13 Must-have, essential shoes every man should own

You can’t build a perfect outfit without the right shoes. Your choice of footwear can both enhance and ruin your overall appearance. However, finding the perfect pair can be challenging. As the fashion industry grows, so do your options. How do you pick the right one for the occasion? And what factors should influence your decision?

In this article, we’ll introduce you to 14 must-have, essential shoes every man should own. Though the information mostly benefits men, ladies will also find it useful. After all, shoes can be a wonderful present for your boyfriend or husband.

Summary

If we could only choose one pair, the must-have, essential shoes every man should own would be Chelsea boots.

Why you can trust us & how we picked

You can trust us because we bought and tested all the pairs of shoes we recommend on this page. We picked different pairs, so there was something for every style and budget.

Must-have, essential shoes every man should own

What you should buy depends on how often you go out. The list of shoes every man should own is quite long. Some are also suitable for only specific seasons and types of events. You can find a concise list of 14 must-have, essential shoes men should own in the following table:

TypeOccasionSeason
Chelsea bootsCasual/formalAll year round
TrainersCasualWarmer months
Chukka bootsFormalWarmer months
LoafersMore formalWarmer months
Service bootsCasualAll year round
OxfordsFormalAll year round
DerbyCasual/formalAll year round
BoatCasualWarmer months, unsuitable for rainy weather
MoccasinsCasual/formalWarmer months
BroguesCasualWarmer months
Dress bootsFormalWinter
Monk strapMore formal than casualAll year round
EspadrillesCasualWarmer months, unsuitable for rainy weather
SneakersCasualWarmer months

1. Classic shoes for men – Chelsea boots

Named after the eponymous area of London, Chelsea boots date back to the Victorian era. These boots became popular thanks to UK bands such as The Beatles and The Rolling Stones.

Chelsea boots stand out thanks to the comfort they offer. Thanks to their elastic sides, they adapt to the shape of your feet. If you hate retying your shoes every five minutes, consider these boots. Since they are a slip-on option, you’ll never have to worry about laces while wearing them.

Chelsea boots work great for both casual and formal occasions. If you wish to appear more formal, we recommend buying a black pair.

Our choice

Bruno Marc chelsea boots

If you’re looking for high-quality, warm Chelsea boots, consider Bruno Marc.

Pros

  • Elastic and comfortable
  • Good formal option
  • Decent color variety

Cons

  • Suede doesn’t handle heavy rain well
  • It might be too warm to wear in summer
Bruno Marc
Bruno Marc is a good choice.

2. Trainers

Trainers are one of the most casual types of footwear. But that doesn’t mean they’re useless. Trainers are an excellent choice for just going for a walk and running. Designed with comfort in mind, they’re also perfect for doing chores or running errands.

Our choice

New Balance 990 V5 Grey

These V5 trainers have everything you can ask for. Not only are they comfortable, but they are good-looking too.

Pros

  • You can choose from several different colors and sizes
  • Extremely comfortable
  • Made from high-quality material, meaning they will last you a long time

Cons

  • Somewhat pricy for trainers
  • The delivery took longer than expected
Sale
V5
V5 from New Balance is a trusted model.

3. Chukka boots

Chukka boots have their origins in the military, particularly In World War II. British soldiers used to wear them in the desert. For this reason, you may sometimes run into the term desert boots. Chukka boots round towards your toes. They typically feature two or three eyelets. When it comes to height, they may vary. Some may cover your whole ankle while others are much lower than that.

We recommend wearing Chukka boots for formal occasions.

Our choice

Mens Clarks Chukka Boots

Made from quality leather, the Chukka boots from Clarks will make an excellent addition to your collection. With these boots, you’ll appear elegant and sophisticated at all events you attend.

Pros

  • It comes in several different colors that will complement your outfits well
  • One of the best choices for formal footwear

Cons

  • Like most types of boots, it takes a while to break them in
  • They run a bit large, meaning you may have some trouble buying the correct size
Sale
Clarks
Clarks can be trusted.

