How to Wear Boots

by Welcome to Outsons
5 Work Boots You Should Be Wearing Right Now

Men have been wearing boots for a long time and they have evolved into something that’s now so much more than just a practical piece of footwear. We’re here to run through some of the best designs out there, as well as the various ways you can fit them into your look. 

How to Wear Boots

With so many types of boots around it can be trying to figure out exactly what style to go for, and no one really has enough time to try on every single design to see which one they like best. To save you some time and help you keep your sanity, we’ll just go through the most popular designs, and the ones that work best with a whole range of looks.

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The Ankle Boot (aka The Chelsea Boot, Beatle Boot, Dealer Boot)

Best known through The Beatles and their overall 60s popularity, the Chelsea boot is a slim fit, streamlined design that tends to be made from a continuous strip of material. Traditionally made from leather, you can now get Chelsea boots in various materials and colours, making them easy to work into different looks.

How To Wear Ankle Boots

First off if you’re wondering what to wear with ankle boots, just remember that they’re a lot more versatile than you’d think. A full suit or slim chinos will work perfectly with the fitted design, and even ankle boots with jeans is a sleek combination. Just make sure that if you’re going for this look you know how to roll up jeans. You don’t want to drown your boots in denim, so a little cuffing might be necessary. 

You can work these sleek boots into a variety of different outfits, and for a simple formal look try teaming some leather Chelsea boots with an all-black suit. It’s a perfect look if you’re wondering what to wear with black ankle boots. The unique boots will create enough of a contrast with the suit to keep things interesting, while still providing a clean, stylish finish. You can also try out a more casual look with skinny jeans and ankle boots, keeping the colours light and the shape of the pieces less fitted. 

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The Desert Boot

The desert boot is one of Clarks’ proud creations and originated from a traditional bazaar in Cairo. Nathan Clark took the design, reworked it and created the desert boot that we know today. Because of its soft, flexible material and handmade style design, the desert boot is ideal for warmer weather, ensuring your feet stay cool and comfortable.

How To Wear Desert Boots

So desert boots are perfect lightweight shoes and are ideal for spring and summer days, but it’s not just typically ‘summery’ outfits that they work with. Desert boots and jeans are a classic combination that’s perfect for autumn days, and throwing on a leather jacket gives the look a casual, stylised twist. You can also go for a formal style by matching a fitted navy suit or blazer with some light coloured boots, creating a breezy, warm toned look.

The Work Boot

The work boot can be anything from combat boots and hiking boots to construction boots and motorcycle boots, with the main aspect of the style being practicality. While any of these can be worn for fashion they still maintain a functional design, usually have thick soles, and are made from sturdy materials, with strong support around the ankles and feet. If you’re wondering how to wear your combat boots though, then read on.

How To Wear Work Boots

If you’re wondering what boots to wear with skinny jeans, then work boots are the answer. Their chunky shape contrasts well with the slimline jeans, helping the outfit to stand out without looking too out there.

Throw on a leather jacket for a clean, alternative vibe and you’re set and is a great option if you’re wondering what to wear with brown boots. Brown boots and jeans are a staple combination, but for a slightly more formal look you can play around with shapes, working in smart longline coats with less structured loose fit jeans. 

How Boots Should Fit

In order to get the right fit when you’re trying on boots, there are a few things you should keep in mind at first.

  • For the best result, you should try on boots in the afternoon, as feet tend to swell over the day.
  • Make sure that you are wearing boot socks so you can gauge the snugness of them.
  • Make sure you try on both boots as most people’s feet are slightly different sizes.

When you’re in your new boots your entire foot should feel snug and supported, but you should still be able to move your foot and your ankle around without any difficulty or pain. Some boots, like best boots for concrete workers and leather work boots, might feel a little tight when you first have them, but as you break them in the heel and the leather will soften, conforming a little more to your foot.


  • Before lacing, push your foot forward so you’re sure you have enough space in your shoe.
  • One finger should fit behind heel, ensuring your shoe isn’t too small.
  • Lace boots and stand.
  • Wiggle your toes. They shouldn’t be pressing right up against the toe of the shoe.
  • Your toes should not touch the end of the boot.
  • Rock up and down, squat and bounce. Your foot shouldn’t move too much in the boot.
  • Stand on sides of feet to test for ankle support and painless flexibility.

If you have narrow or wide feet, you may need to experiment a little with the sizes. The general rule of thumb is that if you have narrow feet you should go down half a size, and if you have wide feet it’s best to go up half a size.

How To Break In Your Boots

There’s a certain amount of pride that comes from breaking in a tough pair of shoes. Despite the fact that you’re literally just wearing boots, getting them past the initial rigid stage to the comfortable, hardwearing one can take a bit of time, so a small amount of pride is understandable. However, if you’ve just got yourself a good pair of shoes and you’re not quite at the celebration part yet – there are some tricks and tips to help soften up those tough boots and make things a little more comfortable on your feet.

