How should Chelsea Boots Fit- Ultimate Boot Sizing Guide

chelsea bootsChelsea boots are classic ankle boots with elastic side panels that are designed for men and women. First introduced in 1851, Chelsea boots became fashionable and trendy between the 1960s and 70s. Because of their significantly unique construction, many of us get confused about how should Chelsea boots fit. This is why we did some research to help you buy the right size for yourself.

How should Chelsea boots fit?

Boots Materials:

When looking at a Chelsea boot first thing to check is the materials of the boots. If you’re going to buy the suede ones, remember that they don’t loosen up after a few wear. On the other hand, leather Chelsea boots are going to free up at least 1 or 2 cm after you wear them several times.

Purchase the correct size:

Generally, Chelsea shoes are true to size, but because of various types of toe box, design, or shape, it’s normal to doubt about your usual size. So first try out your usual shoe size and you’ll see there’s no need to go for a smaller or bigger size. Just a reminder, when you try out the Chelsea shoes, trial them with socks to find the best size for your feet.

Know your Ankle Circumference:

Before you put the boot on, you can tell the shoe store assistant your ankle circumference. They can help you narrow down the style or brand, and size. Don’t forget to check the gap between your ankle and the boot entrance. The elastic side panel ensures easy put-on and once your feet are inside the boots, there should be no gap and a close fit.


Make sure you know if you have wide feet or not. If you can fit into regular shoes, you can go for a pointed toe style. If you have wide feet, don’t worry, just go for the rounded toe Chelsea boots. The rounded ones have plenty of space to fit the wide feet.

Stretch the Boots:

As Chelsea boots are close-fitting, make sure you stretch your boots before wearing them. You can stretch them up with a boots stretcher as well. This helps to break the boots before you wear them.

Follow these steps thoroughly to find the best fit every time you buy a pair of Chelsea boots.

Should Chelsea boots fit tight or loose?

Chelsea boots are supposed to the most close-fitting boots. When you’re buying a new pair of Chelsea boots, make sure they snug or hug around your feet properly. If they feel too tight or too loose, do not buy that size or style.

When you’re just entering your feet inside the boots, make sure there is some sort of resistance. If your shoes just slide right in, that is not a good sign. Ankles need to be your focus point, when you are putting the Chelsea boots on, check whether they fit nicely to your ankle, and of course not too tightly which might cut off your blood circulation. Also, if you struggle to get your feet inside then that pair isn’t right for you either.

If you are confused even after putting the shoes on, just follow the step by step guideline mentioned above.

When should You wear Chelsea boots?

The best thing about Chelsea boots is they are unisex. Both men and women can slay their look with a pair of these stunning boots. For example:

Men can wear Chelsea boots with Skinny/Narrow cut jeans, Boot cut jeans, Fitted classic suits.

Women can wear Chelsea boots with a Skater skirt and top/blouse, a Shift dress, and stocking, Fitted trousers/jeans, Suits. You can find the dress boots here.

Chelsea boots are great for their versatility. As you can see, they are great for both casual and formal occasions. Here are some of the places where people with Chelsea boots are seen very often.

  1. Slight cold to warm weather: Ideal for fall when the weather isn’t too cold or too warm. As they’re ankle length you’re getting good air ventilation.
  2. Evening outs/dates: For a fun evening/night out, put on one of these boots, and enjoy the time of your lives without worrying about your feet.
  3. Workplace: Chelsea boots are amazing for the workplace. You can pair them with suits or any formal attire and slay the day.
  4. Cozy walks: You feel like going for a like walk? Just put on one of these bad boys and enjoy the cozy walk.
  5. Festivals: Whether it is a music fest, art exhibition, 4th of July, or beer fest, you can wear Chelsea boots in almost all of them and look stylish.


Besides the boots’ sleek design and super versatility, they’re also great for your health. The heels aren’t too high which makes the boots comfortable to walk. The fit is also on point to give you an all-day-long comfort. So with our guidelines, find the best fitted Chelsea boots for yourself and enjoy the look. Good luck!

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