Boot Upgrade: The Jodhpur

October 16th, 2014

The footwear purchase that’s going to enhance your entire wardrobe this fall: the suede “Jodhpur” ankle boot.

It’s a kind of blend between a chelsea boot and a monk strap. Originally designed for horse riding, they were slang-named after the traditional equestrian pant style that was often worn along with them.

Today they’re available in all price points, from classic benchmade cobblers, to high-end designers, to fast fashion chain stores. But as usual, when you’re looking for something very specific, eBay has the widest selection.

Find a pair in a chocolate suede and you’ve found yourself a boot that will enhance virtually any look this season. Here my main man Will and I give you just a glimpse of their versatility.

    1. All Business


    You already know we love a sharp dress boot, and the shape of these is extra sexy. They’re sharp enough to wear with just about any well-cut suit, including a three-piece bespoke micro-houndstooth flannel by Ariston.


    The proportions aren’t exact here (the tie is slightly narrower than the lapels), but it’s pretty close.

    The angle of the cutaway collar blending smoothly with the gorge line of the jacket (where the lapels meets the collar) is one of those subtle details that creates an added flow and symmetry to the look.

    With a cutaway collar it’s fine to show a little of the tie noose. Some people recommend tying a fat ‘ol windsor to “fill the collar gap” but I think that just looks silly, especially on a relatively narrow tie. Stick to the four-in-hand, go around twice if you need some extra beef.


    I don’t design a lot of three-button jackets, but this English-country-feeling fabric called for it, along with leather-wrapped buttons.

    And patch pockets. On the jacket and the waistcoat. You can pack some serious cargo in this suit.


    2. Rockin’ Weekend


    The ankle strap also gives the Jodhpur boot a polished rocker vibe, which is absolutely perfect for a weekend night out.

    Just avoid the rain, and too many drunkards stepping on that suede.


    The suede o-ring belt is a perfect match, and the cream/brown striped crewneck ties together the white jeans and the two different brown tones.

    With Will’s skin tone & hair color, the color palette here makes everything fluid. More on that later…


    Had your pants and jeans cropped this summer for that no-break look, but feel a little silly showing so much ankle in the Fall/Winter?

    Problem solved. Show off some mean ankle boots instead.


    • Vintage Ralph Lauren Sunglasses from Kings of Past
    • Tan leather motorcycle jacket by Boda Skins
    • Linen crewneck pullover by Hugo Boss
    • White denim jeans by Helmut Lang
    • Brown suede Ring belt by Brooks Brothers
    • Suede ankle boots by Jack Erwin

    3. Hitting the Road


    These Jodhpur’s are not only super versatile (you could basically wear them with any outfit), they’re also very comfortable.

    When traveling, pack your lighter second pair of shoes (maybe loafers, or sneakers) and wear these to save space in your carry-on, but give you plenty to work with on your trip.


    Here’s an easy recipe for a great casual look for the man on the move: felt hat, trim henley, beefy cardigan, tailored flannel jeans, dress boots.


    Flannel jeans: the perfect “in-between” pant. Wear them as jeans, as trousers, or anywhere in between.


    • Brown Felt hat by Stetson
    • Navy cardigan by Steven Alan
    • White henley by J. Crew
    • Brown American Bison Belt by Trafalgar
    • Grey flannel Jeans by Zegna
    • Suede ankle boots by Jack Erwin
    • Brown leather tote by Frank Clegg x Dan Trepanier
    • Watch by Montblanc Timewalker

    Thanks, as always, for reading.

    Yours in style,

    Dan Trepanier

    Shop Custom Menswear Made in America


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    • Alex


    • Benjamin Armstrong Howe

      Why are only some of the articles displayed linked to the brand shops? Are some entirely unavailable?

    • Ruby shaikh


    • Rory

      Where did you get the Zegna flannel jeans? I can’t find them in their online store. Thanks!

    • Jhwendland

      Serendipitous timing. Just saw a picture of Sidney Poitier rocking some of these the other day but didn’t know what they were called.

    • Eric

      3 buttons?!? Say it ain’t so!

      • Jeanscuffed

        “More on that later” *in Dan’s voice* lol

    • BougieHippie

      This shoe or the Saint Laurent ankle strap boot is the only thing I’m excited about buying this season!

    • Arden

      Those boots are killer, great job yet again guys. In particular, I absolutely love the second look. That jacket is a real thing of beauty.

      Also, apropos of nothing, Will is a ridiculously handsome dude.

    • cam

      While the jodhpurs are nice, I think the boot of the season is the chelsea (thanks in large part to Mr. West). Those flannel jeans are

      • TO

        Not much difference aesthetically. Cut off the ankle strap and the jodpur is a chelsea.
        I know you know this sorta this killer cam, but just to point it out :)

    • Sean

      Nicely done! Especially the 2 casual looks. That leather jacket is on-point and I love the way the different browns play off the cream shirt and pants. Never thought about using a cardigan with a henley, great for this in-between weather we have right now.

