1 Piece/3 Ways: Leather Espadrilles

July 16th, 2013

Remember our friend Gagan Singh (as featured here and here)?

He recently started producing the perfect summer shoe: leather espadrilles.

These versatile slip-ons are handmade in India, available in black (brown coming soon), and only run $150 a pop.

Here’s three of the hundreds of ways you can style them for summer.

    1. Leisure Suit


    If you haven’t noticed already, I like to wear suits. Even if the situation doesn’t necessarily call for one. The simplicity and tradition of a suit is what appeals to me. I reach in the closet, grab a summer suit (like this olive cotton number), a white shirt, and a couple simple accessories and I can be the “well dressed guy” wherever I go for the day. It’s a simple recipe, really.

    Once you’ve done the work of shopping for the right items and having them properly tailored, being “well dressed” becomes straighforward and a matter of routine.

    The leather espadrilles are perfect for dressing down a lightweight suit; they look like loafers but feel like sneakers.


    This particular suit was an original sample from the DT x MAB collection I designed a couple years back. The fabric has a little stretch it in (3% elastane, if I remember correctly) which makes it much more comfortable (especially for you guys wearing ’em extra-slim)…although, like any elastic, the question is how long will the “bounce back” last. I’ve been pretty rough on it, and it’s holding up well… So far so good.

    My friend Angel Ramos, aka ANGEL BESPOKE (as featured here and here), recently made me this shirt. The guy, a style icon in his own right and fellow winner of Esquire’s “best dressed”, is known for his very strong collars. This one stands at attention and really creates a powerful, commanding look. As he admits, it can take a little getting used to, but after a few wears you can’t go back to wearing those soft whimpy collars.


    2. Business Casual


    If I have to look buttoned-up on those hot & humid days, I usually swap out the blazer for a waistcoat. Preferably a linen one.

    This brown third-piece, for example, keeps my look sharp and neat without the heat and restriction of a jacket.


    When it’s getting nasty out, it’s okay to unfasten a few buttons.

    Typically I leave two shirt buttons open, but in this weather I’ll often dip to three.


    Again, the leather espadrilles are a perfect “in between” dressy/casual compliment.


    3. Damn It’s Hot!


    I’m not much of a shorts guy but NYC has been extra hot-and-sticky lately. That doesn’t mean you need a tank top and flip-flops, though.

    Camp shirts are a favorite of mine for this kind of weather. They’re super lightweight and have an open neckline that looks natural with a few buttons undone (not to mention the chest pockets are great for storing shades).


    When it comes to inseam of shorts, everybody has a different preference. I feel most comfortable with a hem that hits a couple inches above the kneecap. If you have the legs (and balls) for the shorty shorts, by all means, go for it.

    Leather espadrilles are also a great alternative to sandals, for those who aren’t fully comfortable with the concept of open-toes.


    • Gold Plated hand-engraved shades by Matsuda
    • Khaki camp shirt by Brooks Brothers Black Fleece
    • Olive chino shorts by Bonobos
    • Leather espadrilles by Singh and Son
    • Brown leather duffle by Frank Clegg Leatherworks

    Thanks, as always, for reading.

    Yours in style,

    Articles of Style


    Photography by Alex Crawford

    • Daniel Moretz


      I was referring to the shirt on page 2. I didn’t see the earlier comment referring to page 1. My current bespoke clothier is with Astor & Black. Recently, I’ve been working with fabrics from KT what are your feelings on KT vs Ariston? Just curious to hear you opinion.


    • Daniel Moretz


      Great article! Do you happen to know the fabric ID of the shirt or was this something you purchased a long time ago? I really like that fabric.


    • Brandon K


      What a great look. You mentioned the shirt from Angel Bespoke, curious, what type of fabric is the shirt made out of (i.e. twill, egyptian cotton)?

      • http://tsbmen.com Dan Trepanier

        Canclini poplin I believe.

    • Dom

      Dan, look three brought back a memory from a long time ago. It’s all a cycle!


    • TO

      Love the DT x MAB olive suit cameo!

      Was going to ask at first if you were using the wurkin stiffs you recommended a while back, amazing that that is just the regular collar. Those espadrilles are sweet, good on Gagan.

