7 Boot Styles All Men Should Know (and How to Wear Them)

There are all kinds of men’s boot styles from chelseas to chukkas and work boots to dress boots. This article is a deep dive on 7 awesome boot styles for men.

So, do want to know one of the easiest ways to look like you know a thing or two about style this fall and winter season?

Upgrade your boot game.

7 Awesome Boot Styles For Fall/Winter + Styling Inspiration | GENTLEMAN WITHIN

I’m going to cut right to the chase and show you 7 different kinds of men’s boots for fall/winter — that as a stylish man — you’ll definitely want to know about.

In this article you’ll learn the differences between the myriad of men’s boots, get outfit inspiration on how you can wear them and my boot picks for fall and winter.

Additionally you can watch the full video directly below which includes many more looks from me that are not in this editorial.

Let’s get started.


13 BEST BOOTS for Stylish Guys (Chelseas, Moc Toes, Chukkas & More) | Men’s Fashion

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Thursday Plain-Toe Boots | GENTLEMAN WITHIN
President Men’s 6” Lace-up Boot in Brown: Thursday Boot Co.

What Is A Plain Toe Boot?

The casual plain-toe boot is first up. The it’s a clean all-purpose boot style with a timeless design that all stylish men must have in their fall/winter wardrobe. The pair above is an affordable, quality boot called the President from Thursday Boots that is handmade with a Goodyear or Blake welt construction. This allows for you to re-sole the boots when they wear down.

Where to Buy Plain Toe Boots

Thursday Boots Review | GENTLEMAN WITHINRelated: You might like this long-term Thursday Boots Review.

How To Wear A Plain Toe Boot:

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How To Wear Plain Toe Boots 1
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How To Wear Plain Toe Boots 2

How To Wear Plain Toe Boots 3

The plain-toe boot’s casual nature makes it perfect for everyday wear. You can feel comfortable wearing them virtually anywhere besides more formal outings that will require a suit.

It’s versatile enough to wear with everything from a casual button down and jeans to chinos and a cardigan sweater or denim jacket and cords.

I love that the plain toe boot is an all purpose boot that’s perfect with everything from casual looks to smart casual getups. You can feel comfortable to wear them with everything from top layers like leather jackets to light padded vests or lightweight Harrington jacket.

Down low you can opt for jeans to match the boot’s casual nature or elevate them slightly with a pair of slim fit chinos.

Plain-Toe Boot Style Inspiration:

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Thursday Midnight Suede Cap-Toe Boots | GENTLEMAN WITHIN
Captain Men’s 6″ Lace Up, Cap-Toe Boot in Midnight Suede: Thursday Boot Co.

What Is A Cap Toe Boot?

This casual boot style is similar to the plain-toe version with the difference being the cap across the toe boot. It’s slightly more casual than a plain-toe, and is a viable alternative if you’re seeking something similar, but with an added subtle detail.

The pair above is in a navy suede. Not only is the color unique, but the suede adds texture which is perfect for fall/winter seasons. Personally I prefer cap-toe over plain toe because it adds more visual weight to the boot which ups the rugged factor.

Where to Buy Cap Toe Boots

Taft Rome Boot Review | GENTLEMAN WITHINRelated: You might like this in-depth Taft Boots Review.

How To Wear A Cap Toe Boot:

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How To Wear Cap Toe Boots 1
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Just like the plain-toe, the cap-toe boot can be worn virtually anywhere. I wouldn’t wear it with a traditional suit, but it can work with a suit with more casual fabrics like flannel or tweed.

You can rock it with a sport coat and jeans or chinos as well. I like mixing textures, so the suede can go well with wool trousers and other winter fabrics like tweed. I featured this navy pair in my holiday party/New Year’s Eve Lookbook.

A pair like the Taft Rome Boot is perfect to wear with smart casual looks. In the example above I’m wearing 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 stuffy at all.

Cap-Toe Boot Style Inspiration:

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How To: Heel Lock Lacing Technique (Prevent Blisters & Black Toenails) | GENTLEMAN WITHINRelated: You might like this step by step guide on how to heel lock lace your boots to help prevent blisters.


