Who Wore It Best: Timberland Moc Toe Boot

November 15th, 2013

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As we mentioned in our last “Who Wore It Best” style-off, we’ve been working with Timberland and highlighting some of our favorite styles from their new collection.

For this segment Towni, Wes and I chose the Men’s Earthkeepers Rugged 6-Inch Waterproof Moc Toe Boot and we each put our own spin on them.

Use the poll at the end of the post to vote for your favorite look and don’t forget to check our Timberland’s full line-up of boots for the season.


1. Dan – LA Rocker


Photography shot with the Canon EOS 70D digital SLR camera, with Dual Pixel AF technology and built-in Wi-Fi

As you may know, I love leather jackets. A leather vest is something new to me, but it’s a great alternative until the weather cools off a little more here in LA.

There’s definitely a strong Rock & Roll vibe to the style out here – great feature on that coming soon!


The plaid wool shirt was originally purchased for the TSB Shop (which we’re completely revamping, along with our website as a whole) but it fit so well that I decided to keep it.


These boots really are built to last, and the fact that they’re fully waterproof makes them an even better investment for those looking for a boot that can trudge through anything.


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  • http://undefined Dick Lickerson

    I voted for Towni eventhough he looks like “Earl had to die”. Stay away from the black eyed peas bro (the food not the Fergie).

  • http://beeranddenim.wordpress.com/ Brian

    Looking forward to Dan’s “west coast/socal” updates. I really enjoy the articles here but definitely a different vibe out here. Especially when winter temps can still be in the 70s.

    Tsb fan in San Diego

  • http://anorexicescapades.com BougieHippie

    Danny my boy I must say though Wes is my fav when it comes to styling you brought it this time. I like that this is a bit different from your personal aesthetic and you didn’t take the expected approach to the shoe as did the other two fellas.

    Granted I like each look but it’s nice when you get some inspiration from a look. Good job guy!


  • Cam

    Not one bad word to say about any of these looks. Went with Wes just on gut reaction. In the words of Jim Carrey, “Killer boots man!”

  • Hen

    Wes got my vote. His look is well put together and the boots are just a very subtle addition.

    I never owned any shoes of this brand but visited one of their stores a while ago. I put the pair of interest back to the shelve after seeing their insole was at least partially made of cardboard. It might not be the case for these boots, still it left a flimsy impression about this brand.

    Hence, recalling that many times quality has been preached in this blog, I would love to also get some comments about the aspect of quality for the featured items in general.


  • http://www.theseals.com.au Desmond

    Some ballin’ looks there.

    I had these in brown about a year ago but ended up flipping them because I just couldn’t get them to work for me. Kudos for putting together some sharp outfits.

    The rolled up pants thing looks great here, but for me it ended up making me look out of proportion.

    Also, mine let in water sometimes (just from walking in the rain) which was a little disappointing.

    Just one man’s experience though – they certainly were tough boots, can’t fault them on that count.

  • Timbaland

    just wondering, would you rock the Timbs featured in your pics, or would you rock Red Wing Moc Toes?
    i want an honest answer

    • TK

      Exactly! In my 2-3 yrs of following the site,I’ve never seen any of the team rock Timberland! I get it that it all comes down to $ but c’mon son…

      • http://www.tsbmen.com Westley Dimagiba

        TK! Listen homie, what would you rather have? 80% of our posts sponsored by Timberland or two out of over a hundred that I’m sure you’ve enjoyed or commented on. Our growth comes with some risks we have to take and Dan along with the rest of the team will never compromise out integrity having every post sponsored by a brand. We’re about the inspiration first and foremost.

      • http://tsbmen.com Dan Trepanier

        I’ve been wearing Timberland sine the 9th grade.

        • http://www.tsbmen.com Westley Dimagiba

          beef and broccoli’s homie

  • John B

    I can’t decide. I didn’t really like the boots in tan, but in black.. They’re amazing. I’ll probably go with Dan, because I really want a biker leather jacket(with sleeves though)but I’m not sure. Great job!
    By the way, I know it’s hard but you should try to include Alex in wiwt posts too!

  • Sam

    I think Towni’s could be the winner but the floppy, weird curve hat brings it down. He would have won with a samurai bun or nice toque (beanie for Americans) here.

    • http://undefined Mr E

      I couldn’t agree more with this.

      The toque would have been the best topper for this look.

      Don’t believe me?

      Check it out: http://tinypic.com/r/30rnxjt/5

      • Towni

        Bahaha, nice one. That’s some mean blue steel.

  • Kien

    I want Towni’s buffalo plaid shacket! Is it a Pendleton or Woolrich?

  • Michael

    Voting for Towni…..I wore a buffalo plaid shirt jacket, grey crew neck sweatshirt and cap this morning coincidentally (with jeans and brown suede, red-soled brogues) so Towni and I were practically rocking’ the very same outfit . Oh and the black, brown thing…I find myself breaking this ‘rule’ more often because 1) it looks fine depending on how they’re combined, and 2) I just don’t give a shit about the rule.

  • http://wideeyestightwallets.com Adam

    Damn! Kinda pissed Wes’ coat is vintage, cuz I want one. Haha, great duds all around though, those boots are killer. I’m shopping around for some to help me deal with what I’m already predicting to be a rough Chicago winter, and these are going to make the list of possibilities for sure.

    Out of curiosity, do you guys recommend investing in a quality pair of rugged boots like these or dress boots as a first pair? I love to dress up (wow, that sounds very effeminate, ha), but like I said, I live in Chicago, so I’m not sure if I’m better off springing for something to help me deal with the elements.

    • http://www.tsbmen.com Westley Dimagiba

      it’s actually J. Crew, will change the credits later

      • http://wideeyestightwallets.com Adam

        Oh nice! Current season? I’ll definitely be taking a look!

  • cam

    I kinda figured towni would win even before I got to his pic based on his outdoorsmen background.

    Dan, what are you looking at on the ground that has captivated you ;)

    • http://wideeyestightwallets.com Adam

      His boots? Haha just playin…but maybe…

  • Stevesy

    As always, sterling looks by the TSB team. It’s been very cool watching your respective styles develop along bicoastal lines. Quick question:
    You mention rolling a pant leg to accommodate boots, and it works well with this shorter style of boot featured here. Would it be a decent way to wear taller boots (specifically 12 roper style boots that reach to around midcalf), or would it look affected? And if it doesnt work, any suggestions? Thanks!

  • AK

    That freakin vest is so badass. Dan’s got my vote on this one.

  • http://undefined Joshua

    Wes’ layering gets him my vote in this post. Although Dan looks very, “LA ish” in his pic. You can really see how LA is influencing him as of late.