2
1
0
3
4
5
6
7
8
9
10
11
12
13
14
2
1
0
3
4
5
6
7
8
9
10
11
12
13
14
4.8/5 based on 4.700+ reviews

John | High-Top Chelsea Ankle Boots

$195.00 $79.95 Savings: $115.05
/
Limited stock available!
  • 30 day hassle free returns
Colour
Size
US Flag Free shipping to United States
  • Visa
  • Mastercard
  • American Express
  • PayPal
  • Maestro
  • Afterpay

Modern Design Meets Superior Comfort

The John High-Top Chelsea Ankle Boots combine sleek style with practicality, offering a perfect balance of comfort and versatility. Crafted from high-quality fabric and featuring a comfortable leather lining, these boots are designed to fit your lifestyle seamlessly. The elastic strap closure ensures an easy, snug fit, while the solid color design makes them suitable for various occasions. Whether you're heading out for a casual day or looking for a more sophisticated touch, the John High-Top Chelsea Boots are your go-to choice for everyday elegance.

Why Choose the John | High-Top Chelsea Ankle Boots?

  • Premium Fabric Construction: Made with durable fabric for a sophisticated look that stands the test of time.
  • Comfortable Fit: The leather insole and lining provide all-day comfort, making them perfect for long hours of wear.
  • Elastic Strap Closure: Designed for easy wear, the elastic strap ensures a snug fit that accommodates your foot's natural shape.
  • Versatile Style: The simple yet stylish design pairs well with both casual and semi-formal outfits, making them ideal for various occasions.

Product Highlights

  • Material Outside: Durable fabric that combines strength and flexibility.
  • Material Inside: Soft leather lining for a breathable and comfortable fit.
  • Material Insole: Genuine leather insole that provides support and cushioning for all-day wear.
  • Type of Closure: Elastic strap closure for easy, quick fitting.
  • Height: Short boots that provide a modern and sleek silhouette.

Elevate your wardrobe with the John High-Top Chelsea Ankle Boots—perfect for men who value style, comfort, and functionality in every step.

I proudly offer FREE shipping

Each pair of shoes is carefully wrapped by hand and sent directly from my workshop to your doorstep, with love and attention to detail.

Once your order is shipped, you’ll receive a tracking number so you can follow your new boots on their journey home.

If you're not completely satisfied with your shoes, you can return it within 30 days - no questions asked.

Hi, I'm Henry

For over 30 years, I've been crafting leather boots, believing everyone deserves to walk in comfort and style. Each pair blends durability, beauty, and individuality—because every step should feel as good as it looks. From rugged to refined, every boot tells its own story, shaped with care from the finest leather.

As I close this chapter, I'm grateful you’ve been part of the journey and hope these boots bring you the same comfort and confidence they’ve brought me.

Lifetime Craftsmanship Guarantee

Every pair of shoes comes with a lifetime craftsmanship guarantee. Not satisfied? Return them for a full refund—no hassle, no questions.

38.787+ MEN ALREADY LIKED MY CRAFTSMANSHIP!

Review Image
★★★★★

I can't get over the quality of this Shoes! The leather feels so soft and durable, and the design is both practical and stylish.

Andrew M.

Review Image
★★★★★

Bought my Boots a few days ago, and They've already been delivered! The leather is soft and the craftsmanship is exceptional.

Jack P.

Review Image
★★★★★

These are hands down the best pair of Boots I’ve ever owned. The leather is top-notch, and they're very comfortable.

Ben O.

Review Image
★★★★★

very pleased with the purchase. Nice looking boots and very comfortable to wear. Arrived very quickly. Excellent service 👏

Jack U.

Review Image
★★★★★

One the best boots I bought. They are good quality and sturdy.. You can wear them for work or on nights out. I definitely recommend. such a great price for such quality boots!

Daniël A.

Review Image
★★★★★

Great product, really comfortable, delivery good, thanks! I'm very happy!

Mark M.

BUNDLE & SAVE

Save $125.05
Thim | Genuine Leather Chelsea Boots
Thim | Genuine Leather Chelsea Boots
$195.00 $69.95
Save $80.05
Harrold | Rugged Leather Lace-Up Boots
Harrold | Rugged Leather Lace-Up Boots
$140.00 $59.95
Save $105.05
Julian | Premium Leather Boots
Julian | Premium Leather Boots
$165.00 $59.95
Save $75.05
Oscar | Men's Chelsea Boots
Oscar | Men's Chelsea Boots
$145.00 $69.95
Save $105.05
Boas | Handcrafted Premium Leather Oxford Boots
Boas | Handcrafted Premium Leather Oxford Boots
$195.00 $89.95
Save $100.05
Jack | Lace-up Leather Boots
Jack | Lace-up Leather Boots
$170.00 $69.95
Save $105.05
Frank | Men's Retro Derby Boots
Frank | Men's Retro Derby Boots
$185.00 $79.95
Save $135.05
Max | Premium Men's Leather Boots
Max | Premium Men's Leather Boots
$195.00 $59.95
Save $110.05
Henry | Retro Winter Boots
Henry | Retro Winter Boots
$190.00 $79.95
Save $90.05
Nick | Zipped Leather Chelsea Boots
Nick | Zipped Leather Chelsea Boots
$170.00 $79.95
Sold Out
Alvin | Men's Leather Ranger Boots (SOLD OUT)
Alvin | Men's Leather Ranger Boots (SOLD OUT)
$215.00 $69.95
Save $130.05
Finn | Genuine Leather Chelsea Boots
Finn | Genuine Leather Chelsea Boots
$220.00 $89.95
Save $150.05
Nate | Leather Voyager Boots
Nate | Leather Voyager Boots
$230.00 $79.95
Save $195.05
Jasper | Genuine Leather Boots
Jasper | Genuine Leather Boots
$295.00 $99.95
Save $100.05
Damian | Genuine Leather Loafers
Damian | Genuine Leather Loafers
$170.00 $69.95
Save $110.05
Rafael | Genuine Leather Boots
Rafael | Genuine Leather Boots
$175.00 $64.95
Save $145.05
Luke | Fashion Leather Ankle Boots
Luke | Fashion Leather Ankle Boots
$215.00 $69.95
Sold Out
Ricky | Men's Leather Ranger Boots (SOLD OUT)
Ricky | Men's Leather Ranger Boots (SOLD OUT)
$275.00 $89.95
Save $165.05
Milan | Vintage Cap-Toe Derby Boots
Milan | Vintage Cap-Toe Derby Boots
$245.00 $79.95
Save $80.05
Dereck | Men's Leather Ranger Boots
Dereck | Men's Leather Ranger Boots
$170.00 $89.95
View all
View all
30 products

Frequently Asked Questions

I am available 7 days a week to answer all your questions.

Opening hours:

Mon - Fri: 9:00 AM - 5:00 PM

Sat - Sun: 10:00 AM - 4:00 PM

I strive to respond within 48 hours.

✉️ support@henry-boots.com

I always offer our customers the option to return their order within 30 days of receipt. Email us at the address below to initiate a return.

support@henry-boots.com

I always offer FREE shipping

You will receive a tracking number once your order has been shipped

Pay easily and securely with PayPal, Amex, Maestro, Visa, MasterCard, Afterpay, Apple Pay, Google Pay, and Shop Pay and so on

All of the shoes on the website are handmade by me

I’ve crafted thousands of shoes, bringing joy to just as many people who wear them happily every day

The very last chance—only a few pairs left in stock!