How to Wear Boots 102

How To Wear Boots 102 – Beyond The Basic Boot Styles

We discuss how to wear boots 102 or boot styles beyond the basics.

If you are new to boots, please check out our other video about the 5 basic boot styles first. Once you have your basic boots covered, it’s time for some advanced styles.

Button Boot, Work boot, suede boot, and windtip boots in brown and tan

Button Boot, Work boot, suede boot, and windtip boots in brown and tan

Button boots

It’s this beautiful two-tone boots with buttons.

Who are they for? They’re for men who like elegant formal outfits; dark suits like charcoal, maybe a stroller suit, or a morning coat.

They’re definitely a statement piece because they’re contrasting like a spectator and so they stand out from the crowd. It’s also a great option for you if you simply don’t want a boot that anybody else has because there’s a very small number of people who actually have them. It’s also great for people who love vintage clothing because it can give you that vintage look.

To learn how to button these boots, please check out our in-depth guide.

Black and off-white button boots with striped trousers

Black and off-white button boots with striped trousers

What colors should you get them in for? Well, traditionally, you have a black box calf leather at the bottom upper and then a contrasting white or off-white suede top. Today, you can also find them with fabric inserts such as tweed. Maybe in some contrasting leather, you have brown, or you can have red with black. Basically, the sky is the limit.

Who is this boot not for? Obviously for people who are just starting out with boots but that goes without saying. It’s also not a boot for you if you’re not into formal clothing unless of course, you go with tweed and something in brown but that’s very unusual and only available made to order. It’s also not a terribly modern look so if you want to be cutting edge, this is not the boot for you.

Work boots paired with denim

Work boots paired with denim

Work boots

As you can see, it’s dirty, it has scuffs, because it’s used to work outside and so there are signs of wear. Work boots are perfect if you are in the construction business, if you work outside a lot, if you’re very physical, or if you love your yard and your garden and you just need something that withstands the elements. They’re also good for electricians and sometimes they come with steel toe caps so your feet are protected.

In recent years, these boots have become very popular with hipsters who wear high-end expensive denim jeans and flannel shirts. If they have a tattoo, a beard, and a disconnected undercut.

Work boots leather sole

Work boots leather sole

The most well known popular brand is definitely Red Wing who recognized this trend and so besides the regular work line, it created a heritage line. Even though it emphasizes the craftsmanship of the boots, it’s clearly a more fashion-driven brand.

Redwing Heritage Boots

Redwing Heritage Boots

Outside the US, these kinds of work boot styles for city men are popular in Japan & Germany, and many other countries. Thorogood is another US made brand and it’s very good. I’ve been using those for years and I can vouch for the quality. As you can imagine, I only wear them when I actually work outside.

Other brands you can look into include Eastland, Wolverine, and Danner. For work purposes, a Vibram sole is great because it’s rubber, it gives you extra grip but you can also find them in different kinds of leather soles or rubber soles.

Work Boots in burgundy oxblood

Work Boots in burgundy oxblood

What color should you go for? Traditionally, this is a kind of mid brown. If you want something different, you can go with dark brown, something in burgundy or even sand. Since it has that outdoor work heritage, black can simply be too formal.

Who’s this boot not for? If you wear a lot of suits and you like formal outfits, this is not the boot for you. Ideally, this pairs well with denim, not even well with khakis, so if you’re not into denim, don’t buy this boot.

Moc Toe Boots

Moc Toe Boots

Moc toe boots

Another variation to the classic work boot. It’s inspired by the moccasin and although the construction is not a true moccasin, it has a similar look.

Who’s it for? It’s for men who like the traditional look of the work boot but they don’t need the performance aspect, it’s simply for the looks. The moc toe will usually have a white rubber sole and they’re perfectly fine to wear for a start-up office or a casual office environment.

What colors should you get moc toes in? I personally think mid brown or even better, burgundy because it goes well with colors, not just blue but other shades.

Lace-up wingtip boots with Off White Fort Belvedere Boot laces with Cords

Lace-up wingtip boots with Off White Fort Belvedere Boot laces with Cords

Brogue boots or the Wingtip boots

This style comes in lots of different versions and I just like it because it goes so well with fall/winter outfits and it has a typical full brogue look and as a boot, it’s just slightly warmer and I even prefer it to a regular shoe.

These boots may come in a very thick sole or you can go with something thinner that is more elegant.

Who are these boots for? Men who love flannel suits, or tweed, or any other kind of winter fabric. They pair supremely well and always looks stylish. They also look great with denim, corduroy, chinos, or any other kind of casual pant. Honestly, I can’t think of a man who can’t wear this boot. Obviously, if you’re into brogues, this is the boot for you.

if you get them with a thick leather sole, they can even double duty as a hiking boot.

Tan Wingtip Lace-Up Derby Boot with Blue Grey Boot Laces Round Waxed Cotton - by Fort Belvedere with black corduroy trousers

Tan Wingtip Lace-Up Derby Boot with Blue Grey Boot Laces Round Waxed Cotton – by Fort Belvedere with black corduroy trousers

What colors should you get them in? Personally, I like tan a lot because it’s contrasting so if you have a black, dark brown, brown, or navy blue pair of corduroys, jeans, or chinos, it really stands out.

Maximum versatility, though, I think you should go with a cordovan oxblood color. This here is a cordovan boot and it goes with a lot of outfits, it’s not as flashy but I used some shoelaces to get a different look. Obviously, I did the same thing with this boot. The great thing about having different boot laces is that you can achieve a different look simply by exchanging a very inexpensive pair of boot laces.

