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Five Common Sizing Mistakes

Posted by Wyatt Gilmore on

Five Common Sizing Mistakes

One of our priorities is to help our customers find the size best suited for them. Of course, many variables affect sizing, but the proper selection can be straightforward when avoiding these five mistakes we encounter most often.

  1. Buying snug to “break in” the boot. This is a wildly popular take on how new GYW footwear should fit. This is uncomfortable from the first wear and depending on the season and time of the day, your foot can swell creating an even more miserable experience. Tight footwear restricts blood flow and leads to poor foot health. A new shoe should feel comfortable from the outset.
  2. Focusing on the amount of room in front of the toes. Most people are used to wearing sneakers and try to compare the fit to their boots and shoes. Sneakers generally have a rounded toe shape, which allows the toes to sit closer to the front of the shoe. However, when the footwear has an almond shape, excess space in front of the toes should be expected. Prioritize having the ball of your foot in the widest part of the shoe. The 5th joint (small toe) needs to be sitting comfortably in the shoe, never pinched.
  3. Heel slip. Ah, the dreaded heel slip. It might be the most troublesome issue because customers will size down (too far) solely to avoid it. When a customer is in-between sizes, we encourage the larger of the two for one reason in particular: a tight-fitting Goodyear-welt shoe or boot will not improve with wear. It will shape to your foot with time, but the lack of overall volume will still cause discomfort on a summer day. Heel slip, however, can improve with wear. As the insole and outsole components are being flexed over time, the shoe begins to roll, working with your stride. The upper components, including the leather heel counter, also begin forming to your foot, thus improving the overall fit and minimizing that slippage.
  4. Tight instep. While this fit issue may not be as obvious on a shoe or boot that laces, it’s worth paying attention to from the onset. (If you have ever worn a loafer with a tight instep, you understand the true meaning of discomfort.) When lacing your footwear, observe the instep area and notice the distance between the eye rows or simply unpleasant pressure on the top of your foot. When it feels like you're restricting blood flow in your foot, you probably are.
  5. Sticking to your size. As with clothing, it's easy to continue buying the same size each time before realizing it's not always working. We encourage customers to evaluate their current footwear and how they actually fit today. It's all too common when someone says they wear a 10 in a particular boot, but when we ask how it fits, they will catch themselves explaining how it feels too big or small. Even when clothing sizes may not change over a period of time, areas of the foot can change, requiring a different shoe size.

To sum it all up, our simple rule of thumb is to make sure your new shoe or boot offers enough room from the very first try on. If you have specific questions on fitting, please reach out to our team by phone or email for personalized suggestions.


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6 comments


  • Looking for a boot w/rubber soles and designed to be worn in wet, slippery, icy cold weather. Your suggestions, please.

    James A Boland on

  • I agree all the points mentioned here. I would only add to remember the type of socks you wear most often when considering your size. Also, I like that GS lasts and scale seems to account correctly for the wearer’s clothing and body mass in how the shoe looks fully outfitted. Some shoes look great in store or online, but in person they get swallowed up or look unbalanced, even in tailored clothing on a moderately sized person like myself. 👍

    G.Graham on

  • Truly appreciate this most informative article on sizing and fit. I have yet to avail myself to your expert advise as I don’t even get the chance to get to wear my Diesel boots(no thanks to lockdowns) which by the way was a perfect fit thanks in part to your previous advise. Looking forward to walking in them again and taking advantage of the sale Grant Stone is putting out there. Stay safe.

    Peter Goh on

  • It should be noted the most popular last from a well regarded high-end Canadian workwear bootmaker has had a number of minor tweaks over the years.

    Beau on

  • @ Oleg – If something needs to be addressed on a last, this can be done. That being said, it’s a large undertaking (and cost) to change existing lasts. This is the main reason developing lasts takes a considerable amount of time; you want to get it as close as possible the first time around.

    @grantstone on


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