10 Casual Boot Mistakes Only Menswear Experts Notice

Boot-wearing has become increasingly more popular throughout the years, especially as a more casual style of footwear. But as more people adopt them, those not experienced or without the proper know-how can limit their style potential. Wearing boots casually isn’t as easy as wearing them formally, either. Today, we discuss nuanced errors that any well-styled person will notice.

Note that we’re only discussing casual boots, for instance, no button boots: just learning how to button those is a whole other post in and of itself. We’ll only be focusing on boots that fall within the casual and the business-casual setting, which include options like the wellingtons, work boots, casual cowboy boots, chukkas, and the like.

We’re also thrilled to announce that we have a new face at the Gentleman’s Gazette, Ivan Martinez, who’ll contribute his expertise in the realm of menswear. He runs his own YouTube channel called “I AM MR MARTINEZ,” so check that out, too!

Casual Boot Mistakes

1. Not Investing in a Quality Boot

Just because something is casual doesn’t mean that you have to skimp on the quality. Just like anything else in classic style, you get what you pay for. Cheaply-made boots will use subpar construction in order to keep their cost down.

Cheap boots may have subpar quality.
Cheap boots may have subpar quality. Skimping on quality is among the most lousy boot mistakes!

A boot without a Goodyear welt won’t last as long as one with a welt and will need to be replaced more often, somewhat defeating the rugged appeal of boots in the first place and leading to a higher cost-per-wear as you repair the boot.

Goodyear-Welted Shoes: Myth or Magic?

It is less likely that cheaply-made boots will have the beautiful lines that higher-quality boots will have. When cutting corners, a boot’s beauty is usually the first one to be cut out, so if you have the funds, it is better to invest now for a great pair of boots that will last you a lifetime.

2. Getting Formalities Wrong

One of the easiest ways to stand out for the wrong reason is wearing your boots with the wrong outfit. Combat boots and suits are probably not the best combination for a classic look. While there are more obvious picks, there are some nuance considerations.

Clashing Formalities e1698577941498

Clashing Formalities

Suits and Combat Boots

If you’re trying to go for more of a business casual outfit, a utilitarian boot probably isn’t going to be a good fit. They’ll often be made with materials that will clash with more formal outfits and have a chunky silhouette that is not suited for an office environment.

Likewise, dress boots aren’t the best for casual settings as their sleeker lines, and more precious materials probably aren’t as adept for handling wear and tear. In other words, you may not want to go on that hike in your Chelsea boots.

Look at the purpose and the occasion when picking out your boots. If you want to relax your boot options, you might want to consider some broguing elements to your boots or more casual garments like jeans. You might be wondering if denim is smart-casual, so check out another post on this topic for our verdict.

Should You Pair Dress Shoes with Jeans?

3. Using the Wrong Sole/Subpar Sole

One of the great things about more casual boots is their rugged style and their practical design; however, the sole that you use has a massive impact on the formality and utility. For example, if you have a more formal dress boot and you put a chunkier sole to it, this will only make it more casual.

For a more formal-appearing option, we always suggest using a V-tread or a less chunky sole. A leather sole on a boot that is meant to be worn for dirty or rough terrains will break down more quickly because it’s not meant to be worn in those environments, especially without a storm welt. Much like formality, purpose and location will help you determine the type of sole that you’ll want to use for the occasion.

4. Picking the Wrong Trouser

Not all trousers are meant to be worn with boots. Skinny jeans and boots may not be the most flattering look. Consider the silhouette and the leg opening of your trousers: for instance, straight or boot-cut jeans go very well with boots. Hey, they’re called “boot-cut jeans” for a reason, right?

Raphael in boot cut jeans and boots.
Raphael in boot-cut jeans and boots.

As a general rule of thumb, the taller the boot, the wider the leg opening has to be on the trouser. For example, chukka boots don’t require as much space, while cowboy boots need to have more room so they don’t bunch up and get uncomfortable.

Also, consider trouser material; jeans and chinos might be better for casual boots paired with something like a leather jacket. Their coarser materials make them more casual and even harder-wearing: it’s all about trying to harmonize formalities.

Corduroy with dress boots

Trouser Materials matter

Corduroy and Dress Boots

Avoid jarring combinations by looking at the purpose or formality of the trouser and boot materials. For instance, corduroy and flannel trousers might look better with dress boots than fresco pants would.

Did you know that Fort Belvedere carries corduroys?

5. Socks Not Harmonizing with Boots

You probably already know that white socks with boots are usually not a good idea, but too many men underutilize dress socks when it comes to wearing boots. We cover the basics of how to avoid your footwear and socks from clashing in another guide, but harmonizing them for an exceptional look is more nuanced.

White socks and boots aren't a good combination!
White socks and boots aren’t a good combination!