    • SoFloStyle

      Love these boots Dan! They’re not available on Jack Erwin’s site though. Any insight on this?

      •!/wonkinakilt Joe Colucci

        They disappeared from JE a while back. Seems like they just ran out of that style and haven’t restocked – dunno if they’re just out of stock/on hiatus, or permanently discontinued.

    • VitaminCM

      I like a nice boot, just not very into these. They kinda have a 90’s lady-boot feel to them.
      Still interesting to see the different ways to mix them up.

      • John

        90’s lady boot feel. Thank you for articulating my thoughts.

        • Daniel

          I can see that too. Maybe it’s due to (what appear to be) small feet, or the streamlined cut of the boot?

      • Jefe009

        Yup, this. ^^^^^^^

        Not very manly. Chelseas, Brogues, no problem. But these are a little too ‘lady boot’ for my taste. Also, remember who popularized these. British colonizers playing polo while their Indian subjects worked the fields. Not a good look, bruh.

    • Andrew


      Unrelated to post – Do you ever get sick of clothes? Been into menswear for awhile and the more time passes in my life and the closer I get to my ideal wardrobe, the less I feel clothes have any earnest purpose in life. I was just wondering if you ever share the disdain for the materialistic. As somebody who does it for a living, it must wear you out sometimes.

      Menswear is a bittersweet hobby. It’s nice to be knowledgeable of all things clothing – but, when it comes to what matters in a life well lived, clothes hold no value.

      • Owen

        The same can be said for any hobby. There are people dying from incurable diseases, wars, terrorism etc all over the world, so in the grand scheme of things, of course hobbies hold no value.

        As for a life well lived, well I believe (and I’m sure Dan shares this point of view) that clothes can create opportunities to allow us to fulfill our goals and lead more successful lives. It’s a fact of living in a world where outward appearances do actually matter, and that can either be embraced or seen as a failing of mankind.

        • ChrisD

          Music and other forms of art are a hobby for some, do they hold no value in the face of international plight? I think many would disagree..

          Wearing nice clothes and engineering an outward appearance to achieve success in other arenas is a tactical move. And this blog supports that intention for that type of reader.

          There are other types of readers, with other intentions, perhaps appreciating the clothes themselves.

          “..that can either be embraced or seen as a failing of mankind.”

          That is a bit harsh. I would warn against judging others by the outfit they’re wearing. You can miss out on some truly high-quality humans in your life.

          • Owen

            I’ve been playing the drums on and off as a hobby for the last 15 years. I’m not sure how that benefits anybody other than myself? If what you do as a hobby has any international recognition, then it probably can’t be considered as a hobby any more.

            I agree about not judging people by their outward appearance, and I don’t, if I am given the opportunity to meet those people. But we can’t get to know everyone we see, and sometimes a first appearance can open doors. Maybe through one of those doors are some ‘truly high quality humans’ that you wouldn’t have met otherwise.

      • AFH

        I called peak #menswear a few weeks ago, and I think it’s good to take a pause to reflect. It’s interesting that people travel around the world with a backpack and….live their lives. And there is some truth that the things you own can end up owning you.

        But I still like most of my clothes. I’m not really buying any more at the moment though.

      • ChrisD

        In addition to picking up practical tips here and there, I read this blog as an indulgence in a hobby. It’s like walking through a vintage guitar store and touching a real 60’s Fender. I’m not a professional musician.
        Hobbies are something I consciously make time for in my life because I’ve noticed they bring me happiness. That’s about as complex as it gets.

        If you’re chasing something that has left you feeling bittersweet, I suggest a little introspection.

        • Tom

          Life leaves most bittersweet. That’s why religions are so prevalent. You live a little and then you die like everything else of earth. Bittersweet is the nature of life.

        • Tom

          Spending any amount of time on materialism is bittersweet unless you’re not thinking critically.

      • John

        Substance and form. An argument that has existed phenomenologically since the beginning of thought. I totally hear what you’re saying. This blog, however, despite being absolutely wonderful in the capacities that it chooses to be, is not really set up to contemplate things of that nature.

      • mligon

        The law of diminishing returns.

      • PdxTony

        coming in late but what you are talking about is part of a normal growing up phase. I think of men’s wear as a hobby, a way of expressing my own emotions. The nice part about it is unlike a family , child, work etc you can leave a hobby alone or make a mistake and the world will not come to an end. Like a sport fanatic you can have heated discussions about what is right or wrong or the best and deep down we know that it wont effect waking up the next day.
        In the end IMO ask if spending 300 on a pair of shoes (or more, its all relative) or a pair of court side seats is more beneficial in the long run. Anyone else ever had the experience of making someone smile because you took a little extra time on how you dress?