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Pikolinos Moc-Toe Boots | GENTLEMAN WITHIN
Alpes Moc-Toe Men’s Boot in Cuero: Pikolinos Alpes Boot

What Is A Moc Toe Boot?

The moc-toe boot is more rugged than the previous two men’s boot styles. It’s distinguished by the crescent shaped seam running across the top of the shoe, which believe it or not was inspired by moccasins worn by the Native Americans.

American Heritage boot brands like Wolverine, Redwing and Thorogood have their own versions of the moc-toe boot. They often come with the ubiquitous white polyurethane outsole. The pair above is by far the most comfortable pair of boots that I own.

Where to Buy Moc Toe Boots

How To Wear A Moc Toe Boot:

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A Minimalist Summer To Fall Transition | Transitioning Your Style

How To Wear Moc Toe Boots 2

The moc-toe boot is primarily rugged, but it can still be dressed up to a point, depending on the boot’s silhouette. The moc-toe boot’s rugged nature compliments thick and heavy layers, so feel free to pile ’em on for a stylish seasonal appropriate look.

Personally I prefer the slimmer silhouette of Spanish brand Pikolinos. I’ve featured it in my denim jacket guide and in my piece on early fall style. They’re the most comfortable pair of boots that I own to date.

The Pikolinos moc toe boots look great with the minimalist basics, slim jeans and t-shirt look as well as rolled up jeans with a long sleeved henley shirt. It’s the simple, casual cool nature that I love most about the looks above.

Moc-Toe Boot Style Inspiration:

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Thursday Chelsea Boots | GENTLEMAN WITHIN
Duke Men’s Chelsea Boot in Honey Suede: Thursday Boot Co.

What Is A Chelsea Boot?

The chelsea boot is a laceless boot style that is as popular as ever. A distinguishing feature of chelsea boots is the elastic band around the ankle, extending up to the tip of the boot opening. It’s a unmistakable, utilitarian feature as it allows for easy slip on and off.

It’s super comfortable with a clean, minimalist aesthetic, making it one of my favorite boot options at the moment. This coming from someone who hated the design for the longest time, but it grew on me.

Where to Buy Chelsea Boots

How To Wear A Chelsea Boot:

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The classic chelsea boot is one of the more popular boot types these days. It’s classic design lends itself to dressing up or down. Wear it with jeans and chinos or if you’re feeling up to it, rock it with a suit and tie. They’re that versatile. A word of advice, chelsea boots (especially suede) may stretch a little bit and so it may be a good idea to size down a half size when purchasing a pair.

I love a suede pair of chelsea boots because of its relaxed nature and versatility when pairing with casual outfits which has been my bread and butter over the past several years. I wear them everything from with bomber jackets to field jackets and more refined top coats.

Quick Note: You might like this long term review of Ace Marks Troy Chelsea Boot.

Chelsea Boot Style Inspiration:

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7 Awesome Fall/Winter Boot Styles For Men | My Boot Collection + Styling Inspiration

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Clark's Chukka Boot | GENTLEMAN WITHIN
Originals Men’s Desert Boot in Brown Suede: Clarks

What Is A Chukka (Desert) Boot?

All desert boots are chukkas, but not all chukkas are desert boots. What makes a chukka a desert boot is basically 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 typically find this ankle-high boot in suede or leather. Chukkas were popularized by the iconic Clarks Originals desert boot.

Where to Buy Chukka Boots

How To Wear A Chukka Boot:

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Chukkas can be much more dressy and worn with a suit. A desert boot leans more rugged and is more suitable for wearing with cuffed jeans, flannel, and a light vest. Either way, know that similar to chelseas, you can easily rock chukkas both casually and more formal. It’s also the reason why chukkas are on my list of shoes every man needs.

Chukka boots are also great for multi-seasons, appropriate for the cooler months of autumn all the way to the warm spring and summer months. Get a classic pair in suede for a true “desert boot” style.

Chukka Boot Style Inspiration:

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Quick note: If you’re enjoying this article on men’s boot style, then you’ll probably find my other writing on all things men’s style useful. Each week, I share updates, style tips and other things not shared on the blog through my free email newsletter.

