25 Years Ago, Biggie Smalls Predicted How We’d All Be Dressing Today

Welcome back to Vintage Gold, a recurring segment where we here at Esquire HQ collectively lose our shit over some of the best throwback looks in Fit History.


I’m not going to lie, I initially stumbled across this blessed of the Notorious B.I.G. while scouring the internet for some Halloween inspiration, but this isn’t so much a costume as it is a HUGE fucking mood. Everything Biggie’s doing here you should be doing, too. I mean, shit. The dude looks like he’s absolutely swathed in soft-shouldered ’90s Armani excellence (and, hell, he very well might be). In other words, he’s dressing exactly the way we should all aspire to right now.

Snapped arriving at the 1995 Billboard Music Awards only two years before his untimely death, the Brooklyn-born rapper came through in one of the biggest (heh) fits I’ve seen in a minute. You got eyes, man. Take a look for yourself.

In a pristine white turtleneck layered underneath a richly textured double-breasted blazer that gently cocoons around his body and relaxed trousers that puddle elegantly over a pair of scuffed Wallabees, Biggie effortlessly epitomizes the type of cozy luxury that remains a defining element of how menswear’s most prescient designers are thinking about clothing right now. (When hubcap-sized buttons and a chunky gold crucifix necklace are only the proverbial icing on the cake that is your outfit, you know you’re doing something right.)

That’s a 10 out of 10 fit right there, folks, no matter what year it is. Someone give this man a posthumous medal for his services in the name of menswear today. This is king shit, done by the king of all MCs. And gentleman, with this outfit as your lodestar there’s no way you can go wrong once you really start dressin’ this fall.

Poppa been smooth since days of Underroos, baby!

Double Breasted Blazer Cardigan

Lardini farfetch.com

$519.00

Super Soft Supima Turtleneck

Land’s End landsend.com

$39.95

Houndstooth Wool Dress Pants

BERLE nordstrom.com

$165.00

Wallabee Maple Suede

Clarks Orginals clarksusa.com

$150.00

Avidan Grossman is the Style eCommerce Editor at Esquire, covering men’s fashion, shoes, grooming, and accessories.

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Source : Esquire