Here are 32 of Princess Diana's off-duty outfits that never went out of style, from varsity jackets to cycling shorts

Away from the red carpet and royal engagements, Princess Diana's off-duty outfits show off her innate sense of style to a T. In fact - forget the glamorous ballgowns and sleek skirt suits - the looks the mother-of-two wore in her downtime are some of her most memorable.

From gym workouts to the school run and polo days to the ski slopes, the Princess of Wales ensured her attire was always on point - and her looks were some of the best royal off-duty outfits. While she loved to make a fashion statement - with her 'black sheep' jumper, Philadelphia Eagles varsity jacket and pink gingham trousers being three of her most iconic wardrobe items - she was also a fan of the classics. Her go-to items included blue Levi jeans, black oversized blazers and chunky white trainers.

Prince William and Prince Harry's mother may have been a princess, but she sure knew how to mix things up - and the outfits she wore away from royal engagements enshrined her as the queen of cool. What's more, many of the looks we've rounded up for you here, are so good they'll simply never fall out of style...

32 of Princess Diana's off-duty outfits

1. Virgin Atlantic sweater

One of Princess Diana's best fashion moments was rather unexpected. The royal mother-of-two was snapped wearing a navy sweater - branded with her friend Sir Richard Branson's Virgin Atlantic company - while departing the Chelsea Harbour Club gym in London in 1995. She paired it with orange cycling shorts and white trainers in a look that has become iconic.

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2. 'Black sheep' jumper

Many speculated that the then-Princess of Wales was trying to make a point when she wore a 'black sheep' jumper to the Guards Polo Club in Windsor in 1983 - two years after her royal wedding. She paired the Muir and Osborne piece with a pair of white trousers and tan-brown ballet flats.

3. Philadelphia Eagles jacket

Princess Diana brought serious style to the school run. In 1991, she dropped off Prince Harry at Wetherby School in London in a green Philadelphia Eagles varsity jacket, which she dressed up with a black pencil skirt and gold belt.

4. Leopard print swimsuit and sarong

Princess Diana looked chic holidaying on Sir Richard Branson's island of Necker in the British Virgin Islands in 1990. She was seen playing barefoot on the sand with her sons in a leopard print swimsuit and matching sarong.

5. Blazer-over-sweater combo

As the years passed, Princess Diana became more confident with her sense of style. She swapped floral tea dresses for a cooler look at Guards Polo Club in Windsor in 1988 - wearing a black blazer over a white British Heart Foundation sweater with a navy baseball cap, blue jeans and brown boots.

6. Tie-dye strappy mini-dress

Just weeks before she was tragically killed in a Paris car crash in 1997, Princess Diana was seen on holiday in St Tropez, France. The royal mother-of-two looked stunning in a green and purple tie-dye effect mini-dress that was perfect for the hot weather.

7. Pleated blue midi-dress

Princess Diana may have been off-duty, but she was the epitome of elegance in a pale blue midi-dress - featuring large gold buttons and pleating - at the Cartier International Polo match in Windsor in 1989. She paired the Catherine Walker design with white heels.

8. Sweatpants and boots combo

For the school drop-off in London in 1989, the Princess of Wales opted for a particularly head-turning ensemble. She wore a white sweater beneath a black blazer, which she paired with white sweatpants tucked into brown boots - sweeping up her blonde hair into a baseball cap.  

9. Red varsity jacket

Princess Diana looked sharp as she dropped off her youngest son Prince Harry at Wetherby School in London in 1992 - the year she separated from Prince Charles. She paired a red and black varsity jacket with a pair of blue jeans, and added gold hooped earrings and brown boots.  

10. Belted pink midi-dress

For a summer's day in London in 1989, the Princess of Wales kept cool in a pale pink button-through midi-dress - cinched in with a tan-brown belt. She accessorised the look, for collecting Prince Harry from nursery, with a pair of gold ballet flats.

11. Suede brown skirt

In a seriously stylish autumnal look, Princess Diana did the school drop-off in 1988 in a slouchy cream turtleneck tucked into a brown suede A-line skirt - a look that is the essence of quiet luxury. She accompanied Prince Charles to Prince William's London school, and the then-couple departed with Prince Harry.

12. Cobalt blue scarf

Princess Diana knows the power of a carefully chosen accessory. In 1986, she was spotted dropping Prince William off at nursery in London in a black jacket with polka dot-print trousers and knee-high black boots. However, she added a dash of colour in the form of a cobalt blue scarf.

13. White pleated skirt

We love the elegant but relaxed ensemble that Princess Diana wore to the polo in 1987. She was seen guiding her youngest son across the grass in a white and navy printed sweater over a long pleated white skirt, which she dressed up with gold ballet flats.

14. Straight-leg floral trousers

While it may not have been the most practical attire for hanging out with horses, Princess Diana looked stunning while leading a Shetland pony on the grounds of Highgrove House in 1986. She paired a pale pink ruffled-neck blouse with a pair of floral trousers and wore a cream jumper tied around her waist.

