How to Wear Men's Boots - A High Level Guide

In this week's Style Advice for the Everyday Guy, Chris and Eric from Cladwell discuss how to wear men's boots.

Guys if you're not sure how to wear men's boots- we've got an app that will help dress you, and you can try it for free here. It sends you expertly styled outfits every morning using the clothes you already own.

Find out why men's boots are more popular than ever, why they tend to be higher in cost than other items in your wardrobe and which styles work best for certain occasions.

Video Transcript:

I haven't bought a new pair of boots since 2002.

Eric, I think it's time for some new boots.

So, if you're in the market and you're thinking, "I need a new pair of boots. I need some help. I have some basic questions." That's what we're going to cover today.

Yeah, we're going to hit some styles. Some prices. We're not going to go too much into the nitty gritty, but we'll give you a good idea of boots.

Why are men's boots so popular right now?

So, the first question I have Chris is that it seems like boots are really growing in popularity lately. What's going on with that? Why is that happening?

Yeah, I think, you see guys on the streets wearing boots really a lot more in the last four or five years. I think a couple of things have contributed to this. One, men are just becoming more interested in how they dress. So, it's nice to have options, especially in the winter. A couple of other things, I think outdoor activities - an emphasis on healthy living and a healthy lifestyle is becoming really cool. That's a great thing. So, you see more outdoor oriented clothing.

Just being outdoors. You've got the lumberjack or lumbersexual look. It's coming. (The lumberjack look is a thing, yeah.) And that's the look with maybe a big plaid check, the scarf, the boots. (Exactly.) Denim, etc.

Yeah, we're exhibiting this right now. I think another thing is that people in our generation. I'm 29. You're 40? (I'm 33). People in our generation are really searching for authenticity in their clothing. So, we're seeing a lot of throwback things in your wardrobe. So, American workwear style is really popular right now. So, workboots and things like denim shirts are great for that kind of style.

Yeah, so we've seen sites like the ArtofManliness for example. There's a real resonance to that of getting back to previous generations and boots are kind of a bridge back to those previous generations. Would you say that?

Absolutely. And he's doing a great job communicating that stuff that I think we all really long for deep down, and now it's like cool. It's good to talk about that stuff.

Why are boots more expensive?

All right, so let's talk about pricing a little bit. It seems like when I'm shopping for boots, they are more expensive than your everyday shoe. Why is that and what price ranges should I be thinking about?

That's a really good questions. First of all, let's think about the materials. Boots are typically leather, suede. So, they're going to be a little bit more. They're going to cost more than a man made material you may find on a sneaker or something like that. The other thing is that even against a dress shoe, which might also be leather, there's a little bit more material. They're coming up your ankle to protect you from cold weather, rain and that sort of thing. So, those both contribute to the extra cost.

How should I be thinking of boot price ranges?

So, what are the prices if I'm in the market. If there's a low end, etc. And, there's a quality component to the pricing too. So, walk me through what I should be thinking about here?

I've said it before, and I'll say it again. Shoes are a good investment if you have a little bit of money to spend on the clothes you are buying. That's a good place to spend on, especially boots. I'd say, as far as actual prices go, I'd tend to stay away from anything that is below $100. I think it's really not worth your money at that point. It's just going to fall apart. It may last you one or two seasons.

So, you think you're getting a deal, but really, you're going to be shopping for boots again next year.

You will, yes, depending on how much you wear them. If you can get up to $150, you start to get into some decent quality boots. And then after that, the sky is the limit. I'd say you kind of hit the price ceiling, as I call it, around the $300 or $350 range. Once you get above that, the quality doesn't really go up that much for what you spend.

And so it kind of depends, and we're going to walk through right now a couple of different styles of boots. Because you have these different categories, right? You've got your workman's boot, which is a very functional boot. You've got your casual boot that's maybe in the middle. And there's a dress boot. And so all of those are going to have their own different price ranges. (Yeah, they can. I mean, you can probably find any range in any of those styles.) But, it will basically lay out to those general rules you just set out for us.  Under $100 is no good, etc. So, let's look at some different styles.

Show and tell: Eric's "experienced" boots

Can we first show, maybe, something that I believe you brought with you today?

