These friends shared more than just the odd boyfriend, they also shared a serious love of expressing themselves through style.
Blair opted for more preppy, almost regal looks that incorporated plaid, lace, florals and tweed and that were always topped off by a picture perfect accessory whether it be a beret, wide belt, pea coat or, yes, a headband.
Serena, meanwhile, preferred a more Bohemian vibe that was said to be inspired by Kate Moss. For S, it was all about layering jewellery, Grecian-inspired gowns and trendy blazers paired with jeans and boots, with splashes of stripes or sequins occasionally thrown into the mix.
It’s no wonder that these two are still regarded as some of the most influential style icons to date, with outfits that we’d honestly still wear today.