      • Gagan

        Thanks TO! Appreciate the kind words.

    • In Seoul


      Espadrilles should have roped or fabric soles, or at least shaped to look like them, right? What you have is a fine, hand made lightweight leather slipper/loafer.

      • Brent Kuz

        100% my thoughts.

      • http://tsbmen.com Dan Trepanier

        Not necessarily, but you’re right…the mini-heeled leather sole makes them a sort of cross between an espadrille and a slipper.

        Perhaps Gagan can chime in on how he officially categorizes them…


        • http://tsbmen.com Dan Trepanier


          “I wouldn’t refer to them as espadrilles as they are more of a leather slip-on.”

          I should have clarified this prior to publishing, since it impacts the expectations of price and quality.

          • Gagan

            I mentioned this below but figure I might as well post it here as well.

            I agree, Espadrilles is not the best word to describe them but let me give you a little background on how we got to where we are. When I first gave Dan a preview of the shoe, there was no accurate way of describing them without using the word espadrille. The shoes are distinct from espadrilles and more of a leather slip-on as mentioned by Dan above.

    • Noel

      The first post is excellent. Very stylish yet approachable. #Tsbmen #Fashion

    • http://undefined Steven

      Fantastic Dan!

      Noob question: In looks 1 & 2, the trousers are cuffed. Is this called something other than cuffed when it is done with dress pants? Is this just flipped and ironed or are they sewn that way?

      Thanks for everything

      • http://tsbmen.com Dan Trepanier

        Yup. Trousers are hemmed with a cuff (yes, they’re sewn to keep their shape).


        • Steven

          Thank you again!

    • Brandon

      Aaaaand I’m a size 14 and can’t get these shoes…:(

      • Gagan

        Sorry Brandon! Hopefully we can offer more sizes next year.

    • Sergio

      Look #2 is my favorite for the fact that mixing different pieces is great, especially with the waistcoat and trousers! Two I’ve tried that same color combination before and I will say plenty of compliments.

    • AARJ

      You know, as much as I like the looks, showing chest hair is a huge NO….why showing chest hair? that’s just terrible.

      • Brent Kuz

        Great looks. As for chest hair by all means if it isn’t like jungle vines growing up your neck do it. We are men, most of us have some form of chest hair. Most ladies I know have no gripes about the average chest hair and most I know detest men that shave their chest. It is 100 degrees by all means show it(casually of course).

        As for the shoes Dan you had a post wearing them earlier in June. I loved the shoe but I was waiting to see the price point and at “just $150 a pop” welp that isn’t a deal when I can get Tom’s for $50 and H&M for $11-$20. A true Espadrille just isn’t worth more than $50 max. Light weight shoe that will take a beating and just toss them later on. $150 is cole haan JM and AE (at the rack) prices. Just can not pull the trigger when my black h&m ones look quite similar but in canvas.

        • http://undefined Steven

          I agree that if they were cheaper I would jump on them ASAP. But I assume what we are paying for is also the fact that they handmade and have high quality materials… Interesting though!

        • Gagan

          Brent –

          These are handmade in India and very few around still make them in the country. Also, the shoes are 100% leather both upper and sole. I have been wearing them for two years now and they hold up great.

          The closest offering Tom’s has are these (http://www.toms.com/mens/shoes/classics/black-perforated-leather-men-s-classics/s) and it looks like it has a rubber sole and is about $50 cheaper which isn’t much. As for H&M, I don’t consider them to be a fair comparison.

          I wouldn’t refer to them as espadrilles as they are more of a leather slip-on.

          • Brent Kuz


            I might be lost on the translation of the word Espadrille. But correct me if I’m wrong these are not true espadrilles but more a alternate leather loafer (driverish) all espadrilles I have bought have had cord soles not leather. Are they glued, Goodyear welted, etc. construction very well could be a make or break here. Also my aunt made me some hand made socks when I was 10, they lasted one wash. Handmade does not equal a superior product as many factors come into play quality control is one that comes to mind. To a point I’m playing devils advocate here but id love to see these go for $75 not $150

        • http://tsbmen.com Dan Trepanier

          Gagan can weigh in here, but I wouldn’t compare these to Toms or H&M by any means – considering the quality of the leather uppers and soles, as well as the exclusivity. After your third pair of Toms I’ll likely still be wearing these…and the leather will look awesome.

