11 Best Men’s Chelsea Boots: Your Buyer’s Guide

chelsea boots

123rf Evgeny Ustyuzhanin

Finding the best men’s Chelsea boots is following in a tradition brought to you by the hip, on-trend cool kids in the 1950s and 1960s England. Men’s Chelsea boots (get it? Chelsea, a district in London) are among the most popular boots a guy can wear and they work very well as men’s summer boots.

 

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Our Unbiased Reviews
  1. 1. Calvin Klein Men’s Christoff Epi Leather Chelsea Boot

    Pros:
    • Slip-on and off
    • Casual or formal
    • Comfortable
    Cons:
    • Hard to break in
    • Scuff easily
    • Sizing

     

     

    In the intro, I mentioned the origin of the name Chelsea for this style of boots. It was the fashion-forward people in the Chelsea district of London who started wearing the style, which was popularly then referred to as “Chelseas.” You can include “Beatle boots” in the glossary because those four lads wore something very similar.

    These men’s Chelsea boots from Calvin Klein are pretty dang close to those Beatle boot styles. These are definitely a street boot which will be great men’s summer boots.

    The upper is tumbled leather and the sole, which is very streamlined, is synthetic. Shown in dark brown, also available in black. 

  2. 2. Frye Men’s Jones Chelsea Boot

    Pros:
    • Multiple colors
    • Slip-on and off
    • Trusted name in boots
    Cons:
    • Price point
    • High maintenance
    • Sizing

    This is a very good looking pair of men’s Chelsea boots that you’ll probably not wanna wear out on the trail. Frye makes a huge range of footwear and these boots definitely fall in the “dressy” category. In turn, it makes them a perfect candidate for the men’s summer boots category.

    These have leather uppers and a leather sole. Shown in black, the boots are available in three different colors, but all sizes are tough to come by unless you’re going for the black or the chocolate colors.

  3. 3. Blundstone Men’s Summer Boots

    Pros:
    • Comfortable
    • Slip-on and off
    • Durable
    Cons:
    • Price point
    • Protective spray needed
    • Loose fit

     

     

    How do you say “I love you” in Australian? (Insert smiley face here.) The fact is, I have a pair of these and they’re awesome. Besides being great looking men’s Chelsea boots, these are incredibly comfortable: I was recently on vacation in London (big city vacations are always “working vacations” because of all the walking) and I pretty much exclusively wore my Blundstones.

    For me, they’re the epitome of men’s summer boots because they’re so light. Blundstone just recently introduced its lineup of summer boots, although they do have a wide range of Chelseas and other styles available. The summer boots are the company’s lightest weight boots, with Blundstone’s Featherflex soles and a leather upper that features a reduced height through the ankle.

    According to Blundstone, the new line of men’s summer boots “was designed for comfort and shock absorption, with added durability to the sole tread for improved wear and tear.” They’ve got two logoed pull tabs, one in front and one in the back (the tabs are conveniently long, making the boots even easier to get on). Shown in “rustic black,” the boots are available in four different colors: sand, rustic brown, suede olive, and the rustic blacks.

  4. 4. Timberland Mens Britton Hill Chelsea Boot

    Pros:
    • Trusted name in boots
    • Very durable
    • Comfortable
    Cons:
    • Heavy
    • Bulky
    • Clunky

     

     

    Timberland is the very popular streetwear brand that’s mostly known for its iconic Timberland Premium Waterproof Boot, but these Brook Parks make it abundantly clear that Timberland knows its way around a category about the best men’s Chelsea boots.

    The upper is leather while the goring (the stretchy part at the ankles) are elastic fabric. The sole is from Green Rubber, a company that recycles Vulcanized tires. There’s a small heel here (just .75″) and the boots have a convenient (and contrasting red) pull-on strap at the rear.

     

  5. 5. Dr. Martens 2976 Chelsea Boot

    Pros:
    • Trusted name in men's footwear
    • Very durable
    • Comfortable
    Cons:
    • Heavy
    • Scuff easily
    • Sizing

     

     

    These men’s summer boots from Doc Martens are made with the company’s “Airways” original leather, which they call a “firm, finished leather with a smooth, semi-bright appearance.” The boots are Goodyear-welted, meaning the upper and the sole are heat-sealed and sewn together, which is obvious because you can easily see that classic Doc Martens style.

    The heel is one-inch and the boots feature the classic Doc Marten’s logoed pull-on loop at the heel. Shown in “black smooth,” the boots are available in nine different colors.

     

  6. 6. Skechers Men’s Blaine Orsen Ankle Boot

    Pros:
    • Comfortable
    • Rustic look
    • Casual or outdoor
    Cons:
    • Fit
    • Sizing
    • Limited colors

     

     

    This is a very popular men’s Chelsea boot from Skechers. This might be the most rustic looking on this list of men’s summer boots.

    It’s an oiled leather upper with a rubber sole, which is very “tready.” The goring panels — the elastic panels at the ankles that make it easy to get in and out of Chelseas — are “hidden” with leather that’s got a lot of stylized vertical stitching going on. The boots have two pull tabs, a regular sized one in the back and a smaller one in the front.

    Shown in dark brown, they’re also available in black.

  7. 7. Bruno Marc Men’s Casual Chelsea Ankle Boots

    Pros:
    • Formal boot
    • Great look
    • Unique design
    Cons:
    • Hard to break in
    • High maintenance
    • Sizing

     

     

    Another dressy pair of men’s Chelsea boots that work very well as men’s summer boots. This pair, from Bruno Marc, has the classic Oxford styling on the upper, with the very recognizable punch holes and stitching.

