What to Wear with Military Boots Men

During winter season, you will find these military boots very essential because they cover your feet very well and they ensure that your feet stays warm the all day. These military boots differ in style; we have the short military boots and those which go above the ankle.

For beginners, I suggest you opt for short military boots, the ones which stop just around the ankle; the best example is boot (1). Knee high military boots are for those who are comfortable with heavy boots; however, these boots are warmer than the ankle military boots because they cover almost the all leg, so they tend to be the best boots for winter.


What to Wear with Military Boots Men

What to Wear with Military Boots Men



The good thing is that these boots come in many colors and styles, so you can have more than one option of styling them. For those who want to wear these boots in a British style, you might opt for British colors like blue, black and brown.


If you want to wear boots with suits, then you should opt for Chelsea boots not military boots. Chelsea boots are formal boots so they match well with suits, yet military boots are casual boots, they only match with casual outfits.

Today on Olixe, I have compiled a list of the best military boots every man would love to wear, at least you will find a boot of your interest on this list, i have listed both knee high and ankle military boots with tips on what to wear with them.


NOTE: Links to stores where you can buy these Military Boots for men are listed at the end of this post.



  1. 1.

    ‘Baggy’ Leather Roll Down Boot

Military Boots 1


  • Polo Ralph Lauren Men’s Ranger Lace-Up Hiking Boot – $95.00
  • Polo Ralph Lauren Men’s Ranger Lace-Up Hiking Boot – $36.99
  • Mens Boots – Forced Entry Tactical W/Side Zipper – $59.99
  • Timberland Men’s Earthkeepers 6″ Lace-Up Boot – $97.19
  • Bates Men’s Delta-9 GTX Side Zip Work Boot – $139.99

This fold-over tongue and collar military boot is good for everyone, it does not matter if it is your first time to wear military boots, you will feel comfortable in this fold over boot. Folding them over will make them look like ankle boots, and for those who want to wear above the ankle military boots, all you have to do is to re-fold the boots and tie the laces up to the top. These boots feature lace-up style, vegetable-tanned leather upper and a rubber sole which makes them light and easy to wear on both hot and cold days.

What to wear with fold-over military boots men?

Tip 1: My first guess will be jeans. Due to the fold-over style, you can wear these boots with skinny jeans because these jeans have a narrow bottom, so you can wear the boots over these skinny jeans, this will allow you to show off the fold-over style. If you decide to wear buggy jeans with these boots, it will require you to tie-up those laces, because buggy jeans don’t look good on fold-over boots.

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Tip 2: Do you like skinny cargo pants, if yes, these military boots will match well with those skinny cargo pants. You can complement the trend with a round-neck t-shirt and a casual biker jacket.

Tip 3: Now let’s go to shorts, ware these fold-over boots with shorts, my best guess will be cargo shorts or denim shorts. Khaki shorts will not match well with these boots.

  1. 2.

    Basket Butch’ Boot

Military Boots 7

With its rugged look and sneaker style, this basket butch military boot will make you look fashionable. It is true, good things come to those who wait upon them, now you can wear a military boot which feel like a sneaker, it is too light and comfortable, so whoever has issues with wearing boots for long hours, this is not just a military boot. This boot features leather upper, synthetic lining and a rubber sole.

Tips for styling this Butch Military Boot:

Tip 1: Judging from their rugged style, you can wear them with damaged jeans. To add value to your trend, you can opt for a v-neck slim fit t-shirt and a black leather or biker jacket. Make sure you complement the boots with a big buckle black leather belt. Since they have laces, you can loosen up the laces so that you tuck-in the jeans in the boots.

  1. 3.

    Post’ Boot

Military Boots 2

This post boot looks great and it has a perfect fit, the boots are light weight and comfortable so you can wear them for longer hours, they have supper soft leather which makes them versatile. This Post Boot features leather upper, lace-up style, man made leather sole and a round toe which will ensure that your feet gets no pressure.

Styling Tips for this Post Boot:

Tip 1: I will go with skinny jeans; the slim design of these boots makes them compatible with skinny jeans. To look fashionable, you can wear the boots over your skinny jeans, and then complement the trend with flannel shirt or slim-fit t-shirt.

Tip 2: Since these boots have a classy style, you can also wear them with slim fit pants or trousers, to look stylish, you will need to tuck in the pants with the boots, then wear a causal shirts and a blazer over the shirt.

  1. 4.

    Leo’ Boot

Military Boots 3

After putting on these Leo’ boots, you will feel like your putting on dress shoes, they feel so comfortable and their leather is too soft. Some times it is very hard to rate a shoe until you own them, but judging from their design, I can tell that these are great boots. They feature a zip on the side which makes them easy to wear, so if you don’t want to go through the hassle of lace-ups, you can use the zip on the side. These Leo boots feature lace-up style, leather sole, soft leather upper and leather lining.

What to wear with this Leo Boot?

