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What to Wear with Ankle Boots

Versatile, effortlessly chic and ideal for transitional dressing, here's how to style ankle boots between the seasons

Content editor

Ellie Spicer

How to wear ankle boots with jeans

Understanding how to wear ankle boots with jeans can unlock a series of low-effort, high-return outfits. It's all about finding the perfect pairing.

Let's start with how to wear ankle boots with skinny jeans. The figure-skimming shape of these jeans opens up a range of ankle boot styles to choose from. Consider suede or leather stiletto ankle boots for an elevated look, or create contrast with chunkier styles inspired by rock 'n' roll stars.

What about how to wear ankle boots with straight-leg jeans? Here we face the conundrum of whether to wear the hem over or inside of the boots. In general, wearing your straight-cut jeans over your ankle boots helps to maintain their shape, however cuffing your hems by rolling them up buys you more space for taller boots.

For looser cuts, such as flares and palazzo jeans, look to pointed-toe boots to help elongate your legs. Round and square-toe ankle boots give an edgier finish, so try contrasting your colours for a modern feel.

Published 7.23.2025