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Wolverine 1000 Miles Work Boot | GENTLEMAN WITHIN
Brown cap toe boots in brown: Wolverine

What Is A Work Boot?

The work boot goes way back. Miners way back in the day, talking over a hundred years ago wore work boots for their toughness and durability, but also comfortability. The defining characteristic of these boots though, was their double layered cap-toe to protect the miner’s feet from injury as they worked with hand tools and heavy machinery.

Overall, they’re bulkier with a more heavy duty aesthetic. Some popular American brands are the Red Wing Iron Ranger, Wolverine 1000 MileThorogood, and Timberland. Work boots can double as a great winter boot as well.

Where to Buy Work Boots

Wolverine 1000 Mile Review: 3.5 Years Later (Does it Hold Up?) | GENTLEMAN WITHINRelated: You might like this in-depth Wolverine 1000 Mile Boot Review 3.5 years later.


How To Wear A Work Boot:

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One word comes to mind when talking about work boots; rugged. I’d rock work boots with plaid flannel, light or heavy vests, hoodies, denim jackets and anything that leans casual. And unless you’re Nick Wooster, I wouldn’t recommend wearing them with a suit.

Don’t be afraid to dirty them up either, they are work boots after all. Out of all the types of boots on this list, I’d say that work boots are appropriate to wear with boot cut jeans because of the boot’s more heft nature. I know, the boot cut style may not in fashion these days, but some men still swear by it.

I personally love rolled up or cuffed blue jeans to pair with rugged work boots like the my Wolverine 1000 Mile boots or Thorogood 6″ moc toe boots. Feel free to rock them with bomber jackets, field jackets, denim jackets and especially canvas jackets that already have a workwear aesthetic. 

If you’re feeling a bit more fashion forward, go ahead and pinroll your pants to show off the boots in all its glory like I’ve done with the tobacco Thorogoods above.

Thorogood Boots Review: 4 Year Update | 6 Inch Tobacco Moc Toe Boot | GENTLEMAN WITHINRelated: You might like this long-term Thorogood Boots Review.

Work Boot Style Inspiration:

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Allen Edmonds Dalton Brogue Dress Boot | GENTLEMAN WITHIN
Men’s Dalton Boot in Dark Chocolate: Allen Edmonds

What Is A Dress Boot?

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

This pair in particular I had my eye on for years and finally pulled the trigger. It’s the Allen Edmonds Dalton Wingtip Dress Boot in a chocolate brown color. I chose dark brown because it’s the most versatile dress shoe color and shade. It’s crafted with premium calfskin leather upper and Goodyear welted construction which makes the soles recraftable after they wear out over time.

Where to Buy Dress Boots

How To Wear Dress Boots:

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Valentine's Day Look 4: All Tied Up 1 | GENTLEMAN WITHIN
Valentine's Day Look 4: All Tied Up 2 | GENTLEMAN WITHIN

If I had to choose between a normal dress boot or one with broguing, I’d choose the latter simply because it’s more versatile. It can be worn formal with a suit and with more casual looks, including jeans, cords and wool trousers. I featured these brogue dress boots in my Valentine’s Day Lookbook. The brogue dress boot is underrated and one of the best boots for men, in my honest opinion.

Dress boots are the most refined pair of boots on this list and so you can wear them with a suit and tie, no problem. In the winter time, I like to rock my Allen Edmond Dalton’s with outerwear like a topcoat or pea coat that fits perfectly with a dressier aesthetic.

Brogue Dress Boot Style Inspiration:

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All stylish men know the value of wearing boots come fall and winter seasons. It’s taken me years, but I’ve built up a pretty solid boot collection, and I’m glad to have a pair for virtually any occasion from date nights to hikes and ball games to running errands. Still hesitant on those cowboy boots, though.

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

Catch ya on the next one!

7 Awesome Boot Styles For Fall/Winter + Styling Inspiration | GENTLEMAN WITHIN

Editor’s Note: This post was originally published on November 12, 2017 and has been revamped and updated for accuracy and comprehensiveness.


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