Unseen Images of Harry Styles and Olivia Wilde

By Juliet Smith 1 year ago

Their First Meeting

Harry and Olivia Movie

Image Source: uk.finance.yahoo.com

This shot shows one of the earliest meetings between Harry Styles and Olivia Wilde, on the set of Olivia's movie Don't Worry Darling. In the film, Harry plays Jack, who works for a mysterious company in the idyllic town of Victory. Olivia said she was ecstatic when Harry took the role in her film, and the pair clearly hit it off right away.

Kisses on a Boat

Harry Styles Olivia Wilde Kissing

Image Source: Twitter @holiviacandids

This is the life: reading on a boat in the sun with your boyfriend doting on you. Harry took the opportunity to give his girlfriend a loving kiss as she read on the deck of their boat in Italy, though perhaps she was also making sure she didn't lose her page!

All Loved Up After A Few Months

Harry and Olivia Wedding

Image Source: Twitter @holiviacandids

Just a few months after Olivia announced that Harry would be appearing in her film, the two appeared for the first time as a couple! Olivia and Harry attended his agent's wedding in Montecito, California, and judging by his face in this picture, he only had eyes for Olivia.

Fun in the Sun

Olivia Wilde Holiday

Image Source: Twitter @BestEdits_

Fast-forward a few years and Harry and Olivia took a romantic trip to Italy with friends. Though the two naturally spent time sunbathing and chilling out, Harry also took a chance to have a bit of fun, including leaping from their boat into the sea. Olivia's gleeful face says it all; these two are really meant for each other.

Candlelit Dinners

Harry and Olivia Date

Image Source: Twitter @StylesAnnoyingg

This intimate moment was snapped by a fan, and it's a picture that you rarely get to see of celebs. Here, Harry and Olivia choose to dine at a corner table in the restaurant - to be as near to each other as possible. Have you ever seen a cuter picture?

Smooches in the Sea

Harry Styles Olivia Wilde Italy

Image Source: pinterest.com

Back on their Italian holiday last year, Olivia and Harry locked lips in a passionate instance of PDA on their boat. The vacation happened right after Harry finished filming his film
My Policeman
, and it seemed the two couldn't wait to spend some solo time together again.

Romantic Walks in the Park

Harry and Olivia Park

Image Source: Twitter @Holiviaa1

Harry and Olivia have both been spending a lot of time in London recently, where Harry has a house. As Harry gears up for his stadium tour of the UK, Harry and Olivia were spotted taking relaxing walks through London's parks, which included hand holding and cheek kisses. Cute!

Finishing Filming

Harry Styles Olivia Wilde London

Image Source: Twitter @eonlineRP

This photo was taken to celebrate the end of filming on Olivia's film
Don't Worry Darling
. According to others on set, Harry and Olivia had immediate chemistry but took care not to mix their personal and professional lives while working together. Here, they both look very happy with their work - and perhaps hopeful that they can spend more time together now.

No Smiles for the Paparazzi

Image Source: Twitter @AirBrushClub_

Olivia and Harry are known for prioritising their privacy, which sometimes means actively avoiding the paparazzi when they're out and about together. This time, though, they didn't manage it, though neither of them look very happy to have been caught during a relaxed morning coffee walk.

Getting Ice Cream Together

Image Source: popsugar.co.uk

Harry and Olivia spent May last year enjoying a romantic holiday in Italy, which included frequent trips to the beach. Here, Harry and Olivia walk back to their accommodation after a day on the beach, looking very tanned and chilled. Later, Harry even offered to carry Olivia's tote bag for her - aw!

Spotted at a Restaurant

Harry Paparazzi

Image Source: Twitter @StylesAnnoyingg

It must be hard being a celeb - especially when you're as popular as Harry. When the cameras are on you at all times, you must have a sixth sense as to when you're being photographed. Here, Harry and Olivia are caught at a restaurant dinner, with Harry immediately spying the paparazzi - oops!

Cheering on Her Love

Image Source: dailymail.co.uk

Like a dutiful and caring girlfriend, Olivia always makes an effort to attend Harry's shows when she can. She's even been caught bringing her two children to them! Here, Olivia watches from the sidelines as Harry wows the crowd, singing and dancing like the rest of them.

Loving Glances

Harry and Olivia Boat Italy

Image Source: Twitter @H_Endlessly

Every girlfriend wants their boyfriend to look at them like this. After a day in the sea, Harry and Olivia unwind in the shade, and can't resist those longing glances at each other. Though they're barely touching, you can sense the love between them - even if Olivia is 10 years older than Harry.

