The warm air of summer has been replaced with brisk fall winds and with it a whole new wardrobe for us to indulge in. Cable knit sweaters, classic black tights, plaids and tartans, and of course, a really great pair of boots. From combat to knee-high to suede to bootie, fall’s boot options are bountiful.
We asked our editors to give us their take on the perfect boot—which ones stand up to the wear of New York City’s unforgiving streets and which are most in sync with their personal style. Some opted for more practical pairs while others were swept off their feet by pairs that made a statement. Commerce Writer Alexis Bennett has her eye on a pair of fall boots from Ulla Johnson—they’re infused with a touch of the Southwest but built for city living. (See her up above.) Executive editor Jessie Heyman was inspired to purchase the safari leather boots by Loeffler Randall after spotting Margot Robbie sporting the same pair last year. Market Editor Naomi Elizée went for a statement-making-pair of Dries Van Noten boots that’ll make onlookers green with envy. No matter the look, this post serves as proof: fashion and function can be friends.
Alexis Bennett, Commerce Writer
I need a boot that can take me from the office to dinner and everywhere else. That’s why these fun, moccasin-inspired boots are at the top of my list this fall.
Alexandra Michler, Director, Fashion Initiatives
This jaunty little pointy toe leather boot by Khaite is a fabulous fall staple with trousers for the work week, with jeans for weekend lunches, and bare legs for Saturday night.
Celia Ellenberg, Beauty & Wellness Director
These Gianvito Rossi boots are the stuff of my dreams, literally. I just got an unintentionally 90s haircut and have been envisioning Fall wardrobe staples that feel era-compliant but not too retro. I started an extensive online search with these terms in mind and found this classic style as if Google was actually reading my mind—which it very well may have been. (I try to disable Cookies as often as I can, but I’m fairly certain all of my devices are not only listening to my conversations, but intuiting my every desire as well). Anyway. The narrow toe has the perfect amount of squareness as not to appear clownish, the 3″ heel is high but not too high that I can’t take them on (short) subway rides, and the mid-calf shaft is just right under straight-leg jeans, and with dresses. The online description referred to them as a “timeless investment,” and I couldn’t agree more.
Chloe Malle, Contributing Editor
I’m prepping for another winter spending more time outdoors than I’m used to and these Larroude lug sole lace ups are the perfect boot to get me around the city in any weather.
Lilah Ramzi, Commerce Editor
It wouldn’t be an overstatement to say this: I really, really struggle with boots. Every year when is gets too cold to bare my ankles, I get flustered. My style skews incredibly lady like (if I do say so myself) and so the idea of chunky, clunky boots makes me want to run in the opposite direction in my pointed toe kitten heels! A couple years ago, I picked up these suede boots by Sarah Flint and their loveliness did everything I needed them to do: keep me warm without adding any weight whatsoever to my look. When I shop for my next pair, I’ll basically be trying to recreate them.
Jessie Heyman, Executive Editor
It was love at first sight: Two years ago, I saw Margot Robbie in the most perfect below-the-knee boot—and I’ve coveted these Loeffler Randall beauties ever since. This season, I’ll finally make them mine.
Rickie De Sole, Executive Fashion Director, Vogue.com
These Celine boots are an investment, but they’re totally worth it. I bought these boots three years ago on a trip to Paris, and they pair with just about everything. They hit at exactly the right spot above my calf, and while the heel is high, I can still walk in them quite easily. I have been eyeing them in a hunter green color too. When you find the perfect pair, why switch for anything else?
Julie Tong, Senior Commerce Editor
I’m a loyal fan of the Chelsea boot and currently have my eye on this Proenza Schouler version for the fall season. Another one of my all time favorite boots is this set of Loewe lace-up boots, although they’re no longer readily available, you can still find them at Yoox and a few consignment shops like Vestiaire. With their shearling lined interior and suede exterior, they’re a plush way to transition between seasons.
Madeline Fass, Market Editor
These are by far my most comfortable heeled knee-high boots—no pun intended. I love wearing them with leather shirt dresses and midi-skirts by day, and under wide leg trousers or jeans with a vintage t-shirt for after hours. When I am after an edgier square-toe moment, Miista makes the coolest, exaggerated options.
Eliseé Browchuk, Production and Marketing Manager, Experiences
Fall is by far my favorite time of year. This season, I’m investing in a pair of black leather ankle boots. I’ve been eyeing these equally sophisticated and stylish Jimmy Choos. The subtle sparkle detailing around the sole matched with the chunky silhouette make this pair stand out.
Emily Farra, Senior Fashion News Writer
I have some cognac suede Loeffler Randall boots that I’ve worn to death, so I’m eyeing this pair to add to my rotation. It’s really hard to find classic, simple, comfortable boots that don’t have a weird heel or flashy hardware, so LR is my go-to!
Mai Morsch, Associate Market Editor
Every couple of years, I invest in two pairs of classic black boots—one heeled and one flat—and wear them until they have all but fallen apart. I am in need of a refresh and don’t think I could ever grow tired of these timeless pairs from Marion Parke and Wandler.
Naomi Elizée, Market Editor
I’m not afraid of color and love a bold boot to transition into Fall!
Elise Taylor, Living Writer
Jenni Kayne’s canyon boots are inspired by vintage hiking gear, but I’ve found they fit in just as well on a city street as they do a nature trail. I’d know—I’ve worn them on both.
Sarah Spellings, Fashion News Editor
I wear these boots at least once a week. Yes, they’re cowboy boots, which I know is daunting to some people, but they’re sleek and subtle cowboy boots. The stitching and steel toe are two great details that make them feel special as well.
Chioma Nnadi, Vogue.com, Editor
As soon as fall rolls around, I feel like my hunt for the perfect boot resumes. Thankfully this season my colleague Carlos Nazario made it a whole lot easier by curating a collection from the archives Italian boot makers Buttero. I’m really into the curved detail on these knee-high riding boots. And the best thing is they’re flat, so I can pretty much wear them all day long.
Christian Allaire, Fashion and Style Writer
I have never been a Margiela Tabi person, but lately I’ve found myself drawn to the (very polarizing) split-toe boots. I think they’d look so cool with a simple white tee and black pants. They’d for sure turn heads on the street and I live for it.
Lauren Sanchez, Business Manager and Contributing Editor
I feel most at home in a boot—which I attribute to childhood growing up on a ranch in the Texas Hill Country. It feels like I live a million miles away, trading in taxis for pastures but when I slip on a pair of cowboy boots, it’s like I never left. Texas born and handmade—City Boots come in just about every color under the sun. I refuse to believe cowboy boots will ever go out of style (evidenced by Fashion and Style Writer Christian Allaire’s recent article) which is why I have big plans for a pair of bone white boots this fall.
Arden Fanning, Contributor
There’s something very electro soft about P448’s white teddy boots, I don’t know how they’d stay clean for more than a few city steps, so I imagine they’re more like an indoor party boot. It’s hard to find options with sizes that go beyond 40 or 41, so I’m looking.
Clarissa Schmidt, Commerce Producer
The only boot that truly seemingly lasts forever is, of course, the beloved Dr. Martens! I have owned my floral pair for years now, and they still look (and feel) good as new. Docs are a great year-round shoe, but fall is the best time to pair them with my favorite jeans and dresses.
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