Princess Diana’s Bike Shorts and Slouchy Socks Look is Back in 2025

September 3, 2025

Princess Diana was more than royalty - she was a global style icon. One of her most casual outfits has now become one of the biggest trends of 2025: bike shorts with an oversized sweatshirt, slouchy socks, and sneakers.

This look, once just Diana’s relaxed off-duty uniform, is suddenly everywhere again. From influencers to street style, the Lady Di bike shorts and socks outfit has become the go-to transitional weather look.

Why Diana’s Outfit Still Inspires

In the late ’80s and early ’90s, Princess Diana was regularly photographed in this exact combo. She paired black bike shorts with collegiate sweatshirts, chunky sneakers, and slouchy socks (also called slouch socks, scrunch socks or scrunchy socks). The result was effortless and chic while still being practical.

Today, the same formula feels just as fresh. It balances sporty and casual, comfort and style - something fashion is craving in 2025.

The Key Piece: Slouchy Socks

While bike shorts and sweatshirts may seem simple, the detail that made Diana’s look stand out was the socks. Slouch socks added texture and balance, softening the streamlined fit of bike shorts and giving the outfit its signature retro vibe.

Fashion cycles always bring back the good stuff, and slouchy socks are now trending again. They are being styled with sneakers, loafers (hello Michael Jackson vibes!), and even boots, proving that scrunch socks are more than a throwback - they’re essential for 2025.

How to Wear the Princess Diana Look in 2025

If you want to channel this timeless style today:

Start with classic bike shorts in black or another solid color.
Add an oversized sweatshirt with a graphic, vintage logo, or bold color.
Finish with slouchy socks and sneakers, letting the socks scrunch around your ankles.
For a polished twist, swap the sweatshirt for an oversized blazer but keep the slouch socks for authenticity.

The Timeless Balance of Comfort and Chic

The bike shorts and slouchy socks outfit works because it is practical, flattering, and fashionable all at once. Princess Diana wore it naturally, and decades later it still sets the standard for laid-back streetwear style.

Whether you call them slouch socks, scrunch socks, or scrunchy socks, they remain the accessory that pulls the whole look together. That’s why this Princess Diana outfit isn’t just back for 2025 - it’s here to stay.

Get the Look

If you want to recreate Princess Diana’s bike shorts and slouchy socks outfit, the perfect pair of slouch socks, scrunch socks, or scrunchy socks is just a click away. You can shop them right here and add that authentic Diana-inspired touch to your transitional weather outfits.