Best Men’s Chelsea Boots
Stephanie Patterson
Table of Contents
If boots make the man, and to be the man you gotta beat the man, then the only way to survive the dog-eat-dog world of men’s footwear is by having the best boots possible.
There are plenty of boot styles and shapes, but the Venn diagram of high-quality boots and Chelsea boots is more like two overlapping circles.
What better place is there for you to commence your vision quest towards unmatched masculinity than our list of the best men’s Chelsea boots. We’ll cover the hottest boots from the hottest brands for the hottest boys on the block.
How to Choose The Best Men’s Chelsea Boots
It’d be nice if we could choose the best men’s Chelsea boots for you, wouldn’t it? It’d also be nice if we could pay for them, deliver them straight to your house, and maybe even put them on for you.
We’re not fairy godmothers, buddy, but we are able to give you some tips as to how to choose the right pair of boots for you.
You can’t just freestyle footwear purchases. You have to consider what it is you’re looking for before you insert your credit card number at the checkout screen.
For example, are you the type of guy who wants men’s Chelsea boots with buckles, or would you prefer suede men’s Chelsea boots (both very good choices)?
We’re not trying to scare you by overloading your brain with considerations. That’s why we’ve isolated the three most important factors that go into selecting the best men’s Chelsea boots for you. They are as follows:
- Brand
- Material
- Price
Brand
Most Chelsea boots follow pretty strict style requirements. They’re laceless, easy to slip on, and shapely.
However, that doesn’t prevent the brands lining this list from experimenting with the format.
Each company brings their own touch to the Chelsea boot design, resulting in this list where every item highlights what distinguishes the brands from one another.
Material
Chelsea boots are usually made from either suede or leather. These materials have their advantages and disadvantages as well as changing how the boots look.
Keep in mind that some of the best Chelsea boots are built for winter months, thus they’re insulated with extra material, while some keep things light so that you can sport them in the summer.
Consider when you’ll want to wear a pair of Chelsea boots during the year to help guide your decision-making process.
Price
Footwear should be considered the biggest investment you can make in regard to fashion. That’s because, unlike other clothing garments, a discount or bad pair of boots can negatively impact your health.
You want a pair of Chelsea boots that can support your body without crumbling in disgusting weather. Furthermore, you don’t want to invest in a shoddy set that will give you back problems due to their poor insoles.
Thankfully, some of the options we’ll feature deliver reliability without an outrageous price tag.
12 Best Men’s Chelsea Boots
This section of our best men’s Chelsea boots ranking will cover what you came here for; here are our picks for the Chelsea boots that put other boots to shame.
#1 – New Republic Sonoma Suede Men’s Chelsea Boots
There’s no need to rush for leather when it comes to Chelsea boots. In fact, the New Republic Sonoma Suede Men’s Chelsea Boots proves that the opposite is often true.
These are among the best men’s suede Chelsea boots because they’re so casual. Their exterior lining is a brown suede colorway that is as cool as a morning batch of waffles; decadent and sweet.
Their pale beige color means they could slip into fall or winter outfits easily. Plus, it’s a distinctive color among the blacks and dark browns that usually adorn other Chelsea boots for men.
- New Republic Sonoma Suede Men’s Chelsea Boots: SALE – $90, Regular price – $128
#2 – Steve Madden Crimson Waterproof Men’s Chelsea Boots
As we mentioned in our introduction, functionality can make or break a Chelsea boot. Thus, a functionless boot can break a man.
The Steve Madden Crimson Waterproof Men’s Chelsea Boots storm out of the gate as one best men’s leather Chelsea boots with their waterproof external layer.
You’re probably searching for the best men’s Chelsea boots for either fall or winter – two particularly wet seasons. These boots can keep your feet dry and your socks safe throughout the colder calendar months with their rubber outsole and warm fleece interior.
Plus, they’re sleek as all heck. The Steve Madden Crimson Waterproof Men’s Chelsea Boots can bring out the bad boy vibes without going overboard with supplementary whips and chains.
- Steve Madden Crimson Waterproof Men’s Chelsea Boots: $190
#3 – Alexander McQueen Tread Men’s Chelsea Boots
Modest boots are great. They’re covert, humble, and ready to work.
Sometimes you just want to stomp about in some thick, so these chunky leather boots are built for war but dressed for the runway. That’s the vibe that the Alexander McQueen Tread Men’s Chelsea Boots exudes.
