OOTD – Princess Diana Casual – April 2022

As a sport, tennis has never been the most fashionable of athletic pursuits. It’s more often associated with khakis than kilts, and is more likely to be played in a park than at a fashion show.

What this has caused most casual fans to miss out on is that some of the game’s greatest players have crafted looks as iconic as any other athlete in the world.

One great example of this is Princess Diana, who was such a fan of the sport that she managed to get both Boris Becker and Andre Agassi over to her house for dinner in their primes. Her favorite player was Steffi Graf, an elegant German player known for her one-handed backhand and extravagant clothing choices—something she picked up from her royal role model. The two famously wore coordinating outfits during Wimbledon: white for day and black for night in homage to each other’s styles.

Princess Di may no longer be with us, but her affinity for bold colors, intricate patterns, and luxurious fabrics lives on in today’s fashionable women—and it can be seen clearly when looking at what you can wear with biker shorts and an oversized jumper like we see here.

Biker shorts have been very popular this summer.

Biker shorts are in, and everyone’s wearing them: the fashion-forward, the sporty, and even those who’d never be caught dead in spandex. Biker shorts have replaced skinny jeans as the go-to summer pant for countless men and women throughout the country. It’s easy to see why—they’re comfortable, fashionable, and more acceptable than spandex. Biker shorts have been popularized by athletes and cyclists alike, but they can be worn by anyone regardless of their fitness level or hobbies. They’re made from a variety of materials including flannel, denim, synthetic fabrics like polyester and rayon blends (sometimes referred to as “technical” or “performance” fabrics), or full-on cotton for maximum comfort (although this does sacrifice breathability). The look is an exaggerated version of mom jeans that definitely doesn’t work for everyone—especially men with larger thighs—but when pulled off well with just enough attitude (and maybe a hint of irony), bikers are both cute and comfortable.

Biker shorts come in all kinds of shapes and sizes these days because their popularity has spread far beyond their athletic origins: you can find everything from high-waisted to low-rise styles; some are super long while others barely cover your bum; some don’t include zippers at all (for those who prefer less fabric around their thighs) while others go all out with extra pockets. There’s no one right way to wear them; it usually depends on your personal taste. For example I prefer my bikers loose around my knees where they’re not constricting—a lot more forgiving than tight bike shorts that really dig into your glutes if you wear them too long before going on a ride.

When I was in London last weekend, I wanted to go for a more casual look inspired by Princess Diana.

I’m sure you, like me, recognize that Princess Diana was always well dressed. She wore designer clothes that would’ve cost a fortune and all of the latest fashions she could get her hands on. Though she had the money to buy whatever she wanted, she never seemed to lose sight of what a “normal” person might wear. Did you know though that there was one thing the people’s princess wore that most people don’t know about?

One of her go-to outfits was biker shorts and an oversized jumper. She loved how comfortable they were for long days of travel. The biker shorts were loose enough not to feel restrictive or dig into her legs as she rode in a car or on a horse, yet tight enough to not be riding up or falling down when mounted on a horse during an official occasion in full formal dress. This outfit also gave her room to breathe when walking around Rome in 100°F heat while wearing several layers of formal couture dresses; plus it looked great with sneakers! No one who saw this outfit thought “Oh my god, this is so casual!” They thought: “How awesome does Princess Diana look today?!”

I paired my biker shorts with an oversized jumper and sneakers.

While some would claim that summer is over, it is still quite warm in the Northeast. There are days where I just want to wear a comfortable outfit like sneakers and oversized jumper. When I want to look more put-together, I pair my oversized jumper with biker shorts and sneakers. A cute headband can also be worn for extra style points and it will keep your hair out of your face if you decide to wear sunglasses. If you want more of an athletic look, you can throw on some athletic pants or shorts instead of jeans and change out the sneakers for running shoes or sandals (you’ll probably get weird looks from other people at the gym).

It’s important to have versatile pieces in your wardrobe so you’re always prepared for what’s ahead!