I Thought I Hated Skinny Jeans, But These 5 Shoe Styles Make Them Feel Cool Again

Skinny jeans have been a battlefield. For years, they were my go-to—sleek, flattering, and easy to style. But then the internet decided they were passé. The rise of baggy jeans, cargos, and every other Gen Z-approved silhouette pushed skinnies into the “millennial cringe” category. Didn’t bother me though. They fit me like nothing else could, and despite the trend cycle, I refused to let them go.

Still, I’d be lying if I said the noise didn’t get to me. There were days I swapped them out for straight-leg denim just to dodge the side-eye. But recently? Something shifted. Skinny jeans are creeping back, and instead of looking dated, they’re starting to feel… fresh again. The trick? Shoes that bring them into the now.

1. Point-Toe Ankle Boots With Kitten Heels

For nights out, I’d go straight to point-toe ankle boots with kitten heels. These aren’t your standard booties; they are sleek, polished, and modern with the low heel and pointy toe. Paired with skinny jeans, a fitted black turtleneck, and chunky gold jewelry this boot and denim look gives off very French vibes.

2. Mary Jane Flats

Mary Jane flats, but not the prim-and-proper kind. Think The Row’s version—minimalist, sleek, and unapologetically cool. I’d style them with a boxy sweatshirt and a slouchy trench. The combination hits the perfect balance between nostalgic and forward-thinking.

3. Loafers

Next up? Loafers. They look great with a pair of skinny jeans, especially paired with a turtleneck and an oversized blazer. The easy of the jeans against the sharpness of the loafers give a totally timeless look.

4. Point-Toe Kitten Heels

The contrast between the skinny fit and the sharp silhouette of the shoes gives off a “don’t mess with me” energy. Suddenly, skinny jeans didn’t feel like a relic. They feel powerful.

5. Slippers