MEN'S JACKETS, RANKED

Sartorial armor for every man.
  1. 1.
    The denim jacket
    The king of iconic jackets. Historically a symbol of youth, adventure, and masculinity, the denim jacket is a classic, rugged, versatile, and practical staple for every man. Works perfectly over a grey t-shirt but also as a layer over an oxford shirt and a slim-knit tie for that signature J.Crew look. Wear it to hell and it only gets better. Just make sure the thing fits.
  2. 2.
    The peacot
    Immortalized by Robert Redford in Three Days of the Condor (1975), the peacoat is the one true winter essential. It's nearly impossible to get this wrong, especially given the abundance of options and styles on the high and low end of the market. Call me old-fashioned, but if you ask me, the simplest peacoats look best. Don't forget to pop the collar for instant cool points.
  3. 3.
    The bomber jacket
    Developed by the US Army in 1917 to keep pilots warm in unheated aircraft cockpits, the bomber jacket has endured as classic redefined most famously by James Dean in Rebel Without a Cause (1955). These days we often see them as a urban streetwear staple, worn notably by Kanye West and The Weeknd. Dress it up in chinos and brogues or dress it down with joggers and sneakers - you can almost do no wrong.
  4. 4.
    The Harrington jacket
    Not too dressy and not too casual, the Harrington jacket is the close cousin of the bomber jacket and is just as versatile. Wear it with a cableknit sweater, chinos, and sneakers for a casual weekend look. Note: if you Google Harrington jackets, they might turn up results that look similar to bomber jackets - while the differences are often subtle, look to the patterned inside jacket lining as a dead giveway.
  5. 5.
    The leather jacket
    This one is a little trickier than the rest, given it's place in the pantheon of iconic menswear but also how easy it is to get wrong. Cost, quality, fit, and function all complicate the plot, which is why I would call the leather jacket the investment piece. You should look to save at least a few hundred dollars for one that you can pass down to the next generation. Also, steer clear of the style a la Marlon Brando in The Wild One (1953)—very few people can pull that one off.