The past few years have given us countless glimpses of Donald Trump’s family. However, one family member remains surprisingly enigmatic: Ivanka Trump.
Perhaps taking a note from her father, Ivanka Trump is constantly rebranding herself. She’s been an executive for the Trump Organization, but she’s also headlined her own luxury fashion brand. She’s a published motivational writer, and she’s also served as Advisor to the President and even made a prominent appearance at the G20 Summit.
Even for Ivanka’s biggest fans, this leads to a simple question: who is Ivanka, really?
It’s tough to get that answer these days. As both politician and celebrity, Ivanka Trump has mastered the art of creating her own narrative and hiding how she truly feels.
But that wasn’t always the case. Photos of the early life of Ivanka, born in 1981, give a rare glimpse into her relationship with her parents, her curiosity about the world, and her growing inspiration to leave her mark on the world just as her famous father did before her.
If you want to get a look at the real Ivanka Trump, look no further than these rare photos of her life as a child, teenager, and in her early 20s. These powerful images give us an interesting glimpse of where Ivanka comes from and quite possibly what her future may hold.
1986: One big happy family
Here, we can see a very young Ivanka flashing her best smile! This is from a family photo taken way back in 1986.
1991: Let’s go to the movies
Donald Trump loves movies… both starring in them and watching them. Here we see him taking Ivanka to the 1991 premiere of the film Stepping Out.
1991: Sports with dad
Donald Trump has never been afraid to bring Ivanka to various events. In this case, he brought her to the U.S. Open in 1991.
1991: Getting dad’s attention
Donald Trump has made no secret that Ivanka Trump is his favorite child. Maybe it’s because she never hesitated to get his attention, which is what she is doing in this photo from 1991.
1991: Not-so-happy camper
Just because Donald took her almost everywhere doesn’t mean that Ivanka always liked it! Here, she seems to be pouting about appearing with dad at the Plaza Hotel in 1991.
1992: Play ball!
Donald Trump played baseball when he was younger and claims to have nearly gone pro. Here, we see him taking Ivanka and Eric to a game at Yankee Stadium in 1992.
1992: Face time with Ivana
The kind of bond that Ivanka and Ivana have doesn’t just happen overnight. This rare photo shows us they’ve been working on this bond from the very beginning!
1993: Ivanka… motorcycle enthusiast?
Thanks to tagging along with dad, Ivanka ended up in some unexpected places over the years. This picture captures her and Donald in 1993 at the Harley Davidson Cafe in New York City.
1995: Daddy’s little girl
This photo comes from a shoot with Donald back in 1995. It was a very vehicular day: Ivanka sat in daddy’s lap on a Ferrari before riding an ATV with her brother Eric!
1995: Riding in style
Ivanka has had a taste of the good life from a very young age. For example, we see her here in 1995 chilling with dad in a limo when she was 13 years old.
1996: Home sweet home
Mar-a-Lago has been Trump’s home away from home for a long time and now serves as his primary residence. Channeling Miami Vice, we can see Donald posing at the resort with Ivanka in 1996.
1997: Punk phase
Ivanka claims she went through a “punk phase” as a kid and was devastated when Kurt Cobain died in 1997. Here she is that same year as a 12-year-old.
1997: Ivanka behind the scenes
Most of the time, we see Ivanka Trump with her wardrobe and makeup absolutely perfect. But this photo lets us get a rare glimpse of Ivanka behind the scenes at New York’s Jill Stuart fashion show in 1997.
1997: WNBA dreams?
While Ivanka has a strong bond with mother Ivana, that doesn’t mean she can’t be friendly with Donald’s second wife, Marla Maples. Here, we see the two of them in 1997 at the Shooting Gallery’s Third Annual Celebrity Basketball Game at Hunter College.
1998: Posing across the pond
Ivanka enjoys a very close relationship with her mother Ivana. And in 1998, these two showed off the family resemblance at Royal Ascot in England.
1998: Patrons of the arts
Ivanka seemingly inherited her mother’s love of arts and culture. Here, we can see the two rocking some stylish looks at the Grosvenor House Art & Antiques Fair reception in 1998.
1998: Bride of Frankenstein look
Ivanka wears her most unusual hairstyle yet backstage at the Thierry Mugler Spring/Summer 1999 COLLECTION fashion show in October 1998.
1998: Pink hair
Bet you’ve never seen Ivanka with pink hair! She wore this look at the Lolita Lempicka Prêt-à-porter Fall / Winter 1998-1999 fashion show in March 1998 in Paris, France.
1999: Ivanka as a brunette
If you thought Ivanka with pink hair was shocking, get a load of this. Here, a rare photo of Ivanka as a brunette at 17 years old. This was taken just before she appeared in a Pamela Dennis benefit fashion show, organized by Sarah Ferguson, in New York City in April 1999.
Ivanka is pictured here with fashion designer Anand Jon at his Fall ’99 fashion show in New York City.
1999: Rocking the runway
Rocking curly hair, Ivanka models the Vivienne Westwood 1999 Fall/Winter collection at Bryant Park in New York City.
1999: Fierce fashion
Ivanka models her fiercest look yet at the Zang Toi Fashion Show in September 1999 at Bryant Park in New York City.
1999: Casual party look
Here Ivanka attends her mother’s birthday party in February 1999 at the Lava Lounge in New York City.
2000: Return to Antiques Fair
In 2000, Ivanka and her mom returned to the Grosvenor House Art & Antiques Fair, but Ivanka is nearly unrecognizable without her signature blonde hair.
2001: Make it fashion!
Ivanka and her mother were no strangers to photoshoots. And this 2001 photo gives us a cute glimpse of the mother/daughter pair showing off their matching hairstyles.
2001: Time for a wardrobe change
Here, we have another great shot from their 2001 photoshoot. But thanks to a quick wardrobe change, their clothes now match almost as well as their hairstyles.
2001: Ivanka shows some personality
This photo rounds out Ivanka and Ivana’s photoshoot from 2001. While their new wardrobe still matches, we can see Ivanka experimenting with new styles and really making this look her own.
2002: Put on those dancing shoes
Fortunately, Ivanka and Ivana share more than a love of photoshoots! In this photo, the two have put on their dancing shoes to attend the 25th Anniversary of Studio 54 in New York City in 2002.
2002: Getting from here to there
Even the very wealthy need to grab a taxi now and then! Thanks to this photo, we get a fun glimpse of Ivanka and Ivana in a London taxi in 2002.
2006: Celebrating her 25th birthday in style
How did you celebrate your last birthday? Probably not like this! Here, we see Ivanka celebrating her 25th birthday in 2006 at the Pure Nightclub in Las Vegas.
2009: Happily ever after
Ivanka Trump and husband Jared Kushner have redefined our idea of “power couple.” This adorable photo captures the two dancing at their wedding in 2009.
2012: Photoshoot with Ivana 20 years later
The image on the left is from a 1992 Town and Country Magazine photoshoot of Ivanka and her mother Ivana. The image on the right depicts them from a 2012 photoshoot for Hello! Magazine, 20 years later!