Boots For Men - What Styles You Should Buy & What Mistakes To Avoid

Boots For Men – What Styles You Should Buy & What Mistakes To Avoid

In another video, we discussed the first two men’s boots every man should buy but today, we’re going to dig deeper and figure out who boots are for, who they’re not for, and what you should look for. Unfortunately, there’s not one boot that works for everybody because we all have different needs and preferences.

Chukka boots, striped socks and pinrolled jeans

Chukka boots, striped socks and pinrolled jeans

Chukka boot or Desert boot

It got its name from the polo field where a one-time slot is called “chukka” or “chukker”.

Who’s the chukka boot for?

Ideally, it’s a great boot for students because it pairs with a lot of outfits so if you don’t have much money, you can invest in one pair of boots and it works with a lot of combinations. It’s also a fantastic boot for men who like to wear denim or jeans because it pairs really well. It’s a boot that pairs well with corduroys when it’s cold outside during fall/winter, or with khakis when it’s warmer outside. It’s also great for men who like a soft boot because the leather is usually unlined and extremely comfortable.

Since these boots are much shorter than others, you can see your socks and it pays to have some interesting combinations to just upgrade your outfit especially when you pin roll jeans.

Overall, it’s a boot that can be dressed down with all kinds of casual wear and even with a not so formal suit or combination, it looks stunning.

Allen Edmonds chukka boots in sand paired with houndstooth flannel 3-piece suit

Allen Edmonds chukka boots in sand paired with houndstooth flannel 3-piece suit

What colors should you go for?

If it’s your very first boot, I suggest you go with a dark brown, a choco brown, or a mid brown because it’s most versatile. If you already have boots in those colors in your closet,  I suggest you go with something lighter which is sand because it underlines the casual character of the boot and it just gives you more versatility.

Who’s this boot not for?

If you wear a lot of suits, it’s not the boot for you because it’s very suited to casual outfits. Also, if you like formal wear, be it a stroller suit or a morning wear or tuxedos, not the right boot for you.

It’s not great for the colder times of the year because it’s unlined and it doesn’t insulate very well. To learn more about chukka boots, please check out our full-fledged guide to get tips about what to buy, the history, and anything else you want to know about this wonderful boot.

John Lobb Jodhpur Boots with upside-down alligator strap

John Lobb Jodhpur Boots with upside-down alligator strap

Jodhpur boots

Personally, I like them a lot because they have a very clean, elegant silhouette yet, they have some history. The characteristic of Jodhpurs is the buckle and it goes around. There are lots of variations of it. Originally, it comes from horseback riding and Indian heritage just like many other menswear garments and boots or shoes.

Who’s the Jodhpur boot for?

I think it works really well with casual suits, flannel suits, and sport coat combinations. You can also pair it with a leather jacket or jeans, or chinos. Because there’s no broguing and it’s a flat boot, you can also pair them with a regular suit. It’s great for men who like clean, classic, elegant lines and you don’t just want to buy a boot anybody else has.

brown jodhpur boots with navy blue trousers

brown jodhpur boots with navy blue trousers

What color should you go for with a Jodhpur boot?

Ideally, a mid brown or something lighter, maybe tan, works best and it’s most versatile.

Who is this boot not for?

If you’re in a hurry and you don’t have the time to buckle the boot every time and take it off, it’s not a boot you should go for. Otherwise, it’s a great boot to have in your collection.

Chelsea boots

Chelsea boots have become a timeless classic because they have that insert and it’s easily recognizable especially if you have a colored insert .

Who are the Chelsea boots for?

They’re perfect for men who look for a convenient, easy slip on version of the boot. Even though they’re quick to put on, they are super elegant and classy and don’t look sloppy at all. They’re also great for eccentrics because you can add green, red, or blue inserts that really give you a personal note. They’re also great for men who want their very first boot that is quite versatile that can be worn with suits or casually and you can adapt it to your needs based on if you need a cap-toe or not, broguing or not, and so you can find exactly what you need.

Dark brown chelsea boots with Light Brown and Blue Shadow Stripe Ribbed Socks by Fort Belvedere with glen plaid trousers

Dark brown Chelsea boots with Light Brown and Blue Shadow Stripe Ribbed Socks by Fort Belvedere with glen plaid trousers

In what color and what style should you get a Chelsea boot?

Well, that depends a little bit on what you already have. If it’s your very first boot, I suggest you go with something darker, maybe dark brown, or chocolate brown. You can have some broguing like a medallion, with a cap toe is good because it’s not too casual and not too formal but can be paired with a lot of things. If you like to wear suits in the evening, you may consider black Chelsea boots. If you already have a few boots in your closet, you can consider getting a little more out there and having maybe a suede Chelsea boot in brown, tan, burgundy, or even blue.

