The Search for the Perfect Ankle Boot

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I thought I had this season's boots all sorted. In July, I purchased the Miista Tyna Brown Ankle Boots, which I adored. Initially, I opted for a size 40, but they felt too big, so I switched to a 39. However, come fall, on my first attempt of wearing them, they were decidedly too small. After selling them, I'm was on the hunt for a new pair of boots, specifically to wear under pants.

Miista Tyna Ankle Boots

Alright, I thought. I've had another boot on my wishlist for quite some time - the Alma boot by Flattered. This seems like the perfect moment to buy them; they look fantastic on my friend, and they're bound to be supremely comfortable and just right. They even bear a resemblance to the Zip boot by The Row, though I haven't had the chance to try those on.

Left: Flattered Alma Boot, Right: The Row Zip Up Boot

I bought them, and they do look great with a mini skirt. However, they don't quite work with straight or tapered pants, which are my go-to during the fall/winter season. Considering my need for something to pair with mini skirts, leggings, or skinny pants is already met by the great Flattered Frances riding boots (which I highly recommend), my search for the perfect ankle boots was restarted again.

My ankle boot criteria seem simple enough:

• The go-anywhere boot: They should work for everything from coffee runs and family meet-ups to work engagements.

• Winter-proof. They need to withstand not just rain, but also snow and messy conditions. Winters here are intense, complete with shoe-damaging salt, so durability is crucial. My Flattered Frances riding boots have been great for the past three years, but now I need something that fits under jeans.

• Works under pants. I have enough tall boots for dresses, but finding a versatile, everyday pair for pants is a tougher challenge.

• Flat(-ish) and Comfortable. They must be flat or nearly flat and provide enough comfort for long walks of at least 5km, without cramping the top of the foot. I would also prefer them to have a non-pointy toe to make it less restrictive.

• Ideally, non-black. Preferably something other than black. Since rediscovering color, I’ve come to appreciate boots that add an interesting color.

Upon reflection, the criteria do appear quite extensive. While there seems to be more options in the tall and/or black boot category, finding a low ankle boot to pair seamlessly with jeans proves significantly more challenging.

Why is this so? In winter, the pants we often wear are either tapered or straight since wide-legs aren't practical and skinny jeans are less popular. This requires a certain boot style. Round toes don't always fit the bill because of postman vibes, and bulky boots can dominate the outfit. I suspect the current market has many such oversized boots at good prices because of the shift from skinny jeans, which they complemented well, to looser, more relaxed bottoms that demand a certain styling acumen to be able to combine relaxed pants and bulky boots well.

On the other hand, pointy-toe boots may offer insufficient room for thicker socks, steering us towards square, almond, or round toes with unique design elements. However, the dilemma is that these narrower toe choices can easily drift into “basic” shoe territory. I've experienced this myself; last winter, I frequently wore slim Chelsea boots with a round toe despite actually disliking them, simply because they worked well with trousers from a practical standpoint.

So, what's the solution? I set out to find a slimmer shoe that also has an interesting yet comfortable toe shape. Here are some boot options I've come across.

Slim(-ish) shoe, interesting shape

From left: Gray Matters Mara Boot, Tibi Mario Boot, M6 Maison Margiela Boot

• Gray Matters Mara boot (650 USD) has several appealing features: it's distinctive, not excessively broad at the front, likely very comfortable, and available in an intriguing color. This boot appears to work well with various outfits due to its vertically flat front, making it compatible with both pants and skirts (for outfit images, scroll down on GM website).

• Tibi Mario boot (695 USD) has a unique shape, and what I particularly like is its apparent design to be worn both open and closed, offering more options. Its patent white option is simply stunning - it definitely has a spot on my wishlist.

• The M6 Maison Margiela Ankle boot (286 EUR), seems to be designed for men. Yet, its shape, low heel, and attractive price point render it an intriguing option regardless.

• The Dear Frances Skye Boot (650 EUR) (not shown above), offers an interesting color and a classic, somewhat slender shape - and the brand itself is know for an exceptionally comfortable shoes.

From left: By Far Slava Boot, By Far Este Boot, Aeyde Lee Boot

In the selection above are another set of boots that present a slimmer, more feminine aesthetic.

• By Far Slava Boot (470 EUR): I appreciate By Far for the diverse range of colors they offer. The higher-heeled Slava boot comes in a rich burgundy/maroon shade, among others.

• By Far Este Boot (470 EUR): There's also a lower-heeled version known as Este, providing a great alternative if you're in the market for a more feminine flair. I own the tall version (see the picture below), and they come in a really stunning color range, though the toe area might feel somewhat narrow, depending on your foot's shape and size.

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• Aeyde Lee Boot (395 EUR): Aeyde delivers the ideal almond or perhaps slightly square toe, coupled with a low heel in the perfect shade of brown. This is one of my favorites from this collection (and seems almost sold out - check its cousin Neil boot for an alternative).

