general | November 01, 2026

Lollapalooza Outfit Photos – Hollywood Life

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Eminem’s daughter, Hailie Jade Mathers, 25, is always rocking some sort of sexy outfit and her latest look may just be one of our favorites. Hailie has been sharing a ton of photos from Lollapalooza in Chicago and for her latest outfit, she donned a black halterneck bikini top that featured a gaping hole at the chest. She styled the top with a pair of tight high-waisted light-wash jean shorts.

Hailie posted two photos of herself to Instagram – one pictures her sitting down in a golf cart while the other sees her standing up posing. She accessorized her look with a gold chain belt, a pair of sunglasses, and a cool pair of knee-high high white leather heeled cowboy boots. She captioned the photos, “these boots were(n’t) made for walkin’ … so i’m just gonna sit here for a minute.”

While in Chicago for the music festival, Hailie rocked a slew of fabulous outfits. Aside from this black swimsuit top, she wore a similar ensemble featuring a light green halterneck bralette top that put her toned abs on full display and only covered up her chest. She styled the tiny shirt with a pair of ultra high-waisted light-wash mom jeans, tan wedges, and a white leather purse.

Some of our other fave looks from her trip were her tight, dark-wash high-rise jeans with a sleeveless white corset top and her tight jeans with a pink and yellow cropped tank top and sneakers.