Copy Princess Diana’s Travel Outfit in 5 Steps

It’s “Princess Diana season,” according to InStyle. The princess is known for her timeless fashion and unconventional pairings of preppy, comfortable looks. Her effortless style is an everlasting source of inspiration. One of her most iconic outfits is a super cozy ensemble for fall travel days: a cotton crewneck sweater, bike shorts, white sneakers, crew socks, oversized sunglasses, and a large shoulder tote.

The outfit recipe has become a fall-favorite classic, beloved for its balance between snug and roomy. The oversized cozy top compliments the flexible, weightless freedom of bike short bottoms. Slip into your most comfortable walking shoes and you have a look that is effortless, athletic, and relaxed.

Here’s how to get the look and enhance it for a day of comfortable travel. 

Cotton Crewneck Sweater

The key to nailing the crewneck sweater component of the look is to size up from your typical fitted size. This way, the sweater is boxy and long and hits at the top of your thighs. Princess Diana was seen wearing graphic crewnecks from colleges like Harvard and Northwestern, as well as from iconic British brands like Virgin Airlines. Wear a fleece that reflects you, be it a graphic title from your favorite school, destination, brand, or band. This Ralph Lauren crewneck is customizable with your favorite crest, city, or Polo Bear, while this one lets you add an embroidery of your favorite dog. Still, you can’t go wrong with a simple solid color crewneck. 

Bike Shorts

Look for bike shorts with a length of at least 7 inches, ensuring the shorts will be long enough to peak out of a long sweater. A standard black bike short will match with just about any sweatshirt color, but a statement color wasn’t uncommon for the princess to wear either. Some bike shorts come with a handy pocket sewn into the leg — a great storage spot for a passport or phone that you always like to have at your fingertips at the airport.

White Sneakers

Any white sneaker will do here, but the key is to prioritize comfortable walking shoes for long days of travel. These Reebok classic high-tops were popular in the ’80s and feel retro yet timeless. But for me, I opt for a classic pair of Converse, while many celebrities are known for their love of Adidas Sambas. 

Crew Socks

Crew height socks are back in again (alert your millennial friends who might still be wearing no-see ankle socks). Princess Diana sported scrunched crew socks in this look, which offers a little height and warmth to the leg. For long travel days, opt for a cotton blend of socks for breathability. I’ll be wearing this Mongolian cashmere blend from Quince which is luxuriously soft and warm for chilly fall travel days.

Large Shoulder Tote

A good travel outfit doesn’t stop at apparel — you’ll need a roomy bag as well for keeping essentials within easy reach. Princess Diana was often seen wearing the biker short look when running from the gym, and a large tote was the choice accessory for carrying what she needed. Look for a canvas or jute tote bag which are durable materials for an item that will be sitting on the floor, going through X-ray machines, and enduring the trials of a travel day.  

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