For the fashion-conscious man, knowing and understanding the ebb and flow of trends is key. Top looks are often heralded by the classic and timeless pieces that stand the test of time: a crisp white tee, a straight-fit pair of gray wool trousers, and a slim-cut navy suit quickly come to my mind. But when you’re in the mood to be a little less “classic,” there are edgier bits that can casually take you from day to night, or weekday to weekend: a pair of dark blue (slim) jeans, a pair of military-esque black lace-up boots, and a bomber jacket can be pulled together (with other pieces, of course) to complete a more laid-back (yet still timeless) look.

Classic and timeless looks aside, we know that in the world of trends, there are some that have more lives than even the most shrewd chat noir. One trend that has re-appeared as of late is the creeper. Yes, the creeper. For those who need no explanation, I nod my head to you (and roll my eyes)… but for those less familiar – creepers are shoes. More specifically, the term technically refers to the weighty crepe sole… a style that rose in popularity during the rise of punk and new wave subcultures. The ultra-thick soles, which cushioned many a shoe for men and women alike, were often deemed an outward expression of rebelliousness and quirky-individualistic style.

Admittedly, I had my own “creeper” moment back in the late 80s/early 90s. I owned a couple of pairs, partly as an homage to my love for Bananarama –who, at the time, sported the style along with all-black outfits and aerosol-sprayed hair. (Thankfully, I have no digital imagery of myself in this look. THANKFULLY.) But eventually, that look ebbed and ultimately flowed out of my life for what I thought was for good. But it seems that is not so much.

In recent years, the top fashion houses have resurrected the shoe back into the limelight. During the 2011 season, Prada’s runway shows were filled with super-thick creepers which teetered the boundaries between chic-worthy and gag-able. Part wingtip, part brogue, and definitely part madness, variants of the shoe were sported by the likes of Rihanna and Jude Law. Other designer labels followed suit, including Thierry Mugler and Dries Van Noten.

With the look being re-pioneered by the world’s runways, in no time creepers could make their way to an Aldo near you. (If they haven’t already.) But would you take the plunge? At the end of the day, sporting anything with an air of confidence can spark a look that even the fashion less-conscious might turn their heads at… in a good way. But nevertheless, and thankfully so, there are more subtle incarnations of the military-inspired look out there, like this pair by A.P.C.

As I’ve always believed, the shoe can definitely make a first impression. And just because a shoe fits, it’s still wise to wear with caution. But so long as you do with confidence, you’ve got to own it… and own it well. (That goes for you creepers, too.)