Tip 1: When it comes to styling these Leo Boots, you will team with both skinny jeans and straight leg jeans. Boot cut jeans will not look good with these boots because they have a wide bottom which might add weight on the bottom when you fold them or tuck them in the boots.

  1. 5.

    Montgomery’ Lace-Up Boot

Military Boots 4

Guys, this is the type of military boot you can wear to work, it has a formal classy design which makes them unique and fashionable. They have a warm insulated liner which makes them comfortable, so you can wear them for longer hours and feel no discomfort or pressure on your foot. The insulated liner makes them perfect for cold winter weather, but I’m no so sure if you can wear them in summer. If you ride a motorcycle, you will need these boots because they fit well and they look fashionable so you can team them with business professional dress codes. The boots feature a round toe, man made upper leather, Rubber / leather outsole, lace-up style and a pull up style which makes them easy to wear.

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What to wear with this brown Lace-up military boot?

Tip 1: If you want to wear them to work or any professional activity, you can team them with straight leg denim jeans. Make sure the jeans have simple fade because the boots look a bit formal. To look stylish, you can wear a dress shirt or check long sleeved shirt and complement the boots with a brown leather belt.

  1. 6.

    Locke’ Plain Toe Boot

Military Boots 5

Now, this is what I call a real military boot, forget about those short ankle boots, this one rocks, if you want to hit the streets this weekend in a trendy style, then these toe boots are the best option. During cold days and winter, you will need to wear boots which will keep your feet warm, and this above the knee military boot will do that job. You can wear it with both skinny jeans and straight leg denim jeans. They feature a raised toe, a rubber sole, leather / suede upper, side zip and a lace-up style.

Their so many ways of styling these boots; for example,

Tip 1: You can team them with a narrow leg denim jean, then complement the trend with a long sleeved shirt, to look fashionable, wear a buscoat and a casual blazer, you can fold the sleeves of the blazer and the shirt.

Tip 2: You can also wear them with shorts or Capri pants. Since these boots go above the ankle, you will look smart if you team them with either shorts or Capri pants. For example, you opt for a leather Capri pant, then wear a slouchy long sleeved t-shirt and a black leather buscoat.

Tip 3: For those who love leather pants, this is the best military boot you can wear with leather pants. Opt for skinny leather pants, black or gray will look good. Complement the pants with a long sleeved sweater t-shirt.

Tip 4: Since they have a real military look, you can wear them with military pants. But this will depend on the laws in your country, some regions they don’t allow civilians to wear military clothes, but if it is okay in your region, then complement the military pants with a v-neck t-shirt and a long tweed jacket.

  1. 7.

    Morrison’ Cap Toe Boot

Military Boots 6

This is a cap toe military boot, it has a very soft upper leather which almost floppy, its rubber sole makes the boots durable. For those who love ankle military boots, this is a great option for you. You can wear this Morrison’ Cap Toe Boot with jeans. To look stylish, you can match your jeans with a biker jacket or denim jacket, and then complement the boots with a black leather casual belt.

  1. 8.

    Diesel Men’s Mil Boot

Military Boots 10

Diesel is a pioneer in both denim and casual outfits, so if you think of rocking the club and streets this weekend with something crazy and unique, i guess this Diesel Men’s Military Boot will be a good choice. It is very comfortable because its leather is soft, so you will feel no weight , the side zip makes it easy to wear these boots. You can team these boots with skinny jeans and narrow leg denim jeans.

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You might call this color brown or Licorice, what ever the case; the boots are classy and fashionable.

I know of some men who want to be noticed once they enter a room, these boots have a sole which is sturdy, so they make a great sound when you walk.


  1. 9.

    Mens Boots Military Combat Style Shoes

Military Boots 9

What ever you need in a military boot, you will find it in these short military combat boots for men. I might not know your needs for a military boot, but when it comes to things like comfort, durability and style, these Polar Fox boots rock. They feature a rubber outsole, faux leather upper, lace-up style, ankle length. The boot comes in two colors, brown and black.

You can wear them with denim shorts, damaged faded denim jeans, skinny jeans , leather skinny pants and skinny cargo pants.

  1. 10.

    Rocky Men’s C4T Tactical Boot

Military Boots 8

Rocky Men’s C4T Tactical Boots are real military boots, the one you can wear and go hunting, you cam also wear them as fashion boots, but they only look good with cargo pants, military pants and jeans. Don’t wear shorts with these tactical boots, you will look awful. What is funny, they look like boots, but once you wear them, you will feel like your wearing sneakers, the laces are well spaced which makes them easy to tie. They feature leather textile, rubber sole and spaced lace-ups.


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On this list you have seen both short and above the knee military boots. Judging from the picture above, the best way to wear these boots is by teaming them with jeans. I like the guy who wore twisted faded jeans with a flannel short and military boots, he looks casual and smart. Complementing your trend with a tweed jacket like the guys in the picture above is also a wise idea, but if you don’t have a tweed jacket then opt for biker leather jackets.

Feel free to ask a question or leave your comments and thoughts below…

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