Easy Method

There are slow and steady ways of softening out your boots, or slightly faster ones that can be a tad more painful on your feet. One simple way is to slip your boots on in the morning, wear them around the house, and once they start to take a toll on your feet, take ’em off. This is a fairly slow way of softening up your boots, and it could take a couple months till they’re ready to wear, but on the plus side it’s unlikely you’ll get blisters or bruising, so it’s all about the balance.

Standard Method

If the gentler methods aren’t working in softening up your boots, then it’s time to take more drastic measures. One method just requires water, a plastic bag and a freezer. All you need to do is fill your plastic bag up with water, tighten it securely and fit them into your boots. Cover your boots in another plastic bag to protect them and pop them in the freezer. The water freezes and expands, the leather stretches, and you’ve got yourself some slightly less rigid boots.

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Best Method

If you are serious about your boots and don’t mind some hands on work, using mink oil is your jam. If these are brand spanking new boots, you don’t need to do any prep work. Using a hair dryer, soften up the mink oil until it is melted, then using a clean rag or sponge, work it into all the seams and surface areas of your boot. After you have finished coating it, use the hair dryer to melt any last bits of the mink oil. Once you have finished this, let them rest for at least 24 hours. During this time, flex the boot at the toe and the rear, as this is where the natural bends will form.

When 24 hours have passed, take another clean rag and work in the last of the mink oil that is on your boot. Move your cloth-covered finger in small circles, working the oil in as much as you can.  When you finished, buff the whole boot with a pad or rag to remove any remaining oil. If you’ve done this much, you might as well go the full monty and finish it up with some polish. Not only will they be nice and pliant, but they’ll be protected from the elements, giving you many years of fine wear.

How To Clean Your Boots

Most boots can take a bit of a kicking, and some rain, mud, and dust isn’t going to beat them to shreds. However, this doesn’t mean they won’t get dirty, and even if you like a rugged look, boots caked in mud and grime might still be a little too much. Regardless of if your boots are made from there are ways to clean them up without causing any damage to the material, even if you’re dealing with the more sensitive suede.

How to Clean Leather Boots

Leather is one of those materials that can soften up without thinning out and handle water without getting damaged, making it a little more resistant than other materials. It’s therefore a lot easier to clean them without causing any damage, and although you can’t throw them in the washing machine, you don’t have to worry too much about tidying them up.

You only really need a few basic products to keep your leather boots in good condition.

  • A stiff brush.
  • A soft cloth.
  • Detergent.
  • Leather polish.
  • Shoe protection spray.

How to Clean Suede Boots

So suede is a little more sensitive and needs to be handled more carefully than leather. If you’ve just got a pair of suede shoes, before you do anything, grab a good protection spray and spray all over your boots. This will basically help to repel water and dirt, and ensure you can just give your boots a quick brush over from time to time to keep them clean. Re-spray every couple months and you shouldn’t have much trouble with dirt or cleaning.

However if you’ve missed the option to use the spray, and your suede boots are looking a little worse for wear, there are a few ways you can smarten them up. You’ll need:

  • A soft brush.
  • Newspaper to stuff the shoes.
  • Suede eraser.

How To Store Your Boots

If you have seasonal boots and you fancy storing them away for summer or winter, there a few ways you can make sure your shoes are in the best possible condition by the time you take them out next season.

However clean and damp free your home is there’s always a chance that your boots or clothing will get a little musky when they’re in storage, and on top of that there’s always the risk of moths (they get everywhere) ruining your precious items. A few good ways of keeping your boots fresh are:

  • Use cedar chips to help absorb moisture, keeping your boots free from damp.
  • Moth balls have a bit of a weird smell, but they’re something that keeps the clothes destroying insects away, so they’re worth the investment.
  • If you’ve got a particularly expensive pair of boots, in something like suede for example, it’s a good idea to add a shoe tree to them to help maintain their shape.
  • If you don’t have a shoe tree, stuffing your shoes with some good old fashioned newspaper will do the job as well.

How to Wear Boots

  • Chelsea boots can easily be incorporated into both casual and formal looks, and even go with a neatly tailored suit.
  • The desert boot has a relaxed shape and can be worn with casual outfits for a clean look, or with formal looks for a unique twist.
  • Work boots are stronger and more practically made, can take a while to break in, but give outfits a striking finish.

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On That Note

Boots are the perfect day to day footwear and different designs can be worn in the height of summer to the coldest winter days. Men’s jeans and boots go perfectly together, but it’s easy pair your men’s boots with sleek suits and relaxed chinos as well. On top of that, while footwear like brogues and certain kinds of loafers need a little more care to keep in good shape, boots are generally more hardwearing and don’t require as much attention. A good shoe protection spray, a polish and a soft brush can be enough to keep your boots in top shape, so even if you’re lazy about shoe care you don’t have to work too hard to keep them looking sharp.

Feature image from Pinterest

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