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How Should Chelsea Boots Fit?

Chelsea boots are a wardrobe staple and are the perfect balance between style and a rugged pair of shoes. They’re super versatile and can be dressed up or down but one question that a lot of people keep asking me is how should Chelsea boots fit?

Chelsea boots should have a snug fit but they shouldn’t make you feel as though your feet are restricted or constricted.

Of course, there’s tons more to learn about the fit of Chelsea boots and how to choose the right fit for your feet. I’ll cover all your most burning questions in this guide.

Styling Chelsea Boots

What Are Chelsea Boots?

The Chelsea boot used to be called the paddock boot and they weren’t all that popular until the Fab Four brought them into the spotlight in the 1960s. Once people saw John, Paul, George and Ringo donning these laceless boots, they took the world by storm.

Chelsea boots are also popular because they are so easy to put on. Without complex lacing systems, it’s merely a case of slipping them on and heading out the door.

They also come in a range of colors and can be worn by guys and girls of all ages and for any occasion. It’s perfectly easy to dress your Chelsea boots up for a more formal occasion or you could wear them with jeans and a sweater for a casual look.

What’s The Right Fit For A Chelsea Boot?

When wearing Chelsea boots, the fit is probably going to be a little different to something like your Dr M’s or your Timberland boots. That’s because they’re a totally different style and are intended for a smarter and sleeker look.

This means that your Chelsea boots should have a fitted feel but not be so snug that they feel overly tight on your feet. Your feet should feel supported but free without a feeling of being constricted.

One of the best pieces of advice I ever heard regarding the fit of Chelsea boots was to try them on while you are wearing thick socks. While you may normally be able to choose your regular size, you may find that new Chelsea boots are difficult to get on because the leather needs to loosen up.

On the sides of a pair of Chelsea boots, there are elasticated panels and you should feel that these fit nicely against the ankle. The reason for this is that the boots have no sort of fastening so if they slide around, there’s nothing you can do about it. But one thing I would recommend is to think about the style of Chelsea boots. Some are slightly wider which allows you to tuck your pant legs in whereas others are more fitted and designed for trousers to be worn over the top.

On the flip side, you may find that your Chelsea boots are a little tight, in which case, you can use a boot stretcher. This doesn’t mean that you can just settle for a pair of boots that are too small; for this, you will need to size up.

How should chelsea boots fit?

Are Chelsea Boots True To Size?

One of the things that can make buying shoes such hard work is that some styles aren’t always true to size. For example, when I buy sneakers, I always have to size down, no matter what the brand. Sometimes, I can even get away with fitting into a kid’s pair!

But that’s not the case with Chelsea boots. This type of shoe is almost always true to size so you can go into a store and choose your normal size with confidence. That said, I’d always recommend trying on shoes before you buy, just to be sure.

How To Get The Right Fit With Chelsea Boots

Earlier, I talked about how you should initially try on Chelsea boots wearing a thicker pair of socks. But I have some other great tips on getting the right fit with these stylish boots.


When you are purchasing a new pair of Chelsea boots, it’s really important to ensure that the shape is right for your feet. You can do this by looking at the instep which should be in line with the middle of the boot.

Chelsea boots are almost always made from leather or some other similar synthetic material. One of the problems with leather is that it can take some time to stretch so be sure to wear the shoes in gradually otherwise you may end up with blisters and sore spots.


The last thing you want with a pair of Chelsea boots are constricted toes. When trying on your new boots in the store, check that there is plenty of room in the toe box. You should be able to wriggle your toes around easily and there should ideally be around ½ inch between the tip of your big toe and the boot material.

Of course, comfort is a personal thing and some people may find this gap too much. For this reason, it’s important to go with what feels good for you which is why I always suggest trying on several boots in various sizes to make sure you have the perfect fit.


Another important consideration when buying Chelsea boots is that they fit properly around the heel. Let me tell you that there is nothing worse than shoes that don’t fit your heels properly. When they’re too big, they’ll move around and rub your heels whereas boots that are too small will put friction on the skin of the heels and this is painful too.

When you wear your Chelsea boots, you should feel just a little bit of resistance in the heel. Initially, you may feel some discomfort because the leather is still stretching out but this shouldn’t be to the point where it becomes painful or prevents you from wearing the boots.

Tips For Buying Chelsea Boots In The Right Size

  • For people that use orthotics or insoles, be sure to take these with you when trying on Chelsea boots in store. Using these may mean that you need to size up in order to comfortably fit the insoles into the boot.
  • When you go to the store to try on Chelsea boots, make sure that you wear socks that you’d normally wear. There’s no point in wearing a thin pair of dress socks if your day to day footwear includes thick hiking socks.
  • Once you have the boots on your feet, spend a bit of time in them. Walk around the store and pay attention to how the boots feel. Do they chafe? Do they slip around or move on your feet? Do they feel tight? Asking yourself these questions will help to ensure you choose the right boots.
  • Go to the store with an open mind. I know you might have your heart set on a specific pair of boots but it’s always best to try on different brands in different sizes so you can really get an idea of what feels good.

Merrick’s Art Video On Chelsea Boots

A “Getting Dressed with Merrick” video on Chelsea Boots – this is a great, insightful, short video.

Another great video from Merrick’s Art!

Final Thoughts

If you’re into fashion then you’ve probably got at least one pair of Chelsea boots in your wardrobe but a lot of people aren’t sure how to wear them because of the fit. These boots should feel snug but not to the point that they restrict the natural movement of your feet.

Usually, they’ll have a comfortable fit around the ankle but there are some Chelsea boots that leave a bit of extra room here for you to tuck your trousers into.

Jenna Reign
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