I Spent Months Hunting for the Best Black Ankle Boots—7 I'm Putting My Money Behind

If I can put you on to a single black ankle boot in this story, let it be this one. The inventory speaks for itself—nearly every size is sold out, but honestly, it was too good to not write about. I spent nearly three weeks, walking around fashion week in New York and Copenhagen, with these Madewell boots. In most other cases, I'd groan about how uncomfortable heeled boots are, or how clunky they can look when paired with three pairs of tights and jeans in the winter, but I simply had zero complaints wearing these. They're now a permanent part of my wardrobe.

Widths: Standard

Sizing: 5 to 11

Heel height: 1.75-inch heel

Customer review: "I bought these amazing kitten heeled boots for the winter holiday season. They are the perfect boot to dress up or down with either dress pants or a pair of dark wash Madewell jeans. I’ve worn them a ton already and they are so comfortable!"

After dozens of reviews poured into my Instagram DMs from fashion people singing the praises of these Toteme boots, I knew I had to see what all of the hype was about. While in Copenhagen, I had the pleasure of trying these on in Denmark's sole Toteme store, right on one of my favorite shopping streets. If I wasn't on a major no-spend endevaor due to my upcoming nuptials, I 100% would have walked out of the store with these on. They're sleek, sophisticated, and simply stunning. If you have wider feet, though, be prepared to size up due to the elongated toe box.

Widths: Standard

Sizing: It 35 to 42

Heel height: 1.5-inch heel

If you're looking for a sleek, low-profile elongated boot, this one's for you, diva. I've been taken by the long toe-box trend sweeping across all black ankle boots, and I haven't found a single one quite as approachable as Steve Madden's. The trend can tend to be a little bit clown-ish if not done correctly, but this pair balances the trend with wearability quite well. They're also a IYKYK reference to another ultra viral pair for a fraction of the cost. I will say, though. if you have a wider foot like I do, the wear time on these might be less than expected since the footbed is on the narrower side.

Widths: Standard

Sizing: 5 to 12

Heel height: 1.5-inch heel

Customer review: "These boots were exactly what I was looking for. The shape of the toe box is quite chic and height of the shaft makes it perfect under pants or with a skirt. The boots are well made and the suede is a nice quality and color. The boot is a bit narrow but nothing that won’t adjust with a few wears."

I'm already a big fan of Dolce Vita's boots (their wide-calf knee-high riding boot is in my Greatest of All Time list!), but, to be honest, seeing this pair at first made me nervous. Me? In a heeled boot? I usually prefer low-to-the-ground options, but I slipped on these Dolce Vita black ankle boots that my friend had while over her apartment the other day and I fell in love. They gave me the perfect height boost while still being comfortable. While the pair I tried on fit perfectly, several reviews recommending ordering a full size up.

Widths: Standard and Wide

Sizing: 5 to 13

Heel height: 3.5-inch heel

Customer review: "Love these boots! They are so cute and easy to walk in! They honestly go with anything for any occassion. They are a tad tight so if you like looser shoes, I suggest sizing up!"

I'm often dubious of an Instagram-beloved product—I've often fallen victim to them and spent way too much money on an over-hyped product that over-promised and under-delivered. But these Reformation boots proved me wrong. They're on the pricier side, sure, but they felt like an instant upgrade from the dozens of black ankle boots I tried on and tested while reviewing shoes for this story. Clearly, I saved one of the best for last.

Widths: Standard

Sizing: 5 to 11

Heel height: 3-inch heel

There's something special about Margaux. The brand is, by far, my favorite shoe brand I own (Not joking, I own 8 pairs of their shoes, from ballet flats to sandals.) So, when I was able to see these boots up close and personal during the brand's preview earlier this year, I jumped at the chance to try them on. They're ultra comfortable, stylish, and an investment that will last in your wardrobe for years to come.

My favorite part about the Margaux Downtown black ankle boots is that they come in various sizes and widths, accommodating everyone's fit so they can last on your feet all day.

Widths: Medium, wide, and narrow

Sizing: 3.5 to 14

Heel height: 2.5-inch heel

Customer review: "I tried these shoes on when they arrived and didn’t take them off the rest of the day. Gorgeous and extremely comfortable out of the box, and I say that as someone who wears clogs and sneakers most of the time."

Everyone who's anyone knows Tabi boots. The split-toe style has been around for ages in the fashion scene but has only had a resurgence amongst the general population post-pandemic. While they can be a bit jarring to wear for the first time, these split-toe Tabi black ankle boots scream New York City fashion kid to me. They're just freaky enough to wear every day without being boring. Plus, I find my pair to be roomier than the rest of my black ankle boots, so they're wide-foot friendly.

Widths: Standard

Sizing: IT 35 to 41

Heel height: 3-inch heel