For the wonks of workwear, authenticity trumps all. And it doesn't get more authentic than Filson's Mackinaw Cruiser. Crafted from 100-percent virgin wool in a Seattle factory, the unlined jacket features four front products and a larger "cruiser" pocket on the back—just like when it was introduced in a red and black plaid back in 1914. Now in six colors, the durable weather-resistant wool wears like iron and will absorb 30-percent of its weight in water without even feeling damp. Meaning it's just as suited to protect you from the elements whether your hunting grounds are in the woods or at the bar. $280, at Filson
Ray-Ban just relaunched their classic Clubmaster frame. $129, at Ray-Ban.