Ankle-Length Trousers, Jeans and Leggings are Notoriously Tricky to Style—These 6 Shoes Suit Them Best

As much as cold weather is an invitation to show off your collection of sophisticated bottoms, there’s really one style that reigns supreme throughout the season: ankle-length trousers.

Indeed, floor-grazing styles will always look polished, but they’re simply not practical when you have to combat countless puddles and dirty pavements. Instead, jeans, leggings and woollen trousers cropped right at the ankle truly come into focus once the temperature drops, but this length can be tricky to style, so what are the chicest shoes to wear with ankle-length trousers?

I’m of the opinion that you can go in two very different directions. The foremost choice would be to lean into the crisp cut of the shape by embracing more refined footwear styles like heeled boots, ballet flats or slingbacks; a trifecta you’d definitely find in any French woman’s wardrobe. Or, the alternative is to reject this notion altogether and go for something relaxed and casual to offset the graceful length of the trousers.

If you need some visual styling inspiration, you're in luck. As autumn continues its slow descent into winter, fabrics are starting to get thicker and hemlines longer, so there are quite a few ankle-length-trouser outfits around that are proving my point. What you’ll notice from these looks (including an effortlessly elegant ensemble from Kendall Jenner featuring a sheer slip skirt from St. Agni layered over graceful trousers) is that they all feature one of just a few styles.

Like how there are specific shoes that complement ankle-length trousers most, there are some that aren’t necessarily the most compatible, simply because of the proportions that they create. And whilst I’m not suggesting that you need to go out and purchase the below pairs, these combinations might spark some ideas about how to style your ankle-length bottoms—or other styles altogether, for that matter—in new and fresh ways.

So, keep scrolling through for the six shoe styles that work best with ankle-length trousers.

The 6 Chicest Shoes to Wear With Ankle-Length Trousers

1. Loafers

Style Notes: Whilst loafers originated in 19th-century Norway, their sleek shape and discerning style have made them a beloved staple for minimalist dressers. Given that ankle-length trousers allow you to show off slightly more of your shoes than most, bonus points if you opt for a suede iteration or a pair that gathers around the edge of the foot.

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2. Ballet Flats

Style Notes: With a lower profile and graceful connotations, ballet flats are a versatile enough shoe to enhance almost anything they’re paired with. However, what I love most about them with ankle-length trousers is the way they subtly subvert each other. Given the delicate nature of the dance-inspired shoe, you’d think that whimsical dresses and floaty skirts would be the perfect match, but the tension between practical bottoms and a dainty shoe is one I’ll always endorse.

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3. Heeled Boots

Style Notes: One of the more functional options is heeled boots, which will particularly appeal to petites, thanks to the way they elongate the leg. Plus, I find that anything with a slight heel intensifies the poise of ankle-length trousers. Personally, I think that a razor-sharp pointed toe is the best shape, but round or almond toes work well, too.

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4. Slingbacks

Style Notes: Ask any Parisienne what they’re wearing with ankle-length trousers, and they’d probably tell you it’s a slingback. A favourite since Coco Chanel introduced them to the mainstream back in 1957, with an elasticated strap that wraps around the heel and shows off a hint of skin, this style is the most elegant and timeless of the bunch.

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5. Trainers

Style Notes: One style that doesn’t adhere to seasonal volatility is trainers. Rain or shine, sneakers can always be relied upon thanks to their all-around resourcefulness. This season in particular, however, opt for pairs with retro accents and slim soles.

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6. Sandals

Style Notes: Another lesson in contrast, especially for those with shorter frames where cropped trousers naturally finish at the ankle, sandals provide a great way of balancing out ankle-length tailored trousers with something light and breezy. Save this one for when the weather warms again.

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