How to wear men’s Chelsea boots with style

Shiny chelsea boot on grey

Chelsea fit perfectly into formal or casual wardrobes.
Featured product: Prestige Chelsea Boot

Worn by rock stars, mods and fashion aficionados, Chelsea boots are one of the most popular boot options available. But many men are wary of boots, or simply don’t know how to wear them.

Chelsea boots can be worn casually with moleskin trousers or jeans, or with a quality dark suit as part of a snappy formal outfit. With smooth lines and unique gusset detailing, Chelseas are considered by many to be the most stylish boot out there.

Fear not, with this simple guide you’ll soon be able to wear Chelsea boots with the hip shaking swagger of Mick Jagger.

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5 top tips when buying (and wearing) Chelsea boots

Chelsea boot worn by The Beatles

Image source: Flickr
Chelsea boots: popularised by the Beatles in the 1960s, and in fashion ever since.

Chelsea boots make perfect partners for a wide range of formal and casual outfits, surely deserving a place at the heart of every well-dressed gent’s wardrobe.

Instantly recognisable by their ankle-high fit and the elasticated side panels, Chelsea boots were invented by Queen Victoria’s shoemaker, J. Sparkes-Hall, in the 1850s as a hassle-free alternative to the tall, laced riding boots of the day.

Originally called paddock boots or jodhpur boots, they were relaunched in the swinging ‘60s when the Beatles, started wearing them on the famous Chelsea scene. With the celebrity seal of approval, Chelsea boots soon became the footwear of choice for mods and rockers alike.

Here are our five top tips to bear in mind when buying Chelsea boots.
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Chelsea boots, Paisley and other British clothing conceptions

Have you ever wondered where your clothes got their names from? Like Beckham’s babies, lots of tots are named after the place of conception.

Here’s our guide to some thoroughly British clothing conceptions, and the foreign imposters.

Chelsea boots

Chelsea Boots – Made in Britain
Source: Samuel Windsor

It was the vulcanisation of rubber that enabled the creation of the footwear we know today as Chelsea Boots.

Charles Goodyear invented the process of rendering naturally soft, sticky rubber into the tough, stretchy, hard wearing substance we know today. The elasticated gusset that sets mens Chelsea boots apart from other types of shoe was a revolution in Victorian footwear.

The ease with which the boots could be put on and off wasn’t lost on Queen Victoria herself, who is reported to have worn them regularly. As to why they’re named after the London borough of Chelsea – they weren’t.

Chelsea boots were originally called paddock boots or jodhpur boots and only got their current name as a result of a 1960s relaunch.

Oxford shirt

Not just for boffins – Oxford shirts
Source: 4.bp

An Oxford shirt is a classic garment made from cloth of the same name. The fabric has a basket weave that produces a soft, breathable material that holds it’s shape well and requires only light ironing.

Often two different coloured filaments are woven together to create a dappled effect. The yarn used to weave Oxford cloth tends to be heavier than that used to make poplin shirts, so it’s hard wearing too. The good news for the majority of us is that you don’t have to be a genius to wear it.


From Persia to Paisley
Source: Wikipedia

Paisley cloth is named after the Scottish town in which it was produced during the height of the Victorian era. Used to make ties, bandanas, pajamas and many other clothing items and accessories, the fabric comes originally from India, Persia and Mesopotamia – modern day Iran and Iraq.

The highly colourful patterned swirls are thought to represent the date palm – or the ‘tree of life’ and began to be exported to Britain by the East India Company in the 17th century.

The cost of the cloth was greatly reduced by the replacement of imported woven fabric with mass produced printed imitations from Scotland, making Paisley affordable to the masses.

Harris Tweed

From the Highlands – Harris Tweed
Source: The Vintage Showroom

For a miracle of preservation of an ancient way of life in our mass produced, mechanised world, look no further than Harris Tweed. Every inch of the world famous cloth is woven by hand by crofters working from home.

They use only yarn dyed and spun from virgin sheep’s wool processed in the Outer Hebrides. And what a product. Only the best cloth gets the unique orb trademark. And just in case you’re still not sure, it’s tested to 50,000 rubs to make sure that a Harris Tweed garment will literally last you a lifetime.

Jersey Sweater

Fishing Jerseys
Source: Stitched and Stitched

Jersey is a name given to almost any type of knitted pullover, but the original garment does in fact get its name from the channel island of the same name. Jersey and Guernsey have been famous kitting centres since at the middle ages and a proper Jersey jumper is a pullover with a difference.

The wool yarn used to make a Jersey is tightly spun and dyed using a technique that doesn’t strip the wool of its natural oils. This gives the pullover the remarkable water resistance necessary for its original role as a fisherman’s sweater.


Le Denim
Source: Little Scandinavian

Famous the world over as the fabric used to make American blue jeans – we couldn’t resist including it in this line up. But denim doesn’t get its name from the USA or from Great Britain.

In fact we have to look to France for the origin of this hard wearing, practical cloth. Denim is the abbreviation of ‘serge de Nîmes,’ a town in Southern France.