Hiking - If you plan on doing a lot of hiking, you’ll want a good pair of sturdy hiking boots, quick-dry hiking pants, and insect repellent. Because Portland has a lot of standing water in the forests, the mosquitos can be a bit nasty so you’ll want to stay protected as much as possible. And, as mentioned before, it can be a bit wet so if you choose to take a rainy hike, you’ll want a light raincoat that is still going to be comfortable and breathable.
Snow Sports - When going skiing or snowboarding, you don’t want to have to worry about the weather which means wearing the appropriate layers is important. Start with a base layer and add on either a snow bib or ski pants, a thick winter coat, gloves, a helmet, and goggles. And while it may seem silly, SPF is extremely important when on the slopes. The light reflecting off the snow can seriously sunburn your face.
Nightlife - Portland is a very casual city so getting extremely dressed up for a night out on the town isn’t necessary. For men, jeans and a nice button-up with a pair of loafers will do. For women, stick to jeans and dress it up with a blouse and wedges.
Sightseeing - If you’re set on walking around the city and exploring all of its hip shops and coffee houses, you’re going to want to be dressed comfortably. Go for layers (depending on the season), a thin jacket if needed, and most importantly, a good comfortable pair of walking shoes. I typically like to go with close-toed shoes such as sneakers for maximum comfort.