Leonardo DiCaprio was spotted ‘giggling’ with Lottie Moss at Chiltern Firehouse 30 years after ‘fling’ with her sister Kate – but the OnlyFans star has taken a VERY different path to her supermodel sibling

• Both Kate Moss and her half-sister Lottie partied with Leonardo DiCaprio at 25
• READ MORE: Leonardo DiCaprio, 49, heads to five star hotel as he arrives in Paris after partying into the early hours with Lottie Moss, 25, at Chiltern Firehouse

Leonardo DiCaprio has become known – and in some cases, mocked – for his preference to date supermodels in their twenties.

Indeed, the Oscar-winning actor’s dating history has even been recorded in bar charts that compare his age to the ages of his girlfriends and rumoured flames while he dated them.

This week, the 49-year-old partied the night away with model Lottie Moss at Marylebone’s celebrity hotspot, Chiltern Firehouse. 

Rewind some 30 years ago, and it might have been Lottie’s half-sister, Kate Moss, in her place – as the pair were rumoured to have had a brief fling in 1993 when they were both 19 years old.

Yesterday evening, Lottie, who at 25 years old is just within the age bracket consistent with Leo’s dating history, was ‘chatting’ and ‘giggling’ with the actor.

Lottie Moss and Leonardo DiCaprio partied together yesterday evening. 30 years ago it was Kate with Leonardo. Here, FEMAIL explores whether it’s just a taste in men that the half-sisters have in common 

Lottie, a TV personality and OnlyFans star, added to her following recently with her appearance on E4’s Celebs Go Dating.

But at the beginning of her career, she was often compared to her supermodel sister. 

In fact, Lottie was dubbed ‘the new Kate Moss’ at just 13 years old when she featured as a bridesmaid in her supermodel sister’s wedding to Jamie Hince in 2011.

Yet the once close relationship they might have shared seems to have vanished, with Lottie hitting out at her famous half-sister Kate last year, saying she has ‘never really supported me’ in a scathing Instagram post.

While there are definitely differences between the pair as Lottie carves out a new career for herself, some similarities between the half siblings remain – but is their taste in men one of them?

Here, FEMAIL takes a look at Lottie and Kate’s career trajectories as the once-close siblings have taken very different paths… 

EX PARTNERS  

Lottie Moss went public with The Vamps Tristan drummer Evans (pictured) in 2021. The pair are pictured above in London in 2021

Made in Chelsea star (pictured) Alex Mytton had a brief romance with Lottie Moss back when she was 18. The pair are pictured above in 2016

Lottie and Adam were romantically involved after Celebs Go Dating. They are pictured above leaving Chiltern Firehouse earlier this year, the same spot Lottie was at yesterday evening with Leonardo DiCaprio 

Lottie Moss has had numerous relationships with people in the public eye, including Made In Chelsea star Alex Mytton. 

The pair got together in 2017 when Lottie was 18 and Alex was 25, with the pair frequenting top London nightclubs and putting on loved-up displays.  

However, the romance appeared to come to an explosive end after a few months when the pair were recorded arguing in a nightclub, with Lottie heard telling her love: ‘No Alex, I’m done!’

In 2021, Lottie and The Vamps rocker Tristan, 27, went public with their romance after it emerged that they had secretly been dating.

But the sister of supermodel Kate Moss clarified that things were over on Instagram later that year when responding to a fan’s question on Instagram asking if she is single, she replied: ‘Yes and actually very happy for the first time ever and here are the reasons why.’ 

Kate Moss and Johnny Depp dated in Kate’s early twenties for three years, their separation was allegedly heartbreaking for Kate. The pair are pictured in 1995

The pair quickly developed the title of the ‘It couple’. The pair are pictured above t the The Academy in Beverly Hills, California in 1995 

Opening up further about her dating history and her preferences with boyfriends, Lottie told her fans what her ‘type’ was, joking that her type has now changed from ‘malnourished men with tattoos’.

She explained: ‘I feel my type has changed so much in the last few years – don’t look at my track record but if you do, it is malnourished men with tattoos’ she quipped.

She continued: ‘Men with any type of drug problem or trauma – not my type anymore – obviously apart from like a guy that I’ve dated, but… musicians.’

More recently, Lottie Moss was linked to Love Island star Adam Collard, 28,  since meeting on the E4 reality series Celebs Go Dating. 

On one episode, Adam told the dating agents that he felt a ‘spark’ with Lottie, which came after it was revealed the pair had slept together.

But in a later episode, things got heated very quickly as drama unfolded between the pair. They soon parted ways. 

By the age of 25, Kate, on the other hand, had only had one serious relationship with Johnny Depp. 

Moss and Depp met at a popular New York City café called Tabac in 1994, a year after he split from Winona Ryder – when the model was 20 years old and the actor was 31.