Combining Socks, Shoes & Pants

Instead of matching colors, include other colors, too. Try to match them to an accessory or try to even incorporate it with other parts of your outfit instead of blending in with your pants. It’s just a way to showcase that you put time and effort into your outfit. Options like Fort Belvedere shadow-striped socks will help you with this.

6. Picking the Wrong Material for the Occasion

Boots come in a number of unique materials – such as alligator, suede, and Cordovan – yet some materials, like suede, have various situational purposes. Unless waterproof, they might not work in rain or mud. They’re also more casual and less versatile than calfskin.

Alligator is a bolder material – also making it more memorable and, thus, not nearly as versatile. Cordovan is an extremely hardwearing leather, but can be tough to care for, and its sheen won’t fit all boot styles.

We also have to consider how the leather is treated. A more glossy leather won’t look as good with a more casual outfit, while a waterproofed upper won’t be as formal. The more refined and shined the leather is, the more formal it will be. The more matte the leather is, the more casual it will be.

7. Poorly Shined Boots

While a novice might notice that your boots weren’t cared for, a seasoned enthusiast will notice a bad shine job. Not treating the edges, a botchy and improperly set polish, missing spots, not moisturizing or conditioning, which leads to cracks, or leaving bits of dirt under the leather on the polish.

Poorly maintained boots are not a good look for gentlemen.
Poorly maintained boots are not a good look for gentlemen. [Image Credit: Ariat International]

Worried you might have made one of these mistakes? We have a guide that will show you how to shine your shoes properly.

Mirror Shining Your Shoes

8. Wearing Boots That Are Too “Out There” for You

As we develop our boot skills, we want to wear more elaborate styles. For example, if you are a fan of Western style, you might want to consider some cowboy boots; however, if you’ve never worn them before, jumping into some blue alligator skin might not be a great idea. That’s not to say that you could never wear these styles, but we recommend more of the classics first.

Start with classic boot styles

Getting Started

Classic Boot Styles

When starting out your boot-wearing journey, consider classic and more middle-of-the-road styles to boot, such as the chukka or Chelsea, and then you can work up to bolder options.

As you get more comfortable with boot-wearing and what you like and what you dislike, you could gradually work up to bolder styles. Style and confidence take time to develop.

9. Tucking (or not Tucking) Your Pants Into Your Boots

This one could start an East Coast versus West Coast debate. Traditionally, pants were tucked into their boots in order to protect them from any debris from the countryside roads and fields. This has been popular since the Middle Ages and can still be seen today with cowboys. However, dress boot styles tend to have a more slim design less suited to tucking.

Ultimately, the choice to tuck or not tuck your pants is really up to you. There is no right or wrong answer in this in most cases. But, as a rule of thumb, lace-up styles and boots with taller uppers can be warm with your pants tucked in; dressier boot styles will work better with your pants untucked.

10. Boring Boot Laces

Finally, a style element that many men overlook is their bootlaces. While the standard brown and black shoelaces aren’t wrong, they aren’t the most interesting choice. Instead, you could look to add color laces that complement your outfit. This will give your looks an extra dimension, making everything much more visually stimulating.

A lace-change can help elevate your boot game.
A lace-change can help elevate your boot game.

Fresh laces can bring new life to an old pair of boots, giving them a unique character. It can even change the formality as bright, playful laces make your boots more casual, a more rounded one will only elevate the formality. We believe our options at Fort Belvedere are excellent choices.

Add Boot Laces To Your Collection!


In conclusion, boots are a great addition to any man’s wardrobe, but men can easily miss out on wearing them properly. So, by avoiding these mistakes, you could further elevate your style and gain that X-factor that people will notice even if they can’t quite put their finger on why it looks so good.

Do you have any style pet peeves for boots we might have missed? Let us know in the comments which boot mistakes you see wearers make.

Outfit Rundown

Today, I am wearing a navy suit jacket from a navy suit that I have. It is by my brand, By Mr. Martinez. Same with the pants, they are brown and white. I am also wearing a white shirt with a spread collar, just kind of keeping it all classic.

At the time of this recording, it is 90 degrees in Minnesota, so I am not wearing boots. On my feet, I am wearing a pair of burgundy horse-bit loafers from J. Butler. Although you can’t see them, I am wearing socks. I’m just wearing no-show socks.

On my wrist, I am wearing a Timex Marlin watch. For my pocket square, I wanted a little bit of a pop of color, so I went with a red and kind of a blue, just kind of incorporated into my outfit.

For fragrance, I decided to wear this Roberto Ugolini scent. I thought it was appropriate since it’s the loafer, and I’m wearing some loafers. If you want to check out this and other fragrances, as well as our menswear accessories, make sure you check out our shop.

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