So who are the Chelsea boots not for?

Actually, I believe every man should have at least one Chelsea boot in their wardrobe because they are so timeless, versatile, and easy to use.

Brown and Purple Balmoral boots

Brown and Purple Balmoral boots

Balmoral boot

The Balmoral boot is a classic dress boot that works well with formal outfits.

Who is the Balmoral boot for?

It’s basically the choice of elegant gentlemen who want something like an oxford shoe as a boot version. It’s a fantastic boot if you have lots of formal outfits in charcoal, navy, and grey. It’s also fantastic with three-piece suits or you can wear it with a morning coat, or with a stroller suit. If you live in a moderate climate, it’s a perfect boot for winter because it’s warm enough and always very elegant.

black balmoral boots with dark grey socks with houndstooth trousers

black balmoral boots with dark grey socks with houndstooth trousers

What colors should you go with?

I suggest you start with black with black suede insert. If you are more advanced, you can have a contrasting insert in beige or buff or off-white and if you have that, you can move on to something in brown, burgundy, or other colors. It’s a great alternative for a button boot especially if you’re not quite sure about the whole buttoning process and it’s a little more subdued.

Who is it not for?

It’s not for people who like country outfits, who like to wear tweed, chinos, browns, and corduroys because it’s just too formal for those kinds of outfits. Luckily, there are lots of other options.

Winter Boots with corduroys with Fort Belvedere over the calf socks in charcoal and orange

Winter Boots with corduroys with Fort Belvedere over the calf socks in charcoal and orange

Winter boots

If you live in a climate where it gets close to freezing outside, you need winter boots. They may just look like regular boots but they have a wonderful fur lining. With fur, I usually mean sheepskin or lamb skin. It’s quite plush and insulating and cozy warm especially if you’re outside a lot when it gets cold. Of course,

Of course, there’s lots of ugly boots in polyester but as an elegant gentleman who wears a suit, those kind of boots would ruin your entire outfit. For added traction, those boots should always have a rubber sole. Obviously, they come in different styles. If you are more of a casual guy, get them in tan, if you’re more into suits, you should go with a version that’s kind of a balmoral, it’s just like an oxford but with the fur lining that keeps you warm.

Who is it for?

It’s for every man who likes warm feet and does not want to sacrifice style.

Who is it not for?

Winter boots are a high budget item and they are much harder to find so if you live in warmer climates or you’re never outside for longer than 5 minutes, you can skip them otherwise, I strongly suggest you invest in one of them.

No matter what boots you buy, one item that you should invest in is a shoe horn. If you go in without a shoe horn, you’ll damage the shoe and it’ll wear out much more quickly.

That being said, most boots would only come with black or brown shoelaces. While that works, it doesn’t give you much versatility. That’s why we offer more than a dozen different boot laces in different colors because with an investment of a few bucks, you can change the entire look of your shoe and your outfit. This comes particularly handy when you’re just starting out and you have enough money for one boot. if you invest in five or six different pairs of laces, it creates a different look and people may think you have a different boot even though it’s the same just with different shoelaces.


These are just five basic men’s boots that I think should be the first five every man should invest in. Once you have those, there are a lot more boots out there to experiment on. We’ll cover all of those in another video. So stay tuned!

Boots For Men - What Styles You Should Buy & What Mistakes To Avoid
Article Name
Boots For Men - What Styles You Should Buy & What Mistakes To Avoid
An in-depth guide to five essential boots for men; styles to go for and how to combine them.
Gentleman's Gazette
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16 replies
  1. Desmond Jackson says:

    I prefer the wingtip dress boot,in dark brown,oxblood ,walnut and black.It works with all my outfit combinations except for my formal wear.Great job.Every day is a dapper day

  2. Matt D says:

    Had my share of Chukka’s over the years, and while comfortable, mine always seemed to sag in fairly short order, they’re prone to staining and only seemed to work w/ the most casual of outfits. Of course, they look great fresh out of the box!

    What’s worked best for me is a dark, navy blue Cronmok boot from AE. They go from dress slacks to jeans, cords, everything. And never fail to draw notice and compliments. I’m willing to revisit Chelsea boots, but in my youth these were called “Beatle boots” and tend to look better on more slender types. Which I am no longer.