    The upper is synthetic while the sole is rubber. The heel sole is about one-inch and the heel area of the upper features a slightly contrasting (a deeper color) strip leading to the heel tab. If you shop this shoe online, be aware that it’s listed with several other versions from Bruno Marc, many that aren’t classic Chelsea boots. You can buy these boots in a few different colors so there should be something for every guy and his particular style. 

  8. 8. Clarks Men’s Paulson Up Chelsea Boot

    Pros:
    • Slip-on and off
    • Price point lower than most
    • Lightweight
    Cons:
    • Light color easy to get marks or scuffs on
    • Sizing
    • Fit

     

     

    Clarks is a well-known brand that make some seriously stylish and slick boots. These boots are a traditional Chelsea boot with a nice shine and great durability. 

    Shown in black leather, this men’s Chelsea boot is available in four different colors. The black leather is all leather and it has a rubber sole. The heel measures about 1″. It’s got a pull-on tab at the heel and the boot is lined with leather. A great-looking, low profile boot.

  9. 9. Mark Nason Los Angeles Tamar Chelsea Boot

    Pros:
    • Lightweight material
    • Stylish
    • Slip-on and off
    Cons:
    • Minimal colors
    • Sizing
    • No insulation

    This men’s summer boot from Mark Nason Los Angeles is in a style called “dress knit.” If you want a better idea of what that is — and how popular it is — just take a stroll around the internet and look at designs by Pharrell Williams, Kanye and more. Knit has been super popular for the past couple of seasons. It’s quite unique to find it in a men’s Chelsea boot.

    While the upper is knit, the sole is synthetic. The insole features air-cooled memory foam. Shown in charcoal, the boot is available in three different colors. This is a great candidate for the additional protection of Scotchgard.

  10. 10. Rockport Men’s Wynstin Chelsea Boot

    Pros:
    • Trusted name in boots
    • Slip-on and off
    • Design quality
    Cons:
    • Sizing
    • Heavy
    • Arch support

     

     

    Rockport is the shoe brand that made its name on producing comfortable shoes. These men’s Chelsea boots from Rockport feature a leather upper and the goring panels are attractive (without being distracting) in a herringbone pattern.

    The boots feature a pull tab at the heel and contrasting stitching on the upper, as well as at the welt (where the boot is attached to the sole). There’s also the contrasting stitching on the back heel area, which is in a brushed leather, contrasting with the smooth leather that makes up the predominant part of the upper. The sole is synthetic and features Rockport’s “truTech” technology for lightweight shock absorption. The boots feature a removable Ortholite footbed with an EVA (a synthetic material) heel cup.

    Shown in dark bitter chocolate, they’re available in two different colors.

  11. 11. Thursday Boot Company Duke Men’s Chelsea Boot

    Pros:
    • Great looking
    • Added height
    • Multiple color combos
    Cons:
    • Stain easily in this color
    • Heavy
    • Sizing

     

     

    The Thursday Boot Company says they started their company to offer “ridiculously high-quality footwear at honest prices that could handle our busy lives in New York City.” Wherever you are, these will work great.

    The boots feature premium suede uppers (which look great in the “honey suede” color because they contrast with the dark goring panels). They should be plenty comfortable because the footbed is cork and it conforms to the wearer’s feet. Thursday Boot Company says they did “more than 20 re-designs to optimize the slope for comfort and aesthetics.”

    The sole is rubber and Thursday recommends ordering this boot one size smaller than you would normally wear in athletic shoes.

    Shown in “honey suede” color, they’re available in three different colors.

     

Summer doesn't always mean wearing sneakers or sandals. Chelsea boots work great all year and for a ton of outfits, even shorts or, certainly, jeans.

History - As you poke around researching the history of the Chelsea boot, you'll see Great Britain's Queen Victoria mentioned repeatedly. Her personal cobbler made her a pair of boots suitable for her horse riding habits. The key element in those boots -- and Chelsea boots today -- is the addition of rubber (or, now, any flexible material) in the ankle cuff area. (To get all booty and technical, it's called "goring," which is the process of adding an elastic element to slip-on footwear that doesn't have any other sort of closure. It makes the boots easy to get on, easy to get off.)

But also in the 1800s, some boot makers in Australia were creating a style that has continued to maintain its worldwide presence. The company, called Blundstone, has an interesting timeline about the evolution of its boots here. (Blundstone provided me with a pair of Chelsea boots to try out. They're listed below in item #3.)

Men's Summer Boots

As we have talked about previously in the intro to our curated list of men's chukka boots, men's summer boots are defined by a lighter touch. For our list, we're avoiding the heavier boots that often have a warm lining, etc. Men's summer boots are usually made of lighter materials, both for the upper and the sole.

Chelsea boots have become almost a strictly "city boot" because they're so on-trend and fashionable, although their history is decidedly in outdoor wear. In sum, men's Chelsea boots work anywhere. If you want to keep rocking the Chelseas when the bad weather hits, consider treating them with Scotchgard.

Each style shown is in a particular color but just about every one of these models of men's summer boots comes in a wider assortment of colors, and we make note of that. Be sure to check the links. Also, if you're shoe shopping for something other than Chelsea boots, check out the links at the very bottom of the list for some other footwear options.

One last word on fashion. While you can definitely wear your jeans over the Chelsea boots, they're also commonly worn lately (thanks to the cool, on-trend kids everywhere) with rolled up jeans or jeans that are tucked in. They're all great looks and you'll look great in something from our list of Men’s Chelsea Boots 

See also:

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