4. Best men’s summer dress shoes – Loafers

Although they resemble moccasins, loafers typically come with no laces. Originally worn by fishermen in Norway, they eventually became an everyday footwear option. Loafers don’t reach higher than your ankle, which makes them ideal for summer. While they may be formal, they’re surprisingly comfortable.

Our choice

Vostey loafers

Every man will appreciate the loafers from Vostey. They’re an excellent choice for summer, especially if you pair them with nice shorts. They’re also the perfect blend of comfort and elegance.

Pros

  • Very comfortable
  • Affordable
  • Compatible with machine wash
  • Come in several different colors

Cons

  • You can’t wear them in the rain, not even in light showers
  • Not a good choice for colder seasons/climates
Sale
Vostey
Vostey are classics.

5. Service boots

Service boots date back to world wars. They were originally designed for rugged terrain and featured good ankle supports. Today, men wear them in everyday scenarios. They feature a welted construction, which makes them more durable than other boot types. They’re typically made of leather and come with a capped toe. Like most boots, they have an elevated heel.

Although they lean more toward the casual side, they can also go well with certain formal outfits.

Our choice

nortiv 8

The Nortive military boots are a must-have addition to your collection, especially if you like hiking a lot. No other type can match their level of durability.

Pros

  • They’re waterproof, meaning you can wear them even in the rain
  • They will last you a long time, even if you wear them a lot
  • They feature an anti-slip sole

Cons

  • Not the most fashionable option out there
  • You won’t find much use for them outside of hiking, or motorbike riding
Sale
NORTIV 8
NORTIV 8 are popular.

6. Oxfords – the best formal shoes

This type is a must-have for every man. Considered the pinnacle of formal footwear, Oxfords shoes command class and respectability. They are extremely versatile and complement most types of formal outfits well. Oxfords are usually low-cut and come with a closed lacing system. Though they may not be the most comfortable option on this list, they’re certainly the most elegant ones.

Our choice

The Oxfords from Bruno Marc scream prestige and elegance. If you attend a lot of formal events, you can’t go without this pair.

Pros

  • The best dress shoes you can buy
  • Great choice of colors
  • Very affordable

Cons

  • Little to no slip resistance
  • It can be a little uncomfortable
Sale
Bruno Marc
Bruno Marc also makes Oxfords.

7. Derby shoes

Derby shoes are a good choice for both casual and formal occasions. Though they resemble Oxfords, they come with an open lacing system. It is the biggest difference between the two styles. The open lacing makes for a more relaxed fit, making this type of footwear much more comfortable than Oxford’s. You can wear them for a day without getting foot cramps.

Our choice

If you’re looking for a mixture of elegance and comfort, consider going for these Derby shoes from Clarks.

Pros

  • Very comfortable despite being formal
  • Compatible with machine wash

Cons

  • Somewhat expensive
  • It doesn’t come in many color options
Derby shoes
Here's another pair from Clarks.

8. Boat shoes

As the name implies, these shoes were designed to be worn on boats. They provide a better grip on the slippery deck for sailors. Nowadays, they’ve become a casual but fashionable option for men. Since they aren’t very thick, we recommend wearing them in the summer. Due to their design, they look best when worn with shorts or tapered pants.

This type of footwear is incredibly comfortable once you break it in. You should avoid wearing socks with these shoes to look as fashionable as possible. One downside is that they’re not waterproof. Thus, we don’t recommend wearing them in poor weather conditions.

Our choice

sperry loafers

The boat shoes from Sperry offer good value for money. We consider them the most comfortable summer shoes you could ever buy.

Pros 

  • You can wear them either as tie shoes or as slip-ons
  • A very comfortable summer option
  • Come in several colors

Cons

  • Unwearable for formal occasions
  • You likely won’t wear them outside of summer
Sperry
Sperry is a brand that's loved.

9. Slip-on shoes – Moccasins

Moccasins have origins in Native American history. Although they have laces, these are purely decorative. Moccasins are slip-on shoes, meaning you don’t have to worry about your laces coming undone. Depending on the model, you can pair them with casual and formal outfits.

Our choice

The Hanes moccasins will keep your feet warm and fuzzy during winter. You can wear them both indoors and outdoors.

