3 Boot Styles Every Man Needs

Ditch the sneakers, gentlemen. 

A sure-fire way to elevate your style is to strap on something a little more formal, more classy, more masculine. Yes, I’m talking about a pair of boots. 

But with so many types of boots available, which ones are must haves and which are just nice to have? 

Today, I’m diving into the three most essential boot styles for the stylish man. 

#1. Chelsea Boots

First up is the Chelsea boot. Typically made with just one or two pieces of leather around the upper with elastic gores at the side, this slip-on boot is an excellent balance between formal and casual. 

There are two predominant styles of Chelsea boot: the chunkier English style, typically done with a rubber sole and Goodyear welt, and the slimmer European style with a leather sole and Blake stitching. 

If you like to pair your boots with jeans, try the English Goodyear welted style. But if you really want to impress, try the slim, European Blake stitch boot paired up with a tailored suit. 

I’ve added this as the #1 most essential boot for men because of its versatility in your wardrobe. One word of caution, however: these really look best if you’re wearing tapered slim trousers or jeans. With straight cut pants, the slim, sleek silhouette of the boot tends to drown. 

#2. Service Boots

While Chelsea boots have a more contemporary vibe, service boots recall the 1940s with their military aesthetic. 

But make no mistake, these boots aren’t just utility. Service boots from companies like Oliver Cabell and Thursday Boots are made with slimmer profiles than their military-grade counterparts. 

This makes for a rugged and masculine boot that’s quite stylish. 

This style is often made with a cap toe and features a steel shank. Some folks prefer nickel eyelets, which is a feature commonly found on miner’s boots many years ago. 

Service boots aren’t quite as versatile as Chelsea boots; you probably can’t get away with a rugged pair of boots tucked under your suit. But with a cuffed pair of jeans, there’s hardly a more manly look. 

#3. Chukka Boots

And to round out your collection, consider a simple pair of chukka boots. There are so many varieties of chukka, ranging from the super simple Desert Boot to more elegant versions made with tighter construction. 

I’m biased toward a more simple chukka. 

These make for ideal footwear in casual situations. Say you need to run some errands — sure, sneakers are a safe bet, but why not snazz things up a bit with a boot? Chukkas often slip on so you can jet out the door. And like most leather boots, they pair with nearly any trouser you can think of. 

Before investing in a pair of chukka boots, get clear on what type of shoe sole you’d like. Many are made with crepe rubber soles, which can lead to some surprises if you haven’t had any experience with the material. 

Crepe rubber is unusually porous and picks up a lot of dirt. Don’t be surprised if that cream-colored sole turns grey within a few months. And if that doesn’t sound appealing to you, find a chukka with a more standard vulcanized rubber sole. They last longer and don’t discolor as easily. 

What Will It Be?

How many of these boots do you own? All 3? 

Elevating your style is a journey, and remember to buy quality over quantity. It’s better to have one stunning pair of Chelsea boots that you wear daily than to have three shabby boots that you regret buying. 

And if you need any help choosing the right pair of boots for your style, make sure to hit the contact button above and drop Adam a line!