ASOS Chelsea Boots
Buy It Now at ASOS, $56

This footwear was made popular by The Beatles, and while it hasn't necessarily fallen out of style, it's safe to say they aren't as popular as they used to be. Menswear collections have been attempting to revive this style for the past few years, and we think this is the season they start coming back into prominence. Don't be surprised to see a lot more of these popping up soon, which why we'd advise hopping on the trend now—so you can say you were up on it first.