How Should Chelsea Boots Fit?

With the weather looking like it won’t be improving any time soon, it’s not quite time to put those boots away just yet. Usually reserved for autumn and winter fashion, Chelsea boots are actually the best style of boots for all year round. Bulky and lace-up boots feel too heavy for summer when the rain is drizzling down. Chelsea boots take less than a minute to pop on and feel secure on your feet without being cumbersome. 

At Rydale, we are big fans of our Chelsea boots. They’re versatile enough to wear to the office, when out running errands or to casual nights out. This is our ultimate guide to Chelsea boots: how they should fit, when and where to wear them and our all-seasons guide to them.

Getting the perfect fit for your Chelsea boots

Chelsea boots should fit a little differently to other styles of boots. These are meant to look sleek and smart, rather than practical and sturdy. Whilst they are extremely versatile, there are still some considerations to make before purchasing a pair. We’ve rounded up some of our top tips on how to get the perfect fit for your Chelsea boots.

They should be fitted but not snug. We recommend trying a pair on whilst wearing a thicker pair of socks. You will more than likely get away with your regular size but the leather boots can be tough initially to get on. 
The elasticated panels should fit against your ankles. With this style of boot, they need to be fitted against your foot and ankle because there is no zip or buckle to tighten them with. 
Use a boot stretcher if they’re too tight. Obviously, if they’re far too small, you need to size up. If they’re just tough because they’re new, using a boot stretcher or wearing them in will stretch them in a little. Always use the tag at the back of the boot to help you put them on.
Tuck in your jeans to see how they look. Many styles have a wider top to enable you to tuck in any trousers whereas some are a more fitted style. Some trouser styles look better untucked though, such as smart work trousers. 

Where to wear Chelsea boots – ladies

As we’ve said above, you can wear your Chelsea boots for more occasions than you might think. Some people seem to think they’re just for smart-casual occasions and the office, some people think they’re purely for casual occasions and have no idea how to smarten them up! Below are some instances where you might be going where you can most definitely wear a pair of Chelsea boots!

The office – Here it is best to stick to the classics, leather and patent styles, as they look the most smart when dressed up. Whilst coloured boots can work for the office, a traditional brown or black helps to smarten up any look. Whether you wear smart trousers, a full suit or dark wash jeans, a pair of dark brown leather Chelsea boots will keep the look classic and chic.

Black leather can be harder to style so a softer brown shade helps to soften the look whilst still keeping it smart. Adding a country checked shirt, such as our Laura Tweed in Navy, adds a pop of colour to an otherwise neutral outfit. 

The outdoors – Easy to clean shoes are a must when outside so leather or patent again should be your go-to. However, if it’s rougher terrain than usual, a pair of nubuck Chelsea boots might be more suitable. With a grippy rubber sole, this style is designed for working and walking outdoors. Pair with a waterproof jacket or coat in a neutral or bright colour and you’re all set for the great outdoors!

Everyday errands – A practical pair of boots that are also fashionable can be a bit of a struggle. This is where a pair of beautiful suede Chelsea boots can come into play. A pair of tan suede Chelsea boots are some of the most versatile footwear you will find out there and as long as you look after them (by cleaning them regularly), they will last you for ages! Whether you’re doing the food shop, popping to the bank or picking the children up, these boots are super comfortable and oh so stylish. Tan shades go with just about every other colour so you’ll never have to think about whether they’ll go with your outfit of the day. Keep them by the front door so you can just slip them on and get on with your day!

Days out – With anything from a day shopping to a theme park and everything in between, the odds are you’ll be on your feet for most of the day. You might even go for lunch out somewhere so you might need practical but dressy boots on. Instead of regular Chelsea boots, why not give a brogue style pair a go? In traditional tan and navy hues, they will dress up almost any outfit (apart from loungewear) without looking too dressy. Wear with a wax jacket for the ultimate ladylike smart-casual look. 

Evenings out – For casual nights out to the pub or a night at the theatre or a concert, you will want to be dressy but comfortable, especially if you’ll be eating or sitting down for a couple of hours! A pair of suede heeled Chelsea boots are the perfect blend of dressing up but not too much. They’re versatile enough to wear with jeans and slim-leg trousers but also look great with dark tights and a skirt or dress. 

Where to wear Chelsea boots – gentlemen

Chelsea boots for gentlemen are the perfect alternative to formal footwear, such as brogues. They’re still smart but can be more versatile; you can get away with wearing them to work and then keeping them on to nip to the pub for after-work drinks! They can be worn casually too so keep reading for some useful outfit tips!

The office – When it comes to office wear, keep it as classic as possible with a pair of brown leather Chelsea boots. Brown is a warmer tone to match with others compared to black and it feels less formal too. Brown compliments blue, green and brown tones so is incredibly versatile. It also goes really well with tweed, whether that’s a full three-piece suit or just the trousers. 

The outdoors – Sturdy, grippy soles are a must when outdoors, whether you’re working or walking. Our Carlton style is a less formal version of the Chelsea boot, meaning it’s perfect for any outdoor activities. They still look smart when cleaned up so you could most definitely wear them all the time!

Everyday errands – Suede is a great option for everyday errands, especially in navy. Navy suede Chelsea boots and dark wash, straight leg jeans are the perfect pair as a foundation for an outfit. You can then add as much or as little colour as you want on top. Add a polo shirt or a half-zip jumper if it’s particularly cold!

Days out – You’ll probably need to be prepared for all kinds of weather so leather Chelsea boots are a must here. For a day out, we love to add a pair of tan boots because they’re a bit more casual than a dark brown pair. They also go with any wash of denim and can be dressed up or down pretty easily. You’ll probably need a waterproof jacket or coat with you too, just in case!

Evenings out – A classic pair of brown leather Chelsea boots are the smartest pair to choose but we prefer a pair that look a little more worn in for nights out. Whether you’re at the pub with friends, a meal out with your partner or a family gathering, you can dress brown boots up or down as much as you want to! If you’re feeling smart, a tweed blazer is simply a must for any night-time country gentleman’s outfit!

Chelsea boots are some of the easiest types of footwear to style, whether they’re leather, patent or suede. They always come in classic colours, such as brown, tan and navy, so you also don’t have to think about colour clashing too much either! If you don’t have a pair already, just think of how many outfits you could pair with a pair of Chelsea boots and go and grab yourself a pair!

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