          Nevertheless, we all have our own budgets and have to make decisions accordingly.


          • Gagan

            Brent –

            I agree, Espadrilles is not the best word to describe them but let me give you a little background on how we got to where we are. When I first gave Dan a preview of the shoe, there was no accurate way of describing them without using the word espadrille. The shoes are distinct from espadrilles and more of a leather slip-on as mentioned in another comment above.

            Still, the shoe itself is distinct in design and feel. I apologize if the usage of the word espadrille primed you to think in a certain way.

            Hopefully both mine and Dan’s comments can help you understand what the product I spent a lot of time building exactly represents.

            As Dan mentioned, everyone has their own budgets and the reason fashion is so versatile and diverse is that there is something available for everyone.

      • jerry feinstein

        you’re smoking crack AARJ, gotta put that pipe down brother.

        • http://undefined Steven

          I agree, chest hair FTW

      • massimo

        dude, a little chest hair is fine, a smooth hairless chest, is also fine i suppose, if that is your thing….and showing a bit of hair is perfectly acceptable as well.

      • http://tsbmen.com Dan Trepanier

        Really? What’s your beef with chest hair?

        I like showing a little, in the right context…

    • http://undefined Daniel

      The first look is one of the best this website has featured in a long, long while. To think that you were wearing something from KMart!

      • http://tsbmen.com Dan Trepanier

        I did a whole look from KMart a while back, to prove that you can be stylish on any budget :)

    • http://urbsuburbstyle.com/blog/ Paul

      All 3 great looks – love the shoes.

    • Oisik

      this damn shoe costs $150? i know they are less than $5 a pair here in India.

      • http://tsbmen.com Dan Trepanier

        Send me a pair!

    • AK

      Looking sharp as always, Dan. Those espadrilles are definitely killer. My only hesitation with ever buying espadrilles is that they seem like they might be kind of flimsy. I understand they’re meant to be a light weight shoe, but I’m slow to pull the trigger on something that may fall apart in a year of moderate use. Can you weigh in on these particular espadrilles and their sturdiness?

      • Gagan

        Hey AK,

        You’re right, they are a lightweight shoe but the construction is absolutely solid. I have been wearing a similarly constructed pair for almost two years now with no issues.

        • AK

          That’s great to hear! Thanks for the response, Gagan.

        • http://tsbmen.com Dan Trepanier

          Agreed. They feel surprisingly sturdy (granted, I’ve only had them for a few weeks).

    • http://undefined TimL

      I like all 3 looks Dan.
      The shoes look great with all of them.
      Very comfortable looking and still dressy.

      • http://tsbmen.com Dan Trepanier

        Thanks Tim

    • Shawn

      Great post Dan, you look super sharp as usual!

      • http://tsbmen.com Dan Trepanier

        Thanks player

    • Alan

      They’re pretty nice those Espadrilles, but they’re only available in black on the website right now.

      I’m rocking some $20 H&M black cord slipper/espadrilles at the moment. It’s a solid look for sure, but the brown ones are probably easier to wear.

      • Gagan

        Hey Alan,

        Brown will be out for next year!

    • Alex

      Awesome post! All of the looks are super clean and simple. What brand is the watch in the second and third look?

      • http://tsbmen.com Dan Trepanier

        Montblanc Timewalker

        • Alex


    • Calvin

      We can tell you’re not much of a shorts guy. Your legs are bright white haha. Like always great post guys!

      • scott


        Why is the color of white people’s skin okay to make fun of, when any other race would be racist?

        • jerry feinstein

          ……..probably because dark skinned people don’t get noticeably tan. relax scott, it’s all going to be okay i promise.

          • scott

            I just found myself wondering that the other day, as I hear it all the time. I am proud of my SPF100 complexion :)

      • http://tsbmen.com Dan Trepanier

        Haha word. We’re moving to LA in two weeks…so this may change