The Pioneering Preppy Style of Boyz II Men

You probably know the Boyz II Men story. A quartet of guys from the Philadelphia High School for the Creative and Performing Arts with four incredible voices got together and delivered a string of hits that, especially in the first half of the 1990s, you couldn’t escape. “Not too hard, not too soft”: words to live by. The popularity of their sound was one thing, nestled snugly into the rise of new jack swing, a mishmosh of sounds that comfortably fused hip hop and R&B, jazz, doo wop, club music and whatever else had a good beat, they spent the kind of time atop the charts reserved for names like Michael Jackson or the Beatles. But they also had a look: red Brooks Brothers blazers and jeans; tennis sweaters and chinos that look straight out of the Alex Mill ad on your Instagram feed; striped oxfords popping with pink and blue; great eyewear and baseball caps, lots of those.

Going through old pics of the group is like a glimpse of the present. They were way ahead of the big suit revival. You’ll find rolled up pleated khakis with a pair of Timberland 3-Eye Lugs over 25 years before brands like Alife would breathe new life into the shoe. Basically, look at any picture of Boyz II Men in their heyday and you’ll see all the looks brands are rediscovering or the stuff people are likely to pay big money for at the best vintage stores. And the best part, to me, at least, is they’re always wearing hats. The band could wear anything and they’d almost always top it off with a hat and somehow it always worked. And the whole look had one person to thank: Michael Bivins, the former member of new jack swing originators New Edition and Bell Biv DeVoe, who pivoted from singing to managing, saw an opportunity for the group to stand out with a look that was all their own. Their “trademark collegiate duds,” as one 1992 Spin profile put it.

“We weren’t really into it at first,” group member Shawn Stockman told the magazine. “But once we started wearing the stuff and learning how to put it together, it started to feel good.

Prep is once again everywhere: Tyler, the Creator dresses like he’s ready for a day at the golf club, people are trading sneakers for loafers and I can’t wait to see what preppy expert Michael Bastian does at Brooks Brothers. But the role that groups like Boyz II Men played in the preppy revolution—and their influence now, with the look on the rise again—is under-discussed. In the 2012 Yale University Press book Ivy Style, the few paragraphs dedicated to Tommy Hilfiger explain that the brand’s clothing was popular among “young urban men.” Yet there is more to the story than that: it’s one that is about taking a style and elevating it, making it modern and accessible for more people, and Boyz II Men played a big role in that, serving as a bridge between the preppy boom of the 1980s and the comeback in the aughts.

“The preferred mainstream narrative is that the '90s was all about oversized sportswear, baggy jeans and Carharrt jackets — but that's only part of the story,” says Jason Jules, the “Patron Saint of English Ivy.” The author of the forthcoming book Black Ivy, Jules is focused on bringing attention to the fact that our obsession with Ivy overlooks the style’s indebtedness to the likes of Malcolm X, the poet ​​Amiri Baraka, or the artist Charles White. “There's a kind of reticence about recognizing the contribution Black culture has made to that style because the style, in essence, is all about maintaining a kind of status quo,” Jules says. “And the ways in which generations of Black consumers have worn these clothes undermines the solidity of that establishment ideal.”

Rappers wearing the occasional piece of Tommy or Ralph was one thing. Boyz II Men took it to another level. Look at any picture of them in the ‘90s and you get a smattering of tennis sweaters and cardigans, turtlenecks, blazers and ties, the Easter pastels and Nantucket reds swapped out for colors that popped out of photos or videos. The group would often show up dressed the same, like they’d just stepped out of the coolest prep school in the world. Look at them showing up to the 1994 VMAs, wearing clothes you could pull out of a contemporary Todd Snyder or Rowing Blazers collection: jeans, white oxfords with colorful striped, and red three-button Brooks Brothers blazers. To top it all off, each one is wearing a Mississippi State hat.

Boyz II Men made played out styles look fun. They helped usher in a new kind of emerging fashion sensibility, one that was very of the time, but also incredibly forward thinking. They announced that anybody could wear this stuff—but you really have to make it your own in order to make it stand out.