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
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, there is something about these beautiful boots that immediately beautify your gait.
But you don’t need to shell out for this look, either. These beautiful brown Sam Edelman Drina boots are similar, and I know this style 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, European 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
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. Trust me, 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
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 with their cool street-style looks, paired with flirty dresses or skirts. I even brought my red and black cowboy boots over from New York as a fun nod to American culture and was photographed out and about during Milan fashion week with them. While wearing cowboy boots to a friend’s bachelorette party in Nashville can be a little kitschy or too on the nose, 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 this boot is reminiscent of the perfect pair of jeans. Extremely comfortable and with a reasonable 1.5-inch heel height, these boots are great for exploring an Italian city and the side pull tabs make them easy to get on and off. 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
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 recently, 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 I have to say, 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, I think I found the best boot for living in Bergamo and the surrounding hills. Get the look for less with these Dream Pairs boots that are only $35 at Amazon.
The City Hikers
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 admittedly heavy, these boots are nevertheless comfortable enough for me to travel in 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, especially with the Napa leather lining that breaks in easily. A zipper up the side makes this pair easy to take on and off. Pair with leggings or jeans you’ve found another wardrobe staple.
The Hiking Boot
Now what if you’re actually going hiking, say in the Dolomites? These Adidas waterproof hiking “boots” that toe the line between a stylish sneaker are especially comfortable with a sock-like upper, but they’re also lightweight and stylish, too. Plus, the brand says they’re especially made for the cold, so they’re perfect for chilly fall hikes. Even Amazon shoppers are noting how good they are for hikes, highlighting their grippy traction and lightweight feel while still being functional.
The Combat Boot
Skiing the Italian Alps on your radar this year? Maybe you’ve booked a trip to a luxury Italian ski resort like Cortina? I must admit that a trip to a luxury European ski resort this winter converted me into a major fan of the luxury combat boot. Some of your favorite Italian designers, like Gucci and Prada make ski collections and you really see them in action on the streets of a resort like Cortina. I actually have these stylish and practical (but heeled) Gucci quilted leather lace up ankle boots. The slight platform and chunky leather sole of these boots, or Prada chunky sole version, makes for stylish trekking with easily cleaned leather. Pair with jeans or ski pants!
But for much much less, you can get the combat look with just as much function in a classic pair of Dr. Martens. These can last what feels like a lifetime as these lace-up combat boots never go out of style. I see them quite regularly on the streets of Bergamo, spanning across all age sets. And if you happen to go gaga for cool fashion collabs, this Dr. Marten and Marc Jacobs Jadon boot is a stylish pick to show off in Italia, especially with the on-trend looser fitting jeans for a very ’90s look.
The Stylish Rain Boot
If you’re traveling to Italy during the fall, there’s a strong chance that you’re going to encounter some rain. Here in Northern Italy, it rains a lot during this season. But, I don’t see that many people walking around with wellie style rain boots. Perhaps that trend came and went? What I have seen is more subtle and stylish rain boot options like a Chelsea boot shape in a waterproof or gortex material like these cool Jeffrey Campbell platform rubber Rain-Storm rain boots. At $70 in a cool red, the leather Chelsea boot look of these rain boots makes them great for packing and city exploring on non-rainy days. Another cool rainy day Chelsea boot option are these 90 percent plastic Dolce Vita Stormy rain boots in onyx. Pair these boots with a great boyfriend jean or midi skirt.
The Lace Up Knee-High Boots
I am so thrilled to see these lace-up knee-high boots from Theory on major sale. In a beautiful black, these knee high boots are super 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 more delicate feminine pieces. The soft, supple leather has rave reviews, and as a bonus for light packers, the mix of leather and elastic allows for a little less weight when tucking away these boots in a suitcase. These boots with a classic lambswool peacoat or an Italian wool long-line blazer is a perfect pair for exploring a coastal city like Venice in the fall.
The Suede Over-the-Knee Boot
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, making a complete outfit, or with a mini skirt, giving your legs the appearance of miles high length. The block heel of these boots makes them the perfect sophisticated boot for travel as they add a little height but are still comfortable to walk around in all day. The adjustable ties at the top make for the ability to 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. When I think of brown suede thigh-highs, I think of sweater weather, cozy fall knits, and pumpkin spice lattes. Well, Starbucks is taking Italy by storm, so you can order one over here to complete your fall pics, too.
The Thigh-High Patent Leather Boot
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 as they are warm, flat, and elegant on days when I have meeting around NYC and Milan. And when it rains, I pair them with my patent leather Eric Javits rain hat! I definitely recommend packing a stylish rain hat like this for your travels, by the way — here’s a cute one at Amazon for under $20!
Similar to these Schutz over the knee patent leather boots, my boots have served me well over the years and definitely worth the splurge. However, currently on-sale at Kohl’s for under $50, these comfy Journee Collection patent leather thigh-highs lined with true comfort foam are a great way to test the look without breaking the bank. Also available in wide and extra-wide calf sizing, these boots could be your perfect fit. For a very glam Milanese look, pair them with a cape.
The Kitten Heel Boot
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 or questionable, with some naysayers asking, “What’s the point?” it seems that kitten heels are here to stay. Here in Italy, there is a strong trend called scuiraglam (that roughly translates to “wealthy married woman fashion”) and you’ll see wearers sporting kitten heels a lot. After all, the elegant mature women of Milan are the inspiration behind brands like Prada, so let’s appreciate their heels, too!
These The Dimes ponyhair kitten heel boots from Madewell are statement-makers. Jeans and a white T-shirt? Throw on these booties and suddenly it’s a look. Looking for a more subtle kitten heel boot? Try these J. Crew booties in the beautiful café latte color. And if you’re not completely sold on kitten heel boots but want to try the trend without investing too much? At under $50, these Zara booties are a safe test drive — and the ultimate in Italian style.
Love a great deal? Sign up for our T+L Recommends newsletter and we’ll send you our favorite travel products each week.