Chukka vs Chelsea Boots: Comparing Business Casual Boots

We all love chunky, casual boots like Red Wing Iron Rangers and Timberlands, but when someone is looking up info on chukkas versus Chelsea boots, it’s because they’re the best boots for the office — or because they’re ideal smart casual boots.

Chukkas and Chelseas are both great for when you want to look a little nicer than jeans-and-t-shirt but you want to keep things a little more relaxed than suit-and-tie, so whether you’re after smart casual or business casual boots, you’re looking at the right models.

I’ve spent years traveling the world visiting boot factories and menswear factories, so I’m good to break down the types of each model, their versatility, the differences in fit, and which one’s right for you. I mean, you’ll have to decide that last one, but I’ll give you the tools you need to do so.

Real Quick: What’s a Chelsea Boot?

• Chelseas are laceless boots that secure to the foot with elastic panels

Brands that make boots in the United States are actually pretty unlikely to make Chelseas; they’re a distinctly British boot.

Originally a walking shoe made for Queen Victoria, they became especially popular across the pond when they were the suit boot of choice for The Beatles (for a time, they were better known as Beatle Boots.)

Chelseas have no laces: they secure to the foot with elastic panels on either side of the foot, called “goring.” Because they’re laceless, they were usually pretty slim, and the sleekness combined with the simplicity led them to be worn in somewhat dressy environs.

But as time went on, more people became enamored by the Chelsea’s ease of use, and casual Chelseas like Blundstone (above) became widespread.

So, today, Chelseas come in many shapes and sizes. But they tend to be fairly slim and sit in the smart casual or business casual category.

Real Quick: What’s a Chukka Boot?

• Chukkas are short boots with just two or three pairs of eyelets

Chukkas are easy to spot because they have just two or three pairs of eyelets and they have quite low shafts, sometimes considered ankle boots.

You could say chukkas and Chelseas are similar in that they have fewer laces and fewer details than your average lace up boot.

Chukkas tend to have pretty simple designs consisting of fewer pieces of leather than other boots, so they’re often a pretty cost effective boot.

Chukkas vs Desert Boots

Desert boots are a kind of chukka made with suede uppers and crepe rubber soles.

Made with suede that’s often unlined, desert boots are very breathable and make great summer boots.

All desert boots are chukkas, but not all chukkas are desert boots. While some chukkas are casual and some are dressy, if it’s called a desert boot it’s pretty much guaranteed to be casual.

Chukkas vs Chelseas: What’s Best for a Suit and Tie?

• Chelseas.

Chukkas can be pretty smart, but not smart enough to wear with a tie.

Most boots aren’t quite smart enough to wear with a tie either, but there are plenty of Chelseas that will make the cut if you want a suit boot. If there’s one boot you can wear with a suit it’s a Balmoral boot like this, but the right Chelsea can work great with a suit.

That’s the end of the list of boots that work with a suit and tie, though!

What to Look for In a Dressy Chelsea

• Black calfskin leather is the default choice for formal or professional footwear. Brown is less dressy; since you’re toeing the line already by wearing a boot with a suit, I’d stick to black.
• A flat, low profile sole, ideally leather.
• A slim, sleek silhouette.
• As few seams as possible: a seam behind the heel and under the elastic is fine, but there should be no seams or details around the vamp.

Best Chelsea Boots to Wear With a Suit

• Carmina’s Simpson Chelsea ($550), pictured all over this section, is the standard. Made in Spain with box calf leather, it contours the foot just right and has a great closed channel leather sole. It’s also made with a durable Goodyear welt, but it has none of the chunkiness that this build tends to confer.

• Koio’s Trento ($365) is a cheaper option that I like a lot. It’s made with Blake stitch construction, so while it’s a little harder to get resoled than Carmina’s Goodyear welt, it helps keep the boot slim and lightweight.
• Thursday’s Cavalier ($190) is a great option that’s under $200. It’s not made with calfskin and it does’t have a fancy (and breathable!) leather sole, but it nails the slim silhouette and it’s very easy to resole.

