Skip to content
There are no items in your cart
Home / How Should A Chukka Boot Fit?

How Should a CHukka Boot Fit?

If you’ve never purchased a chukka boot before, it may be difficult to tell if the boot fits correctly. Chukka boots fit differently from that of a typical shoe. They may feel loose on your foot even when the fit is spot on.

Unsure if your new chukka boots fit as they should? Try them on and examine the fit in these four areas.



When trying on chukka boots, the fit of the flex point and heel are the most important.


Flex point


Dark Blue Chukka Boot


The flex point is incredibly important when finding a chukka boot that fits correctly. To find the flex point of the boot, feel for where the shoe bends when you take a step. Many leather chukka boots will have a stiffer flex point than that of a typical leather shoe, but the sole should still have some amount of give while walking.

Your natural flex point is just below the toes and above the ball of the foot. Your chukka boot should fit so that its flex point aligns with that point on your foot. This will allow the boot to flex with you with each step.

If the chukka boot does not bend with your feet, it could cause problems later for both your foot and the boot. You will probably begin to feel pain when wearing the shoes, as the shoe is preventing you from bending in a way that is comfortable. The boot may also crease and twist, causing damage to the leather.

Determine if the flex point is positioned correctly by slowly walking in the shoe, feeling where the shoe bends as you walk. You can get an idea of the fit at a glance by seeing if width of the shoe aligns with your foot. The widest part of the shoe should line up with your foot’s widest point.



The heel of your chukka boot should be snug with only a small amount of heel slip. While heel slip in typical dress shoes is seen as a sign of a poor fit, some heel slippage when wearing chukka boots should be expected. However, the heel slippage should be minimal and not distracting. Chukka boots that have no heel slip could be too stiff and become uncomfortable over time.

A small amount of heel slip should fix itself within a few months once the chukka boot is broken in. If the heel slippage is uncomfortable when walking, then the fit is probably off.



You can expect more room in the toebox of a chukka boot than that of a typical shoe. A half-inch to an inch of additional room after the toes of a chukka boot is considered normal.

Never size down in order to reduce the amount of toe room in a chukka boot. If the flex point of the boot aligns with your foot, that is much more important to the fit than additional room in the toe.

However, too little toe room can be a problem, as the shoe could rub against your toes and cause pain. Size up if this is the case, though make sure the flex point continues to align with your feet after increasing the size.


Shoe Width

The width of a chukka boot should fit comfortably against your foot. While boots will stretch slightly as they are worn in, stretch is usually minimal. Don’t buy a chukka boot expecting it to stretch. Choose the correct size out of the box and adjust if any stretch occurs later.


Tips For Trying on Chukka Boots


Moral Code Dress Shoes


Keep in mind the following when trying on your chukka boots for the first time to help accurately determine their fit.


Start with your Normal Shoe Size

Your boot size is usually similar to that of your shoe size, so begin there. If you typically purchase shoes in a half size that is not available for the chukka boots you are trying on, size up. If your foot is narrow, you may find that sizing down is more comfortable.


Wear The Right Socks

Think about what types of socks you would typically wear with your new boots. Chukka boots are often worn with thick socks. If you intend to wear your chukka boots with thick socks, make sure that you have similar socks on when testing the fit, so that you know they will fit comfortably. A thick sock could add a half size to your feet.


Try On Your Chukka Boots at Different Times

Your chukka boots will fit differently depending on the time of the day you are wearing them. Typically, feet will swell slightly at the end of the day. Try them on in the evenings, as well as the mornings, to ensure that they fit comfortably throughout the day.


Once you’ve found your fit, chukka boots can be a great addition to any man’s wardrobe. Looking for ways to wear them to the office? Read our recommendations for pairing dress boots with suits.  

Leave a Comment