These boots combine combat boot bulkiness with the refinement inherent to the Chelsea boot shape. The rubber sole will grant you an additional inch or so of height, so shorter guys should save this item to their Karma wishlist.
We’d call these cowboys one of the best men’s black Chelsea boots for how effectively they combine style and size.
- Alexander McQueen Tread Men’s Chelsea Boots: $790
#4 – Aldo Carangue Men’s Chelsea Boots
The pointed toe is one of the Chelsea boots’ most distinctive features. It elevates their classiness, and these Aldo Carangue Men’s Chelsea Boots are some of the classiest rancheros in this saloon.
Combine that accented pointed toe with this item’s smooth exterior and we believe these men’s brown Chelsea boots should be a regular at high-society get-togethers.
What’s better is that they don’t sacrifice any functionality for their formality. These boots have a convenient pull-back tab and a forgiving mouth so you can slip them on easily.
- Aldo Carangue Men’s Chelsea Boots: SALE – $120, Regular price – $195
#5 – Beckett Simonon Bolton Men’s Chelsea Boots
The Beckett Simonon Bolton Men’s Chelsea Boots are the Chelsea boots.
If you were to visualize an item and inspect the totality of its being, doing away with all the fluff to hone in on the key components, you’d likely envision these boots when trying to imagine a Chelsea boot.
That fussless design is what cements this product as one of the best men’s Chelsea boots. These boots are as slick as oil, as cool as the Marlboro Man, as tough as a 2-dollar steak, and as timeless as the Queen of England.
Their Italian craftsmanship is likely the largest factor that sets these boots apart from the pack. This item looks like it’s the product of over a century of hard work.
- Beckett Simonon Bolton Men’s Chelsea Boots: SALE – $239, Regular price – $400
#6 – Thursday Boots Cavalier Men’s Chelsea Boots
These are the first men’s grey suede Chelsea boots we’ve covered thus far, but they’re available in multiple colors too.
The Thursday Boots Cavalier Men’s Chelsea Boots’ black, sandstone, dark brown, and dusty color options are all as appetizing as the grey option.
There’s even versatility in the material. The Thursday Boots Cavalier Men’s Chelsea Boots comes in a hickory leather exterior as well.
No matter what color entices you, know that each one features a smooth leather interior and a forgivingly flexible opening. The opening should accommodate all manner of feet.
Since they’re only lined with leather we’d slate these boots as one of the best men’s Chelsea boots for warmer weather. They lack the thickness a wool interior would provide, but it’s nice to have a classy boot you can still wear during the summer.
- Thursday Boots Cavalier Men’s Chelsea Boots: $190
#7 – Browns Blundstone Men’s Chelsea Boots
The Browns Blundstone Men’s Chelsea Boots bring the thunder from down under. Walk through any intersection between September and April and you’re bound to see at least a baker’s dozen of Blundstones carrying people where they need to go.
The brand’s ubiquity speaks to their quality, but it doesn’t reveal everything that makes the Browns Blundstone Men’s Chelsea Boots one of the best Chelsea boots for men. Here’s a quick list of this item’s highlights:
- Water-resistant exterior
- Insulated to conserve heat
- Unique and rugged brown colorway
Is there anything these boots can’t do? Maybe wrangle a couple of loose broncos, but who needs Chelsea boots in the heart of cowboy country anyways.
- Browns Blundstone Men’s Chelsea Boots: $240
#8 – Fryre Bowery Men’s Chelsea Boots
You can’t be the toughest man to walk the streets without the toughest boots on your feet. Thus, the Fryre Bowery Men’s Chelsea Boots should round out that desired tough look.
They’re one of the best men’s Chelsea boots for a few reasons. Firstly, their leather and rubber compound sole supports a Goodyear welt exterior, delivering a product tough enough to survive an atomic bomb.
Next, we’re particularly drawn to their original take on black. It’s not a solid color, no sir.
Instead, the Fryre Bowery Men’s Chelsea Boots has a glossier stonewash undertone. It makes these boots look like they’ve already lived through tough times and lived to tell the tale.
- Fryre Bowery Men’s Chelsea Boots: $392
#9 – Dr Martens 2976 Smooth Leather Men’s Chelsea Boots
Dr Martens are better known for their punk-rock adjacent looks. You’re probably expecting this entry to be one of the few men’s Chelsea boots with buckles or chains.
However, like this product’s name proclaims, the Dr Martens 2976 Smooth Leather Men’s Chelsea Boots keep it cool and casual.
