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.

  • Brown micro-houndstooth flannel suit ·
  • Navy ducks tie by Friday Tieday ·
  • Suede ankle boots by Jack Erwin ·
  • Brown leather briefcase by Maxwell Scott
  • · Blue cutaway collar shirt by Twillory

Sky Blue Broadcloth Shirt

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

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