For three years, the pair were practically inseparable, and they couldn’t keep their hands – or lips – off one another. 

While it certainly appeared to be filled with many ups, their whirlwind romance also had some downs, as the two stars were seen shouting at each other in public on more than one occasion. 

They ultimately split in 1997, after Depp said he struggled to balance his busy work schedule with his relationship, and Moss later admitted that the breakup left her devastated for ‘years.’ 

INCOME 

Lottie Moss has secured deals with fast fashion brand Pretty Little Thing. She is pictured above from a recent shoot for the company 

Lottie was once signed with Storm Models Management. She is pictured above in PrettyLittleThing X Lottie Moss Red Dress Halloween Shoot

Lottie has had a lucrative modelling career throughout the years, and has worked for Vogue, Calvin Klein, and Harper’s Bazaar. 

However, last year she claimed she had been dropped from her agency, Storm Models Management, with sources telling MailOnline the decision was made due to her partying habits. 

Industry insiders had warned for months that Lottie was putting her promising fashion career in jeopardy by selling raunchy photos of herself on the adult website OnlyFans.

Sources close to Storm Management suggested that the firm, which has nurtured the careers of many successful young models including Cara Delevingne , 31, had finally run out of patience with Lottie and permanently cut ties with her.

As well as deleting her portfolio from the company’s website, Storm had not posted about Lottie to their Instagram profile, which is followed by 439K fans and industry professionals, since September 2020.

But Lottie continued with her career on OnlyFans, where she also sells her underwear – and even claimed she can make up to £30,000 a month on the website. She has also worked for fast fashion website Pretty Little Thing. 

By the age of 25, Kate Moss was one of the biggest names in fashion. She is pictured above at a motor show in Earls Court, London, in 1999

Kate was scouted in an airport while travelling back from a family holiday. She is pictured above at London Fashion Week in 1999 

By 25, Kate, on the other hand, had a very different career. The supermodel also signed to Storm Model Management as a teenager. 

Coming from humble beginnings in Croydon, the then teen was scouted by Sarah Doukas, the owner of modelling agency Storm, at JFK Airport in New York following a holiday in The Bahamas.

And while the talent scout believed in her looks, neither Kate nor her mother had the confidence that her appearance would propel her to the big time with Kate stating in a 2022 interview that she didn’t think she was ‘modelling material’. 

While her mother Linda stated that she ‘wasn’t photogenic’, with Kate agreeing before both then concluding that she ‘might as well try’ to make it in the modelling industry.

She soon rose to prominence in the early nineties thanks to her images by Corinne Day featured in youth style magazine The Face, with her radiant features and unstyled shots going on to pique the interest of those in the industry.

FAMOUS PALS  

Lottie Moss went to Ibiza with pal Millie Court (pictured left) to celebrate Chloe Burrows 27th birthday 

Lottie donned a black bikini with a cute cropped co-ord and silver belly chain to celebrate her friend’s birthday at O Beach Club 

Lottie is often spotted out on the dancefloor with a group of pals who share her love of partying. 

Earlier this year, Lottie was snapped enjoying a clubbing holiday in Ibiza to celebrate her close friend Chloe Burrows’s birthday.

Chloe, a reality personality, 28, invited Lottie to O Beach Club along with several other close girl pals, including Millie Court.

Chloe and Lottie met earlier this year while both looking for love on the E4 dating reality show Celebs Go Dating.

While Lottie calls many familiar faces her friends, a younger Kate Moss tended to keep a slightly smaller inner circle – in particular, she was close friends with fellow supermodel Naomi Campbell. 

Kate Moss and Naomi Campbell instantly hit it off. They are pictured above at a Versace event in 1999 

Naomi defined their relationship as a ‘long friendship’, having mmet in Los Angeles in 1992. The pair are pictured at during an auction for Mandela’s Children Fund at the Grooteschuur estate in Cape Town in 1998 

The two girls who hail from South London met on a shoot in Los Angeles in 1992, when Kate was 15 and Naomi was 18, and have been close pals ever since. 

‘It was a brief meeting but I remember her being strikingly quiet, she hardly spoke. She can be very shy at times — if she doesn’t know you she doesn’t speak. The other striking thing, obviously, was her beautiful face. 

‘I knew she was special from that first minute I saw her,’ Naomi said in a birthday tribute post in The Standard. 

The beauty added: ‘Some months later in 1993 we were both working in Madrid and that’s when I kidnapped her. I said: “You can’t be here on your own! You’re coming with me.” That was the start of a long friendship.’

FASHION   

Kate is known for her effortless yet chic style. She is pictured above at the CFDA Fashion Awards, New York

Lottie is bold with her style choices, and isn’t afraid to show some flesh. She is pictured above earlier this year at the Glamour Women of the Year Award

If there’s one thing the Moss sisters know about, it’s fashion. 

