Kick Around: Chelsea Boots

I’m a big fan of chelsea boots.  I like everything about them.  They look slick, and can be dressed up or dressed down.  Chelsea boots come in a variety of styles, with leather bottoms for a dressier look, or rubber bottoms that are built for comfort.  When shined up, they look like dress shoes – good dress shoes.  Be careful, though, go for a pair that has a traditional or rounded toe.  Avoid squares at all costs.  Think of these as a cool replacement for wing tips.  Well, that’s how I look at them.

Want to get fancy?  Try a pair in dark brown suede for a really good cool-weather look, or get a pair of black chelsea boots to wear with a dark suit or a tux.  Today, though, we are going to focus on the tan leather jobs.  Here are some of my favorites:

Clockwise from top left:

1. RM Williams Chelsea Boots: They’ve probably been making these boots forever, and had no idea that these options from the outback would be such a big hit.  Essentially, they don’t make them any better.  There are tons of sole options…so knock yourself out.
2. Sid Mashburn Chelsea Boots:  Of course Sid would have a chelsea boot.  Makes perfect sense.  His have a leather sole, so it’s essentially a dress shoe.  Wear these with anything from jeans to khakis to wool trousers (2″ cuff preferred).
3. Dubarry Kerry Leather Chelsea Boots:  Dubarry makes some outstanding stuff…and their Kerry boots are no exception.  The feature a rubber sole, so I’d avoid wearing them with wool trousers.  However, they will be comfortable all day long.  College football tailgating approved.
4. John Lobb Misty Leather Chelsea Boots:  The Rolls Royce of cheslea boots (and most other shoes).  It doesn’t get any better than a pair of Lobbs…and from their perspective – proven by the Dianite sole, these should be worn often, and for many hours at a time.
5. Ted Baker Camroon Chelsea Boots:  A lower profile option, but a super-sharp natural sole.
6. Wolverine Garrick Chelsea Boots: A great cost-friendly option, complete with football-grain leather and a really nice toe.

What did I miss?



  1. Harry
    10/14/2014 / 10:31 AM

    I’ll plug for my pair of Alfred Sargent Belgrave chelsea boots. The last is killer.

  2. Josh L
    10/14/2014 / 12:54 PM

    How can you miss Blundstones?!

  3. CCL
    10/14/2014 / 4:50 PM

    Josh, Blundstones are not Chelsea boots, they are simply pull-on work boots and lack the refinement to wear with a more dressed-up look.

  4. Charles
    10/14/2014 / 7:28 PM

    Got a decent pair from Cole Haan.

  5. Roger C. Russell II
    10/14/2014 / 10:53 PM

    The R.M. Williams boot is the best fitting most durable boot that I have ever owned. However, I have used the boot for its intended purpose which is for horseback riding. These boots are all basically what equestrians refer to as a paddock boot. A lot of pilots like this style boot as well. In the World War II movie that John Wayne did titled The Flying Tigers he wore The R.M. Williams Craftsman. Recently R.M. Williams was purchased by a fashion company. I hope that they don’t start cutting corners with their products. The Yard Boot lasted me almost 10 years of use 5 to 6 days a week. I stupidly never took the time to preserve the boot with leather treatment of any type. I simply sprayed it off with water. I have heard that R.M Williams has resoled boots that were over seventy years old.

  6. Josh L
    10/15/2014 / 1:42 PM

    @CCL Actually, that’s not correct. Chelsea Boots are a style of boot, which feature an elastic side panel and tab of fabric on the back of the boot, enabling it to be slipped on or off. Therefore, Blundstones are in fact a variation of the Chelsea Boot.

    Take note of their Chisel Toe styles, which, in my opinion, are refined enough to wear with a dressed-up outfit.

  7. 11/07/2014 / 7:58 PM

    I don’t own a pair of Chelsea boots, but I have been looking into them and thinking about adding them to the lineup.

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