The '90s It-Girl Backwards Hat Is Back & Brad Pitt's Girlfriend Is Owning It
This is far from breaking news, but the '90s are back in full force. Whether it's finding yourself reaching for your skinny jeans due to the edgy revival of a '90s basic or putting on your slip dress for an evening out, the decade is having quite the influence on our current wardrobes. And that includes the way we're wearing our hats. When you think of the '90s, Carolyn Bessette-Kennedy, TikTok's quiet-luxury fashion icon, might come to mind. Bessette-Kennedy embodied it-girl style, and if there's one piece from her catalog that is making a comeback right now, it's the backwards hat.
Bessette-Kennedy perfected the backwards hat and gave her polished, tailored outfits an instant dose of effortless cool-girl vibes. Decades later, Brad Pitt's girlfriend Ines de Ramon is completely owning the trend in 2026.
Perfect for a modern summer, de Ramon styled the '90s it-girl backwards hat with light and breezy sunny weather staples. While we loved Bessette-Kennedy's ability to pair a sporty accessory with a tailored look, it can be quite the contrast to pull off. de Ramon's 'fits are proof that the cool-girl accessory can be just as impactful with a basic white top and jeans or a feminine lemon-print sundress.
How to incorporate the '90s it-girl backwards hat into your wardrobe
Whenever a trend feels too far-fetched to wear in real life, the trick is always in how you incorporate it into your wardrobe. The backwards hat look can feel like you're trying too hard to give off an edgy vibe, but the secret is making it look like an afterthought. It's something Ines de Ramon and Jennie, who had one of the best beauty moments from Lollapalooza, pulled off so well in 2026.
The key? They kept their basic outfits completely grounded, and the headwear simply added that extra punch. Whether it's de Ramon throwing on a cap with her yellow sundress or Jennie contrasting a navy Aimé Leon Dore cap with an oversized statement knit from Chanel and dark sunnies, the backwards hat should simply be the final, effortless addition to your outfit.
Opt out of styling a backwards hat with a sporty 'fit, because that might feel like a uniform. Instead, think out of the box and contrast it with elevated, unexpected pieces. We love the sundress and knitwear routes, but it would also look so effortlessly chic with your favorite jeans and basic tee combination or even a blazer during the colder months.