Chelsea Boots

Wear This: Chelsea Boots Keep your feet warm in this classic style

A great pair of boots is a dynamic choice for both dressy and casual occasions.  One boot in particular that we’ve got our eyes on this time of year is the Chelsea boot.  Endlessly versatile, this shoe is as easy to style as it is timeless. And, with the sheer variety of materials, colors, and finishes available, there’s bound to be a pair to work with any man’s personal style. Here is everything you need to know about the Chelsea boot. 

Read: The Essential Guide to Men’s Boots

Table of Contents


Chelsea Boots; History

The Chelsea boot was invented in Victorian-era England by J. Sparkes-Hall, official bootmaker to Queen Victoria herself.  Using then-recently-invented vulcanized ( a chemical process that converts natural rubber into more durable materials) rubber, the Chelsea boot was designed to be slipped on and off.  This may not sound like a big deal to you now, but in a time when boots were characterized by intrinsic lacing, slip-on boots made things a hell of a lot easier.  While the boots were originally made for the Queen, their popularity grew so much that men of the time eventually adopted the trend as well.  Nearly a century later, the boot got its iconic name from socialites in the Chelsea neighborhood of London who frequently sported the shoes day in and day out.  Its popularity grew even more once the Beatles started wearing them.  The rest is history.


Chelsea Boots; Fit

Unlike other boots that you can simply lace up tighter if they’re a little loose, Chelsea boots need to fit perfectly in order to be comfortable.  Find a boot that fits tightly around the ankle and still leaves room for your toes. Additionally, you’ll also want to consider your socks. If you wear thick socks a lot, you’ll also want to consider going a half size up. Wear the socks you plan to wear with your boots while trying the shoe on.


Chelsea Boots; Materials

Chelsea boots are as dynamic as they are timeless, and they can be found in a wide variety of materials to suit your needs. You’ll want to pick the material that works best with your lifestyle.  If you’re looking for a shoe for casual or indoor wear primarily, you’re fine rocking suede. However, if the weather’s a bit temperamental where you live, leather might be the way to go.


Rounded vs. Pointed

Chelsea Boots; Pointed vs Rounded

Chelsea boots are usually shaped with either a rounded or pointed toe.  The rounded toe is a great option for everyday use as it’s way more casual and easy to pull off.On the flip side, pointed toe Chelsea boots are, in general, more formal and edgier.


Chelsea Boots; Colors

Blacks and tans are great classic options, especially if you’re going for a polished, urban look. Brown suede is best for casual wear, while brown leather could make for a great office-appropriate addition. If you’re looking for an office-appropriate shoe that’s not black or brown, you can never go wrong with burgundy. Additionally, different colors like indigo, green, and copper are great options to add to your wardrobe when you’re trying to make a statement.


Chelsea Boots; Quality

Chelsea boots aren’t going out of style anytime soon, so you can rest assured that your investment will be good for the long haul.  If you want to go for a more trendy style or in a nontraditional color, go with a cheaper pair ($50 – $150).  However, a more expensive pair that will last you longer is a safe bet if you’re looking to expand your shoe staples. So, even though a $400 pair might seem unheard of in the moment, these boots will be a go-to for years and years to come. We’re not saying you should splurge, but we’re also not not saying it, either…

Our Picks:


Chelsea Boots; Save

Houston Chelsea Boots, New Republic $99


New Republic | Men’s Sonoma Chelsea Boot with Crepe Sole

  • Suede/Leather
  • All-day Comfort
  • Classic style


Chelsea Boots; Spend

Liverpool Chelsea Suede Dress Boot, Allen Edmonds $445


Allen Edmonds Men’s Liverpool Chelsea Boot

Iconic British chelsea boot with American attitude. Authentic ‘60s style. Dress it up or down, perfect any way you style it. Classic Fit, fits true to size.

Since the eighteenth century, the Chelsea boot has been a timeless footwear staple.  Chelsea boots are a great alternative to the typical work boot and come with the added benefit of transitional use.  Next time you’re looking to dress up your office outfit or put together a look for a night out, opt for the classic Chelsea boot.  

Read Next: The Essential Guide to Men’s Boots

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