But the pair have quite different takes when it comes to clothes and shoes.

It’s no surprise that Kate, who was walking the catwalk for luxury fashion houses and posing for top-end designers, was donning clothing with class by 25.

The supermodel was known for her effortless rocker chic attire in that era, sporting sophisticated silk cami dresses and adding a touch of flair with a biker leather jacket.

On the flipside, Lottie takes a different approach to fashion.

She is often dressed in revealing two-pieces and girly ensembles.

The Celebs Go Dating star does seem to have a love of mini dresses and pastel shades.

Opting for a more glamorous style than Kate, Lottie is known for more out-there styles.

TATTOOS 

Lottie Moss has revealed that her face tattoo was her way of expressing her ‘freedom’ after ‘years of being so controlled’

Bold move: The model and OnlyFans star, 24, shocked as she showed off her new ‘lover’ face tattoo after a wild night out

Lottie shocked fans in recent times with her decision to get a tattoo on her face.  

She later revealed that her face tattoo was her was of expressing her ‘freedom’ after ‘years of being so controlled’.

Last year, the model and OnlyFans star surprised her fans as she showed off her new ‘lover’ face tattoo after a wild night out.

But in a candid new chat with Glamour magazine in which she opened up about growing up in the ‘toxic’ fashion industry, Lottie told how the inking was her way of ‘expressing that I am free’ after embarking on a ‘self-discovery’ journey.

The interview saw Lottie detail her years feeling traumatised after being body-shamed a young model, before she later stepped back from the industry and went on to launch a successful career on X-rated subscription site OnlyFans.

After falling into a state of depression and self-medicating with drink and drugs to quell her anxiety amid the backlash of her joining OnlyFans, Lottie checked into rehab last year. 

Lottie told the publication that after finally finding the peace and freedom from her former life, she got the tattoo to symbolise her new found liberation from years of feeling suppressed in an ‘intense industry’.

During the interview, she explained: ‘Since rehab, I’ve been on a journey of self-discovery. I’ve spent a lot of time in Bali, surrounded by nature, reading alone or spending time with like-minded people – and learning to love myself again while finally being free from my former life.

‘That’s why I decided to get my face tattoo; the word ‘lover’ under my eye. Yes, it was impulsive, but after years of being so controlled, it was my way of expressing that I am free. I’m no longer controlled.’

Kate, who currently has a number of small and intricate tattoos, did not have any before the age of 25. 

SCANDAL 

One thing the Moss sisters do have in common is there love of partying. Lottie is pictured above this year

Kate earned herself a party girl image in the ’90s. From L to R is Leah Woods, Kate Moss and Sadie Frost At Supergrass Party, Astral Club, London, in 1999

Scandal surrounded Lottie when she was supposedly dropped from Storm Models Management. 

A fashion source told MailOnline that the company was forced to distance itself from Lottie after she confessed to having a ‘really bad addiction to cocaine’ and checked herself into rehab.

There was also growing concern amongst industry bosses over the amount of cosmetic surgery she has undergone when Storm models are banned from drastically altering their appearance.

An insider revealed: ‘Lottie got caught up in the world of partying and drug taking and even confessed to having a cocaine addiction on social media.

‘She left Storm Management with no choice but to sever ties because that’s not the way they operate.

‘They are known for launching the successful careers of hundreds of models and the association with Lottie was beginning to tarnish their reputation.

‘Her partying lifestyle, sexualised content on Instagram, and her OnlyFans profile, made it impossible for Lottie to be signed for high fashion campaigns with the likes of Chanel and Calvin Klein, who she’s previously worked for.’

However, last year, Lottie claimed that she was given alcohol and drugs to get through modelling shoots.

The model said she thought taking drugs was ‘normal’ in the modelling industry as she alleged that she was given drugs when she was ‘exhausted’ at events.

Lottie claimed she didn’t feel like people ‘cared’ about her ‘wellbeing’.

Speaking about drug use in the industry, Lottie told the Call Her Daddy podcast: ‘I think I just thought it was normal and I was going to these events and parties and I was exhausted, that was the only way I was getting through it.

Supermodel sister Kate isn’t free from scandal either. At the start of her career,  Kate was hitting the clubs in London with her new best friends, rock star Liam Gallagher and actress Patsy Kensit. Her two-packs-a-day smoking habit also started to take its toll.

By 1998, and reputedly earning £3million a year, all those late nights — and the break-up of her relationship with Depp proved too much, and in November Kate checks into rehab at The Priory.

Rumours of drug-taking were rife, but Kate insisted she simply ‘partied too much’.

In 1999, the scandal didn’t harm her career — climbing to 18th in the list of Britain’s richest women, she racked up a six-figure fee for a L’Oreal hair commercial and closes the year on the cover of American Vogue. 

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