TSBmen x Timberland x Esquire

September 17th, 2013

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Esquire magazine was the original catalyst to my career in fashion. Had it not been for their “Best Dressed Real Man in America” contest in 2009, I likely would not have found the confidence, or credibility, to pursue style blogging as a career. Honestly, I’d probably be investment banking or just finishing law school.

Esquire has been a great partner and it’s great to be back in the October issue of the magazine!

One of my favorite outdoor heritage brands, Timberland, is releasing some new style-conscious designs this Fall. I used to live in the classic 6″ boots, which I still rock from time to time. My style is more refined now, but so is the Timberland collection. Alex and I teamed up with the brand to creative direct their new styles and Esquire campaign.

The new goods are slightly more style-forward than what Timberland has done in the past (think slim leather bombers and sharp-but-tough boots), while remaining true to the brand’s rugged “outdoor performance” roots.

I’ve been slowly breaking-in their new Men’s Earthkeepers Tenon bomber jacket, a versatile piece that is great for commuting to business meetings in NYC, and even better for a weekend getaway far outside the city.

Here’s how I styled it.


1. Office Commuter


As you may know, I collect leather jackets and they’re one of my favorite things to wear/purchase… This washed bomber is slim-fit and soft to the touch, giving it that “broken-in” feel from day one.

For the “business casual” crowd, or those who leave their suit jackets at the office, a simple “trucker style” leather is a great choice your morning commute through the Fall/Winter. Personally I rock it with the collar up, like most of my outerwear.

The best part is, once you leave the office, simply remove the tie and you have a versatile outfit for wherever the night may take you.


For this collaboration I paired the jacket with the Men’s Earthkeepers Tremont boot in oxblood, a rugged but clean plain-toe lace-up.


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  • Owen

    I just bought a medium, and these jackets fit big…you definitely want to size down if you are in between sizes or unsure.

    • http://tsbmen.com Dan Trepanier

      Agreed. Thx for sharing

  • Sam

    What size are you wearing in the tenon leather bomber. How do they fit. I want to get it but am usually between a M and L depending on brand

  • August

    the timberlands are only okay for me i much prefer redwings. The last pair didn’t seem like something you would wear. don’t sell out.

  • John B

    Happy Birthday Dan! Keep up the great work!

    Congrats on being featured on Esquire again! To be honest, after seeing the first look, I thought this jacket was a bit long, but on look three, it’s perfect!

  • Dan R

    Dan, what styling product do you use on your hair to get that nice shine ? Thanks

  • LouCaves

    The looks: nice. I don’t sport Timbs but my after-work “uniform” usually includes a pair of khaki-colored, leather & canvas boots that I love. Originally bought ‘em for casual wear but they’ve even become my boots for motorcycle riding as well.

    As for TSB’s expansion: Great job, Dan and Co! I’ve been hooked on TSB ever since I saw a yahoo video featured with you, Dan, about a year ago. My game has definitely stepped up because of TSB.

    Thanks and blessings, TSB.

  • Joe

    Glad to see the continued success and feature in Esquire. Can’t wait to see what’s in store for TSB.

    That said, I can’t get with pleated chinos. Higher waisted and a little meatier, fine, but pleats on chinos, I refuse. I liked the other looks though.

  • TK

    Huge fan of the site and love your hustle but Timberland is a favorite brand of yours?? That’s news to me seeing in a couple of years of following this site I can barely recall you using this favorite brand of yours in any looks! I may be wrong but keep it real homie!(C’mon son face)

  • Brent Kuz

    Those earth keeper moc toes are sick I love them. They come in black?

  • Harvey

    Good stuff brotha!
    I’m from southern cali, so I’m excited to see some east coast influence down here. My personal style is very classic, and my friends call me too “grown up.” Then again they’re still stuck in the skinny jeans, graphic tee, and hoodie style even in their 20′s.
    Also, if you’re looking for new places to shop, Desert Hills Premium Outlet and South Coast Plaza (super high end though) are pretty damn awesome. Plus Morongo Casino is right next to Desert Hills.
    I’m really happy that you guys are expanding, and I continually look forward to new posts, and the socal style infusion!

    P.S. I’m trying to be an investment banker dawg, don’t hate :(

    • http://tsbmen.com Dan Trepanier

      Hey Harvey,

      Thanks for the tips! We’re working on some great West coast content, still figuring out the culture and context…

      As far as the line about investment banking or law school…I didn’t mean there was anything wrong with that! Both very respectable, lucrative, careers :)

      All the best,

      • Harvey

        Anytime man. Really looking forward to new content!

  • http://undefined TimL

    Very cool Dan!
    Congrat’s to all your hard work and to this great website you created.
    Nice to see you back in print again!

  • BF

    Ha ha dan.
    Congrats buddy.
    Not a boot guy but you look solid.

    Look 2 is Indiana jones all day..

  • Alex

    Props to Dan and Esquire! That 2009 issue is when I first read about TSB and have been following this blog ever since.

  • Nick

    Absolutely awesome!

    Congrats Dan

  • Andrew Oppenheimer


    Good to see you back in the featured posts. Reminds me of past years/posts on TSB. Love what you’re doing now but your style is what drew me to the website.


  • ACE Fajardo

    The 2nd one is the “Dappered Indiana Jones”!

  • http://wideeyestightwallets.com Adam

    Congrats on the feature! Great post as well, I’m in the market for some new boots this season, so I really enjoyed this.

  • http://www.thingsaboutkyle.wordpress.com Kyle Leon Norville


  • http://thekacar.com Mustafa Kacar

    Congrats Dan on your success. You’ve been on your grind for a few years now so you deserve all the good things that are happening.

  • Carter

    Glad to see everything continues to go well for you and the team. The Esquire spread looks great! Continued success with your west coast relocation and future business endeavors.
    Be Well,

  • Tom

    Congrats! Without your advice, I’d still be stuck rockin’ square toed shoes

  • Vic

    Those are some seriously good looks Dan! Being from Sweden where boots are a necessity about 2/3rds of the year I really appreciate this rugged but stylish look.

  • http://undefined Robert

    Good stuff, congrats on your continued success. Can’t wait for the evolution of the site as well, now being on the west coast.