Merrells, I find they have flimsy “uppers” and are too roomy. Which proves my point that personal preference, foot shapes, along with the fit configurations of the various shoe brands, vary greatly. The best thing to do is try on a bunch of different pairs and see how they feel as best as you can in the store – imagine them on steep uneven terrain (REI stores have a great artificial rock ramp for practicing this). REI is also a great place to purchase the other layers mentioned in this post. Their staff are generally knowledgeable and willing to help. Happy shopping!

Keen on Keens?

People often ask us if it’s ok to wear “Keen style” shoes on their hike. Keen makes many styles of hiking shoes, the most popular being styles that are a combo hiking shoe/sandal with openings on the sides. While this certainly makes them more breathable, the holes leave your feet more vulnerable to injury. Another drawback to the openings is that on steep, muddy trails your foot is likely to slip & slide inside your footwear, especially when going up or down steep grades (visualize muddy feet slipping around inside a waterlogged loose shoe). If your hike is on a less steep trail, your keens are securely fitting and have good traction, and/or it’s a dry day – you should be fine 🙂 Another consideration is that sharp sticks, rocks, or pieces of uluhe fern stem can potentially gouge your foot through openings in the shoe on more overgrown trails.
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