6 Modern Style Lessons We Learned from O.G. Fashion Queen Princess Diana

From loose-fitting T-shirts and blazers to baseball caps, dad-approved fashion is trending, but Princess Di was nailing the look all the way back in 1988. The only modernizing tweaks we’d make to her outfit above would be tucking in the tee (for a little waist definition) and swapping out the boots for a fresh pair of white sneakers.

High-waisted pants with a skinny belt? Total yuppie move. Instead of looking too yacht-club-untouchable, though, Princess Diana’s version is relaxed, thanks in large part to the slightly slouchy fit of her button-down.

Umm, anyone know where we can buy this exact outfit today? Puff sleeves are also in the midst of a major comeback, and Princess Diana absolutely nailed the look in her day. What sets this outfit apart is how perfectly proportioned it is. Instead of wearing puff sleeves with something voluminous on the bottom, she sticks to a snug skirt and sleek obi belt.

The thought of matching your shoes to your dress (um, and to your bag?) seems dated, no? But can we take a minute to recognize how chic it looks when done right? No, this wouldn’t work for every color or every dress-shoe-bag pairing, but basically, don’t write off matching without at least trying it.

If we’ve said it once, we’ve said it a million times: A flowy dress cinched with a wide belt is foolproof. Not only is it flattering (hey, hourglass), but it’s also a pretty effortless way to look put-together.

Can’t be bothered to match your skirt to your top? Wear all black. Overslept and rushing out of the house? Stick to shades of noir. Wearing black from top to bottom is easy, stylish and—did we mention?—easy.