Pros

  • Warm and comfortable
  • Slip-on
  • Compatible with machine wash
  • It comes in several colors

Cons

  • Not waterproof
  • Only wearable in cold seasons and climates
Hanes
Hanes are very comfortable.

10. Trendy men’s shoes – Brogues

Brogues shoes or simply brogues date back to 20th century Ireland. They’re named after the iconic pattern on their leather surface. Though the holes at the front are nothing more than a decoration today, they once had practical purposes. These holes allowed water to drain from the shoes quickly. Since the Irish workers didn’t have to take them off, they could spend more time on their jobs.

Many actors and performers helped popularize brogues. These shoes lean more toward the casual area, making them an excellent option to wear at work.

But before you invest in brogues, you should know about one major downside. We noticed that the holes in the leather tend to collect dirt and mud quickly, even if you walk on a proper concrete sidewalk. Unfortunately, this calls for regular maintenance. If you don’t like cleaning your shoes regularly, you may want to opt for a different style on our list.

Our choice

The brogues from Dream Pairs are a good everyday choice for men. We particularly liked how easy it is to clean the holes in this pair compared to other products.

Pros

  • Made from leather, making it an excellent choice for vegans
  • Incredible sweat absorption
  • Easy to maintain

Cons

  • You might get uncomfortable after wearing them for more than five hours
  • Not suitable for formal occasions
Dream Pairs
You'll love Dream Pairs.

11. Dress boots

While you can choose from many elegant dress shoes, they all share one drawback – they don’t do well in bad weather. Both rain and snow can ruin them, especially if you have to spend a lot of time outside in these conditions. Luckily, you can invest in dress boots. This alternative reaches up to your ankle, providing better insulation and protection for your feet. The heel is usually higher as well, which can prevent slipping accidents.

We recommend wearing dress boots for formal occasions.

Our choice

The Bruno Marc dress boots are a must-have winter option. Compared to Oxfords, they resist snow and adverse weather conditions much better.

Pros

  • Warm and comfortable
  • Made of pleather
  • The sole absorbs impacts well
  • Very durable

Cons

  • The color options are somewhat limited
  • The width may feel slightly narrower than you’d expect
Sale
Bruno Marc
You'll love Bruno Marc.

12. Monk strap shoes

We know little about the origin of monk strap shoes. According to the popular myth, they originate from monks who once lived in the Swiss Alps. This myth is popular because of how closely monk straps resemble the shoes worn back then.

This style’s popularity then bloomed in the 1900th century in England. While the original design features a single strap, we recommend going for double-strapped options. Not only are they more elegant, but they are also more comfortable to wear. Stylists consider them a formal option, although they aren’t on the same levels as Oxfords.

Our choice

The monk straps from Bruno Marc are a solid formal option whenever you need to appear smart and elegant. And unlike Oxfords, they’re very comfortable. This pair features two straps, which looks much better than one-strap alternatives.

Pros

  • Good blend of elegance and comfort
  • Made of pleather
  • Slip-on design
  • Durable

Cons

  • It takes a while to break in
  • It comes in only three colors
Sale
Bruno Marc
Here are monk straps by Bruno Marc.

13. Slip-on shoes – Espadrilles

The term espadrille is derived from ‘esparto’, a type of grass found in Spain and some areas of Africa. People once used this grass to craft the sole of this type of shoe.

Today, espadrilles can be made of many different materials. Although they are fashionable, they’re quite thin. We recommend wearing them during the summer. These shoes are also not very thick, which makes them unsuitable for rainy weather.

If you want them to fit as many of your outfits as possible, avoid complex patterns. Straight colors will ensure your espadrilles match most if not all, your clothes.

Our choice

The espadrilles from Casmag will soon become your favorite casual summer shoes. Just make sure you don’t wear them in rainy weather – they have zero water resistance.

Pros

  • Very comfortable
  • They allow your feet to breathe
  • Compatible with machine wash
  • Easy to put on and take off

Cons

  • You’re in for a bad time if it starts raining
  • Too thin to wear in winter
CASMAG
Try out a pair from CASMAG.

