The “Princess Diana" Socks Trend Is the Easiest Way to Elevate Your Fall Outfits

There are a few photos of me as a child, circa 1996, where I’m wearing an outfit Hailey Bieber or Olivia Rodrigo would totally copy today: a sweet little dress or pleated skirt accessorized with scrunched-up white socks and a pair of shiny patent-leather loafers. (If you must know, they were Barbie loafers with little Barbie charms. Very chic.) 

Of course, my younger self didn’t invent the socks-and-loafers look, and I highly doubt style stars like Bieber, Rodrigo, and Emma Chamberlain are taking a cue from my childhood photo albums. Instead, they’re probably taking a page from one of the greatest and most influential style icons of all time: Princess Diana. There’s a reason those gym-going outfits went viral, and a lot of it has to do with what she was wearing on her feet. Ahead, we unpack the eternal appeal.

The Trend

Influencers, celebs, and regular folks like me have been copying the late Princess’s post-gym look of an oversize sweatshirt, biker shorts, a luxe handbag, thick white socks, and sneakers for years now; those pap shots of Diana have been pinned and posted over and over again—and even inspired an entire photo shoot starring Bieber.

The socks are key to the look; this isn’t the time for no-show socks, ruffle socks, or shorty ankle-length socks. The Princess wore classic white cotton socks with her gym ’fits: They’re not too thick, not too thin, and perfectly scrunched and slouchy at the calves and ankles. Shortly after the gym pics made their resurgence into our collective consciousness, it seemed like everyone was pulling out their white cotton socks and letting the oft-ignored accessories have a moment in the sun once more.

But that’s not the only Diana outfit sparking some of the best summer-to-fall transition looks. The Princess was also a big fan of classic penny loafers and wore the flat shoes with all kinds of low-key ensembles. When paired with the white cotton socks, you’ve got yourself the footwear trend to follow for this fall and beyond. (Plus socks keep your feet warm on chilly mornings, so they’re practical too. Your mom would be proud.)

But that’s not the only Diana outfit sparking some of the best summer-to-fall transition looks. The Princess was also a big fan of classic penny loafers and wore the flat shoes with all kinds of low-key ensembles. When paired with the white cotton socks, you’ve got yourself the footwear trend to follow for this fall and beyond. (Plus socks keep your feet warm on chilly mornings, so they’re practical too. Your mom would be proud.)

How to Get the Look

Getting the socks right is the most important part, and it’s no easy task. The Princess Diana socks in question need to be very specific white socks—they can’t be too thick or you won’t be able to stuff ’em in your loafers, but they can’t be so thin that you can’t scrunch and slouch to your heart’s content. They need to be calf-length—not ankle- or knee-high. They should hold up to a workout or, at the very least, a long day of running errands or bopping around town. Luckily Diana-style socks are easier to find than ever. The Bombas Hybrid Ribbed Calf Socks ($16) are a quality option, as is this chic two-pack from C.O.S. Get the most bang for your buck with the Old Navy Performance Crew Sock 3-Pack ($13) or slip your toes into AE’s easily styleable Slouchy 10” Socks ($10). For a more dramatic look, try Artizia’s chunky Scrunch Crew Socks ($12) or Skims’ Slouch Socks ($16), which come in a bunch of fun colors.

When styling your Diana socks, you can either dress them down with biker shorts, a Diana-approved Sloppy Joe Zip Neck Sweatshirt ($99), a leather top-handle bag, and sunglasses or lean into the prep aesthetic by slipping them into loafers. (Diana was frequently seen in a brown-and-white pair that looks eerily similar to the classic G.H. Bass Whitney, $175. which I personally own and love.) Bieber and Rodrigo wear their white socks with miniskirts and minidresses, and Chamberlain won over TikTok with a midi skirt, tank, and socks-with-loafers look last summer. Bieber also loves wearing her white socks with baggy denim cutoffs and a sweater or a white T-shirt with a jacket on top. Honestly, the magic of classic white socks is that they look fresh, cute, and totally timeless with any fall outfit. Whether you’re channeling child me with loafers and a pleated plaid skirt or the late Princess of Wales in ’90s jeans and flats or your fave biker shorts and giant sweatshirt, you really can’t mess it up.