Every Autumn I Buy a New Pair of These Expensive-Looking Ankle Boots

I've long been an advocate for stocking up on the items you know you'll wear on repeat, and there are a few pieces I don't feel guilty about purchasing in bulk, multiple colourways or re-investing in. Once you know your personal style inside and out, there just isn't the same wasteful risk associated. I'll wear certain things to the death, mending them over and over, restyling them countless ways, de-bobbling, re-heeling and goodness knows what else to try and lengthen the life span of a favourite.

However, each autumn, I do look to buy a new pair of black ankle boots. Why? Well, they're the backbone of many outfits, and I give mine a real battering over the colder months. You need a decent pair to wear with dresses and skirts, but they work under all sorts of trousers and jeans too (not to mention that the right style can function nicely for both the office and the weekend).

Find the dream black boots and you'll be off to a flying start for A/W 19, even if they aren't the most trend-driven item on the shop floor. Each year, some tweaked versions arrive into the market, giving you a more directional spin on a trusted basic that you know will graft hard. The latest drops indicate that Western influences are going strong and chunky soles are gaining in popularity—two additions my wardrobe could definitely benefit from, I'm sure…

Keep scrolling to shop the best black ankle boots of 2019 in every trend category and price point.


If there's one combination that has ruled London over the past few weeks, it's a pretty dress worn with super-chunky boots. Jessie of We the People Style has worn on Prada Chelsea boots on repeat, and rightly so.


best black ankle boots 2019: minimal black boots worn with jeans and vinyl jacket



From simple stilettos to sleek block-heel styles with square toes, we've noticed a slew of ultra-simple black ankle boots coming in, particularly on the high street.


best black ankle boots 2019: western cowboy boots worn with a yellow maxi dress



The trend for cowboy boots started last winter but has really hit the mainstream for A/W 19. They go with many things, but we like them with a floaty dress very much.


best black ankle boots 2019: platform boots worn with khaki trousers



If the chunky soles feel too grunge for you, perhaps you'll be enticed by the extra height provided on the latest batch of platforms. That slightly '70s shape is back and looking pretty badass.

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