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The Drifter Leather Chelsea Boots Review

Chelsea boots are the perfect transitional boot – from Autumn to Winter, Winter to Spring, day to night. They’re also fantastically versatile, easy to dress up or down and, now, available as a barefoot option thanks to The Drifter Leather. 

Custom fit? You bet

If there’s one thing I’ve learnt since shifting to barefoot shoes, it’s that finding a good fitting pair is a very individual thing. So when a company offers customisation at no extra cost that, to me, is a very big deal.

As every shoe is handmade and all parts hand cut, The Drifter Leather are able to make pairs to fit your individual preference – whether you have high or low arches, narrow or wide heels or even differences in length or width between your feet.

Therefore, I felt it would be mad not to go for a custom made pair, and, as I was keen to have a toe box that would allow my toes more room, I made sure to spread my toes when drawing around the outline of my feet to send my measurements to The Drifter Leather team.

This does mean that my Chelsea Boots do have the look of a wider toe box than the standard style but it’s really down to personal preference – whether you want the look of a narrower fit or the space for your toes.

Another huge benefit of being able to order a custom pair is that it lessens the need for sending returns, which is one of my pet hates when having to buy shoes online. I would recommend taking the time to read The Drifter Leather’s sizing and custom fit guide before ordering a pair. I provided length and width measurements as well as provided an outline of my feet (with toes spread) and am very happy to report that my boots were a perfect fit.

EDIT 26.01.17: Thanks to Melissa and Cara (see comments below) for these two tips:

  • If you decide to send a tracing of your feet, it’s worth having someone do this for you while you’re standing upright as your position affects the shape of your foot – so if you’re bending down and twisting this might not be true to when standing upright, and it’s tricky to keep the angle of the pen straight and even as you go all the way around.
  • Another thing to consider when sending a tracing is that if your feet are shaped from years of wearing conventional shoes then this will be reflected in your outline. For example, if your toes point slightly inwards, then your tracing will lead to a pair of shoes with a tapered toe. Therefore, in some cases, it may be best to just provide your shoe size and ask for a wider toe box to allow your toes adequate space to move.

How to wear them


I have pretty much worn my Chelsea Boots every day since I got them in September. I just find them so easy to wear with my skinny jeans and a chunky knit that I’ve pretty much lived in them for the last few months.

There really are just endless ways to wear them, with tapered trousers, skinny jeans, a little black dress, thick tights, woolly ruched socks, bare legs…

One thing I would say is that as I’ve gone for a wider toe box to allow for maximum toe spread, I do feel that they would look ‘dressier’ if they were a narrower fit.

If you feel like going for something other than a plain black, then The Drifter Leather offer a range of matte and patent options with about 20 different colour choices. If I had a second pair I think I’d go for an autumnal colour – such as a chestnut brown, which I love paired with blue denim, or maybe even a light grey.

If you do have a particular colour / leather combination in mind, it’s worth getting in touch with The Drifter Leather team as they will often be able to customise this for you (in addition to the fit, size, etc.) and again, this usually won’t cost anything extra.

Design details


The Chelsea Boot soles are hand-cut from either 6mm or 4mm Vibram rubber sheets. I decided to go with the slightly thicker 6mm option, as although you don’t get quite as much ground feel, it does provide a little bit more insulation from the cold pavement.

It’s worth noting that as the rubber covers the whole sole, they are attached via piping around the edge of boot and does mean that the boots can appear slightly wider than they actually are as this piping adds about 3mm around the edge. I quite like the look of this but if you’re after more of a narrower style then just bear this in mind.

Another design choice I made was the texture of the leather upper. As mentioned above, there are wide range of colours available but you also have a choice between a matte ‘pebbled’ style, patent and suede upper.

I went for the matte as it tends to easily adapt to the shape of the foot without the appearance of looking ‘worn in’ and I can certainly vouch for this with my pair. To keep the leather in good shape I occasionally protect them with natural beeswax that means I don’t have to worry if it’s wet out.


Due to the customisation possibilities that The Drifter Leather offer, the below ratings can vary depending on your individual pair (e.g. on how wide a toe box you go for). Therefore, the ratings here are specific to my pair, but I’ve made some notes on how this could change and how you can get a more or less minimal fit depending on your preferences.


HEEL – 5/5 for a zero drop and zero arch support


SOLE – 3/5 with the 6mm rubber Vibram but likely closer to 4/5 with the 4mm option. The 6mm are still incredibly flexible but as there are several millimetres between the sole of your foot and the floor you don’t get the most ground feel. However, for an autumn/winter/spring style I feel that a bit of a thicker sole is welcome just to add a bit of warmth, especially as I do a lot of pavement pounding in these.


TOE – 5/5 with a customised toe box to allow for maximum toe spread, but this could vary a lot if you go for a narrower fit.


UPPER – 5/5 although they’re non-adjustable (e.g. don’t have laces you can tighten), the elasticated sides allow for a close fit so I don’t feel that I slip in them at all, or have any desire to grip my toes as I’m walking.


