Herring Shoes

How do I know if my shoes fit me properly?

6 December 2023

At a glance, this seems quite obvious, but the truth is it’s actually a bit more complex than you may think. Due to the number of different last shapes, size options and styles of quality handmade footwear (let’s not forget personal preference too), you can find yourself questioning if you’ve purchased the right size.

I will go through the basics to make sure you feel confident in wearing your new shoes. I will also touch on how to give yourself the best chance of getting the correct size at the first try.

If this is your first foray into handmade dress shoes, the fit and sizing is going to be different to your more casual sneaker/trainer styles. You will want to drop down roughly one whole size in most shoes on our website and expect the fit to be a little more snug. The leather is going to mould to your feet as you wear them as opposed to being slightly oversized. This is just a guide though. Feet come in all sorts of shapes and sizes, as do shoe styles, but it’s a good place to start when trying to get the size right straight away.

The first thing you’re going to do when putting on a new pair of shoes is to see where your big toe sits. This is a good indication of whether they are the right length. You want to have around 15-30mm space between the end of your toe and the end of the shoes (more space in extremely long styles), but how much space will depend entirely on the last shape of the shoes. Some last shapes are longer in the toe than more traditional styles, but this does not mean your toes should be the same distance away from the end as they would with a more rounded style. If a shoe is a little longer in the toe, it is designed to have more space between your big toe and the end of the shoes so there would maybe be 30mm space instead of 15mm.

You ideally want the bottom of your heel to be a gripped by the back of the shoes. It’s important to not be confused between the heel and your Achilles, which is higher up. This will not be tight to the leather. If you think about it, the Achilles does not come straight up from your heels, so expect a little space here. Being able to stick a finger or two behind the heel is not an indication they are too large, but excessive movement when you are walking is an indication they are a touch too big. Some movement is ok though, so if everything else feels good, then you should be ok.

Now, we will think about the width. You want this to be snug, but not tight. You shouldn’t see your toes bulging out the sides of the leather, but it’s ok if you can just make out where your toes are sitting. As above, the leather will mould to the shape of your foot, but if they are too tight then it’s unlikely they will give enough for them to be comfortable. If you don’t feel the leather on the sides of your foot at all, then this is perhaps an indication they are a little large for you. If you feel the length is ok but there is too much width, you likely would get away with half a size down. Again, if you feel they are a bit tight but the length is ok, try half a size up or if possible the same size but in G fitting if available.

We have spoken at length about the instep in previous journals and this one is no exception. It plays a big part as to whether your shoes are a good fit or not. If your shoes are an Oxford-style lacing then you are looking for a nice V shape. You don’t want the two sides too close or touching as, with wear, they are going to move slightly closer and if there is nowhere to go, then you won’t be able to lace your shoes. So if you find that the lacing is closed nearly all the way, this means they are too large for you and a half or full size down is needed. If you find the V shape is excessive and there isn’t much lace left to tie your shoes, this means they are too small. In this instance you could try a Derby style if the rest of the shoes fit you well.

When you take a step in your shoes, keep an eye on where the flex is around the toe area. It should be around the knuckle area of your toes and not further back or on the toe at all. These would be indications the shoes are not a good fit and if you continued to wear them, the creasing would be unsightly.

A quick note about slip-on styles. They will need to be a tighter fit than laced shoes, simply because that is the only way they will stay on your feet. Pay attention to the heel and the instep. If these areas are snug to tight, then this is spot on. But you don’t want them tight around the toes and you can follow the above suggestions if they don’t feel like a good fit.

On rare occasions you will find that some styles just do not fit you well no matter the size, and this is ok. It just means perhaps trying to find a similar shoe on a different last shape is the best way forward. As with all of the above, this is something we can help you with if you get in contact.

Finally, it’s important to remember that with all of the above in mind, a lot of it does come down to how you personally like them to fit. You may prefer space in your shoes in case you wear thicker socks, or you may like a tighter fit. What matters is that you are happy and comfortable with your new shoes.


  • Reply Andrew Cross 27 December 2023 at 9:33 am

    A very informative article, thank you

    • Reply Chris Clark 22 January 2024 at 4:05 pm

      Thank you Andrew, much appreciated. HS

  • Reply Octavio Jorge 14 January 2024 at 12:19 pm

    Hello, It would be good if you go into more detail regarding the different widths of the brands you carry as you stated in the article it is quite complicated to remote purchase.

    • Reply Chris Clark 22 January 2024 at 4:04 pm

      Hello, it is not complicated to remote purchase (we are an online business so all sales are remote). Sadly there are no set widths specific to brands, exact fitting is based on the specific last shape of the style and as there are hundreds of last shapes with their own characteristics throughout the brands we sell, it would be impossible to write about them all in detail, sadly. Generally you should order your usual dress shoe size as most last shapes will fit you well, you can use this blog to help you work out if they are a good fitting or not once received and if they’re not a good fit you can easily change them for a new size. We are also at hand to offer any advice should you need. HS

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