Sneakers every man should own

And last but not least, we have sneakers. The odds are you already own a pair in your wardrobe. Cheap and comfortable, sneakers go well with most casual outfits. However, you can’t just buy any pair of sneakers. Consider one of the following options to ensure the best look and quality.

Our choice

You can’t make a list of good shoes for men without mentioning sneakers. Of all the options we tried, we liked the ones from Skechers the most. In terms of comfort, this pair comes out on top thanks to the air-cooled memory foam.

Pros

  • The most comfortable pair you’ll ever wear
  • Great color variety
  • You can wear them as slip-ons

Cons

  • Somewhat expensive for sneakers
  • Unsuitable for rainy weather

How many shoes should a man own?

This question is too individual to answer directly. Every man has different fashion needs. As a result, some men can do fine with just five pairs while others have over twenty. If you attend many formal events, you’ll need several types of classy footwear. If you attend such events sporadically, having as few as two pairs might be more than enough for you.

What kind of shoes should I wear? 4 factors to consider

Knowing what shoes you should have in your collection is one thing. But choosing the right pair to match your outfit is a completely different story. It ultimately comes to 4 important factors to consider when looking for essential shoes for men.

Casual or formal

When it comes to choosing from the countless types of men’s shoes, this will be the first factor you must consider. Though some options are versatile, most lean either toward casual or formal occasions. Make sure you identify the event you plan to attend correctly. Otherwise, you may be in for a fashion faux pas.

Comfort

Good-looking footwear isn’t necessarily the most comfortable one. It is especially true of formal footwear. Take Oxford, for example. Although they are best for going out, you likely won’t last more than a few hours in them. If you know the event will last longer than that, consider going to another option.

Season and weather

The best-looking men’s shoes aren’t suitable for every season and weather. Some are deceptively thin, meaning they won’t survive rain, let alone snow. Always check the weather forecast before you commit to an option.

Budget

The final faction you should consider is your budget. We don’t mean just going for the cheaper of two options. An important part of being cost-effective is understanding your needs.

Let’s say you plan to attend a wedding. But other than that wedding, you don’t attend any other formal events. In this case, going for the top-rated, expensive pair may not be the best option. But if you go out often, you shouldn’t be afraid to buy a more expensive pair. Expensive shoes tend to be high-quality, meaning they will last you much longer.

Shoes that go with everything for men

Not everyone has room for an extensive arsenal of footwear at their home. And even if you do, you might not want to invest in too many pairs. While it’s nice to have a wide collection of footwear, it’s not necessary. One way to reduce it is by buying pairs that go with everything.

When it comes to versatility, color plays a much bigger role than type. A universal one is black. It goes with every outfit, whether it’s formal or casual. Gray, white, and sometimes beige can also work.

Most comfortable casual shoes for men

Most casual shoes were designed with comfort in mind. But from all the casual options, nothing compares to sneakers. Since they were intended for athletes, they put comfort above everything else. That’s why sneakers became the most popular casual shoes every man should own. Trainers come close second. If you’re looking to buy a decent pair, check out this article’s later sections.

Here is a table that includes the most comfortable options:

TypeSeason
SneakersSummer
MoccasinsWinter
Service bootsWarmer months & best for hiking
Boat shoesSummer
EspadrillesSummer
TrainersSummer

How much do essential shoes cost for a man?

As we tested out the different shoes, we found that you will usually pay between $50 and $150, depending on the quality and style you’re going for.

FAQ

Can shoes be lighter than pants?

As a rule of thumb, your footwear should be darker than your pants. While it’s fine to break this rule in a casual setting, we recommend sticking to it during formal occasions. This rule has essentially become a social norm, meaning some people may find it strange to wear light footwear with dark pants.

What color of shoes goes with everything?

If you don’t like fashion all that much, simply remember that black is the most neutral color out there. Black shoes complement all outfits well and are usually the best value-for-money options. Gray can also work, but only if it is a lighter shade than your pants.

Our final thoughts on the 14 must-have, essential shoes every man should own

This list contains all the types of shoes you should have in your collection. Owning at least one pair of each will help you dress up for every occasion, regardless of the season. Don’t forget to follow our tips when deciding on what shoes to buy.

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