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Your Guide to Wearing Men's Boots
23 · 10 · 2020

Your Guide to Wearing Men's Boots

Written by Tigre Haller

Haven’t you ever wondered what kind of boot to wear with what outfit? I know I have.

Fortunately, there are many options for men’s boots available. You can choose from extremely casual, to extremely dressy and everything in between. But, it can get a little overwhelming and frustrating.

Have no fear, your boot guide is here.

This article will help you understand the different boot styles available, and clear up the mysteries surrounding them. We’ll also look at the different types of leather and suede boots are made from, and how to wear each one. And you can look forward to getting some quick tips on basic boot care.

Are you ready? Good, let’s get started.

How To Wear Work Boots

Dowler Boots - Pull-Up Leather

Inspired by the gear worn by lumberjacks, construction workers and others, work boots found their way into mainstream men’s fashion a long time ago.

Boots like our Dowlers in pull-up leather, pictured above, took their inspiration from work boots and this particular edition performs really well in rough and tumble situations. Pull-up leather is one of the hardiest materials you’ll ever find, it takes on scratches and bruises like nobody’s business and is easy to maintain.

If the pull-up leather isn’t your thing, smooth full-grain leather is amazing. You can either polish it to high shine, or leave it alone to age on its own and it will always look fantastic.

By their very nature, these boots tend to be rugged and it’s always a safe play to pair them with jeans and casual pants. Heavier fabrics and darker colors always look great with these types of boots. The white t-shirt and blue jeans look never gets old. Layer it with a flannel shirt and you’re good to go.

Chukka Boots

Laval Chukka Boots - Brown

As I wrote about in my article, Best Styles For A Versatile Shoe Collection, the origin of Chukka boots are a bit of a mystery. Were they created for polo players, made for British soldiers on tour in the South African desert or for strolls around the Indian countryside?

I love a good mystery, and this is one best left unsolved. It only adds to the allure of the ankle boot that became a mainstay in the closets of royalty, pop stars and everyday people over the last century.

“In any case,” I wrote in the above-mentioned article, “the ankle-length, clean lines, thinner sole, open lacing system and two to three eyelets of the Chukka makes it a great choice for when you just want to kick around, or sport a casual look. The formality factor is influenced by the material the upper is fashioned from. For example, calfskin leather is dressier than suede or rugged pull-up leather... The type of sole also changes the overall appearance with leather being more elegant as can be seen in our sleek Ellis Chukkas, whereas crepe or rubber signals informality displayed nicely with our Laval Chukkas.”

Keep in mind that Chukka boots reside on the casual side of things, and you can wear them comfortably with relaxed suits, lighter fabrics, nice jeans, cords and shorts. Top off your look with polo shirt, a crisp t-shirt and a jacket or sweater.

Chelsea Boots

beckett simonon preston chelsea boots

Many guys consider Chelsea boots to be the ultimate in “cool.” Slender, sleek and sexy, this style always looks amazing.

Just like Chukka and Jodhpur boots, Chelseas were created for purely utilitarian purposes. This time around the boot was made for Queen Victoria as a convenient riding boot, and one she could stroll around her vast estates in.

I also talked about this now famous style in my article noted above,

“With the introduction of vulcanized rubber, the shoemaker had the perfect solution: create flexible, elastic side walls for normally constricting boots. This also eliminated the need for laces which the queen complained about getting caught in the stirrups.” 

They’ve come a long way since the Victorian era, and have been adapted many times. One of my favorite versions are the Bolton Chelseas in Chestnut suede. There’s something rich about the cool combination of color, style and material. The elements all come together to create a boot that’s at once casual yet dressy.

If suede doesn’t do it for you, go with the soft and smooth calfskin leather. Either way, you’ll be stepping-out in true style and comfort.

Chelseas look great with tapered suits, slim fitting jeans and trousers or ankle-length pants. It’s all about symmetry and clean lines.

Jodhpur Boots

Douglas Jodhpur Boots

Jodhpur boots came to life in the 1920s when they were first introduced as a horse riding boot. Just like the Chelseas before them, they caught the eye of fashionable folks and migrated from the playing field to the street.

The signature component of the Jodhpur makes it one of the most difficult men’s boot styles to make: the thin strap that wraps around the ankle and joins a slender solid brass buckle at the top of the shaft. Getting the proportion and length of this strap just right is something of an art in and of itself.

When done right, as you can see in our Douglas Jodhpurs, it really sets this boot apart from others. Not only is the strap significant, the vamp is formed by a single piece of curved, hand-cut full-grain leather for a streamlined profile and the collar has to hug your ankle without being too tight.

Jodhpur boots aren’t for everyone, but if they fit your personal style, enjoy wearing them with tweed, flannel, casual suits, jeans and corduroys. You might even want to try the "biker" look with jeans and a leather jacket.  

Balmoral Boots

Elliot Balmorals

Moving further into the realm of formality, we have the royal household of Queen Victoria to thank - yet again - for this distinguished style.

