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, cargoes, 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.
The 5 Shoe Styles That Make Skinny Jeans Feel Cool Again:
1. Point-Toe Ankle Boots With Kitten Heels
Style Notes: 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 jewellery, this boot-and-denim look gives off very French vibes.
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Opt for a croc-effect boot to add some texture to the outfit.
Such an expensive-looking shade.
A suede boot is a must in winter.
H&M's premium collection has such great footwear options.
The slightly square pointed toe sets this pair apart.
2. Mary Jane Flats
Style Notes: 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.
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One for the minimalists.
Leopard is going nowhere in 2025.
These will look great with lighter denim washes.
A pair you can take from day to night.
Snake print is my newest obsession.
3. Loafers
Style Notes: Next up? Loafers. They look great with a pair of skinny jeans, especially paired with a turtleneck and an oversize blazer. The ease of the jeans against the sharpness of the loafers gives a totally timeless look.
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Don't these look so expensive?
These will never date.
I love this deep red hue.
Iconic.
Brown is just as versatile as black.
4. Point-Toe Kitten Heels
Style Notes: 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.
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This pair went straight into my basket.
Everyone will think these are designer.
Understated and elegant.
These will look good with any wash of denim.
An easy way to add interest to your classic skinny-jean-and-white-shirt combo.
5. Knee-High Boots
Style Notes: And for the really chilly days? Boots, but the tall kind that European fashion girls would approve of. Polished leather or luxe suede, either way, the knee-high shoe trend is giving rich country-housewife aesthetic. Pair them with a boxy oversized blazer for a laid-back and chic outfit that’s perfect for an afternoon on the town.
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These look so premium.
For if heels aren't your thing.
The block heel will add more support for all-day comfort.
So sleek.
The chocolate brown is calling my name.
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