We've got something special today for you guys! We opened up by saying I haven't bought a pair of boots in 12 years. So, um, these are my boots, if you can see them. These are actually my boots. (You're very brave.) No, what, I'm a very practical guy. These have seen a little wear to them. (They're brittle!) Yeah, they're falling apart. The duct tape is actually round 2. My original plan was putting a staple gun from the sole up towards the toe. (Here's my question, were you wearing them at the time?) Come on Chris! No! Who do you think I am? No, but that didn't work out as well. The duct tape is holding strong. Getting a little bit more life out of these bad boys.

Yeah, thank you for that. Let me show you some better options.

An overview of boot categories (dress, casual, work)

Welker Chelsea Leather Slip on Boots - $395

I'm going to start with something that I wouldn't necessarily recommend for you.  This is called a Chelsea Boot. So, what distinguishes this is this elastic band. So, it's actually pretty easy to put on. It falls into the dress boot category. It has a pretty plain upper part. And if you notice, see how thin the sole is. There's not a lot of room. You can tell by the thin sole that it's not meant to be trudged around in the snow. But, it does give you a little extra protection from the cold by the ankle. (Wear it with?) You can wear it with wool slacks. Wear it with some nice dark denim. That sort of thing. It's a dressier look. If you're the guy who wants to dress up, this is the way to go. (Can you wear a dress boot with a suit?) Yeah, you definitely can. That's something that become really popular.


Johnston & Murphy Men's Copeland Chukka Boot - $122

The next example is a classic Chukka boot. This is mine. A nice grey suede. What distinguishes the chukka are these 3 pieces of leather and the way this stitching is. It's pretty prototypical of the chukka. This is a nice in between casual and dress boot. You can dress it up a little bit. You can also dress it down. (What about the suede material?) Yeah, a lot of people have this question. They think suede is not as hard wearing as leather. I think the reason they think that is because cheap leather is often better than cheap suede, but suede can be just as hard wearing as leather. Look for something that's going to be a little more thick. Thicker suede is going to be better. And if you don't know what that is, go to a shoe store and feel a couple of different pairs. You'll notice the difference. And the price range should help you as well. It's a great indicator.

Wolverine 1000 Mile Morley Full Grain Leather Boots - $400

Next, is a great pair of boots, the 1,000 Mile by Wolverine. This is something a little trendier. You can see it has this sort of lugs sole. So, you're starting to get into the more bad weather wearing boot. This is going to provide you a little more protection, and it's a lot higher up on the ankle, which is great. (It's more functional but feels very stylish as well.) This is very stylish, yes. (And, that's what's cool about boots, they border this line where you're wearing them in colder weather, but you can also get a lot of different looks with them.) Totally, so for a guy who is really attracted to the function of the things he wears, these boots are a great option. And, it's very stylish as well.

Red Wing Heritage Classic Work 6" Round Toe

Ok, one more pair to show you. This is a little bit trendier. This is a classic, American workwear style is this Red Wing pair of boots. It's a classic brand. It's going to last a long time. It's very popular lately, but it's more than just a trend. It's a very high quality boot. It's hard to go wrong. This is something I may recommend for you. (That's what I was going to ask! You've seen my boots. I need a recommendation. Something that is versatile, and I can wear a lot. This is what you would go with?) Yeah, it's very versatile. The one difficulty and maybe "watch out" for this is that it's not going to be dressed up very easily because of this thick sole. I mean, this sole really stands out. So, if you wanted something that you thought you could dress up, I might bring the Wolverine pair back - something like this. Because if you have dress pants, they're going to sit right over the ankle. So, you're not even going to see the tall piece. It can be dressed up a little bit more easily.

How do I wear pants with boots?

Ok, a final few questions. When I'm wearing the boot, what do I do with the pants in terms of wearing them over the boot?

Yes, so like I just mentioned, if you're trying to dress up a boot, wear the pants right over the ankle. It's really going to look like you're wearing a dress shoe except for maybe the sole. But if you want to show it off, and you're wearing boots for more of a casual look, you can cuff the pants. That's a great option. Then, you're showing off more of the boot.


  • Boots are very popular right now.
  • It's worth it to invest more in boots. They'll last you longer, and the quality will be a lot higher once you get over $100-$150 price range.
  • Boots are very versatile. Lots of styles. Lots of price points. For lots of different guys.

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