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I dunno, the filson western looks pretty nice, in theory... I haven't seen it in real life. Jkissi recently posted a WAYWT with a vest and a henley underneath that i thought was pretty cool.
I thought Jkissi's WAYWT looked good, but it might be hard to pull of if you're not Jkissi.
Also, if you're dead-set on going with this, I recommend pants with a mid to high rise. It usually looks kind of odd having a massive gap between the bottom of your vest and your waistline.