Who’s this boot not for? Honestly, almost any man can wear it but it’s not for you if you like clean, simplistic lines and a minimalist design. Then, you should rather go with Chelsea boots or the Jodhpur boots.

Blue suede boots with Glen plaid trousers

Blue suede boots with Glen plaid trousers

Suede boots

If you live in a dry climate, I suggest you get a suede boot. Simply because it has a wonderful texture, it’s very different from regular box calf or cordovan boots and it is casual and it oftentimes comes in different colors, they’re not super classic but still very, very good to combine in a classic inspired men’s wardrobe.

Duck boots in the making at LL Bean

Duck boots in the making at LL Bean

Duck boots

If you live in a colder, rainy climate, you should probably invest in a pair of Duck boots. In the early 20th century, Leon Leonwood Bean came back from a hunting trip and had wet feet so he decided to do something about that. He went to a local cobbler and had a regular boot combined with a rubber boot. It turned out, it was a fantastic idea. In 1912, he acquired a mailing list. The ad read:

 “You cannot expect success hunting deer or moose if your feet are not properly dressed. The Maine hunting shoe is designed by a hunter who has tramped the Maine woods for the last 18 years. We guarantee them to give the perfect satisfaction in every way.”

Now obviously, this kind of marketing wouldn’t quite fly today but back then it really worked and people bought the boot, loved it, and that’s why L.L Bean is still around today.

Duck Boots from Schnee's

Duck Boots from Schnee’s

Why are they called Duck boots? Well, hunters in the marshy waters of Maine, Massachusetts hunted for ducks and so this hunting boot eventually became the Duck boot. Today, it’s worn by people who hunt anything, not just ducks. It’s also for people who just want warm feet when it’s cold outside or when it’s raining. It certainly has a very unique aesthetic. Personally, I’m not a huge fan of it but they’re very functional and definitely a classic.

Who are these boots for? They’re good for men in wet or cold conditions. There are lots of companies producing these kinds of boots, one of them that has a pretty high-quality comes from Bozeman, Montana and they’re called Schnee’s. Ironically, Schnee’s the word for snow in German. They promise to make boots that go even to -4 degrees Fahrenheit.

What color should you get? Primarily, the color doesn’t matter but most of them come in a shade of brown.

Who’s this boot not for? Basically, for all people who don’t need a functionality because hands down, it’s an ugly boot.

side zippers are a big No No

side zippers are a big No No

Side zippers on boots may seem like a good idea because they’re convenient but I would stay clear of them because usually, they wear out prematurely and exchanging zippers on a high-quality boot is a difficult thing and it never looks good.

Stick to regular, traditional boots that are lace up. It may take you a few seconds longer to get in but you can keep those for years to come.


How To Wear Boots 102 - Beyond The Basic Boot Styles
Article Name
How To Wear Boots 102 - Beyond The Basic Boot Styles
A quick primer on boot styles beyond the basics, what to buy, & how to wear them.
Gentleman's Gazette
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10 replies
  1. Chris says:

    Nothing about combat boots? What about Gentlemen with a little more piss and vinegar – punk rock sensibilities?

    • Matt D says:

      Arghhh! I actually work at a supply depot for a military base and we get NIB combat boot returns all the time. By reg, we’re not allowed to re-issue personal wear items. Often thought of ways to repurpose and make them more presentable ( the sage colored suede look very versatile ) but it looks more trouble than it’s worth.

      And while the traction is excellent, my experience is they KEEP tracking lugs of dried mud WEEKS after you’ve last worn them outside. The newer models are much lighter so if the “tread” could be ground off, might be useable?

  2. Matt D says:


    Hate to keep sounding like an AE shill but, they have a great drop down tool where the shopper can SEE how the boots/shoes will play against, khakis, grey, black, blue, pin-stripped, jeans, dark jeans etc. BEFORE making any purchase. Saves a lot of heartburn. Also nice to show the wife so she can kind of coordinate what she might be wearing for an event.

  3. Mike Frizell says:

    I am from Oklahoma and I wear hand made JB Hill cowboy boots with jeans exclusively. Oh except the once a year “Painted Pony Ball”. A local charity ball that is “black tie western”. I DO NOT wear jeans and a tux jacket! I have a vintage RR western tux jacket, vintage tartan black and deep green Purple Label trousers that go great with my black lizard boots.

    My point is being and dressing to who you are is way more important than any “rules” of dress. If I were from a large NE city cowboy boots would look to Urban Cowboyish. But living in Tulsa Oklahoma I think it’s a great look. I like to call it “Cosmopolitan Cowboy”.

    Thanks for the blog Sven! I have gotten many cool ideas from it!

    • David Barker says:

      I have the trilogy boot from Heritage Boots in Austin TX. I often wear them with a gray suit. Not all of my boots are western, but my favorite ones are.

    • B Lyles says:

      Absolutely agree with Mr Frizzell. I’m in TX, and appreciate all forms of fine footwear but would want to be buried in my 14 inch tall cowboy boots. It’s who we are. So many leather and style options. Related to Lefty ?

    • Bill Quick says:

      I just acquired a pair of Alden for Epaulet Brixton brogue boots in a medium brown. Love them. But then, I love just about everything Alden makes. A pair of my Alden LHS in shell cordovan are back at the factory right for for their first restoration. At my age, they may never need another.

  4. Bill Quick says:

    Sorry, but Bean Duck Boots aren’t ugly. Or, at least, their ugliness – or beauty – is in the eye of the beholder. And here in northwest Indiana, nothing looks more handsome to me than my toasty warm feet encased in thick woolen socks and my well-used Duck Boots when the wind chill is hitting 30 below zero, as it was a couple of weeks ago, and I’m trudging through 14 inches of snow.

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