  3. Gary W says:

    Maybe a discussion on cowboy boots needs an entire write up alone. I wear a blazer and tie every day for work and have various dress and dress-casual cowboy boots. A good pair of cowboy boots can set you back several hundred dollars. They dress up and dress down.

  4. Gijsbertus van der Heijden says:

    Very much agreeing with Mr. Matt D. Wearing Chelsea boots, however lovely they are, may be a bit over the top for the man who has grown a bit in weight over the years. Like I have done. Actually I have the feeling that Chelseas, just like the Chukka boot and even the Jodhpur boot may be better suited for younger, taller men. Shorter, and also older men should perhaps look for other boots, especially when they’ve grown a little tummy. I myself like the Balmoral and Button boots, although these are not very much suited for wet or (very) cold conditions. Another great choice may be to get oneself a pair of vintage officer’s dress shoes. These are often very well made, well maintained, or even unworn, looking stunning yet restrained and can be worn for both formal and somewhat more relaxed occasions, even if conditions are somewhat wet or cold.

  5. Matt D says:


    Don’t let me color your opinion too much. I’m probably hyper aware of all the Do’s & Don’ts for older, dapper men. Weight is a factor, but the greater evil may be in overall trouser length. Showing too much boot comes off as missing one’s youth a bit much. It would be my preference people didn’t even notice you’re wearing boots until you are seated or cross your legs.

    As for vintage officer’s dress shoes, I’m already there! Stunning yet restrained describes their statement perfectly. And yes, they’ll dress up OR down. Mixing in military uniforms w/ civilian attire has long been a practice of mine.

  6. Gijsbertus van der Heijden says:


    Wholeheartedly agree. Perhaps the whole thing about the gentlemanly is to balance boldness with restraint and to know how to shift this balance when circumstances such as age, occasion or, for instance, physique, change. This may be true not only for the style with which one will dress oneself, but too for how one behaves and handles one’s affairs in business or public life.

  7. Jbp says:

    Please tell me the brand of the chukka boot with a cap toe in the article above. It also has a lot of cool brouging. Thanks.

  8. Matt D says:


    “for how one behaves and handles ones affairs…”

    So true. The difficulty lies in any time we’re confronted with a new crossroad that begs for, a retooling? There’s reluctance as we feel we’re “not being true to ourselves”. Slaves to our own reputations. Your comment is timely in that a younger gentlemen I know away from work actually had business in my office. I didn’t even realize he was on the premises and before he could announce his arrival, he caught me redhanded dishing out a down-dressing to a junior!

    Something better left to those on their way UP the ladder, not one on TOP of it. One can’t help but wonder if it left him w/ an amateurish impression or even of someone “losing their touch”? Either way, it isn’t favorable. Now I’ve no choice but to add yet another Rule for being a gentlemen. “If you wouldn’t want your FRIENDS to see you like this ( why would you ever do it at WORK!? )” The world has enough “Snakes In Suits”, great book btw!

Trackbacks & Pingbacks

  1. […] Moccasins were made from soft tanned hides of deer or buffalo or bison rawhide was used for the hard soled variety.  Today, you can also find moccasins made of deerskin or moosehide. They were assembled inside out and thus the stitching was hidden. Sinew / Tendon was used for the stitching and holes would be punched through the hide to facilitate it. The knot would be kept on the outside to facilitate comfort. The whip stitch and the running stitch were commonly used. Moccasin construction was fairly uniform across tribes however each tribe had distinctive methods of decoration. These differences also included the cut of the moccasins and the some of the common names of the various tribes such as the Blackfoot and Chippewa are derived from their moccasins. Lavish bead work, quill work and painted designs were used to adorn and decorate moccasins. Women of certain tribes often attached thigh length leggings to their moccasins giving them the outward appearance of boots. […]

  2. […] through the thigh and slightly flared at the ankle. Originally they were wide enough to pair with boots, hence the name, but these days boots are paired with nearly every cut of jean. If you have […]

  3. […] on the 4497S last, this boot certainly allows enough room to wear a thick pair of wool socks. The toebox is round and very […]

  4. […] has become more popular lately. We discuss the origins of the term the history behind these boots, types and style and we provide pictures of […]

  5. […] that the name was derived from the fact that the Polo players preferred to stroll around in these boots after a game rather than in their Polo […]

  6. […] of their upcoming Chukka boots. As always, we told them that we had to see, test and truly like the boots before we could commit to anything. About two weeks ago, we received the sand colored Chukka boots […]

  7. […] it is currently undergoing a renaissance and it seems like more shoemakers are willing to add these boots into their Ready-To-Wear program whereas it was exclusively reserved for bespoke or Made-To-Order […]

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