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How to Break in Leather Shoes

6-minute read

Ugh, will these stretch?! The question filling our concierge email inbox almost daily. We’re looping in with Jessica, our Retail Experience Lead, who’s helped thousands of customers find their best fit online, at our retail stores and pop-ups across Canada.

Let’s get started!  

While sizing is completely personal and almost always of differing opinion, we’re noting down a few key points about fit, stretching and the natural journey that your leather shoes will take. 

Understanding the leather’s journey.

Our shoes are all crafted from premium quality leathers, which means that they typically feel a little stiff or structured right out of the box. The amazing thing about leather being a natural, breathable and supple material is that it will soften and mould to the warmth of your foot with just a little bit of wear! Some materials like nubucks and suede will feel a little softer from the get-go, while a polished black leather and embossed prints may feel more firm—but in the end, they’ll all relax in a similar manner. 

Go for a living room stroll. 

Our concierge team always encourages wearing your shoes for 4 to 12 hours, on and off for a few days on a carpeted surface before wearing them outside to ensure you are happy with the fit. This will also allow you to get a feel of how the leather is relaxing to your foot. All regular priced items have a 30-day return policy, created around the idea that we want you to love your shoes and have time to find the right fit for your feet!

Expert Tip: 
I can say from years of experience—if the shoes are uncomfortably tight, you’re never going to get them to “stretch enough”. Not because leather isn't an amazing and forgiving material, but because it takes work and if you don't want to wear your “not yet quite comfortable” shoes out, you're never going to get there with them. 

Our most common questions: 
1. How much will my shoes relax?
2. Do they stretch half a size?


To this, we don’t have a cookie-cutter answer, because, truthfully, it depends. Your shoes aren’t likely to stretch out a full half size. Your size 8 isn’t eventually going to feel like an 8.5 because sizing up in a shoe changes both the length and the width. 

Leather will only relax where there is consistent pressure on it. Shoes typically will only stretch in width, not length. So, if they’re feeling too short, they won’t get any longer, but if they’re feeling snug (and I don’t use that term generously) in width or over the top of your foot, that’s where you will see the most relaxation. As I mentioned, shoes will only relax where there’s consistent pressure from your foot, so it also stands to reason that if you’re buying a shoe that just fits or has a bit of movement you won't see as much relaxation in it. 

Wait, what about socks?

The second most controversial topic: socks! Socks are a tricky one, as they can change the fit of your shoes more significantly than many people realize. It’s always important to consider the thickness of the socks you’ll most typically be wearing with a style of shoes when looking at sizing. Do your feet get cold often? Will you be wearing a thicker wool sock in your boots? Or are you like me and can’t stand them (unpopular opinion) and don’t need any additional room?

Trying on a shoe with and without a thin sock can also give you a rough idea of what relaxation in the shoe might feel like for you. If they’re feeling a bit snug with a sock, but great without, this can highlight for you the feeling of slight relaxation in the shoe after some wear. 

The last resort: cobblers. 

That being said, leather is a natural and porous material. It can relax quite a bit if you push it, but as I said, it takes work. If you’re finding that you aren't able to relax the leather enough on your own and you’ve already committed to the pair (or unwilling to give them up) then there’s always the last resort option and shoe lovers best friend, the cobbler.

Cobblers can professionally stretch shoes using tools more easily and effectively than we can on our own. For a reasonable price, you can save your feet the pain and have them artificially break in your shoes to just the right point! 

Expert Tip: 
If you suffer from bunions or other painful fit related issues you can always have a cobbler relax that one point in your shoes, so you don't have to do it yourself. 

While there’s no secret formula to fit, at the end of the day, just remember that shoes are there to support your feet throughout the craziest parts of your day. It's all about what comfort means to YOU! A little bit of snugness is ok, shoes will soften and mould to your foot with wear, but no amount of stretching is going to change the fit if you buy the wrong size. If you take one thing away from this, always buy what feels the most comfortable regardless of the number stamped on the bottom!

If you have any specific questions about finding the right fit, email concierge@poppybarley.com

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The Harley Heeled Sandal Ankle Size Guide

How To Measure:
The Harley Heeled Sandal: Take a tape measure and wrap it around your foot, right below your ankle bone as that is where the strap will sit (see product imagery and fit video for a visual demonstration). This measurement is based on the last adjustment point on the strap.

Size Strap length will accommodate an ankle measurement up to the size below
5 26 cm
5.5 26.5 cm
6 27 cm
6.5 27 cm
7 27.5 cm
7.5 27.5 cm
8 28 cm
8.5 28 cm
9 28 cm
9.5 28.5 cm
10 28.5 cm
10.5 29 cm
11 29 cm
11.5 30 cm
12 30 cm

The Esther Heeled Sandal Ankle Size Guide

How to Measure:
The Esther Heeled Sandal: take a tape measure and wrap it around your ankle, above the ankle bone, as that is where the strap will sit (see product imagery and fit video for a visual demonstration). This measurement is based on the last adjustment point on the strap.

Size Strap length will accommodate an ankle measurement up to the size below
5 23 cm
5.5 23 cm
6 23 cm
6.5 23 cm
7 24 cm
7.5 24 cm
8 24.5 cm
8.5 24.5 cm
9 24.5 cm
9.5 25 cm
10 25 cm
10.5 25.5 cm
11 26 cm
11.5 26 cm
12 26 cm

Belt Sizes

Natural Waist Measurement Typical Jean Size Belt Size for High‑rise Pant Belt Size for Mid‑rise Pant Infinite Belt Size
23-25" 23/24 26" 28" 1
25-26" 25 28" 30" 1
26-27" 26 30" 32" 1
27-28" 27 30" 32" 1
28-29" 28 32" 34" 2
29-30" 29 32" 34" 2
30-31" 30 34" 36" 2
31-32" 31 34" 36" 2
32-33" 32 36" 38" 3
33-34" 33 36" 38" 3
34-35" 34 38” 40" 3
36-37" 36 38" 40" 3
38-39" 38 40" 42" 4
40-41" 40 40" 42" 4
42-43" 42 44" 46" 4
43-44" 43 44" 46" 5
44-45" 44 46" - 5

Sizing Note: For the most accurate fit, measure around your body where you plan to wear the belt. Choose the closest belt size to that measurement.

Belt Diagram Accent Belt and Complement BeltThe Accent Belt, The Polished Belt and The Complement Belt size measurements start from the beginning of the leather to the middle hole.

Belt Diagram Infinite BeltThe Infinite Belt size measurements cover the entire length of the leather.

Belt Measuring Guide

Belt Measuring Guide

A - High-rise style:

If you plan to wear your belt around your natural waistline, wrap a measuring tape around the narrowest part of your midsection. Then, add 3” to determine your high-rise belt size.

B - Mid-rise style:

If you plan to wear your belt lower than your natural waistline, you will require a dierent size. If you have a particular pair of bottoms you intend to wear your belt with, wrap a measuring tape through the belt loops while in a relaxed position.

When wearing your belt in your preferred style, it should fasten in the middle hole. The belt will relax with wear allowing you to cinch it tighter, as needed.

If you plan to wear the belt in both the high and mid-rise styles, you have two options:

  1. Select your high-rise style and fasten it more loosely when worn in the mid-rise style.
  2. Select your mid-rise style and fasten it more tightly when worn in the high-rise style.