Can (and Should) Short Men Wear Chelsea Boots?

Chelsea boots are super cool, and they happen to be really “in style” right now. But are they a good choice for shorter men? Read on to find out…

Chelsea boots short men

Here's the short answer (pun intended):

Yes, shorter gents can wear Chelsea boots. In fact, they're an excellent choice for men of modest height.

In this post, I'll reveal why I think Chelsea boots are perfect for shorter men and show you how I like to wear them.

Note: Thanks to Thursday Boot Co. for sponsoring The Modest Man and and hooking me up with a pair of great Chelsea boots. Considering the quality, Thursday Boots are priced very reasonably. Check them out right here (if you haven't already).

It seems like most stylish men agree that Chelsea boots are pretty darn cool. They're definitely very popular right now, and I don't think they're going anywhere for a long time.

TBC honey suede Chelsea boots

jeans | boots

According to Wikipedia, Chelsea boots are “close-fitting, ankle-high boots with an elastic side panel” that “date back to the Victorian era” and, historically, have been worn by men and women.

So, even though they're trending now, they're actually pretty classic. That's a good thing if you're the type of guy who wants to build a timeless, versatile wardrobe.

Here's why, as a 5'6″ guy, I like Chelsea boots:

  1. They're very easy to slip on and off (which is not true for most boots).
  2. They add 1.25″ to your height (but they're not elevator shoes).
  3. They can be easily dressed up or down.
  4. They set you apart because most guys don't own a pair.

The only thing you have to watch out for with Chelsea boots is the sizing. Since they don't have laces, they can't be tightened. So you want to make sure to get a nice snug fit.

Slip on Chelsea boots

watch | boots

Unlike some other brands, Thursday Boots are pretty true to size. Their size 7 boots fit my feet perfectly, especially since I like to wear thick socks with boots. They're also lightweight and low profile (not always the case with Chelseas).

All things considered, I think these boots are a great choice for men of modest height – or any man, for that matter.

How to Wear Chelsea Boots

Like I mentioned above, these types of boots can be dressed up or down. But I think they're perfect for more casual outfits. Not “shorts and t-shirt” casual, but “jeans and button up” casual.

Casual Chelsea boots outfit

jacket | shirt | sunglasses | jeans

This light brown “honey” color looks amazing with lighter wash jeans. It also looks good with light neutrals (white, cream, tan) and many different shades of blue and green.

I think suede is a great choice for Chelsea boots, especially if you're planning on wearing them with more casual outfits.

These particular boots are made with WeatherSafe suede, which is water resistant.

This means I don't have to worry about getting caught in the rain. Unlike most of my other suede shoes, these aren't reserved just for sunny days with no chance of rain.

WeatherSafe suede

For me, Chelsea boots occupy the same space as chukka boots. They're a nice blend between casual and dressy. I think the honey color of these boots is a great choice for anyone looking to buy their first pair of Chelsea boots.

I also have a pair of chocolate brown suede Chelseas, but I find myself reaching for these light brown boots much more often.

Chelsea boots outfit

Since this is a pretty simple outfit, I added a couple of accessories to spruce it up, including one of my favorite watches and belts:

Seiko SKX013 dive watch

The Seiko SKX013 is a perfect entry-level dive watch for men with smaller wrists. It goes great with this casual outfit.

Camo canvas Anson belt

The brown and green in this camo canvas belt go well with my boots and windbreaker.

Green nylon windbreaker

These boots will also look great with chinos (khaki, tan, olive or navy) or even wool trousers. They're appropriate for any season, although I wouldn't wear them in snowy, slushy weather conditions.

Do you wear Chelsea boots?

I've had quite a few people ask if Chelsea boots are a good choice for shorter men. Now that you know my opinion, I have to ask:

Do you own a pair? Are you going to buy some? If so, check out Thursday Boots 😉

Questions/thoughts? Leave a comment below!

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  1. Great post. At 5’8 (5’9 on good posture days) I have thought about this and many other “short guy” issues. I’m in search of my first pair of chelseas, and this is a nice reminder of how well they can be pulled off.

    My question is – I am more of a dark denim (I own no lighter denim, actually), so what color would you recommend?

    • I’d probably go dark brown or black, although I’ve seen people wearing this lighter brown color with darker pants. Probably not as versatile, though.

  2. Brock, are these the same as “Chukka” boots? Is the elastic strap the only difference?

    I have a couple pair of Chukka’s… enjoy them for similar reasons, especially ease to take on and put off.

  3. Hi Brock,
    Awesome post!!
    Great pictures!!!!
    Can I wear these Chelsea boots as a formal wear to work or always with an casual outfits?

  4. I’ve had my eye on them for a while now. I think they are really great. Great post Brock.

  5. Great post Brock! I love wearing Chelsea boots, but only have one pair from ASOS. Are there any affordable, but quality, brands you like that make a good Chelsea boot?

    • These are the most affordable Goodyear welt chelseas that I know of. The ASOS ones look pretty good but aren’t as high quality. I’m sure there are some in between options but I’ll have to do some research!

  6. Great post,I own a dark brown pair that I wear with dark blue denim

  7. Great post on Chelsea boots Brock! Agree they are totally under used but always talked about. I tried on a pair in a shoe store recently by the brand Sutro Footwear and really liked them. They are constructed very well, comfortable, sleek silhouette and not too wide or not too narrow, have a Goodyear Welt, and are priced comparably to the ones you posted. There is also a $10 off code that just flashed up when I went to get the link (TAKE10) if anyone is interested:

    Comes in three colors, I tried on the Mason Taupe and Black and really liked the the Mason Taupe one.

    Thanks for the post!

  8. David Schleger says:

    Great post Brock…….will look for a pair here….(Canada)

  9. I’m very picky when it comes to clothes and I like subtle. That’s not to say boring, but there are times when I can’t wear my denim jacket because, in combination with the other clothes I’m wearing, it just looks too trendy. Like I’m trying too hard to be cool. Anyway, I like the boots, but can’t see myself wearing them because of how prominent the elastic part is. There is something about it that bothers me. I would probably wear the black ones because it doesn’t stand out as much, but in black they aren’t as casual.

  10. Great information 👍

  11. Shahed Chowdhury says:

    Like the post a lot , the Chelsea’s have been my Go To for while now. If you can get invest in leather uppers it can go with some dress pants as well. Above all I think comfort is important I feel that when I feel comfortable with the look, fit and colour its a win win….i am hunting for new ones as the ones i have are wearing out a bit…the other tip I has is for folks who live in snow filled areas make sure you clean them for salt and use a good mink oil for keeping leather healthy.

  12. Kenny Shuster says:

    Hey Brock!
    This is a great post, thanks a bunch. I’ve actually had a pair of Thursday (dark brown) Captains for a few months and love them. I’ve been thinking about getting a pair of Midnight Blue Scouts and eventually splurging on Allen Edmonds’s Liverpool Chelseas (I’m a huge AE fan, just a broke student, so it takes a little longer to get money) in brown. Would you say getting both is a little redundant if I already have the 6″ boots?

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