Desperate to be considered an elite member of President Donald Trump’s inner circle, Alina Habba has made quite the name for herself. The former attorney turned Counselor to the President has molded and shaped herself to fit anywhere Trump could find her presence useful. Although, there’s been some indications that the relationship between Habba and Trump is far from rosy, which has often led to Habba acting out in scandalous ways to get his attention. Known for pushing the boundaries with some inappropriate outfits, Habba has struggled to nail her overall look in a way that would impress anyone outside of Trump’s orbit. In fact, there’s been several times her clothes and makeup styling has really missed the mark.

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Not one to shy away from the use of bronzer or an overly smoky eye, Habba seems to be following the general makeup trends of fellow MAGA superstars. Throughout the years, even before Habba was Trump’s lawyer, her sense of makeup and style was often shifting, so it’s been hard to pinpoint where, exactly, Habba went wrong. We reached out to in-house fashion expert for The List, Luna Viola, to get her expert take on where Habba is failing in her makeup routine, what she could swap out, and what alterations would really elevate her look. Here are five of Habba’s worst makeup fails of all time — and what she can do to fix them.

While attending the annual New Year’s Eve party thrown by Donald Trump himself at Mar-A-Lago, Alina Habba was spotted cozying up to some popular conservative players. Seen here in an Instagram post celebrating the event, Habba is caught snuggling up to Ryan Hager and Eric Trump. Whereas at first glance her makeup seems ready for an evening out on the town, one of the many things that’s changed about Habba since she became Trump’s lawyer is her insistence on layering her makeup. Bordering on heavy and cakey, this look has all the foibles: too much eyeliner, too much foundation, and a mismatched blush that isn’t quite blended in.

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According to Luna Viola, a red carpet hair and makeup artist, there’s a few quick tips for Habba that could really turn this look around. First, “I would lighten up her whole … look,” Viola said. “Starting with her foundation,” the expert continued before also suggesting a lighter contour and then “blending the two seamlessly.” This would add a bit of youth back into Habba’s style, as well as aid her in welcoming in a new year with less makeup to wash off.

Taking to Instagram to celebrate questionable bestie Kimberly Guilfoyle, Alina Habba maybe took some faulty fashion advice from the queen of mess. Guilfoyle has had quite a few makeup fails, and it appears some of them might have rubbed off on Habba. As much as Habba might have been “So proud of KG on the cover of Impact Wealth Magazine,” and excited to participate in the event to raise funds for the Marine Toys for Tots, her look is far from professional. Not only is Habba wildly underdressed for a fundraiser, but her foundation is, again, too heavy and doesn’t match her skin tone. Plus, in a moment of clearly trying to copy Guilfoyle, Habba really overdid it with the eye shadow.

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Makeup expert Luna Viola agrees, saying, “Her eye makeup is too dark,” but she does have a helpful suggestion for Habba. “I would use a more natural shade of brown to enhance her eye color.” Which could easily be sound advice for both Habba and Guilfoyle.

Arriving on stage to speak during the Republican National Convention on July 18, 2024, Alina Habba came dressed in white and doing her best Melania Trump impression. While Habba attempted to become a Melania copycat for much of Donald Trump’s 2024 presidential campaign, her makeup here felt more like an insult to the First Lady. Sure, Melania loves a smoky eye, but her overall look has always been understated, especially when compared to Habba. Here, Habba has truly overdone it with the smothering eye shadow, and her overall foundation is too heavy and dark. Once again this makes her skin tone appear off-putting, and the shine coming through the matte makeup feels greasy. 

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We asked Luna Viola what Habba could do to improve this look, and she came prepared with the perfect answer. “I would use a peach cream blush,” the expert said, as “this would add a warm tone to her cheekbones without [darkening] it.” Plus, using a “cream based moisturizing formula,” would help Habba tackle the issue of always looking a bit too matte. According to Viola, this “would give her overall makeup a much-needed dewy feel,” and we couldn’t agree more. 

While everyone within Donald Trump’s inner circle was bustling to get ready for his second inauguration, Alina Habba took it as an excuse to post a selfie to Instagram. The caption, “T-17 hours,” sits alongside a photo of her in a gorgeous sparkling gown and a tacky MAGA accessory Habba should ditch. It appears Habba showed up early, and according to her makeup, she was expecting it to be a long day. Not only is her foundation piled on, but once again the bronzer she used for contouring is too dark and not properly blended in all the way.

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According to Luna Viola, the major culprit that’s not working for Habba is the bronzer. Not only does it clash with the lawyer’s skin tone, but it might be time for her to retire this shade of bronzer all together. Viola suggests, “A lighter earthy shade of bronzer would complement her skin tone more.” She also suggests that Habba try to avoid pink blusher, as it will continue to clash with most bronzers Habba seems fond of using.

Truly, the ultimate makeup fail that Alina Habba has ever boasted was this stunningly leathery look from the January 20, 2025 inauguration of President Donald Trump. It seems that Habba was more focused on preparing her tan than prepping for her new role within the Trump White House. There’s so much going wrong for Habba here. First, the overly bronzed skin looks like she got a comically bad spray tan a la Ross Geller from “Friends.” Second, the purple of her outfit clashes with the tone of bronzer she used, causing her skin to appear sickly. The sheen of her skin is giving more grease than hydration. In fact, the shine of her skin ultimately makes her hair look a bit dirty as well. Not her most polished look.

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Luna Viola referred to this look as, “quite dramatic,” and we couldn’t agree more. Viola continued, “The contour does not look to be evenly blended, especially on her forehead,” which draws the eye to just how accentuated her cheekbones are. According to Viola, “the [contour] shade is too warm … This adds an orange tinge to her skin tone that is not fresh and flattering.” Again, a recommendation for a more cream based and moisturizing foundation would help pull Habba out of Leatherface territory and into the realm of the healthy and glowing.