Who Wore it Best: Wodehouse Chukka Boots

November 1st, 2013

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Since working with Timberland and Esquire on their recent advertising campaign, we had the chance to learn more about the brand, review some of their new product, and develop some additional content with their creative team(s).

Of Timberland’s wide selection of boots for the season, two styles stood out to us. Firstly, since we love black chukka boots for Fall, we thought the Men’s Timberland Boot Company Wodehouse Chukka Boots would be a great pair for our next edition of “Who Wore it Best. Our final piece in the series will be airing later this month, featuring the Earthkeepers 6-Inch Moc Toe Boot.

Here Westley, Townsend and I each put our own spin on the versatile Wodehouse Chukka. Use the poll at the end of the article to vote for your favorite look and check out the rest of Timberland’s boot line-up.


1. Dan: LA Sweater Weather


It’s finally cooling off in LA, as I hoped it would.

It’s not quite time to break out the leathers, but a chunky sweater (like this 3/4 length ribbed cashmere that I stole from my beautiful girlfriend Karyn) is perfect to keep you cozy during a breezy night by the beach.

With a sweater this thick, I usually try to balance it with a pair of sleek boots that aren’t too clunky.


These black/brown chukkas are a nice addition to my boot collection which is still mostly boxed-up since our move from NYC.

They’re also a great match for that perfect pair of grey denim we’ve been telling you about.


  • Clear frame sunglasses by Vintage
  • Black cashmere shawl cardigan by Lauren
  • Grey scoop neck t-shirt by Alexander Wang
  • Light grey wash jeans by Ralph Lauren Polo
  • Wodehouse Chukka boots by Timberland
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  • LouCaves

    I liked all three and it was hard to choose.

    The boots look great with jeans (as I’ve worn mine tons-o-times), but there’s one detail that set Towni apart was that he wore chinos.

    Vote: Towni.

    Thanks, TSB.

  • TO

    Wes, I wondered if you had gotten to cutting off the collars on polos as well- I thought of it inspired by you. Was hoping it was my secret… haha

  • Ryan

    Dan, such a sick necklace. Did you pick it up off a street vendor?

  • Thomas

    Dan Nails it as always. Love the boots.

  • http://www.techmorobo.com Chris

    it was a close call but Towni’s corduroy jacket did it for me

  • Changingman

    Looks like Timbo ripped John Varvatos black chukka boot style, right down to the sole. The Varvatos ones I have are great , except the leather got ruined in the rain and slush last winter. How do you think the leather would hold up on the Timberlands?

    • Dano

      Mine have held up well with rain and what little snow we get down in NC. Never even taken them to be shined in two years.

  • Joe

    Going with Wes with an easy win on this one. That shirt is great. I’m a big fan of thrift workshirts and flannels, just seems like that’s where you find the best ones, or maybe I just appreciate the “find” more. Nice coat as well. I typically don’t like band collars, but cutting the collar of a polo to make a henley, brilliant!

  • http://undefined Dano

    I almost wore mine today, I have had mine for about two years now and I love them. For once I beat the TSB guys to the punch! Great to dress up or dress down. Found that they run on the big side by about two sizes so keep that in mind guys! They did take a little while to break in, but now they are quite comfortable!

  • http://keyboardandcompass.com/ Jeff

    As a sucker for simplicity, I had to go with Dan on this one. I find these Timb sponsored ‘Who Wore It Best’s particularly challenging, as so often my vote is defined by footwear.

  • John B

    Voted for Towni, but I’d prefer a different scarf. The checks on the scarf almost line up with the “stripes” from the sweater.

  • Daniel

    Three strong and very different looks, but Wes takes it because that shirt looks so damn soft and warm

  • http://undefined Jeanscuffed

    The chukka’s are nice. It’s good to see Timberland in an environment where it’s not the tan boots paired with camo or skinnies. This is something you don’t see often. It was between Dan and Towni and Dan edged it out with simplicity, but everyone’s fit looked great and paired well with the boots. Good stuff gents.

  • http://undefined Ishandev

    Wes for sure! Those other guys need to retire!

    • http://tsbmen.com Dan Trepanier

      Haha. Then what would your homepage be Ishan?

      PS. keep a heads up this week ;)

  • http://derbyparkour.co.uk James

    I’m struggling to find these on the UK website, anyone else have a link please? Thanks.

  • http://undefined Nate

    Ooooof tough one this week. Dan, keeping it fresh and simple, with that beautiful cardigan.

    Towni bossing things with that fairisle knit, and pattern mixing. Nice mix of textures.

    And Wes, that houndstooth shirt is a beaut.

    In terms of what I would most likely wear, it’s Dan. But I really need to get out of my comfort zone…. Towni edges this one, but strong work all round chaps.

    Love the boots btw, especially the contrast sole.