There’s no denying that D was essentially the pioneer of this trend of sporting comfortable cycling shorts, as you’d typically wear leggings while teaming them with an oversized top or crewneck sweater. Ideally, cycling shorts would reach the mid-thigh and sit high-waisted.

Women’s Fitness Biker Shorts – Black
$7.90

During European summers, she frequently showcased herself wearing pastel-hued, abbreviated shorts. Accompanied by a set of athletic trainers, such as running shoes or tennis footwear, and black or white socks that rest slightly above the ankle.

Adicolor Classics Traceable Shorts
$42 $60

If you’re going for neutral black or white bottoms, an oversized casual crewneck is the ultimate practical and super comfy go-to. It’s the perfect outfit for chilling at picnics, running errands, or just hanging out with friends. Make sure you order it oversized.

Monki Light Blue Loose-Fit Sweater
$21 $30 30% off

Back in her early days, Diana had a soft spot for her cosy red knitted jumper, which she would sport on slightly chilly days. It’s a versatile piece that can be paired with casual denim jeans or even dressed up with smarter trousers if you’re in the mood.

& Other Stories Mock Neck Sweater
$62.10 $69 10% off

Chunky running shoes have always been a trademark of Dads’ fashion, but recently they’ve made a comeback, thanks to New Balance captivating the attention of trendy young fashionistas on TikTok and Instagram. However, Princess Diana was way ahead of the curve and rocked that trend back in the early days.

New Balance 530 logo-patch low-top sneakers
$166

Princess Diana always played it safe with neutral socks. They were her go-to choice, matching well with any style of shoes. The sporty socks she often wore, with ribbed stitching that extended past the ankle, perfectly complemented the casual running sneakers that she wore with confidence.

Nike Everyday Cushioned Training Crew Socks (3 Pairs)
$25

Well, this isn’t exactly great for Singapore weather, but it’s totally an option you can consider if you’re travelling to a colder country.

When you think of the British Royal Family, one of the first things that come to mind for many of us is their waxed Barbour jackets. And that iconic picture of Diana wearing slightly oversized Barbour jackets on a countryside walk really captures what these jackets are all about.

They might have a hefty price tag, but they’re definitely worth the investment as they’ll last you a lifetime and can even be passed down to your kids. When it comes to maintenance, all you have to do is give it a re wax at home or send it off to get it re waxed professionally. It’s the perfect jacket for all seasons.

Barbour Beadnell wax-coated weatherproof jacket
$570

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