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5 Best Chelsea Boots for Men in 2020: The Thinking Man’s Boot

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I remember standing in a Banana Republic one day, staring at a pair of Chelsea boots up on the wall.

I turned to my wife and said, “I don’t know if I’m ready.”

She looked at me. “What does that even mean?”

See, I’d never owned a pair of Chelsea’s before—I was stuck on the cap toe lace up boot style. I wasn’t sure I was ready to step my style game up.

“Quit being an idiot,” she said, gently. “Get the boots already and let’s go.” Ah, I remember the twinkle in her eye.

Well, I got the boots.

And I’ve been wearing Chelsea boots probably four to five days a week ever since.

In my humble opinion, they’re the best shoe a guy can wear. You can find a sleek dressy pair that works well with a suit, or you can get a rounded toe version that pairs like a charm with all things casual.

Really, it’s hard to go wrong with a Chelsea boot. They’re sophisticated and masculine. They make a t-shirt and jeans combo look classy. What’s not to love?

In honor of my favorite boot, I put together a list of the five best Chelsea boots out there right now.

Warning: if you’re not ready to catch the Chelsea boot fever, stop reading now.

Quick Summary

  • Moral Code Lawry Chelsea Boot product image white background

    Lawry from Moral Code

    • Rounded toe, excellent for casual-wear
    • Goodyear welted
    • Available in suede and interesting dyed leather colorways
  • MGemi Dritto Chelsea Boot product image white background

    Dritto from M.Gemi

    • European, Italian style
    • Blake stitched
    • Lower ankle and slimmer, sleeker profile
  • Johnston and Murphy McClain Chelsea Boot Product Image White Background

    McClain from Johnston & Murphy

    • Full-grain leather and sheepskin lining
    • Squared toe box
    • Mixed leather and rubber sole
  • Thursday Boots Cavalier Chelsea Boot Product Image

    Cavalier from Thursday Boot Co

    • Dressy Chelsea boot that pairs well with suits
    • No pull tab, so no worries about your pants getting caught in the back
    • Cork-bed midsoles that get more comfortable over time
  • Franco Fortini Mens Trevor Chelsea Leather Ankle Boot Shoes, Black, US 8

    Trevor from Franco Fortini

    • Budget pick
    • More of a dressy style
    • Black and brown are only available styles

What Are Chelsea Boots?

ice blue lawry chelsea boots moral code model wearing with charcoal jeans

Chelsea boots are traditionally slim, form-fitting ankle boots with gored elastic sides. They don’t have laces and are easy to slip on and off.

They became wildly popular back in the ‘60s as bands like The Beatles and The Rolling Stones were seen wearing them often.

But while bowl cuts are a thing of the past, the Chelsea boots remains popular.

A lot of guys (myself included) love the style because it pairs well in a huge variety of outfits. Boxier style Chelsea’s, like those from Moral Code, look fantastic under jeans and chinos. Dressier styles, like those from M.Gemi or Thursday, will pop with a suit or under more formal trousers.

In any case, Chelsea boots are an excellent way to elevate your casual style. As I said earlier, they can make jeans and a t-shirt look like an outfit masterpiece.

Originally, these boots were all made with leather soles, but over time, more modern updates became available.

Personally, I wear Chelsea boots too often to stick with the leather sole. I prefer a full rubber sole, or at least a rubber and leather hybrid. You’ll see that preference throughout the list, too, so keep that in mind as you peruse your options.

I take good care of my shoes, but I do a lot of pavement pounding and my shoes have a limited lifespan because of it. For me, rubber soled shoes are a better investment (unless I’m shopping for a formal occasion. In that case, a leather sole is the better choice).

3 Things to Consider When Buying Chelsea Boots

1. What’s the occasion?

I always buy my shoes based on what sort of occasion I’m looking to dress for. For instance, I’ll ask myself: do I want a pair of shoes that are more casual, but I can pair with a suit? In that case, I’d look for a slimmer profiled boot.

Or: did I just get a new bomber jacket that looks awesome with a pair of jeans but needs something sleek to bring the outfit together? A relaxed, durable Chelsea might be the trick.

A slightly boxier style like Moral Code’s Lawry is my top-choice if you’re looking to fill out your casual shoe rack. While I love them for their ability to elevate a pair of jeans, they’re not the best look when paired with a suit.

For that, I’d choose a slimmer, more European style Chelsea boot.

2. How’s the leather?

model with leather rolltop backpack and ice blue lawry chelsea boots from Moral Code

With most Chelsea boots, there’s no brogue pattern, no cap-toe—nothing to hide behind. If the shoe isn’t made with high-quality leather, it can lose its shape quickly and cease to give you that effortless elegance.