Dinner in Italy

Olivia Wilde Harry Styles Dinner Italy

Image Source: pinterest.com

After a day on the beach, where better to spend your evening than an al fresco restaurant? Here, Olivia and Harry enjoy a few Aperol spritzes together as the sun sets. Olivia looks gorgeous in this floral dress, and Harry never fails to impress with his eye-catching shirt choices.

A Night on the Town

Harry Olivia London

Image Source: Twitter @holiviacandids

When Harry and Olivia are in London together, they can't resist going out for the evening. Sometimes, this lands them in a bar having tequila shots (as witnesses can attest!), but sometimes they just want to walk through the city at night. Here, they look very comfortable, even holding hands in public.

Relaxed Days in London

Olivia Wilde Boyfriend

Image Source: glamour.com

Here, Harry and Olivia enjoying a relaxing day of shopping around London. Harry - always the gentleman - carries Olivia's bags for her, as the two leave a glitzy store. We love Olivia's stylish sunglasses, which the two often share. Could Harry even be borrowing Olivia's hair accessories as well?

A Goodbye Kiss

Olivia Wilde Harry Styles Kiss

Image Source: metro.co.uk

As is so often the case for busy couples, Harry and Olivia often have to spend time apart. Here, the two say goodbye in London as Harry heads off on his UK stadium tour. Instead of a full snog, Harry opts for a very gentlemanly kiss on the cheek to show his love and appreciation for Olivia.

Looking for a House?

Harry and Olivia Apartment Hunting

Image Source: Twitter @bestgug

On one of their nightly London strolls, Harry and Olivia are caught looking in the window of an estate agent's office in the city. Eagle-eyed fans have already pieced together that Olivia and her kids could be spending time at Harry's London house, but could they be looking to buy a home together?

Sweet PDAs

Harry and Olivia PDA

Image Source: Twitter @holiviastyles

Though they like to stay out of the spotlight - especially when it comes to PDAs - sometimes the two can't resist it. Though Harry has clocked the paparazzi behind him, Olivia is unaware as she wraps her arms around her boyfriend during a walk in London.

Keeping it Cool

Image Source: pinterest.com

Anyone glancing at these pictures might think this is just a couple of friends out together. But the two are clearly more than comfortable together, and other pictures from this day show Harry with his arm around Olivia and leaning in for a cheeky kiss.

Their First Wedding Together

First Pictures Harry Styles Olivia Wilde

Image Source: hollywoodlife.com

Was it premature to choose a wedding as one of their first public dates together? Clearly not, as Harry and Olivia are still just as loved-up today as they are in these pictures.  We love that even though Harry has his hands full, he still spares one to clutch his girlfriend - so sweet!

Domestic Bliss

Harry Styles Shopping

Image Source: Twitter @holiviabot

Life as a famous singer and director isn't always glamorous. Here, Olivia and Harry do a chore that all of us are stuck with - the weekly shop. The two wander through a trendy London neighbourhood with all the ingredients for a relaxed dinner at home. Once again, Harry appears to have clocked the paparazzi immediately!

Drying Off

Yacht Harry Styles

Image Source: pinterest.com

Olivia doesn't look particularly pleased to have been roused from her nap here! As the two spend a day on a boat in Italy, Harry enjoyed taking dips in the sea while Olivia kept to sunbathing and reading on the deck. Here, she passes her boyfriend a towel so he can dry off.

In-Jokes at a Restaurant

Harry and Olivia

Image Source: pinterest.com

What is Olivia giggling at here? We'll never know, but it's more proof that Harry and Olivia are perfect together. The two love having relaxed dinners together, even when their hair is messy and they know they'll be found by the paparazzi. Olivia's face says it all: these two are in love.

An Intimate Lunch with a View

Harry and Olivia Date

Image Source: Twitter @StylesAnnoyingg

Olivia and Harry clearly have a thing for classy lunch spots. Here, they dine with friends at a huge outdoor table overlooking a picturesque golf course. However, we can tell by Harry's body language that he his focus is all on Olivia - just look at the way he's completely angled towards her.

Gymming Together

Harry and Olivia Gym

Image Source: Twitter @holiviabot

What's the phrase: couples that go to the gym together, stay together? In this case, that's true. This was taken close to the beginning of the pair's relationship, and Harry clearly values his workout time with Olivia. In one interview, he said that he wrote parts of his latest album on the treadmill!

Arriving at the Airport

Harry Styles Airport

Image Source: Twitter @holiviabot

Even when travelling, Harry and Olivia have a way of looking unnaturally stylish. This photo was taken at an airport in New York as they touched down after spending time in the UK together. As always, Harry takes the difficult bags while Olivia wheels a very classy suitcase.

