What Are the Best Forever Boots?

I want to buy one pair of boots this year that will stay in style for at least five more years. I’d like to wear them to a business meeting and out at night with nice jeans or a casual dress. I believe in timeless items and the capsule wardrobe. What would you recommend? —Sharon, Seattle

Why settle for five years? I’d go for 10. That is, after all, when the sustainable apparel coalition writes the environmental impact of a garment down 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 begin?

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

When it comes to height, it should surprise no one that in the current environment, folks are divided on what kind of boots are best: knee-high or ankle. (Thigh-high boots have their own partisans, but I don’t think any of them would claim that the style is a basic; they’re more like the icing on the cake.)

Arguably knee and ankle boots are complementary — I pretty much live in both styles from October through April — but if you have to choose one, the experts I canvassed agreed that it should be an ankle boot. The lower height makes it just a smidgen more versatile.

According to Angela Koh, T’s market editor, “A simple, black ankle boot, free from any excess designs or trinkets,” is the hands-down best option, ideally with a zip up 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 that it is a style that will last.

Paul Andrew, the shoe designer whose namesake collection currently has two different ankle-boot styles, and who has a signature in interesting heels that are also counter-intuitively comfortable, agreed. (If you want to splurge, check out the Curve.)

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

Then, he went on, the choice is really about what identity you want to communicate. If it’s strength, “a flat lug-sole Chelsea boot is the way to go, especially because the luxury sneaker trend is finally waning.” For a subtler, more classic vibe, opt for a streamlined leather bootee 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 name-checked Everlane, Mango and — for a vegan leather option — Nae. She also noted that it was worth haunting stores such as Nordstrom Rack for off-price options, since 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 the time and money to choose a piece that lasts, you need to do your part, too.

Your Style Questions, Answered

Every week on Open Thread, Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or Twitter. Questions are edited and condensed.