This item dates back to the 1970s and captures the timeless Chelsea boot design. Thankfully, Dr Marten infused it with their world-class leather and the small design choices that have made them a household name among footwear fans.
You’ll find the Dr Martens 2976 Smooth Leather Men’s Chelsea Boots features the company’s classic double stitching, heel loops, and deep grooves.
This is the item if you want to preserve what sets Dr Martens apart from the pack while sporting the Chelsea boot shape.
- Dr Martens 2976 Smooth Leather Men’s Chelsea Boots: $158
#10 – R.M. Williams Comfort Craftsmen Men’s Chelsea Boots
The R.M. Williams Comfort Craftsmen Men’s Chelsea Boots might challenge the Blundstones as the best Chelsea boots for men from Australia. Come on, you know a product is confident when they put the word “comfort” in their name.
These boots have the unique feature of two straps at the front and back. These straps make it even easier to slip on this pair of men’s Chelsea boots.
These versatile boots can be styled either formally or casually. They’ve got the square toe and leather finish to suit a formal gathering, but are subdued enough to fit under an old pair of jeans and a flannel.
#11 – Jack Erwin Ellis Men’s Chelsea Boots
These Portuguese-made Chelsea boots are for the romance addicts reading this list. They’re refined and dressed up with a calfskin exterior, a rubber insole that was stitched by hand, and a slim shape.
The Jack Erwin Ellis Men’s Chelsea Boots are a lovely option. We can almost feel them flirting with us through the computer screen.
If the black color isn’t your thing, then check out the brown full-grain or brown suede options. The latter in particular is one of the best suede men’s Chelsea boots around.
- Jack Erwin Ellis Men’s Chelsea Boots: $225
#12 – Diemme Alberone Men’s Chelsea Boots
The Diemme Alberone Men’s Chelsea Boots are Italian-made, winter-ready boots.
You wouldn’t think their Italian heritage would make them one of the best options for cold weather, but that’s before you consider how every material used comes from Italy. That means you’ll be paying for premium manufacturing.
We’re not lying either. Every part, from the calf leather lining to the thick rubber sole to the suede exterior hail from Italy.
Combine that with Diemme Alberone’s esteemed manufacturing, and you’ve got yourself one of the best pairs of men’s black Chelsea boots.
How To Wear Chelsea Boots?
While some boots like the Aldo Carangue Men’s Chelsea Boots and the Dr Martens 2976 Smooth Leather Men’s Chelsea Boots seem tailored towards specific vibes, there aren’t any rules as to what looks good with a pair of Chelsea boots.
You can dress them up or dress them down. The material and shape will determine the overall attitude you should consider before implementing them into an outfit. Suede usually demands a more formal outfit, but that’s more of a suggestion than a hard rule.
What are the Most Comfortable Men’s Chelsea Boots?
Arguably the best part of men’s Chelsea boots is their convenience. There aren’t any laces you need to tie. They’re all slip-on, providing comfortable functionality in addition to a comfortable feel.
If we had to highlight one pair for their comfort levels, we’d go with the Browns Blundstone Men’s Chelsea Boots. Then again, you’re reading a list of the best men’s Chelsea boots, so it’s not like any of these items will feel like you’re walking on needles.
How do you Clean Leather & Suede Men’s Chelsea Boots?
Leather Chelsea boots are forgiving when it comes to cleaning. You can rid most accumulated grime from the boots’ exteriors with a damp cloth or an actual leather cleaning product.
Men’s suede Chelsea boots require more care. Here are some tips to clean them:
- A good brush is a must so that you don’t damage the material
- Line the insides of the shoes with something to help them keep their shape during the cleaning process (we usually use a loose towel or paper)
- Use white vinegar to scrub out any deep stains
- Dry the boots with a towel after you finish scrubbing them
Which Men’s Chelsea Boots are the Best?
Asking us to pick the best men’s Chelsea boots is like asking us to pick which of our twelve children is our favorite – we love them all!
It’s not an impossible task, but it depends on what you’re looking for in a pair of boots. Some of the products on this list are going to suit the classy champagne enthusiast more than they would Johnny Silverhand.
Consider each product’s price, material, and brand, then follow your heart. It’ll guide you to the best pair of Chelsea boots, though you can’t go wrong with any of the boots in this list.
Looking for more footwear and accessories for yourself or that dashing fellow in your life? Check out some of our top picks:
