12 Fall Boots That Locals in Italy Are Always Wearing

You know the old cliché about the person who spends a semester in Europe and can’t stop talking about it? That was definitely me. After studying abroad in Milan, one of the world’s fashion capitals, I came back with a more elevated style than your average student. And it’s really stuck with me, considering I’m now a travel and fashion writer living in Bergamo, Italy. One of the fundamentals of my style evolution was picking up Italians’ love of the perfect fall boot.

Sitting in a café in Milan writing this article, I’ve had boot envy for passers-by numerous times. And it’s true what they say: Italians do judge based on footwear. So whether you’re heading on a hiking trip in the Dolomites sporting supportive, comfy hiking boots or an aperitivo in Milan wearing stylish riding boots, I know just styles to help you blend in with the locals. Here are 12 fall boots that will have any Italian saying questi sono bellissimi!

The Classic Riding Boot

$154 at Zappos

There’s something about a classic riding boot that’s so elegant. Before studying abroad in Italy, I bought a pair that became my Old Faithfuls. Immediately, on the streets of Milan, I fit right in. People even complimented my boots before I knew how to say “boots” in Italian. If you want timeless luxurious elegance, there are few better Italian brands than Brunello Cuccinelli. These Brunello Cuccinelli riding boots perfectly exemplify this. In supple black leather with a curved equestrian-inspired top, these beautiful boots immediately enhance your gait.

But you don’t need to shell out for this look, either. These beautiful brown Sam Edelman Drina boots are similar and will be appreciated by any wearer for years. Though they have stretch stitching in the calves made to accommodate a variety of sizes, these boots definitely run slimmer for a more streamlined style. The bottom rubber tread also makes these boots great for navigating slick cobblestoned streets. Pair either of these styles with pleated Bermuda style shorts and a button-down for a menswear-inspired look.

The Black Ankle Boot

$120 $77 at Zappos

Picture this, you’re heading to dinner in Rome. When paused at a traffic light, the beautiful leather heel of your black ankle boot gently balancing on your Vespa is illuminated by the light of the Coliseum. The polished, buttery soft Italian leather is impeccable. This could be you! It’s been me! My Bally leather heeled ankle boots have been a wardrobe staple for me here when I’ve been looking to dress up jeans or black pants. A sleek leather ankle boot like this Banana Republic Lucca Ankle boot with a two-inch heel can be worn anywhere in a timeless style and shape. For a lower heel that’s also less expensive, these comfy Clarks boots could be just the ticket. Whether you’re a boot-cut trouser person or prefer a flowy chiffon midi, a black leather ankle boot will be your luggage hero.

The Cowboy Boot

$170 at Amazon

Believe it or not, Western style is a thing here, and it’s not just because Yellowstone is a top streamer on Italy’s Sky Atlantic. For the last few years, contemporary Italian brands have been producing cowboy boots that It-girls like Chiara Ferragni have been seen sporting. I even brought my red and black cowboy boots over from New York as a fun nod to American culture. While wearing cowboy boots to a friend’s bachelorette party in Nashville can be a little kitschy, wearing cowboy boots to Milan fashion week is cool, trust me.

I love the mid-shaft, blue suede Dingo Western boots. Italy’s a denim capital, and the beautiful blue of these boots is reminiscent of the perfect pair of jeans. Comfortable with a reasonable 1.5-inch heel height, these boots are great for exploring an Italian city. Pair with a mini dress like your favorite Italian influencer or a cool blue look with an of-the-moment denim midi skirt for a more mature look.

The Versatile Chelsea Boot

$53 $35 at Amazon

Head to a fashion trade show here in Italy, and you’ll see some really beautiful boots. One of the most popular styles? The iconic Chelsea boot. I fell in love with the style while working for a British High Street store and have a patent leather wing-tipped pair that I’ve gotten repaired countless times over the years. When looking to upgrade, I gravitated towards these Blundstone 63 Dress Chelsea Boots in simple leather. The brand says they’re known for being as comfortable on the trail as on the town, and they are right. Sunday lunch at an agriturismo in the hills? These boots are perfect. Sleek for city walking yet with a great tread for trails; they are the best boot for living in Bergamo and the surrounding hills.

The City Hikers

$189 $75 at Amazon

Two years ago while walking in Milan, I saw a great pair of hiking-inspired, embossed lace-up boots that I couldn’t get out of my head. I couldn’t remember the store but I had my husband retrace our steps a week later to find them. Now, I regularly get complimented on these boots from New York to London, Turin to Detroit. Leather and heavy, these boots are nevertheless comfortable enough for me to travel and add a polished look to my corduroys, perfect for the fall.

