This Boot Trend Will Never Go "Out"—It's Timeless and Always Chic

There are a few fall boot silhouettes that are more or less staples year over year and hold strong within the ever-changing trend cycle. Yep, chunky boots are one of said styles. While flat boots are definitely a front-runner for the season, those heeled picks are still in the spotlight as a must-have choice given their timeless and always-chic nature.

While there's a range of styles out there in the market, we scrolled through some of our favorite sites to uncover the chunky black boots we think you'll love the most in case you're in need of a fresh pair. We also pulled some visual inspiration from fashion people in the shoe silhouette to give you a few outfit ideas. We're talking about everything from a laid-back ensemble to something a bit more dressed up. Keep scrolling for the ultimate curation of the boot trend that will never go "out."

1. Ankle Boots


(Image credit: @nicoleocran)

You can't go wrong with a classic pair of chunky Chelsea boots. Pair your favorite pick with a neutral midi dress for a flawless fall outfit.

2. Lace-Up Boots


(Image credit: @smythsisters)

Slip into a pair of lace-up boots with leather trousers and a tank for an effortless vibe.

3. Statement Boots


(Image credit: @_marisamartins_)

Statement boots (like those silhouettes with a contrasting heel) work with just about anything—including a 'fit like this with a polo and jeans.

4. Western-Inspired Boots


(Image credit: @greceghanem)

Into heeled Western-inspired boots? Try a pair with a simple dress and a jacket or blazer if it's chilly outside.

This post was published at an earlier time and has since been updated. Next, These 30 New Steve Madden and Jeffrey Campbell Boots Look Designer

Market Director

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent over seven years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises. He has also worked across a variety of other media brands and fashion retailers like Refinery29, PureWow, Men's Health, and Gilt covering commerce, trend reporting, women's and men's fashion, home, and lifestyle.