I can vouch for the selections on this list (yep, even the budget pick). None of these choices will do that toe indent thing that looks floppy and terrible. You know what I’m talking about.

3. Will it last?

model wearing blue chelsea boots moral code on stair case

If there’s one thing I’ve learned over the past 10 years, it’s that there’s no point in buying cheap clothes that don’t last. When I was in my early 20’s, I’d buy the cheapest stuff I could get away with and still look good.

The problem is, after you wash your clothes or go for a long walk in your shoes, it looks terrible.

I remember the last cheap pair of boots I bought. I stood in a hot parking lot in LA and literally watched my shoes change shape. They were never the same. And I never bought cheap again.

Don’t be afraid to put some cash on the table here. Good leather boots are an investment. And if you care for them well, they’ll last you for many fashionable years.

3 Ways to Wear Chelsea Boots

The 5 Best Chelsea Boots for Men in 2020

1. Lawry from Moral Code

ice blue lawry chelsea boots from moral code with black shoebox

Because they own their tannery, Moral Code gets nothing but the best leather for all of their shoes and accessories. We took a look at their Chelsea boots (sneakers, backpack, and a wallet too) and felt the value was hard to beat.

What We Like

  • The rounded toe and slightly boxier style of this boot makes it an excellent choice for pairing with jeans and chinos.
  • Goodyear welting means this boot is very easy to resole. If you take good care of the leather upper (just keep it waxed every three months or so), this boot will last you many years.
  • I love suede Chelsea’s but Moral Code’s interesting dye patterns were too hard to pass up. Their unique Ice Blue colorway really separates MC from the pack.

What We Don't Like

  • While they look fantastic with jeans and chinos, these aren’t the best choice if you’re looking to pair with a suit. They’re built a little bigger so their silhouette isn’t ideal for thin trousers.

What Other Reviewers Say

Reviews are scattered around the web, but the consensus is that Moral Code is the go-to alternative to Allen Edmonds.

You’re getting the same quality—the Goodyear welt, the premium leather, the cork in the sole, but you’re cutting the price tag nearly in half. That’s a win-win.

The Verdict

For premium quality casual boots that will stand the test of time, the Lawry is your best shot.

While I love the green suede option, the Ice Blue is one of the more unique takes I’ve seen on the style.

Moral Code has a great deal of experience in the shoe industry and they’re showing it all off on this boot.

If you’re planning on wearing your Chelsea’s more casually with jeans and chinos, these are our top pick.

What We Like

  • The Dritto is a slimmer, Italian style boot. It looks excellent with a suit, but you can always pair it with jeans.
  • A leather sole lends itself to dressier occasions.
  • While classic brown and black are available, there are also some beautiful, hand-dyed suede colorways.

What We Don't Like

  • There’s an off-chance that your local shoe-repair won’t be able to resole the leather, Blake stitched bottom. While Goodyear welts are easy to remove and just about any shoe-repair can spruce your favorite boots up, Blake stitch soles require special tools. Most cobblers have the right tools, but you may have to visit two different shops.

What Other Reviewers Say

Reviewers on the M.Gemi site consistently mention the build-quality and comfort. Those factors are especially important with Chelsea boots as they can constrict after several hours of wear. But not one reviewer had any problem with that.

The Verdict

M.Gemi is our go-to for Italian-crafted shoes. We’re big fans of their lightweight loafers (and we can’t wait for spring and summer to come along so we can rock them).

The Dritto is our favorite pick if you’re looking to dress the Chelsea style up with a suit.

While putting a new sole on these might not be as easy as a comparable boot with Goodyear welting, the Blake stitch is the only way to get that classic, slim Italian vibe.

3. McClain from Johnston & Murphy

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Johnston & Murphy has been around since before zippers were a thing. Oh, you can’t recall off the top of your head when zippers were invented? (Hint: 1851).

They’ve earned a reputation for high-quality shoes, and our experience can attest to that, too.

What We Like

  • Full-grain leather upper and a sheepskin lining give this boot a premium feel.
  • These are the slimmer dressy style Chelsea boot. But the McClain has a neat squared toe-box compared to the Dritto from M.Gemi.
  • The sole is a mix of leather and rubber. Leather for the look, rubber for the longevity.

What We Don't Like

  • Johnston & Murphy only offer black and brown leather—no suede, no interesting variations. We love the classics but the other brands on this list have more variety.