In conclusion

I have to admit that I still have a pair of 2” heeled Chelsea Boots sat in my wardrobe gathering dust (that would probably score 0/5 against all barefoot profile ratings). I just couldn’t bring myself to give them away when I transitioned to barefoot shoes as was worried I wouldn’t find a stylish barefoot alternative.

That was, until I got my hands on these.

If you’re looking for a boot that is super easy to wear, can be easily dressed up (or down) and you know isn’t going out of fashion anytime soon then I would highly recommend giving these a try.


Thanks to The Drifter Leather for providing a pair of Chelsea Boots for this review


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Comments (12)

  1. Melissa
    January 21, 2017

    IMHO I think the mistake I made with mine is tracing myself. Next time I order custom boots I’m having someone else trace me. I like my Drifter oxfords, but they are a little loose – I think a cobbler can fix them though.

    • Emma Poppenborg
      January 22, 2017

      Thanks that’s a really good tip and something I hadn’t thought of even though it took me a couple of times before I was happy with my tracing. I’m going to add it in 🙂 as agree it’s really tricky to do it correctly yourself as the way you’re standing whilst your doing it affects the shape of your foot, and it’s hard to keep the pen at the right angle!

  2. Cara
    January 23, 2017

    I got a pair of these–there are so few companies out there making barefoot boots appropriate for the office or going out! I love my Vivo lace-ups for more casual use, but they don’t look right with dressier attire.

    I did the tracing thing but I wore Correct Toes while I took my tracing. I’ve since returned the Correct Toes, but I’m still glad I left the extra room even though the toe box of the boots looks funny as a result. I’m of two minds about getting shoes based on a foot tracing. It makes sense in theory, but if you think about it, it only works if your feet are already the ideal shape. If you’re like me and your toes point slightly inwards from decades of wearing conventional shoes, the shoes based on your foot tracing will also have that tapered outline.

    And of course our feet are three-dimensional and a tracing is two-dimensional. On a pull-on boot there are no laces to adjust the fit to your foot volume. Luckily the leather (I have the pebbled leather like you) is soft and pliable so they adjust easily to your foot shape.

    I think if I had the chance to do my order over I would not provide a tracing, just give them my size and ask for a slightly roomy toe box.

    • Emma Poppenborg
      January 26, 2017

      Am totally with you on loving my Vivo lace ups but feeling they don’t cut it for ‘smarter’ occasions.
      And that is such a good point about the tracing not being ideal if your feet have been shaped by wearing conventional shoes – I hadn’t thought of that but it makes complete sense! Am going to make a note of it above now, thanks for pointing it out. (Also totally true about the whole volume too). Thanks again for your comment – and enjoy your Chelsea boots!

    • Annelien
      February 16, 2017

      @Cara you can provide 3D measurements for The Drifter Leather, it’s not just the foot tracing they use. I’ve measured my ankles, heels, calves and three points of my feet as well- according to their directions.

  3. Alex
    January 26, 2017

    Thank you for writing this review- I’ve actually been checking in regularly to the blog in the hope that you would have something like this coming up! How well do you find they are wearing? I had a pair of plain Drifter ballet shoes last summer in faded pink with just the two patches of vibram on a leather sole. They went with everything from jeans to 50s-style sun-dresses and I loved them to death, but sadly this didn’t take too long as they scuffed at the toe and heel. I’ve been sorely tempted to try for another pair from them with a sturdier sole, but would like them to last a little longer.

    • Emma Poppenborg
      January 27, 2017

      Hi Alex, my boots have worn really, really well – I’m quite impressed seeing as I’ve worn them almost everyday the last 4 months. The only place there is slight scuffing is on the leather piping that goes round the shoe at the very front, but this is the first time I’ve noticed it (I had a good look!) I’ve also worn the sole down a little bit at the very back of the heel – so might need to get these resoled after another season I imagine – but the rest of the sole looks in great condition. I actually have a pair of the ballet flats (my wedding shoes) with the two pieces of Vibram sole and can imagine that they can easy scuff if you wear them a lot. Hope this helps!

  4. Sara
    February 07, 2017

    They look amazing and are trendy too.

  5. Stine
    March 13, 2017

    I thin they look so cool on you, but in the product picture from the side, they look so “long”, and I like more of a chunky look.
    I hope this is because they are narrower than yours.
    Is it possible to see yours from the side, and maybe also from the front?
    Thank you!!

    • Emma Poppenborg
      March 13, 2017

      Sure, will snap some pics and include them in the post and let you know when they’re up 🙂 It’s always so difficult to tell from product pictures isn’t it!?

      • Stine
        March 14, 2017

        Super! Thank you Emma 🙂

        • Emma Poppenborg
          April 04, 2017

          Sorry it’s taken so long, I’ve just included a couple of pics of the upper and side view – hope that’s helpful 🙂

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