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This post was originally published in 2015. 

So close, yet so far away, the first decade of the 2000s were filled with a string of styles that were as iconic as the ‘80s and the ‘90s. Coming off the ‘90s, which at different points were both grungy and colorful, the rapid advancement of new technology brought a variety of sartorial influences for us to wear throughout the decade. Even today, we see artists co-sign clothing brands like Josué Thomas’ Gallery Dept. that have 2000s-era aesthetics, or brands like Palace leaning into all-over-print styles in their current collections.

But for every fire retro fit you had (which naturally matched your coveted sneakers), there were plenty of dudes hitting the streets in bootcut jeans, oxford shoes, and an Ed Hardy V-neck. But even the most tragic of fashion trends of the time left its impact on men’s closets—even if that impact is reminding guys on what not to add to their wardrobes. And despite hindsight being 20/20, we still have to recognize that most of these styles felt hard in the moment—as is the case with most trends—which is all that matters when you’re trying to get a fit off. From the all-over BAPE hoodies to the rise and fall of the Von Dutch trucker hat, these are The 25 Best Trends of the early 2000s.