15. Knitted v-neck jumper

Princess Diana first introduced the world to her wardrobe of quirky jumpers shortly before her 1981 wedding to Prince Charles. She participated in a photocall with her fiancé near Balmoral wearing a bright pink printed number with green corduroy trousers, red socks and Wellington boots.

16. Polka dot-print skirt

We loved Princess Diana's stylish look for a polo match at the Guards Polo Club in Windsor in 1986. She pushed fashion boundaries in a white sweater, complete with red detailing, along with a white and red polka dot-print A-line skirt by Mondi.

17. Denim shirt and florals

If you're after a fresh way to wear a denim shirt, then take inspiration from Princess Diana's 1990 trip to Cirencester Hospital where her husband Prince Charles was being treated for an arm injury. She wore the wardrobe essential over a white T-shirt and tucked it into a floral midi-skirt which she cinched in with a tan brown belt. 

18. Stars and stripes sweater

Princess Diana headed to the Chelsea Harbour Club gym in London in 1994 in a stylish workout look. She paired a sweater that seemed to be inspired by the US flag - printed with blue and white stars as well as red stripes - with navy cycling shorts and finished off the relaxed look with white trainers and ankle socks. 

19. All-red jumper and skirt

For Prince Harry's first day at Wetherby School in London - where he was joining his brother Prince William as a pupil - Princess Diana opted for an eye-catching all-red look. She paired a sweater, featuring gold detailing, over a long red skirt and finished off the smart ensemble with matching ballet flats.

20. Chanel striped cardigan

Princess Diana invested in good-quality classics for her off-duty wardrobe. To visit Prince William's school in 1989 with then-husband Prince Charles, she wore a striped black Chanel cardigan - which she paired with a cream pleated skirt and white heels.

21. 'Polo player' jumper

Given the numerous occasions Princess Diana watched polo, it is perhaps unsurprising that she nodded to the sport in a navy jumper she wore for a 1986 flight. She paired it with a cream pleated skirt and black heels for the journey up to Scotland where the family were heading to Balmoral.

22. Dusky pink accessories

Accessories can make or break an outfit, as Princess Diana proved time and again. The royal made an appearance at the Guards Polo Club in Windsor in 1983 in a printed jacket and pleated white skirt. However, she elevated the ensemble with a dusky pink handbag and a pair of matching kitten heels.

23. 'Koala' print sweater

Princess Diana did maternitywear in style. The expectant mother was seen in 1982  - while seven months pregnant with Prince William - watching the polo at Windsor in a comfortable but eye-catching ensemble. Her koala-print jumper and red trousers were quite the combo. 

24. Double-denim skiwear

Few loved denim quite like Princess Diana - who even wore it on the slopes. The royal mother-of-two wowed in a denim shirt and matching jeans combo while on a skiing holiday with her sons in Lech, Austria in 1993. She kept cosy in a black jacket and white snow boots. 

25. Cream pussy-bow blouse

Princess Diana had a particular knack for smart-casual, a dress code she nailed with aplomb at the polo over the years. She visited Cowdray Park Polo Club in West Sussex in 1983 in a cream pussy-bow blouse tucked into a pair of striped blue and white trousers.

26. Coral bicycle shorts

We loved the gym look that Princess Diana wore to exercise in at the Chelsea Harbour Club in London in 1994. She looked effortlessly cool in a place blue sweater and coral cycling shorts, which she paired with white ankle socks and white trainers - finishing off the ensemble with tortoiseshell sunglasses. 

27. Yellow denim dungarees

Princess Diana looked colourful in lemon-yellow dungarees and a floral top the year she married Prince Charles in 1981. She was seen enjoying the action at Cowdray Park Polo Club in Gloucestershire with her friend Sarah Ferguson, who would go on to marry Prince Andrew.

28. Monochrome puff-sleeved blouse

It was the era of power dressing, and Princess Diana put on a strong look while watching a polo match in Cirencester in 1983. She wore a white and black puffed-sleeved blouse with a white pencil skirt, which she cinched in at the waist with a black belt.

29. High-waisted Levi jeans

You can't go wrong with a pair of classic blue Levis, as Princess Diana proved on the school run in 1992. She twinned in denim with Prince William, while pairing her jeans with a white T-shirt emblazoned with blue stars and a dark brown belt.

30. White sailor blouse

Princess Diana looked elegant in a white sailor-style blouse tucked into a blue floral midi-skirt at the polo in 1985. She accessorised the ensemble, for the sporting event in Cirencester, with a large brown belt.

31. Red puffer jacket

Whatever the climate, Princess Diana was always dressed to impress. Her wardrobe of skiwear was particularly chic, as can be seen from a day on the slopes in Lech, Austria in 1994. She paired a red puffer jacket with black slim-fit salopettes and finished off the chic look with black sunglasses.

32. Pink gingham trousers

One of Princess Diana's most iconic looks was an all-pink ensemble for a photocall at Highgrove with her sons in 1986. The royal mother-of-two paired a fuchsia pink cardigan over a white blouse, which she tucked into a pair of pink and white gingham trousers - adding a pair of white loafers to finish.