The Definitive Style Guide to Mens Boots

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The world of fashion is continually changing. New styles arrive each season that cater to a revolving door of trends. Although it’s exciting to stay in vogue, you should have some staple pieces ready to go.

Boots are something every man should invest in when looking to complete their wardrobe. They’re comfortable to wear all year long and match most outfits. So which boot is the best for you?

Check out our definitive guide for men’s boots to determine your ideal pair. You’ll learn about the different styles, how to wear them and the best ways to customize. By the time you’re finished reading, you’ll have answers to your most pressing questions – and questions you didn’t think to ask.

Think About the Season

You take many things into account when putting together your daily outfits. You might consider how cold it is, the wind chill and other factors. Every piece of clothing you choose is related to the time of year, including your footwear.

For example, it doesn’t make sense to wear insulated hiking boots to the farmer’s market in July. When you’re venturing into a new style, be sure to buy something you know you’ll wear.

Buying the wrong thing will only discourage you. Think about the time of year and what you like. If you’re going to start investing in boots, choose something you can wear tomorrow.

Think about the weather, terrain and what temperatures you can expect in the following weeks. Can you wear an ankle-length style as a fashion statement? Perhaps you’ll need taller boots for trekking through the snow.

Once you have a picture in mind, you’re ready to learn more about the types of shoes and boots men wear every day. Chukkas, for example, are a low-cut style made popular again by younger generations. Created with leather, these shoes can easily transition between looks. Other styles, such as hiking and desert boots, come with different purposes.

The boots you buy will depend on your style, age and the current season. Take time to read up before you head to the store.

Explore Different Brands

Check out some of the best brands available now that you know what you need from your future boots. When you buy from a reputable brand, you’ll gain quality footwear that will last a long time.

Though brand name isn’t always a good indicator of quality, it’s still an indicator. Make sure you’re choosing the right boot from a trusted company in addition to reading the reviews.

Here are a few boots and brands to get you started.

1. Red Wing Worker Boots

Anyone looking for long-lasting footwear should check out Red Wing. This brand has made boots since 1905, so they know what they’re doing. Their worker boots provide ample space, so your knees don’t ache at the end of the day.

Most styles are waterproof and come with a year-long warranty in case of defects. Try them out, and you’ll feel the difference after working on your feet all day.

2. R.M. Williams Chelsea Boots

Known as the national brand of Australia, fans wear R.M. Williams Chelsea boots around the world. They’re a classy shoe you can dress up for a night out or wear to a casual event.

They feature durable rubber soles and high-quality Yearling leather, which requires a bit of care but rarely wrinkles.

3. Clarks Desert Boots

Another twist on the casual style is Clarks Desert Boots. They have a soft, textured sole made for walking, not hiking.

They’re perfect for warmer weather since they have only one layer of leather and no liner. Leather experts make them in Italy and ship all over the world, so it’s easy to find a pair you love online and order them right to your front door.

4. Fracap Hiking Boots

You’ll have tons of hiking shoe options to choose from. For hikers who want to walk a few miles and look great, go with a Fracap boot.

Each pair is crafted by hand in Italy, including the signature sole. Fracaps are known for their extreme ripple, which gives you traction on most hiking surfaces.

Consider Your Outfits

What do your daily outfits look like? Men who wear simple styles like jeans and logo tees will need a different boot than those who like khakis and dress sweaters. Your style will relate to which shoes are best for you. Spend some time researching your style. Start by finding inspirational photos and boards online.

Start on Pinterest. Here, you can type in a simple search term and find millions of photos. When you find a style you like, click the heart to save it to a board. You can even create multiple boards designated for different occasions. Another excellent website is Instagram. Follow male models, fashion icons and bloggers with a keen sense of style.

If a Chelsea boot appears in most pictures of your favorite outfits, you’re safe buying a pair of your own. Establish the foundation for your collection by looking at what the professionals pair together. Then, recreate it in your style.

You can also choose footwear based on the features of what you wear. If you’re pairing a casual button-down with shorts, it will look odd to strap on calf-length hiking boots. Likewise, a shiny Rolex and faded buckle style will look out of place. Think about what your outfit says and how you can choose footwear to match.

Plan Your Activities

Think about what you’ll do while wearing boots. Will you trek through the mountains off the beaten path or head out for a lunch date? Your activities are crucial in deciding what to buy.

When you’re trekking the mountainside, it’s essential to have hiking boots with sufficient traction for slick trails. You won’t get far if your desert shoes slip and slide with each step.

Consider the soles of potential footwear, the material and how much insulation they have. Once you have the answers, you can narrow down which ones are right for you.

Day-to-day boots are easier to plan for since they don’t serve a significant purpose. Most styles will fit these activities, like walking around the office or driving to town. As long as they fit comfortably and aren’t falling apart at the seams, your choice of daily boots should be easy to pick.

Imagine Your Routine

What will your routine look like once you start wearing boots? Do you like to take your time in the morning or rush out the door? The answer will make all the difference between keeping your routine or ruining it. For example, a lace-up style won’t work for someone who prefers to spend little time getting ready.

Don’t mind an extra minute added to your routine? Then consider lace boots, which allow you to get creative. Consider how to tie up your laces in a unique way. Instead of tying them as-is, try out new lace designs, like the lattice, hidden knot, ladder or zipper. Styling your laces is an easy way to personalize your look, even if you purchase a fashionable pair of boots.

Remember the Upkeep

By now, you might have a brand or type of boot in mind. You’re one step closer to walking home in a pair that matches your style. Yet there’s one extra step no one should forget. Brands with quality shoes use expensive materials that may be susceptible to damage where you live.

Remember to clean and maintain your footwear to make it last. If you skip this step, your footwear may experience cracks in the leather and fall apart, even a few months after bringing them home.

Before you make your boot purchase, take time to read about leather care. Cleaning and polishing shoes regularly will do a world of good.  To start, remove dirt with a nylon brush and a capful of leather-friendly soap. Once the shoes are dry, rub in conditioner with a clean rag. The right formula will restore moisture to the material and prevent cracks. After, give the leather a light buff with a horsehair brush.

You’ll know when it’s time to condition your boots. The material will begin to look ashy and dry. Between conditionings, you can polish your shoes with cream. You can also try wax if you want a high sheen.

It’s easy to damage leather. You can be proactive by investing in a weatherproofing kit. Look for a spray you reapply every three to six months. This spray prevents water from soaking into the material and leaving behind stains. Instead, the rain slides right off. Did you already step in an unseen puddle? Experts say you can mask a stain by misting the entire shoe with water.

When it comes to leather, never expose boots to heat to dry them. This method shrinks and distorts the material of any brand. Air dry your shoes after cleaning or if they get wet.

In Summary

Everything in fashion serves a purpose. Will your shoes help you hike or pull together an outfit? Whatever style you decide to buy, take care of them. Boots are a bigger deal than your old pair of sneakers. Look into the material and what kind of upkeep they require. Learn when to wear them and when to keep them at home.

After you’ve flipped through different pictures of your favorite styles, you’ll know about many kinds of boots. Test out each type by trying them on in person. You’ll figure out which ones feel best on your feet and look great with your outfits.

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About the author


Hi, I’m Brian Bradshaw. I’m a super duper mega hiking enthusiast, with a love for everything that has to do with outdoors, hiking, gear, footwear and more.

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