Swoon-Worthy Autumn Boots to Shop for Fall

As pumpkin spice weather begins to swirl around us, I always have two things on my sartorial wish list: new collegiate sweaters and new collegiate boots. (Honestly, I blame Ali MacGraw in the 1970 film “Love Story” for this annual compulsion).

But there are only so many Kate Middleton-approved boots that I can buy, folks. So this year, I’m turning to SwearBy’s well-heeled contributors for ideas, all of which I think our gal Kate would probably like, too. When I buy them I’ll probably run around like Rachel Green a la Friends yelling: “They’re my ‘I don’t need a job, I don’t need my parents, I’ve got great boots boots!’” She really gets me.

Everlane The Boss Boot

These sleek boots with a two-inch heel had me at “Italian leather.” “You’ve heard of a LBD, but these are my LBB (little black boots),” says Stephanie Perry. “They’re my go-to throughout the fall and winter months and look great paired with jeans, leather leggings, dresses, skirts, and more. Plus, the heel height is manageable enough for walking around the city all day.” Amen to that.

Red Wing Shoes Harriet Boot

I have a very serious crush on Red Wing, because almost all of their footwear is made in their factory in Red Wing, Minnesota. These pecan-hued leather numbers with a stacked heel are cute to (ahem) boot. “These were a little bit of a splurge, but totally worth it,” says Caitlin Kimmet. “I was looking for a nice pair of leather boots that would be lifetime-boots. I’ve been steering away from fast fashion and really angling for more sustainable, long-term purchases. These were not cheap, but they are the highest of quality. They took a little breaking in, but are now my ideal shoes. I am totally sold.”

Frye Melissa Button 2 Boots

I’ve purchased two pairs of Frye boots, and they’ll never die. This pair has blessedly low heels and an equestrian’s aesthetic that will do quite nicely on my next jaunt across the pond. Kate Cihon put it best: “Comfort and style all in one gorgeous package!”

Aquazurra Brera Boot 85

“I love this brand, and this is the perfect day-to-night boot,” says Alexandra Loeb of this teetering knee-high number, made in Italy by Aquazurra. “Stacked heel, easy to walk in height, comfy and classic style. Excellent investment piece.” We’ll have to fact-check “easy to walk in,” but it’s not impossible…and worth trying, for a look this 🔥!

Hunter Original High Gloss Waterproof Boot

Everyone needs a solid pair of wellies. And while I personally don Kate Middleton’s go-to brand, Le Chameau, the Queen wears Hunters…and who am I to argue with her?? This high gloss version in maraschino cherry red makes puddle jumping even more fun. “These are the creme de la creme of rain boots,” says Michele Falcone. “They’re super comfy, keep your feet toasty + look great with an array of outfits. Princess Diana rocked Hunter boots, so if they’re good enough for royalty, they’re definitely worth checking out.”

Hi! [Insert waving blonde emoji here] I'm a Colorado-based freelance writer, and I'm Niles Crane-level picky about everyyyyything.