From left: Miista Minnie Boots, Miista Mariela Boots, Miista Cass Boots

Miista stands out for its ultra-modern designs available in various colors and merits its own section. Their styles usually feature a more generous toe area, but here are a few selections that caught my eye with slimmer toe design:

• Miista Minnie Boots (385 EUR): These boots, with their backward heel and attractive patent shade, are strong contenders, especially if you're comfortable with a modest heel.

• Miista Mariela Boots (270 EUR): I'm drawn to the rich burgundy color and the boots' structured and intriguing details. They're among my favorites from this brand.

• Miista Cass Boots (420 EUR): The boots' purple hue is breathtaking, but for those who lean toward more subdued tones, they're also available in brown, brown patent, and black.

I actually contacted Miista to inquire if they had any styles with slimmer toe options. Their suggestions included the Mariela, Cass (detailed above) as well as Aron and Oliana. However, their entire collection is worth scrolling through.

From left: Neute Leonardo Ankle Boot, Neute Ezra Chelsea Boot, Blanca Boot

I also explored more regional websites, such as W Concept, which features numerous Korean luxury designers, and Vagabond, a Swedish brand that earns my immediate trust, given that Swedish winters are notoriously harsh.

• For those whose shoe size is 39 or smaller, Neute presents an intriguing minimalist option with a few selections, including the Neute Leonardo Ankle Boot (310 USD) and the Neute Ezra Square-Toe Chelsea Boot (317 EUR).

• Vagabond has its own compelling offerings, one of which is the square-toed, dark brown Blanca Boot (150 EUR).

From left: Billi Bi Boot, Aeyde Ruby Boot, Jil Sander Ankle Boot

If you're open to a pointy toe, the options expand even further. Tibi offers an excellent Leo boot, but it's largely sold out, so I haven't included it here. Nonetheless, here are a few alternatives:

• Billi Bi Boot (184 EUR): This brand is new to me, but I'm like this design - it's a pointy-toed shoe that's a non-basic basic.

• Aeyde Ruby Boot (395 EUR): Aeyde doesn't disappoint, presenting a gorgeous pointy-toed style in khaki green that brings an extra layer of depth to any outfit.

• Jil Sander Ankle Boot (696 EUR): Jil Sander's take on the pointy toe skillfully blends modern and classic elements.

From left: Aeyde Hester Port Boot, Vagabond Samira Boot, Nella Boot

If you'd like to push the envelope even further, here are a couple of extra options:

• Aeyde Hester Port Boot (445 EUR): Featuring a Western twist, this boot is an outfit maker that stands out on its own yet is versatile enough to pair with many neutral outfits. It's also available in black, if you prefer a more neutral option.

• Vagabond Samira Boot (280 EUR) and Nella Boot (160 EUR): Both boots present intriguing color variations, adding a unique flair to your style choices.

Big boots, interesting shapes & colors

Now, if you're skilled at styling chunky ankle boots, there is so much to choose from.

From left: Bally Clayson Boot, By Far Alistair Ankle Boot, Wandler Rosa Boots

• The Bally Clayson Boot (720 EUR) is one of my favorites — its modern, sophisticated design stands out.

• By Far once again provides a rich color selection, showcased in options like the By Far Alistair Zipped Ankle Boot (332 GBP).

• Also on offer are the Wandler Rosa Boots (245 EUR) at an attractive price, with Wandler's quality and design continuing to be simply stunning.

From left: Jil Sander Ankle Boot, Jil Sander Chelsea Boot, Aeyde Jack in Moka Calf

• Jil Sander has a few great options for the big boot category, including this Ankle Boot in an interesting greenish hue (907 EUR) and Jil Sander Chunky Chelsea Boot (1027 EUR) with a perfectly misplaced elastic element.

• Aeyde also offers compelling choices in the same category, such as the Aeyde Jack in Moka Calf (445 EUR) in the beautiful brown shade that works with everything.

From left: Miista Dahlia Boots, Marni Ankle Boot, Camper Traktori Boot

• Miista doesn't disappoint when it comes to the oversized boot category, offering gems like the Miista Dahlia Boots (235 EUR). They have interesting detail and color scheme, while remaining very much neutral.

• Venturing into the sportier category, Marni presents an interesting Marni Ankle Boot (619 EUR), available in a perfect neutral tone, and an alternative option in blue.

• I would not be myself if I did not mention the Camper Traktori Boots (285 EUR). They're a bold fashion statement and a definite outfit game-changer if you have the confidence to carry them off.

So, what ended up in my shopping cart? As fate would have it, while perusing, I received a notification from Vestiaire about a pair of Jil Sander Chelsea boots up for grabs. I seized the opportunity, but alas, they were too large and quickly found their way back on the resale list. My quest continues, however, with my sights set on possibly the Aeyde Lee or Neil boots in that irresistible brown that flawlessly works with every outfit. But after being embedded in endless choices, I've decided to pause for a few weeks and catch my breath!

How about you? Have you snagged the perfect ankle boots this fall? Feel free to share your finds or challenges in the comments!