To emulate this style, try these Double T Combat boots from Tory Burch or, for a fraction of the cost, these look-alikes from Vince Camuto. Their patent leather croc-embossed style elevates the standard combat boot, and the cushioned footbed makes this style comfortable enough to wear all day. A zipper up the side makes this pair easy to take on and off. Pair with leggings or jeans for a perfect outfit.

The Hiking Boot

$260 $143 at Amazon

Now what if you’re actually going hiking in the Dolomites? These Adidas waterproof hiking “boots” toe the line between a stylish sneaker; they are especially comfortable with a sock-like upper, lightweight and stylish, perfect for chilly fall hikes. Moreover, Amazon shoppers note how good they are for hikes, highlighting their grippy traction and lightweight feel while being functional.

The Combat Boot

$230 $200 at Zappos

Skiing the Italian Alps on your radar this year? I must admit that a trip to a luxury Italian ski resort converted me into a major fan of the luxury combat boot. Some of your favorite Italian designers make ski collections, and you really see them in action at resorts. I actually have these stylish and practical (but heeled) Gucci quilted leather lace-up ankle boots. The slight platform and chunky leather sole make for stylish trekking with easily cleaned leather. Pair with jeans or ski pants!

For much less, you can obtain the combat look with a classic pair of Dr. Martens. These can last a lifetime, and these lace-up combat boots never go out of style. They are regularly seen on the streets of Bergamo, spanning across all age sets. If you happen to go gaga for cool fashion collabs, this Dr. Marten and Marc Jacobs Jadon boot is a stylish pick.

The Stylish Rain Boot

$70 at Nordstrom

If you’re traveling to Italy during the fall, there’s a strong chance you’re going to encounter some rain. Here in Northern Italy, it rains a lot this season. I don’t see many people walking around with wellie style rain boots. Perhaps that trend came and went? What I have seen are more subtle and stylish rain boot options like a Chelsea boot shape in waterproof or gortex material like these cool Jeffrey Campbell platform rubber Rain-Storm rain boots. Priced at $70, their leather Chelsea boot look makes them great for packing and exploring on dry days. Another cool rainy-day Chelsea boot option is in onyx, these 90 percent plastic Dolce Vita Stormy rain boots. Pair these boots with great boyfriend jeans or a midi skirt.

The Lace Up Knee-High Boots

$575 $432 at Theory.com

I am thrilled to see these lace-up knee-high boots from Theory on major sale. In a beautiful black, these knee-high boots are comfortable for wear throughout the day with their elastic side panels. The utilitarian style pairs beautifully with a uniform inspired A-line skirt or even delicate feminine pieces. The soft, supple leather has rave reviews, and the mix of leather and elastic allows for a lighter weight when packing. These boots pair perfectly with a classic lambswool peacoat or an Italian wool long-line blazer for exploring a coastal city like Venice in the fall.

The Suede Over-the-Knee Boot

$148 at Amazon

Another classic fall boot style that I’ve walked kilometers in throughout Italy are my cognac brown suede over-the-knee boots. Sophisticated, these boots pair well over jeans or with a mini skirt. The block heel makes them the perfect sophisticated travel boot; they add height but are comfortable for all-day wear. The adjustable ties at the top help fit a variety of thigh sizes. While my boots are no longer available at Zara, I found a comparable pair at Amazon by Marc Fisher. These are the fall boots, evoking thoughts of cozy knits and pumpkin spice lattes.

The Thigh-High Patent Leather Boot

$130 $44 at Kohls.com

While I’m off to order a pair of those cool Jeffrey Campbell rubber Chelsea boots for rainy days, I’ve also found my Stuart Weitzman patent leather boots to be a fashionable rainy-day option. For some time now, this style has been my go-to winter option. When it rains, I pair them with my patent leather rain hat! I recommend always packing a stylish rain hat for travels. You can find a cute one at Amazon for under $20.

My boots have served me well, definitely worth the splurge. Currently on sale at Kohl’s for under $50, these comfy Journee Collection patent leather thigh-highs lined with true comfort foam offer a great way to test the look. Available in wide sizing, these boots could be your perfect fit. Pair them with a chic cape for a glam Milanese look.

The Kitten Heel Boot

$210 $158 at Madewell.com

I’ve saved one of the most controversial boot styles for last—the kitten heel boot. Despite the backlash this heel receives for being touted as dated, kitten heels are here to stay. There’s a strong trend in Italy called scuiraglam, and you’ll see many women sporting kitten heels. These The Dimes ponyhair kitten heel boots are statement-makers. Jeans and a white T-shirt? Throw on these booties, and suddenly it’s a look.

For a more subtle kitten heel boot, try these J. Crew booties in café latte color. At under $50, these Zara booties are a safe test drive—perfect for Italian style.