We’re happy to report that not only are Chelsea boots still in style, they’ve experienced a resurgence in popularity and a refresh in styling to coincide with the rise in comfort-forward fashion (Dad sneakers, Normcore, Cabincore, etc.). As Reese puts it, “Chelsea boots remain stylish because they hit all of the high points of a timeless design: versatility, comfort, durability and a minimalist aesthetic. Their classic silhouette allows them to transcend seasonal trends, making them a reliable and versatile choice for any occasion year-round.” Chelsea boots are a step up, style-wise, from your everyday comfortable sneaker, yet in many cases offer more support and an equal level of comfort while elevating your outfit.

One of the reasons we (and our fashion experts!) love Chelsea boots is because they can be worn with just about any look in your closet. Abbas swears by Chelsea boots with everything from “a slip skirt or regular straight-leg jeans” (bonus points if they offer “a little height boost”). While one of the benefits of Chelsea boots is their versatility, look for options that have a little something special to set them apart. Reese recommends a lug sole boot (like this one from Soda Pilot, from $30) as we head into autumn weather, or a style with a bit of sheen to keep things interesting (look no further than this heeled pair from Nisolo, $220; $198). If you’re unsure where to start, try something classic and simple like dark-wash jeans and a white button-up shirt for a no-fail look that’s appropriate for whatever you may have on your schedule.

As we enter into the fall season, there’s no shortage of boots to pick from, so we had our work cut out for us to narrow down this list to the best of the best. Using guidance from our experts and shoppers (read: we pored over dozens of reviews from real buyers to get the straight talk on what worked and what didn’t) we assessed it all.  From fit (narrow, wide, etc.), material (leather vs synthetic), claims (waterproof for the win!) and style, we checked the specs to ensure we’re recommending boots that’ll hold up both in function and looks for this season and beyond.

The 6 Boot Styles That Will Rule Fall 2023

If you’ve devoured the list above and are in the mood for a little more backstory on these longtime fashion favorites, here’s everything you need to know about Chelsea boots. Named for the Chelsea neighborhood of London where they first became popular, Chelsea boots are typically a simple ankle boot that includes a stretchy gusset on the side so you can pull them on and off without a zipper or shoelace. The style actually dates back to the Victorian era (Queen Victoria herself was reportedly a huge fan), but was brought back into the zeitgeist in the 1960s, when Mod fashionistas, both men and women, revived them. And after The Beatles started wearing them, there was simply no going back.

One of the other upsides of Chelsea boots is that they’re available at a ton of retailers. Depending on the price point and aesthetic you’re after, you’ve got a number of stores to choose from. Some of our favorite retailers for Chelsea boots are Amazon, Nordstrom, and ASOS, but you can also find chic designer styles from brands like Nisolo and Tory Burch.

I’m a Shopping Editor. Here Are the 17 Items I’m Most Excited to Buy This Fall

Want to know which buzzy products are *really* worth buying? Sign up for our shopping newsletter to uncover our favorite finds.