Ivanka Trump Makeup Mistakes We Just Couldn't Ignore

Ivanka Trump is one of the richest women in the world (she's worn several outfits that cost more than the average rent) and she belongs to one the most infamously notable families ever, giving her access to super-skilled makeup artists. But Ivanka Trump proves that no matter how much money or fame you have, sometimes your makeup won't look good.

That may be why she admitted on The Skinny Confidential's Him & Her Podcast in early 2025 that she no longer wears heavy cosmetics. "I don't wear a lot of face makeup," the former "The Apprentice" star said, admitting she tries to focus on good skincare so she doesn't have to rely on layering heavy foundations and concealers. That makes sense as to why Trump is gorgeous going makeup-free. But she hasn't always taken that approach. In fact, Ivanka Trump has experienced multiple awkward makeup mistakes over the past few decades.

Ivanka Trump had two makeup mishaps in particular that left her (literally) red in the face. In 2003, she attended the premiere of "Born Rich" with a very pink complexion that looked almost sunburnt. Two years later, she wore a similar makeup look for an event at New York's Whitney Museum of Art. Though her complexion was glowing, it wasn't in a way that one should aspire to.

On both occasions, it seemed Trump or her makeup artist chose a foundation with undertones too pink for her skin. That was further highlighted by her odd blush placement. To bring a little more warmth and dimension to the face, we'd normally recommend adding a touch of blush over the nose and on the temples. But, on this occasion, the blush was too pigmented to go anywhere but her cheeks, and the result made her face look red all over.

We appreciated that Ivanka Trump tried something different by opting for deep red lipstick in 2005, but her lips needed more prep to make it work. Before Trump stepped out for the Hugo Boss Spring Summer 2005 Collection Launch, we would've recommended she look over our tips for mastering matte lipsticks (even though her shade had a slight sheen). Trump or her makeup artist should have used a lip scrub to remove any dead skin, then followed up with a moisturizing lip balm. We also would've encouraged her to reach for a more moisturizing lipstick. The product dried out her lips and emphasized texture instead of giving a smooth, even finish. Another way to bring more moisture back to the lips would have been to add a slick of lipgloss, lip oil, or balm over the lipstick. A sparkly product would have helped hide the patchy, dry finish.

When Ivanka Trump attended a Sotheby's benefit in 2006, she tried to give us Marilyn Monroe vibes with her curly blonde bob. But unfortunately, it was her eye makeup that really caught our attention. The businesswoman's heavy eye makeup, which melded dark shadow, thick liner, and bold faux eyelashes, just didn't work together.

When wearing faux lashes, it's of the utmost importance to choose their shape wisely. Trump (or her makeup artist) opted for a pair of lashes that sloped down and were fluffier and heavier on the ends, which ultimately didn't compliment her almond-shaped eyes. Instead of giving Trump a sultry cat-eye effect (which was probably the goal), they made her eyes look smaller and downturned instead of lifted. We would have recommended lashes that opened her eyes up, with longer strands distributed more evenly across the band, and not just focused on the ends.

Speaking on "The Skinny Confidential Him & Her Podcast," Ivanka Trump admitted, "I don't love so much foundation." And we can see why, in the wake of her 2007 Met Gala mistake. At first glance, the socialite looked glamorous as she hit up the annual New York fashion event. However, the camera flashes didn't work in her favor. Trump's face looked several shades lighter than her tan body, which made her complexion appear washed out next to her sun-kissed décolletage. To avoid the same mistake, have a couple of foundation shades on hand for the changing seasons, as using a slightly darker color when you're tanner will prevent such a harsh face/body contrast.

Trump's issue may also have been down to sunblock. She knows how important SPF is, even in the winter, sharing, "I have sunblocks for every occasion. I have the heavy sunblock when I'm out doing water sports, or surfing, or doing something in the hot Florida sun during peak hours." However, some SPF products contain zinc oxide or titanium oxide for sun protection, which can cause flashback when photographed. Most of the time it won't show to the naked eye, so it's a good idea to snap a flash photo before you step out the door. To avoid the problem, don't ditch sunblock; simply look for SPF products without those ingredients.

Ivanka Trump made a major bronzer booboo while attending "The Apprentice" finale party in 2007. The star walked the red carpet with cheeks that looked decidedly darker than the rest of her face. And the placement didn't work for her face shape. 

To give a glowy, skin-kissed look, bronzer should be applied to the highest points only. Instead, it was applied where Trump's contour should have been, on the hollows of the cheeks. The product was too warm to be applied as a contour, so the result was orange and muddy. Trump would have benefited from a cooler-toned contour stick under her cheekbones to give her face more dimension, then bronzer over the top of her cheekbones, the bridge of her nose, and around her forehead. Clearly, this mistake runs in the family, evidenced by dad Donald Trump's increasingly bizarre bronzer looks.