7 Best Boot Styles Men Should Know & How to Wear Them

There are many types of men’s boot styles from Chelsea’s to Chukkas and work boots to dress boots that every man should know how and when to wear them. In this article, we will cover 7 amazing boot styles for men that will keep you looking sharp and stylish for any season.

When you are being introduced to someone new, the first thing people will notice is your eyes and smile, and the second, your shoes. So what would be one of the easiest ways to make a great first impression and let people know around you that you know a thing or two about fashion?

Upgrade your boot game.

If you are looking for men’s boots for fall/winter, this article will show you 7 different kinds of men’s boots that every stylish man should want to know about.

You’ll learn the variations between the many styles of men’s boots today, and understand how you can wear them and my boot picks for fall and winter.

I have researched the internet on the latest men’s boots fashions and interviewed several clothing designers in my area to come up with this of the 7 awesome men’s boot styles that will always make a great first impression.

boot style
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Plain Boot Style

Boot Styles

President Men’s 6” Lace-up Boot in Brown: Thursday Boot Co.

What Is A Plain Toe Boot?

The casual plain-toe boot is the first on the list. This fresh all-purpose boot style with a classic design is what every man should have in their fall/winter wardrobe. The boot style pictured above is the President from Thursday Boots, they are an affordable, characteristic boot that is handmade with a Goodyear or Blake welt construction. This enables you to re-sole the boots when they wear down.

Where to Buy Plain Toe Boots:

How To Wear A Plain Toe Boot

plain toe boot style boot style

The plain toe boot offers a stylish casual look that is perfect for everyday wear. You can feel comfortable all day wearing them, plus they are extremely versatile.

This boot style is adaptable enough to wear with everything from a casual button-down and jeans to chinos and a cardigan sweater or denim jacket and cords.

Why I love the plain toe boot is that it’s an all-purpose boot that looks sharp with everything from casual looks to smart business casual looks.

They are the perfect style addition to when you need to wear top layers like leather jackets to a lightweight Harrington jacket when the temperature dips.

For everyday use, your can wear this style of boot with jeans or elevate your look slightly with a pair of chinos.

Cap Toe Boot Style

boots styles
Photo Credit: Olivercabell.com

What Is A Cap Toe Boot?

The Cap Toe Boot Style is comparable to the plain-toe version with the exception being the cap across the toe boot. This style of men’s boot is more casual than a plain-toe, and is a great option if you’re looking for something similar, but with an added subtle detail.

The pair above is made of genuine leather boots carefully crafted from hand-selected materials so you can go the extra mile with confidence; high-quality leather upper provides a finished look that gets better with age. 

I prefer cap-toe over plain toe because it adds more visuals to the boot which ups the strong factor.

Where to Buy Cap Toe Boots:

How To Wear A Cap Toe Boot

Bootstyles
Photo Credit: Jcrew.com

Just like the plain-toe boot style, the cap-toe boot can be worn essentially anywhere. 

It’s perfect with a sport coat and jeans or chinos as well. 

A pair like the Thursday Captain Boots is perfect to wear with smart-casual looks. For example, wear them with a button-down denim shirt underneath a woolen crew neck sweater and then layered a corduroy blazer over top. It’s a smart look that’s not conservative at all.

Moc Toe Boot Style

Moc Toe Boot Style

What Is A Moc Toe Boot?

A moc-toe boot is more rugged than the previous two men’s boot styles mentioned above. The moc-toe boot style is characterized by the crescent-shaped seam running across the top of the shoe, which was inspired by moccasins worn by the Indigenous peoples of North America.

American Heritage boot brands like Wolverine, Redwing, and Thorogood have their own different versions of the moc-toe boot. They often come with the universal white polyurethane outsole. Redwing Boot (Pictured Above) is one of the most comfortable pairs of moc boots available today.

Where to Buy Moc Toe Boots:

How To Wear A Moc-Toe Boot

Moc Toe Boot Style

The moc-toe boot is essentially a rugged boot, but it can still be dressed up a bit depending on the boot’s profile.

The moc-toe boot’s rugged character compliments thick and heavy layers, so feel free to add these boots for a stylish seasonal appropriate look.

For a slimmer profile, the Pikolinos moc toe boots look great with minimalist fall basics, like dark jeans, a t-shirt, a long-sleeved henley shirt, and a jean jacket. It’s a simple and casual fall/winter look.

Chelsea Boot Style

Chelsea Boot Style boot style boot style

What Is A Chelsea Boot?

The Chelsea boot is a laceless boot style that is as extremely popular as ever. A distinctive feature of chelsea boots is the elastic band around the ankle, reaching up to the tip of the boot opening. It’s a distinct, functional feature as it enables it to easily slip on and off.

