We Designed the Perfect Fall Boot—Here's How 3 Editors Have Been Wearing It

All the Ways to Wear is a monthly series where we round up the personal twists the Who What Wear team is putting on one particular item, style, or trend. Whether it’s the trending denim of the moment or the season’s It print, we hope to inspire your daily outfits and up the cost per wear on some of our favorite items.

It's that time of year when I take inventory of my current wardrobe before shopping for new seasonal pieces. And when it comes to my shoe collection, I'm pretty set on boots. I have dozens of pairs that range in style: heeled, lug-sole, cowboy, combat, Chelsea, sock boots, and so, so many more are sitting in my closet as we speak. I was all but convinced I wouldn't want to add more boots to my lineup this season, but apparently, I was wrong. (Oops.)

As soon as I saw the first sketches of the boot that our Who What Wear team designed with Sperry, I knew I would have to break my "no new boots" rule. This duck boot comes in two colors and features all of the on-trend details you'd expect a team of fashion editors to select, including a chunky sole, a cool zipper, and exposed stitching. And of course, it has the durability and comfortability that only a heritage footwear brand like Sperry can pull off. I had to make a little extra room for them in my closet, and I'm so glad I did. See how my fellow editors and I are styling the Sperry x Who What Wear boots as we start to dress for fall.

"During the fall, I'm a boots girl through and through. I'm always on the hunt for new styles to add to my collection, so you can guess how excited I was to try this new Sperry x Who What Wear collaboration. These boots aren't only chic (can we take a moment for the white stitching?) but practical as well. Gone are the days of ruining a pair of shoes in unpredictable weather—I know these will hold up no matter what. Plus, the black color is so easy to style. You can dress them up with a cool midi dress or keep them more casual like I did here with some leather shorts and a knit vest. Either way, you're bound to get compliments." — Anneliese Dominguez, editor

SHOP THE LOOK

"I'm really into the contrast between the gorgeous brown leather and the black EVA base (which, by the way, is waterproof) on these boots. It feels very cool and modern while maintaining the look of a traditional duck boot. My favorite way to style them is with any type of pant that can be tucked into the shaft (think skinny jeans or faux-leather leggings) and an oversize top or sweater. It's the perfect everyday fall look, rain or shine." — Michaela Bushkin, associate fashion director

SHOP THE LOOK

"I can't pretend that I'm even remotely happy about summer ending, but fall in NYC is like no other, so I'm prepared to dress accordingly. These boots are my new go-tos. The rubber and leather hybrid with the white contrast stitching is a unique twist on the classic black duck boot. I kept this outfit super neutral and edgy, leaning into the punk aesthetic that's been trending lately. I'd wear this to a casual dinner with friends or even a concert since these boots are so comfortable and easy to walk in." — Aniyah Morinia, associate editor

SHOP THE LOOK

SHOP MORE SPERRY BOOTS