What are the best Forever boots?

Why settle for five years? I would go for 10. That is, after all, when the sustainable clothing coalition writes down the environmental impact of a garment to zero. And like sneakers, flats, and a pair of heels, boots—the everyday kind, not the rain or snow kind—are one of the basic building blocks of a footwear wardrobe. Finding the right pair can solve a myriad of dressing problems, not to mention provide some welcome ankle support. But where to start?

There are choices to be made in height, heel and material.

When it comes to height, it shouldn’t surprise anyone that in today’s environment, people are divided on what kind of boots are best: knee high or ankle. (Thigh-high boots have their partisans, but I don’t think any of them would claim the style is a basic; they’re more like icing on the cake.)

Knee and ankle boots are arguably complementary—I pretty much live in both styles from October to April—but if you have to pick one, the experts I tried agreed it should be an ankle boot. The lower height just makes it a bit more versatile.

According to Angela Koh, T’s market editor, “A simple, black ankle boot, free of excess designs or trinkets,” is the best option, ideally with a zipper on the side. As she pointed out, “labels like Hermes and Saint Laurent have this style in their ‘carry over’ collection, meaning it’s in stores year-round, season after season,” which is as good a sign as any of , that it is a style that will last.

Paul Andrew, the shoe designer whose namesake collection currently features two different ankle boot styles and whose signature is interesting heels that are also counterintuitively comfortable, agreed. (If you want to roll over, check out the curve.)

Regardless of height, black calfskin “should be your material of choice,” Mr. Andrew said.

So, he continued, the choice is really about which identity you want to communicate. If that’s a strength, “a flat Chelsea boot with a heavy sole is the way to go, especially since the luxury sneaker trend is finally winding down.” For a subtle, more classic vibe, choose a streamlined leather boot with a pointed toe and a small heel (the blockier the heel, the easier it will be to walk).

As for where to find boots, Ms. Koh suggests “brands that prioritize longevity versus trends,” and the namecheck Everlane, Mango and – for a vegan leather option – Nah. She also noted that such shops were worth visiting Nordstrom Rack for affordable options as these styles are seasonless.

And then, to ensure further longevity, add taps to the soles, remember to use protective spray on top and keep your boots polished. Great design can only take you so far. If you’re going to spend time and money choosing a piece that will last, you need to do your part, too.

Every week on Open Thread, Vanessa will answer a reader’s fashion-related question, which you can send to her at any time e-mail or Twitter. Questions are edited and condensed.

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