It’s a remarkably comfortable boot style with a clean, minimalist aesthetic, making it a favorite boot option for many men’s fashions today. 

Where to Buy Chelsea Boots:

How To Wear A Chelsea Boot

Chelsea Boot Style

A classic chelsea boot is the perfect boot style for when you need to dress up or even dress down to casual wear. That is why the chelsea boot is one of the more popular boot types today.

You can wear them with jeans and chinos, or even when you have to slap on a suit and tie. That’s how versatile this boot style is. Keep in mind when looking at buying a pair of chelsea boots, is they may stretch a little bit. So it might be a good idea to size down a half size when purchasing a pair, especially with suede chelsea boots.

A suede pair of chelsea boots give off a relaxed feel and offers versatility when pairing with casual outfits. You can wear this boot style with almost everything, from bomber jackets to field jackets and more refined topcoats.

Chukka (Desert) Boot Style

Chukkas boot style

What Is A Chukka (Desert) Boot?

What makes a chukka a desert boot is essentially the crepe rubber sole and overall a more casual appearance. The chukka boot is a dress casual shoe with open lacing and two or three pairs of eyelets. You’ll usually find this ankle-high boot style in suede or leather.

Where to Buy Chukka Boots:

How To Wear A Chukka Boot

Chukkas boot style

Chukkas are a boot style that lends itself to a more dressy look and can be worn with a suit. But they are rugged enough for a casual look with cuffed jeans, flannel, and a light vest.

The ability to be able to wear chukkas for both casual looks and more formal looks is the reason why chukkas need to be in every man’s wardrobe.

Chukka boots are also great multi-season boots, meaning they are appropriate for the cooler months of fall/winter, and leading into the warm spring and summer months. Grab yourself a classic pair of suede for a true “desert boot” style.

Work Boot Style

Work boot style
Photo Credit: Redwingshoes.com

What Is A Work Boot?

The work boot is an institution that goes way back to Miners over a hundred years ago. They wore work boots for their toughness and durability and comfortability. The defining feature of these boots back then was a double-layered cap-toe to protect the miner’s feet from injury as they worked with hand tools and heavy machinery.

This boot style is bulkier than the boot styles in this post so far, and offers a more heavy-duty aesthetic. Some popular brands are the Red Wing Iron Ranger(pictured above), Wolverine 1000 MileThorogood, and Timberland

For fall and winter, work boots are the perfect cold-weather boot.

Where to Buy Work Boots:

How To Wear A Work Boot:

boot style

This is a rugged boot style built for the casual fall and winter look. Throw on a pair of work boots with plaid flannel, light or heavy vests, hoodies, denim jackets, and anything that tips towards a casual look. A work boot is not recommended for suits or formal wear.

Plus, being a work boot, you don’t have to worry about getting them dirty as that is what they are built for.

If you are thinking about what style of jeans would go well will a work boot, and it would have to be the boot cut style of jeans. Boot cut may not be in style in the fashion world, but who cares, they are the perfect jean style for this boot style.

Feel free to dress them up with bomber jackets, field jackets, denim jackets, and especially canvas jackets that already have a workwear look.

Brogue Dress Boot Style

thursdayboots.com boot style boot style
Photo Credit: thursdayboots.com

What Is A Dress Boot?

The brogue dress boot is somewhat more casual than a plain-toe or cap-toe dress boot. But the slim silhouette, leather sole, and overall refined aesthetic make it a dress boot. I enjoy broguing on boots, which are the perforations that you see along the boot.

The Thursday Wingtip Dress Boot (pictured above) is in a chocolate brown color is a very versatile dress shoe color and shade for that dressy look. 

Where to Buy Dress Boots:

How To Wear Dress Boots

boot style
Photo Credit: thursdayboots.com

If you had to choose between a normal dress boot or one with broguing, the Brogue Dress Boot Style is more versatile. It can be worn formally with a suit and with more casual looks, including jeans, cords, and wool trousers.

This is a very underrated boot for men. The brogue dress boot is the most refined pair of boots on this list and you can wear them with a suit and tie, with no problem. In the wintertime, you can jazz up outerwear like a topcoat or pea coat for a dressier aesthetic.

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Summary

If you want to look stylish without trying, wearing a boot style to fit a casual or formal look during the fall/winter season can be your ace in the hole.

Throughout my research and countless interviews to create this post, I am now starting to build a pretty solid boot collection. All of these boot styles can help you for any occasion from date nights to hikes and ball games to running errands. 

I hope you understand now the difference between men’s leather boots styles and are inspired by the many of ways you can wear them.

Stay classy!

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About the author: Trent (IMDB | Youtubehas spent 10+ years working on an assortment of film and television projects. He writes about his experiences to help (and amuse) others. If he’s not working, he’s either traveling, reading or writing about travel/film, or planning travel/film projects.

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