Legend has it that the queen’s consort Prince Albert, an avid outdoorsmen, preferred rambling around the wet grounds of their Scottish castle Balmoral to dealing with courtly activities. And, he really didn’t enjoy the constant changing of clothes his office required.

So, to help ease the pressure, the prince had the royal shoemaker J. Sparkes Hall create a boot he could wear indoors and out. One that had to be useful and stylish.

And the prince was presented with what would become known as the Balmoral boot, or the Bal. Boy, was he one happy prince.

Looking at our Elliot Balmorals above, you can see that the bottom half, called the golosh, is attached to the upper by a row of stitching running from the facing to the the quarter. This is unique to Balmorals. The row of hand-punched broguing adorns the toe-cap adds an elegant accent and the closed lacing system gives the Elliots the appearance of an Oxford shoe.

Wear this rare style with smart suits, tweeds, flannel and tapered jeans.

Side-Zip Boots

Easton Side Zip Boots

Rounding-out our lineup of men’s boots styles, is one of the dressiest you’ll come across: the side-zip boot. Actually, that’s a bit untrue since not all side zip boots are dressy, unlike our Easton Side-Zip Boots.

What distinguishes the Eastons from other side-zip boots is their slender, sleek profile and the appearance of an almost wholecut shoe. Also, the zipper itself is discreetly hidden by a flap of full-grain leather. You’ll know its there, but no one else will unless they really look closely. The flap also adds a neat decorative element to the overall appearance.

The ankle hugging shaft lends itself so well to the tapered look. Wear these dress boots with bespoke or highly tailored suits, nice chinos and fitted jeans for an attractive look day or night.

How Your Boots Should Fit

It really doesn’t make much sense having a pair of boots that look amazing if they don’t fit correctly, does it?

When testing your boots to make sure they’re right for you, keep these tips in mind:

  • Wear the type of socks and inserts you would normally wear with them.

  • Try both boots on at the same time (be sure you are on a soft surface to avoid scratching or damage in case you need to exchange them.)

  • Walk, trot, dance and move in anyway you would when wearing the boots out in your daily life. The idea is to really understand how your feet feel in them.

  • Your heel should fit comfortably without coming out of the boot or rubbing against the back.

  • There should always be about an inch of room between your longest toe and the front of the boot.

  • Make sure the boot bends where your foot bends.

  • Your feet should feel secure, not pinched or squeezed.

  • Roll your ankles side-to-side so you can make sure they won’t twist.

  • Keep in mind that your feet will swell throughout the day so, ideally, you should try them on at the end of the day.

Caring For Boots

Much like leather shoe care, you should carefully look after your boots after each wear. That means taking some basic steps to ensure they are in the best shape possible:

  • Always insert cedar shoe trees after each use to wick away excess moisture and help maintain the boot’s shape.

  • Remove any dirt or flaking mud with a soft-bristled brush.

  • For caked-on mud, dilute dish soap in warm water and wipe down the area with a soft cloth until the mud is gone.

  • Always let air dry away from direct heat or sun to avoid the leather getting too dry or cracking.

  • However, once dry you can heat the boots under direct sun to soften the leather just a bit before conditioning.

  • Treat your leather boots to a nice conditioning every two weeks or so, depending on the need. Then polish them up with a natural compound like Saphir Cream Shoe Polish.

  • Suede requires a little special attention, but it’s actually pretty easy to care for. Click on this link to find out How to Care for Suede.

  • Pull-up leather requires the least amount of looking after and you can remove most scratches by rubbing the surface with your finger. The heat of your touch will activate the waxes and oils and the blemish will disappear. That area will also become a little lighter and the boots will start to develop a highly unique patina unlike what you see in other types of leather.

  • You can find out much more about shoe care and maintenance in this informative article article written by my colleague Gavin.


I hope you found this guide useful and inspiring. There are so many boots to choose from, and you can start by checking-out Beckett Simonon’s exciting collection of Lace-Ups, Chelseas and Jodhpurs. Whatever style you choose, remember these guidelines and let yourself have fun.

Please let us know how you wear your boots by leaving a comment below.


David macy Aug 26, 2021

I really enjoy these articles, they’re very interesting and informative. Thank you!

Mark L. Aug 26, 2021

I am thoroughly enjoying wearing my Douglas Jodhpur boots from Beckett Simonon. I chose the Bordeaux color and couldn’t be happier. They look terrific with gray or navy dress slacks, as well as deep indigo blue jeans. One of the very best things about Beckett Simonon boots and shoes for me has to do with the last—no matter what style I have purchased, each pair has fit my feet perfectly, securely, and comfortably. These really are all-day (and half the night) footwear, even when brand new out of the box. I cannot recommend Beckett Simonon enough. The quality and craftsmanship obvious in each pair is phenomenal. And through emails and their website they open the door to their customers, exhibiting their high standards and transparently sharing their mission and commitment to excellence, while at the same time being welcoming and friendly. I can’t say that I won’t try footwear from other quality companies in my life, but I could be completely satisfied if I only had Beckett Simonon to choose from!

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