Chukkas vs Chelseas: What’s Best for Business Casual?

• Chukkas are better than Chelseas here, but both can work well

Business casual: you’re in the office, you’re wearing a nice jacket, you’re probably wearing a tie, but your jacket and trousers aren’t made from the same material. What boots are you picking?

Both options can work well but ironically enough, while Chelseas are the best dressy boot, I think this level of formality works better with chukkas. If you aren’t wearing smooth black calfskin, you want some laces to keep the boot a little smarter looking.

What to Look For in Business Casual Chukkas or Chelseas

• Brown leather is king of business casual boots. Any color of suede works too, but it’s best to stay away from smooth black leather.
• A flat sole: it doesn’t have to be a dressy leather sole, but this is still too smart for crepe rubber soles (like desert boots) or chunky Commando soles (too outdoorsy). Recessed lugs (like Dainite) are cool.
• Minimal details: You’re dressing them down with the brown leather (or suede!), but keep the seams and details to a minimum. This is still office wear!

Best Business Casual Chukkas

• Crockett & Jones is a British brand well known for their range of high end chukkas; for US-made options, Alden (above) is probably the best known luxury brand.

Best Business Casual Chelseas

• Meermin have great value, resoleable Chelseas that are wholecut, giving it fewer seams and extra smartness. They’re also sold in multiple lasts so you have more control over the fit.

Chukkas vs Chelseas: What’s best for smart casual?

• Both chukkas and Chelseas are great for smart casual wear.

Once you’re down at this level of dressiness, the main smart casual rule you need to follow is to wear leather footwear that isn’t black and dressy. Both chukkas and Chelseas can be worn like this! The rest of the guidelines for smart casual have more to do with the rest of your outfit, which is outside the scope of this article (but inside the scope of this one).

What to Look For In Smart Casual Chukkas or Chelseas

• Just don’t wear smooth black leather: it’s a bit too nice
• You can wear a crepe rubber sole, though it’s a little better to pick a flat rubber or leather sole for that “smart” factor. But if you’re in a nice button down and chinos, desert boots will be fine.
• Avoid very worn in, patinated, work boot style leather like these Red Wing Work Chukkas. Beat up work boots are great but they’re casual casual, not smart casual.

Best Smart Casual Chelseas

• I think Grant Stone makes a great smart casual Chelsea: it’s a little stumpier than your sleek suit boots but it’s still super high quality.

Best Smart Casual Chukkas

• Thursday’s Scout is a solid option, although to be honest, there’s not a ton of difference between smart casual and business casual chukkas: both should be brown or suede with flat rubber soles.

Chukkas vs Chelseas: What’s Best for Casual Wear?

• Desert boots are best.

Listen, casual Chelseas exist, and I’ll name some below, but the fact is that Chelseas are just a lot more likely to be a little too slim to look great with old jeans and a t-shirt. Chukkas are easy to look too smart as well, but the solution is the desert boot: suede uppers and crepe rubber soles make a boot really casual and while you can get that on Chelseas, the desert boot is the more widely recognized way to pair these elements.

Best Casual Chukkas

• For desert boots, I like Astorflex’s balance of quality and casual. See also Red Wing’s Weekender Chukka for American made.
• For casual chukkas that aren’t desert boots, Jim Green’s Vellie is as casual as you can get.

Best Casual Chelseas

• Astorflex also make a great casual Chelsea with a roomy fit, suede upper, and crepe rubber sole that’s both lightweight and resoleable.
• For casual Chelseas that don’t have crepe soles, check out Blundstone.

What’s Better for My Style: Chelsea vs Chukka?

If you’re going all the way up to a suit and tie I’d have to sternly tell you to opt for a Chelsea in black calfskin, but for the rest of the dress codes here, you’ve got a lot of freedom.

Sometimes, one model will inch ahead of the other (desert boots are just more timeless as casual boots than the Chelsea is), but so long as you’re following the basic guidelines of “brown is more casual, chunky soles are even more casual,” then you can find ways to wear your favorite model in almost any situation.

Chelsea or chukka: which one did you pick?