What Other Reviewers Say

Two things jumped out at me when looking at reviews for the McClain—the first is that they last seemingly forever.

But something important to note is that one reviewer mentioned the toe box rising a good amount. This is part of the dressier style, and I’m personally a fan of the look. But if you don’t want any rise in the toe, it’s best to check another brand.

The Verdict

It’s hard to go wrong with Johnston & Murphy. Their shoes are durable, comfortable, and an excellent value for the price.

I’d say this most closely competes with M.Gemi’s Dritto boot. They’re both made with premium materials and can be worn all day with no trouble.

It really comes down to whether you like a squared toe box (McClain) or a rounded toe (Dritto).

Both look fantastic paired with a suit, so no worries there. In either case, the value is there.

4. Cavalier from Thursday Boot Co

Thursday Boot Co has been taking the shoe world by storm. Their value-driven boots seem to be popping up everywhere. Like Moral Code, they have two different versions of the Chelsea boot: the Cavalier, and the Duke.

Between the two, the Cavalier is the dressy one, while the Duke is the more casual silhouette.

What We Like

  • Cork bed insole moulds to your feet after a few days of wear and will increase the overall comfort.
  • No pull tabs so your pants won’t get caught in the back (but they’re slightly harder to put on).
  • Two beautiful suede colorways.

What We Don't Like

  • We’ve noticed that Thursday Boots tend to scuff easily. It’s not a major issue, but you’ll want to consistently care for these Cheslea’s so they don’t look too rugged.

What Other Reviewers Say

Over 500 reviewers on the Thursday site give the Cavalier a 4.7 star rating. Many people like them better than the Dukes (Thursday’s more casual Chelsea boot), but that’s due to the shape and silhouette.

Many reviewers also mentioned that the Cavalier wasn’t their first Thursday purchase. That’s always a good sign.

The Verdict

We’re fans of Thursday Boot Co in general, not just for their Chelsea boots.

And we had a tough time deciding between their Duke and Cavalier for our favorite of their two offerings.

Ultimately, the Cavalier won out because of its sleek design and beautiful rustic suede colorways. These hit the balance of classic and modern better than most other boots on the market.

5. Trevor from Franco Fortini

Franco Fortini Mens Trevor Chelsea Leather Ankle Boot Shoes, Black, US 8

There’s nothing handcrafted or Italian about these. They’re almost certainly made in China and have inexpensive cemented rubber soles.

But you know what? I’ve owned a pair of these for two and a half years and they still look fantastic. This is the best budget pair of Chelsea boots you can find.

What We Like

  • The price is right. If you’re in the market for a budget pair of Chelsea boots, these are your shoes.
  • They’re fairly durable and hold shape well. I’ve owned a pair for two and a half years and still have no problems. 
  • You don’t have to worry about taking them out to bars or getting them scuffed up. I still believe you should take good care of your shoes at any price point, but you can afford to be a little more lax with these.

What We Don't Like

  • The leather isn’t the highest quality and the rubber cemented sole can’t be redone. So when the sole wears out, it’s time to buy a new pair.

What Other Reviewers Say

If you buy from Amazon, reviews say the boots run large. For instance, folks who were size 11 bought a size 10 or 10.5 and were satisfied.

I bought mine from Rack Room Shoes and didn’t run into that problem.

Adjust your sizing according to which place you’re shopping.

The Verdict

Okay, Franco Fortini aren’t the best Chelsea boots in the world. But for under $60, I’m really impressed.

I’ve had my pair for over two years and they’re still in good condition. Some cheap leather shoes collapse in the toe-box and look terrible.

I’ve put tons of miles on my Franco Fortini boots (and spilled a few beers on them, too), and they’re still going strong.

I wouldn’t compare these to anything else on the list—they don’t hold a candle to the quality of the other boots here. But if you’re on a tight budget, these are your best shot.

Ready To Get Your Chelsea On?

If you’re looking for a great new pair of Chelsea boots to elevate your casual style, try one of our five favorites.

The Lawry from Moral Code is our go-to when it comes to boosting a jeans and jacket outfit. With rugged Goodyear construction and premium leather, a little care will go a long way with these puppies.

If you want something a little more slim and sleek, take a look at M.Gemi, Johnston & Murphy, or Thursday Boots. These styles are a little thinner through the middle and will play beautifully with a suit.

And if you’re on a tight budget, check out the Franco Fortini’s, which will have you looking stylish but leave you with some cash leftover for drinks with the guys.

Chelsea boots are widely available, but still not too many guys wear them. Hop into a pair now and give yourself that style boost you deserve.

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