Ankle Boots Buying Guide: Choosing the Right Pair for Autumn/Winter

One well-made pair of ankle boots will outlast and outperform several cheap ones — here's what separates the two.

Construction matters

Look for a stitched and riveted outsole (a GoodYear welt construction, specifically) rather than a glued sole — it's what allows a boot to be resoled instead of replaced, and it holds up far better to wet Dutch autumns. Our Ankle Boots in midnight blue soft leather are fully lined in calfskin with exactly this construction, plus tone-on-tone topstitching and a side elastic panel for an easy on-off fit.

Styling for the season

Ankle boots this shade work equally well under wide-leg trousers, with a midi skirt, or cuffed over straight denim — the kind of neutral-but-not-boring color that goes with a full autumn wardrobe rather than one outfit.

Caring for leather boots in wet weather

Condition the leather before the first wear of the season, and let boots air-dry naturally (never on a radiator) if they get caught in the rain — direct heat is the fastest way to crack leather.