5 Best Chelsea Boots of 2025

Ah, the Chelsea boot—one of the most popular and versatile styles of boots, and my personal favorite. They're stylish, incredibly versatile, easy to slip on and off, and usually pretty comfortable. Over the years, I've tried countless brands and styles of Chelsea boots, and these are some of my top picks. If you're in the market for a new pair, keep reading to find your perfect match!

1. KOIO | Fermo

The Fermo boots in the pinecone colorway by KOIO have quickly become one of my favorite pairs of Chelsea boots for 2024. They’ll definitely see plenty of wear this winter in 2025 and beyond. I think they strike the perfect balance of high craftsmanship, style, and comfort.

The signature PerformLUG sole is a standout feature—it provides excellent traction in winter weather and adds a touch of comfort for long walks. As an Italian myself, I truly appreciate that these boots are crafted in Tuscany. They’re constructed from LWG-certified Italian suede (cowhide) and lined with LWG-certified Italian leather, showcasing impeccable attention to detail and quality.

Overall, these boots exude sophistication and quality, making them a worthy investment at $365. The pinecone colorway, in particular, is versatile and timeless.

$365 at KOIO

2. Thursday Boots | Cavalier

Next up is one of the first brands that comes to mind whenever someone mentions boots: Thursday Boots. This brand has really taken off over the past five years, and for good reason. They've mastered the art of bootmaking with countless styles and variations. Naturally, their Chelsea boot is top-notch. It's high-quality, stylish, and offered at a great price point.

I'm especially a fan of the sandstone colorway pictured above—it pairs perfectly with a dark pair of jeans. And while these boots don’t have a pull tab, they’re surprisingly easy to slip on and off while still providing a snug, comfortable fit.

$190 at Thursday Boot Company

3. Beckett Simonon | Silva

The Silva boots from Beckett Simonon are another favorite of mine. Unlike the others I’ve mentioned, these are the first non-suede pair on the list. Crafted from water-repellent pull-up leather, they’ve become my go-to choice for days when the weather takes a turn.

With a combination of water-repellent leather, a lug sole, and a waterproof membrane lining, these boots are built to handle tough conditions. The rounded toe box adds extra comfort, and the pull tabs on both sides make them easy to slip on and off.

These boots are quickly becoming my everyday pair—the black leather is incredibly versatile and suits a wide range of occasions. Just keep in mind that they’re made-to-order, so there’s a bit of a wait time before they arrive.

$299 at Beckett Simonon

4. Amberjack | Honey

Amberjack's Chelsea Boots are advertised for their comfort, and they absolutely live up to the hype. These boots are incredibly comfortable and perfect for all-day wear. Much of this comfort comes from their unique sole, which stands out from the rest of the Chelsea boots on this list.

Amberjack uses a proprietary TPU outsole that gives the boots sneaker-like qualities, along with heat-activated arch support that molds to your foot for a customized fit. The honey-colored full-grain leather is top-notch, adding to the premium feel. At $199, this pair offers excellent value for the quality and innovation they deliver.

$199 at Amberjack

5. IDRESE Shadbolt

Rounding out the list is the Shadbolt Chelsea Boot from IDRESE. I’ve been testing these over the past few weeks and came away thoroughly impressed. The dark brown color is refined and versatile, making it a perfect choice for fall and winter.

IDRESE is a brand that exudes luxury, with every pair handcrafted and made to order in Spain—so be prepared for a bit of a wait. These boots are Goodyear welted and made with premium Italian roughout leather, ensuring exceptional quality and durability. This is a high-end option that’s perfect for when you want to make a statement.

$375 at IDRESE

And there you have it—that’s the list! From leather to suede, ultra-comfortable to ultra-luxurious, we’ve covered it all. I truly believe there’s a pair on this list for everyone, and I hope it’s inspired you in your search for the perfect Chelsea boots.

If you have any questions, feel free to reach out to me on Instagram @joe_sanfilippo—I’m always happy to help with your Chelsea boot questions and more!