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.
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.
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.
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.
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.
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.
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
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.
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.
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.
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.
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.
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 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.