When it comes to areas like Seattle and Portland, the right gear is incredibly important. You can't walk off the plane in swim shorts like it's San Diego or Mexico and you certainly can't be caught dead using an umbrella---a sign of weakness as far the locals are concerned---despite any convenience or practically it might bring. That said, these tools of the trade should get the job done nicely...
Aether Cloud Jacket: A good looking rain jacket that will keep you warm, dry, and looking like James Bond on a camping trip.
Gallet Multichron Pilot Chronograph: A quality pilot watch isn't a bad thing to have on your wrist anywhere, but this one is an especially good look in the PNW. This particular piece, called a Multichron Pilot, features the legendary Valjoux 72 manually-wound chronograph movement and dates from the mid 1980s. Its price tag won't (totally) break the bank either.
EDC Keychain: Because you never know when you might need something, and it's always good to be a man who's prepared.
2015 Lexus NX: A cool-as-hell crossover that can handle any kind of weather mother nature throws at you, any place or mountain you need to get to, and does so with the kind of style Lexus is known for? Sure, that'll do. We had the opportunity to test drive this bad boy before its release in Q4 2014. It's smooth, has plenty of cargo space for outdoor activities, and some seriously impressive tech like wireless iPhone/Android charging and an automatic parking break. Will you be racing your friends at the track with this thing? No. But it's still a damn fine adventure mobile if you're in the market for a crossover.
Aether Knitted Hat: Combo this with the waterproof jacket hood and you'll stay both dry and warm when that unfriendly rain hits almost daily October through June.
Green Soccer Journal: Both Portland and Seattle are the two biggest soccer towns in the USA, so reading up on some amazing stories from this great magazine isn't the worst idea you can have when relaxing on this trip.
Adidas Originals Boston Super: Suede desert boots aren't gonna cut it in the rain, and just like nobody uses an umbrella in the Seattle and Portland areas, almost no one seems to be wearing rain boots around town, either. These stylish sneakers from Adidas should do the trick though, and because of the low-key dress codes in the PNW, you can get away with these practically anywhere that isn't a steakhouse or a lame bottle-service-y club.
Topo Designs Klettersack: A good looking bag for all your stuff that uses 1000d Cordura for the exterior and coated pack cloth for an entirely lined inner compartment.
Leica T: There are plenty of drool-worthy locations littered throughout the northwest, and you need a damn good (and awesome looking) camera to capture 'em all.
Braven BRV-1: This rugged and waterproof wireless speaker is the perfect thing to bring when out exploring as it can handle pretty much any element thrown at it---rain, mud, snow, etc. The sound? Not so bad either.