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 with a pair of high-quality boots.
I’m going to cut right to the chase and show you 7 boot styles for fall/winter—that as a stylish gent—you’ll definitely want to know about.
In this editorial you’ll learn the differences between boot styles and also get inspiration on how you can wear them.
Additionally you can watch the full video directly below which includes many more looks from me that are not in this editorial.
7 AWESOME BOOT STYLES FOR MEN
Now, let’s get started.
1) CASUAL PLAIN TOE BOOT
What Is A Plain Toe Boot?
The casual plain-toe boot is 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 that is handmade with a Goodyear or Blake welt construction. This allows for you to re-sole the boots when they wear down.
How To Wear A Plain Toe Boot:
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.
Plain-Toe Boot Styling Inspiration:
2) CASUAL CAP TOE BOOT
What Is A Cap Toe Boot?
The casual cap-toe boot 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.
How To Wear A Cap Toe Boot:
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.
Cap-Toe Boot Styling Inspiration:
3) CASUAL MOC TOE BOOT
What Is A Moc Toe Boot?
The moc-toe boot is more rugged than the previous two 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.
How To Wear A Moc Toe Boot:
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.
Moc-Toe Boot Styling Inspiration:
4) CHELSEA BOOT
What Is A Chelsea Boot?
The chelsea boot is a laceless boot that is as popular as ever. A distinguishing feature of a chelsea boot 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.
How To Wear A Chelsea Boot:
The classic chelsea boot is a popular option 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.
Chelsea Boot Styling Inspiration:
5) CHUKKA (DESERT) BOOT
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.
How To Wear A Chukka Boot:
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 Boot Styling Inspiration:
6) WORK BOOT
What Is A Work Boot?
Work boots go 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.
How To Wear A Work Boot:
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.
Work Boot Styling Inspiration:
7) BROGUE DRESS BOOT
What Is A Brogue 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.
How To Wear A Brogue Dress Boot:
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.
Brogue Dress Boot Styling Inspiration:
IN THE END
All stylish men know the value wearing boots come fall/winter. 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 ballgames to running errands.
I hope you now understand the difference between boot styles and are inspired by the myriad of ways you can wear them.
Catch ya on the next one!
QUESTIONS OR THOUGHTS ON ANY OF THESE BOOT STYLES?
Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.
Looking forward to seeing you in there.
LIKE WHAT YOU READ?
Get more posts like this plus style tips & advice delivered straight to your inbox.