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Wear something you can move it and shoes that fit the hike (waterproof if necessary). Don’t wear anything that you have to constantly adjust or jeans that don’t have major stretch. Make sure your shoes are broken in before you head out. Comfort beats cute for footwear. Leggings only if they’re technical and won’t snag on everything, unless you want a hole in your butt. Last hike I did with friends unexpectedly had several downed huge, old growth trees that we had to clamber over and water crossed the trail in several places. We all had Chacos so water crossing was easy. But the one woman in a “hiking skirt” had some issue with going over the trees. So: research your hike, check the weather, read recent trail reports, pack a light day pack, and go from there.
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