Boot Season

I make one exception for wearing socks: boots.  You can’t do boots without socks.  There really isn’t a boot season anymore, as they are a part of any long-pants wardrobe.  That said, colder weather lends itself to many more boot options.  I like to think there are three categories of boots:

First, dress boots.  These are the boots that are essentially tall dress shoes.  Typically leather bottoms or some sort of dress rubber sole, like Dianite.  These are typically treated just like dress shoes: polish, brush, shoe trees, etc.  Suede for extra points.

Second, work boots: Boots that only look sort-of out of place on a hipster wearing skin tight black jeans.  Brands like Red Wing, Wolverine, Truman, and Blundstone all fit here.  Don’t let the bearded hipster scare you off, they are great boots for us in the middle 80%.  Good with jeans and khakis, or with a more rugged pair of canvas pants.  Keep them clean, while allowing the patina develop.

Lastly, utility boots:  These are the boots that serve a specific purpose.  Duck boots and field boots fit this mold.  Gore Tex is a must.  Easily transitioned into normal, non-dressy wear.  My entire pledge class wore duck boots because, well, we needed to wear duck boots.  You get it.

Here is a rundown of some great boot options.  Some you know, some you don’t.  Here we go:

From top left:

1. Cobbler Union Chukka II Boots:  A very dressy option for colder months  The ankle height gives these boots a somewhat heavier feel, but the sleek vamp and toe  give them a sleek and sophisticated look.  The price point is right on for a boot of this quality.
2. Loake 1880 Chatsworth Suede Chelsea Boots:  Chelsea boots have become my post-grad way to maintain some level of cool.  I lived in boots back in the day, and while something like #10 isn’t appropriate for an office environment, these give me a a chance to keep it real.  And suede…bring it.
3. Alden Unlined Chukka Boots:  I have a couple pairs of these and wear them to death.  They look great with jeans and khakis, and are much more dressy than a normal desert boot.  Treat these like dress shoes (cedar shoe trees) and they will do you right.
4. Frye Weston Chelsea Boots:  I’ve started wearing black dress shoes more and more.  I’ve got a nice pair of cap toes and some Barker Black Wolfes that I love, but want to add some black Chelsea boots to the arsenal.  Not only are they great around the office, but they work with a tuxedo when it’s too wet for velvet loafers.
5. Blundstone 561 Work Boots:  Easy-on work boots with a style all their own.  Will this be the year you add a pair of Blundstones to your rotation?  Be sure to try them on before buying – the sizing is tricky.
6. Bean Boots by LL Bean:  What is there to say about the iconic Bean Boots that hasn’t been said?  When it’s wet, this is what you need.  Period.
7. Truman Boot Company Iceberg Kudu Pull On Boots:  These look completely badass.  I love the Truman story, and want to support an American-made company.  The grey Kudu will patina extremely well.  I like these with dark jeans, an oxford, and a lambswool sweater.
8. Dubarry Kildare Boots:  The utility boots you need to own.  They are lightweight, very comfortable, and Gore-tex lined.  Great for walks with the dog, fly fishing on the bank, and sloshing through some nasty winter weather.  Need to keep your feet dry?  Here you go.
9. Tecovas Earl Boots:  While I have a pair of cowboy boots, I’m easing into ropers.  The simple fact is that I wear them more.  Quite a few of my friends have ordered the Tecovas, and all of them rave about them.  Mine will arrive in October, and needless to say, I can’t wait.
10: Red Wing 1178 Work Boots:  I just got a pair of these to replace my old work boots from college (they were also Red Wings – of the 1155 variety).  You know what you get from Red Wing: tough, and cool boots.  These fit the bill.  If these last as long as those, then I’m in for a very good value proposition.

What did I miss?



  1. HMB
    09/07/2016 / 9:39 AM

    Just ordered a pair of Tecovas last week!

  2. Landy
    09/07/2016 / 1:26 PM

    Timely post – I’ve got some desert boots which I wear with chinos and jeans but can’t pull off with dress pants. Thinking the Chelsea boots could work in this role, depending on the style

  3. Cory
    09/07/2016 / 5:08 PM

    Fall and winter are my favorite times of year because I get to wear my myriad collection of boots. It’s still 95 degrees here in the ATL, so I’ll have to wait a bit longer. After all, technically it still is summer.

  4. Sam
    09/07/2016 / 9:38 PM

    I do love living in New England during duck boot season, which is any day at all. I once worked for a Senator whose Chief of Staff wore duck boots with his suits and he wasn’t the slightest bit out of place.

  5. Grant
    09/07/2016 / 10:40 PM

    You missed Chippewa Snake boots. A must-have during Texas dove season.

  6. GWH
    09/08/2016 / 9:23 AM

    My Tecovas Earls came in yesterday. They will be getting their first action in the office tomorrow.

  7. GWH
    09/08/2016 / 9:24 AM

    My Tecovas Earls came in yesterday. They feel great so far. They’ll be getting their first action in the office tomorrow.

  8. Townes
    09/08/2016 / 1:25 PM

    ML Leddy’s

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