Hello, Boots Season—5 Trends We're Investing In and 5 We're Retiring

Welcome to boots season! Over the past few months, we've made predictions based on the fall and winter trends we'd want to wear and planned out the outfit combinations we'd be trying. But now that we're well acquainted with our cold-weather wardrobes, we have to admit that, well, we've been playing favorites. Of all the boot trends on deck this season, each of our editors has cherry-picked the styles that speak to them the most and have been prioritizing those top picks. The change in seasons comes hand in hand with our desire for a wardrobe refresh—starting with a winter-boot upgrade.

To find out what we'll actually be wearing throughout the winter, we discussed the winter boot trends we're phasing out due to their somewhat outdated nature. Chunky lug-sole boots aren't making the cut this season for these editors, but instead, many of us are leaning toward sleek stiletto and riding boot styles this season. Keep scrolling to uncover the boots—from the 2023 update to shearling (yep, they're back) to cool moto options—we're considering to inspire your next winter shopping haul.

"Over the past few seasons, we've seen chunky lug sole knee-high boots reign supreme, but I'm ready to sunset the silhouette in lieu of something more streamlined. Don't get me wrong; I still find the idea of flat boots appealing; however, with so many F/W 23 collections (e.g., Tory Burch) featuring sleek riding boots with statement hardware, I'm ready to make the switch. What I love about these boots is that they walk that fine line between tapping into the low-key luxury aesthetic and being a timeless silhouette." — Jasmine Fox-Suliaman, Editor

"I just overhauled my entire shoe wardrobe and purged tons of outdated style from it. Among them were a pair of slouchy suede boots that I hadn't touched in a solid two years and, well sorry, but they were first on the chopping block. Recently, I've been overlooking the slouchy style for more structured knee-high boots that give off a much more polished effect. The runways are on my side, too, seeing as versions popped up in Loewe and Bottega Veneta's F/W 23 collections." — Anna LaPlaca, Editor

"This season, I’m setting aside shiny patent boots that I don’t gravitate to as much these days, and instead opting for more rugged, lived-in Moto boots which feel of-the-moment—and a trend we’ve been seeing all over the fashion set this season. Whether it’s an ankle silhouette or knee-high style, I’ll be styling Moto boots with silky and sheer long skirts for a cool contrasting look." — Judith Jones, Senior Market Editor

"I know they're comfortable, but I find that my outfits look far sleeker and more refined when I'm wearing a pair of pointed-toe, '90s-inspired stiletto boots than I do in anything with a block heel. All the proof anyone should need arrived at Ferragamo's S/S 24 show in the form of patent-leather stiletto boots. Plus, unlike most boots, this particular style is alarmingly easy to wear with jeans or trousers because there's no bulk to it. The more fitted the boot, the better, if you ask me." — Eliza Huber, Editor

"I have always had an admiration for furry boots, but while that footwear trend soars in temperate weather, it is not built for NYC, IMHO. Shearling boots, however, are slightly different but still give off the same vibe and can somehow outlive a bad weather day. Definitely check whether the boots you’re purchasing are weather-proof or not to be totally sure, but overall, I’m telling you that you won’t regret a shearling or sherpa pair of boots." — Sierra Mayhew, Associate Editor