Time on the Ocean

Harry and Olivia Holiday

Image Source: Twitter @AirBrushClub

These two clearly crave solo time together. With hectic professional lives, the time they have together is precious. On their Italian holiday, the pair spent some time away from their boat to take a dip in the sea together, with Harry taking charge of driving while Olivia enjoys the ocean breeze.

PDAs in London

Harry and Olivia Holding Hands

Image Source: Twitter @fanclubcelebrit

These two love being private, but sometimes they just don't know they're being photographed. That's almost certainly the case here, as the two hold hands while enjoying a relaxed walk in London. They're clearly totally comfortable with each other - this isn't a forced hand hold or one for the paparazzi.

Beach Day

Harry and Olivia Car

Image Source: Twitter @ratethefilter_

These two even manage to look totally fashionable even during a trip to the beach. As they return to their car, Harry takes charge of packing everything away while keeping his focus totally on Olivia. Every girl wants a boyfriend as attentive and loving as Harry!

Getting Frisky In The Sea

Image Source: YouTube
Here, the pair can be seen on holiday getting a b it frisky in the sea. They simply can't keep their hands off each other - which is really quire romantic when you think about it. I wonder whether the snorkelling got a bit boring for them and they were more interesting in each other?

Taking A Stroll In LA

Image Source: dailymail
The flawless pair are pictured here going for a stroll round the sunny city of LA. Their PDA has always been a topic of conversation - just proving how in love they really are. They're both in hats to protect themselves from the sun, but also to probably make themselves as discreet as possible.

Helping Olivia On To Their Private Boat

Image Source: popsugar
Here, the gorgeous pair are spotted in Italy. Harry is always there to help Olivia when she needs it and can be seen helping her step over onto their private boat. Life seems pretty sweet when you can just spend your summers travelling around Europe!

At Home In LA

Image Source: Lipstick
It looks like the paparazzi person who was taking this photo might have tried to get a little too close to the couple. Here, they are pictured getting into their home in LA together. Does anyone else thing that the paparazzi maybe took this a little bit too far and invaded their privacy a bit too much?

Walking To The Beach

Image Source: ElEspectador
It seems like the pair just can't get enough of each other, so they love to go on holiday so they can spend some time just on their own. Here, Olivia is dressed in an oversized shirt (could this be Harrys?!) paired with a cute ribbon in her hair. Not sure about wearing jeans to the beach though Harry!

Lunch Date In London

Image Source: Entertainment Tonight
Having to split their time from London and LA could be quite difficult. But, it looks like they still manage time to fit in cute dates together - no matter which city they are in. Here, they are pictured on a gorgeous balcony out for lunch together in the city of London.

Harrys Birthday in London

Image Source: dailymail
Despite the image quality not being amazing, here the pair are pictured out and about in London to celebrate Harrys birthday. Apparently, he decided to take her to an art gallery for the day. I wonder if they were pictured in the previous image on the same day?!

Another Picture in Italy

Image Source: exclusive
Here, the pair are pictured once again in Italy. They are walking over a bridge in the baking hot sunshine. Obviously, the paparazzi had to get in a funny place when getting this shot! The pair seem to be giggling at something that Olivia has up on her mobile phone.

Harrys Birthday In The Gallery

Image Source: dailymail
Olivia and Harry are actually photographed inside a gallery in London. This was back when masks were mandatory everywhere, which probably played a huge part in helping them to keep a low profile when they were out and about. It was probably the only chance they could do things like normal people!

On Vacay

Image Source: eonline
Caught off guard, it looks like Olivia has something to say to Harry. But, no matter what face she is pulling you can just see how much he loves her. The pair look like they're suited and booted for the sunshine, especially with a pair of sunnies on each and beach bags!

Out Shopping

Image Source: hollywood life
The couple are pictured here going out shopping together. but, they are not alone - it looks like they are with someone else too but we're not sure who that person is. Whatever they are out shopping for, Harry has decided that he wants to carry the shopping bags - but they're using reusable tote bags which is great to see!

Out With Friends

Image Source: Pinterest
Look how comfortable this new couple is together. Not only do the two of them get on together like a house on fire but they also share a lot of mutual friends and are really comfortable hanging out in a  group as well as a romantic couple - Olivia can't contain her laughter.

Caught Out And About

Image Source: Twitter
This is not Harry's best look we'll admit. The two of them have no idea that the paparazzi  are watching and following them. The sun is out, the shades are on and Olivia Wilde is clinging onto her hat. These two are clearly just out for their daily stroll.

