The graphic sweatshirts, biker shorts and sneakers that Princess Diana immortalized in her iconic and most laid-back look is the weekend vibe, perfected. The look telegrams two things at once: 1) “I’m off duty–leave me alone,” and 2) “Even though you’ve caught me in my most casual down-time, I still have impeccable personal style.”
I’ve thought about this particular Diana look in all its variations more than any sane human should, so forgive me for this rabbit hole. There’s just something about this look, a simple sweatshirt with a bold graphic, biker shorts, chunky socks and sneakers. Unlike her highly polished royal persona, it’s so simple, anyone could pull it off. It wasn’t about expensive bags or a celebrity stylist complicating things. Anyone could pull it off and attain the effortlessly chic style of a princess. Where Queen Elizabeth mastered the look of aloof professionalism, unattainable by design, Diana made approachable, yet always inscrutable style, look easy. And this was decades before celebrity stylists started dressing their celeb clients not only for the red carpet but for the Saturday morning Starbucks run. Call her the seminal street-style star.
It’s no wonder that style celebs like Hailey Bieber and Kendall Jenner have made versions of this particular look their style coda. Using this iconic fashion moment as a style guide for off-duty elegance, here’s our dressed-down-but-not-out Weekend Essentials Guide.