My Hunt for Ankle Boots I Can Dance in From Dusk Till Dawn

I already own a pair of black ankle boots from Reformation (the Remy stretch), which fit the bill sans the pop of color I was looking for. I’ve owned and loved them for a couple of years, during which they’ve carried a lot of casual outfits through to something more refined, so I had high hopes for my Reformation selections. Stepping into the Claudette, the first thing I noticed was the wide-mouth ankle; I could fit all my fingers in the space between my leg and the boot. This left me feeling like I was slipping out of them when I tried to walk. What stood apart? The distressed brown color, created from two-tone sheep leather, and how they can be styled with almost anything. However, the heel was less kitten and more catwalk at three inches, so I didn’t trust my ability to stay out all night in these.

Of the two Reformation styles, I like the Gillian ankle boot better. And of the three including the Remy stretch I already own, the Remy is my top pick. The “stretch” — not a criterion for this particular hunt but nice to have nonetheless — hugs the foot best; the Gillian, by comparison, wasn’t snug enough. Reformation didn’t have a smaller size or insert in store so ultimately I couldn’t imagine them being wearable from day to night. (Although if they did fit perfectly, I’d love to wear these from the office to a casual happy hour.) The website recommends sizing down, which I recommend as well, to get the exact fit you’re after. One bonus was the block heel, sturdy and strong, but at $398 for the pair, I didn’t think the leather felt high-quality enough in look or touch.

Having Sézane so close to home is a plus in my life — it’s chic, affordable, and classically Parisian. These ankle boots caught my eye, and although the rich chocolate color veered off brief from my initial mustard, I liked the shine of the polish. Unlike my other options, these boots had a much pointier toe. Visually, this made them stand out, particularly when I imagined them with a pair of jeans andthe perfect white tee. I liked the kitten-heel height (two inches), the price ($260), and the seam that ran up the center, but they didn’t leave me feeling my wardrobe would be improved. The search continued.

Putting on these boots was akin to areallygood kiss. Like my option from & Other Stories below, these have a second-skin sock effect, made from 100 percent stretch patent lambskin leather. They fit my foot and leg perfectly. The heel, at 1.5 inches, makes them simple to style first thing in the morning without looking overdressed, while the burgundy patent leather — made from goat, calf, and lamb leather — adds a layer of sophistication for an evening out. On the back, the silver zipper has a delicately engraved hand that adds a nice touch no one will notice, but I did and I loved this soft detail. Wearing these, I feel a little rebellious, a lot feminine, and ready to dance. Unfortunately, the $712 price tag gave me too much pause. If my writer’s budget could justify multiple pairs of boots, I’d happily have taken these home too.

I’m not typically a stand-in-line girl, but I wondered what all the fuss was about outside the Bobbies shoe store in Le Marais. As soon as I walked in, I understood the quiet hype; almost every pair of ankle boots, knee-high boots, and mary janes across Bobbies’ collection look ultraluxe and ultrachic but at a fair price point I didn’t often see on this kind of boot in New York. The first pair that caught my eye had two-inch heels and were in Manzanilla — the color of a classic martini olive. Although I prefer a negroni, the pop of color and crumpled patent-leather exterior almost won me over on the spot. Its 1.5-inch heel sits across the entire sole, making these a top contender for wearability and comfort.

In general, I am really attracted to the concept of sock boots, which hug the foot as closely as possible, a bit like a second skin. They’re incredibly comfortable, which makes them feel like a sensible choice. A warm espresso brown, these looked more autumn countryside than dancing in the city to me. As with the other styles I gravitated toward, I liked the square toe, which I find more unique than a pointy one. Most important, the heel was chunky and slightly offset, making them very comfortable to walk around the store in. For a moderate price point, these boots were a great find overall, but they didn’t make the cut because they lacked the personality I was looking for.

[Editor’s note: The brown color Simone tried is out of stock, so we’ve linked to the black leather pair, which has most sizes available.]

My favorite boots were sitting at home all along, waiting for me to get dressed. Sometimes you don’t know how good you already have it until you take a walk around the block of comparison. After my hunt, which brought me from the streets of Le Marais to the department store Galeries Lafayette, I returned home to the Reformation boots I bought three years ago. And you know what? They’re everything I was looking for — comfortable, reliable, and effortless. These are truly good boots. I love how snugly they fit on the ankle and how easily they dress up any outfit. To fit my color brief, I’d recommend the espresso stretch leather over the black.

After trying on my first pair of Bobbies, I was nearly determined to have martini-olive-colored boots. I tried a different style that got closer to an evening vibe than a daytime one. The Hazel has a 2.7-inch heel, so it was at the higher end of what I was initially looking for. At first glance, these boots were an instant showstopper — sexy enough to elevate any pair of jeans. I was attracted to the blunt, square toe and liked that these boots hit above the ankle rather than on it. (They are .8 inches taller at the back than the Eline style.) My main pain point with Bobbies was sizing: The brand does not carry half-sizes, so the size 7 was too small, the size 8 was too large, and I was left longing for a 7.5. Adding an insert was the perfect solution. All in all, the quality is well constructed and the look is elegant. I took them for a night about town doing my usual barhopping around Belleville, passing time with friends and meeting strangers after midnight. I am still on the hunt for a Frenchman, but one hunt at a time.

[Editor’s note: Simone’s preferred Manzanilla colorway has low stock, but more sizes are available inVinyl BlackandIrish Coffee.]