Running The Errands

Image Source: Pinterest
Even in Harry Styles and Olivia Wilde's worlds it's not always glitz and glam, sometimes you have to do the daily errands. This was during the aftermath of the pandemic when it was still mandatory to wear masks as we can this couple were fully masked up.

Can't Keep His Hands Off

Image Source: PopSugar
It's clear just how smitten this couple is, the two despite trying to remain as private as possible and refrain from PDA just clearly can't stay away from one another and they cannot help having their arms around each other. Just look at how Harry is looking at his girlfriend.

An Attempted Mask Kiss

Image Source: 24UR
Masks were certainly effective tools for stopping the spread of the virus. But, when it comes to the spontaneous displays of affection and loving little kisses they definitely got in the way - literally. But, that is not holding back these two who are attempting it none the less.

Breakfast On The Balcony

Image Source: Pinterest
Here the couple are enjoying a nice and relaxed breakfast on the balcony. Harry is still wearing his hotel robe with his matching white scrunchie and Olivia Wilde is mid way through munching her breakfast whilst Harry shows her something on his phone.

Cross Words?

Image Source: MSN
We know by now that a picture says a thousand words - and these can be totally out of context. Because here, it looks like the two of them are having cross words by the look of their body language. Yet it would be unusual for this couple in love so perhaps it was just a discussion...

Relaxing On The Yacht

 
Image Source: Hollywood Life
Harry Styles is seriously showing off his body in the holiday snap. It's another paparazzi show from their private yacht vacation. Harry, whose just recently got out of the sea is heading straight back in while Olivia relaxes in the sun whilst hydrating with her bottle of water.

Smooch In The Sun

Image Source: Popsugar
Olivia's attempt to shield their private moment from other people with the book is pretty fruitless. Harry is leaning over whilst Olivia had been sunbathing and reading on the deck of the boat. These two are clearly so in love it's clear to see - no matter how much they try to keep their love life private.

Moving In

Image Source: DailyMail
This was the moment when Olivia Wilde moved her last of her things into their shared house with her big red suitcase. Harry Styles is wheeling it in to the LA mansion where the two of them live as Olivia Wilde looks around checking for any paparazzi.

A Passionate Kiss

Image Source: Popsugar
Here is a very passionate kiss between the couple. Often we see celebs PDA all the time. But with this couple they are much more refrained in public. But not here. In fact the couple are so caught up in one another that we cannot see either of their faces.

All Smiles Before The Tour

Image Source: Twitter
This picture was taken during the day before one of Harry's tours. Olivia Wilde stuck with her boyfriend during his tour taking time out of her busy schedule to support him and she was pretty much as excited as he is as we can see here. This is the true sign of a solid couple.

Pre-Show Quality Time

Image Source: The Irish Mirror
Olivia is walking a few steps behind Harry as the two of them walk closer to the sea. This was just a little vacation together for a couple of days of couple quality time ahead of Harry Styles concert in Dublin recently which Wilde accompanied him to.

The Picture That Sparked The Rumours

Image Source: Popsugar
This was one of the initial pictures which first sparked the pictures that the two were dating - which of course they were. They are about to step into Harry's house after being dropped off by their car. The two of them are peering around to check that they will not be spotted.

A Bum Grab

Image Source: Popsugar
There's no hiding the affection and love between these two. Often things are kept very much low key between the mum and the singer but things are a little bit more cheeky here with Harry holding her rear as they share a hug on their romantic getaway.

At The Airport

Image Source: Southandlastingwealth

The couple are about to catch a flight as they walk through the airport here in New York ready for security, on their way to catch a flight out of NYC for a few days. They are keeping a very low profile and are almost unrecognisable in their masks and shades.

Under Cover Selfie

Image Source: Southandlastingwealth

This student from Ireland is clearly a fan and had spotted who these two are and taken a (not so discreet) selfie. It turns out that not many others recognised the two and she even claims that they were rejected from a few restaurants with nobody recognising who it was and because they had no reservation.

Coffee Strolls

Image Source: Hawtcelebs
This couple do everything together, and going out shopping and grabbing a coffee is one of the things that this could love to do the most. They can often be spotted around a variety of cities wandering and enjoying one another's company and testing their local coffee shops.

Italian Vacay Strolls

Image Source: Twitter
Harry Styles and Olivia Wilde recently took a holiday to Italy. These two were fully engrossed in taking in the sighs and enjoying one another, completely unaware that they are being followed by the paparazzi as Styles drapes his arm over his girlfriend.

What To Read Next

Load More