The thing that bothers us most about faux workwear is that it has no legitimate blue-collar pedigree; it's a sham created by and for urban hipsters. The thing that bothers us most about dark or raw denim is that by two or three washes it's well on its way to losing its colour and grain. Levi's classic denim jackets get around both issues by being based (more or less) on proven workwear, and by needing far less cleaning than your jeans. Skip the much-hyped Thom Brownesque shrunken cord variant by Opening Ceremony and go for a standard issue like the Vintage Trucker (left) or the slightly fitted Tanker variant (right). The shirt-like collar and the contrast stitching will never go out of style; the only things you'll have to change over the years are how you button it and what you wear underneath.