Updated June 07, 2020 by Brett Dvoretz

The 10 Best Chelsea Boots For Men

video play icon
Best High-End
Best Mid-Range
Best Inexpensive

This wiki has been updated 7 times since it was first published in July of 2018. Known for their versatility, Chelsea boots have been a staple menswear item for decades. Whether your style skews toward retro rocker or sophisticated, you’re sure to find something to complement your wardrobe on our list. We’ve included options to meet a range of budgets and uses, from hardwearing designs to casual, chic selections that will finish off any outfit nicely. When users buy our independently chosen editorial choices, we may earn commissions to help fund the Wiki. Skip to the best chelsea boot for men on Amazon.

10. Dockers Ashford

9. Steve Madden Highline

8. Ariat Spot Hog

7. Timberland Carter Notch

6. Dr. Martens Hardie

5. Frye Jones

4. Ted Baker Camroon 4

3. Ecco Crepetray

2. Stacy Adams M2 Wingtip

1. Cole Haan Kennedy Grand

Special Honors

Johnston & Murphy Warner Wingtip With classic brogue detailing,the Johnston & Murphy Warner Wingtip are a stylish choice that can just as easily be paired with jeans as slacks. A sheepskin textile lining makes them breathable, while well-cushioned footbeds and flexible rubber outsoles make them very comfortable. johnstonmurphy.com

Allen Edmunds Liverpool Ready for formal events, the Allen Edmunds Liverpool are handcrafted in Washington from soft and supple calfskin that is burnishable. They boast an authentic 60s style, have shock-absorbing cork insoles that mold to the shape of your foot, and feature V-tread tap soles that provide good traction without deterring from their professional look. allenedmonds.com

Editor's Notes

June 04, 2020:

With the ability to be dressed up for work and formal events, as well as paired with jeans or chinos for a more casual look, Chelsea boots are a must have for every man's wardrobe. Our selections showcase the versatility of this footwear.

If you are looking for something professional enough to be worn with a suit, but with a touch more flair than the average pair, we highly recommend Ted Baker Camroon 4, with their paisley-embossed elasticated panels. They also boast a natural leather sole, which many wearers will find more comfortable than a synthetic sole, since it is flexible and tends to mold to your foot over time. The Stacy Adams M2 Wingtip, while perhaps a bit too elaborate to wear to extremely formal occasions, also boast a natural leather sole, and there is no question they too, offer a very stylish flair. They would like great paired with some jeans, a blazer, or a leather jacket.

When it comes to long days on your feet, the Cole Haan Kennedy Grand and Ecco Crepetray are very good options, as they both feature quality cushioning that retains its loft through plenty of use. Of these, the Kennedy Grand are a bit more formal, while the Crepetray have a slightly more casual appearance, though either of these would be more than suitable for work and other business events. The Dockers Ashford also offer decent cushioning, and while perhaps not made with as high-quality of leather and other materials as the two options above, they are affordable and perfect for those on a budget.

If you need something rough and tumble for casual daily use with jeans and chinos, the Dr. Martens Hardie, Timberland Carter Notch, and Ariat Spot Hog definitely stand out. All three have pull tabs on the front and back for easy donning, and have thick soles that offer excellent traction in a variety of conditions. The Timberland Carter Notch are also waterproof.


Brett Dvoretz
Last updated on June 07, 2020 by Brett Dvoretz

A wandering writer who spends as much time on the road as in front of a laptop screen, Brett can either be found hacking away furiously at the keyboard or, perhaps, enjoying a whiskey and coke on some exotic beach, sometimes both simultaneously, usually with a four-legged companion by his side. He has been a professional chef, a dog trainer, and a travel correspondent for a well-known Southeast Asian guidebook. He also holds a business degree and has spent more time than he cares to admit in boring office jobs. He has an odd obsession for playing with the latest gadgets and working on motorcycles and old Jeeps. His expertise, honed over years of experience, is in the areas of computers, electronics, travel gear, pet products, and kitchen, office and automotive equipment.


Thanks for reading the fine print. About the Wiki: We don't accept sponsorships, free goods, samples, promotional products, or other benefits from any of the product brands featured on this page, except in cases where those brands are manufactured by the retailer to which we are linking. For more information on our rankings, please read about us, linked below. The Wiki is a participant in associate programs from Amazon, Walmart, Ebay, Target, and others, and may earn advertising fees when you use our links to these websites. These fees will not increase your purchase price, which will be the same as any direct visitor to the merchant’s website. If you believe that your product should be included in this review, you may contact us, but we cannot guarantee a response, even if you send us flowers.