The 5 Shoes Every Man Should Own To Look Good

Want to know what the 5 shoes every man should own are? These should form the foundation of every well-dressed man’s shoe wardrobe.

This post is all about the 5 shoes every man should own to look attractive and well put together.

1. Black oxfords

Black leather oxfords are probably one of the most classic men’s shoes. The Oxford shoe has its origin in the 19th century, when students at Oxford University wanted a more comfortable version of the Balmoral boot. The solution was to start to wear a low ankle version of the boot, which was the creation of the Oxford shoes that we know today.

The Oxford shoe is characterised by its closed lacing system in contrast to, for example, a derby shoe, which has an open lacing system where the quarters section of the shoe is sewn on top of the vamp and not into it like the Oxford.

Oxford shoes are available in three main styles: cap toe, wingtip and the plain style Oxford. For a man who buys his first Oxford shoes, the cap toe is highly recommended, as this is the most versatile version of the black oxfords.

One rule that we should follow when wearing Black oxfords is that they should only be worn with suits. For most men, it won’t be the most worn shoe, but you need to have it either way.

2. Dark brown penny loafers

If a pair of black cap-toe oxfords is some of the most formal footwear you can get, a penny loafer offers a bit more versatility without moving too far down the casual ranking.

A leather penny loafer can be worn just as well with a pair of tailored trousers and a knitted polo as it can with one of your suits. Note that if you pair penny loafers with suits, they will pair best with the more casual end of the suit spectrum. Like, for example, a linen suit.

The penny loafers have their origin in Norway, where a guy, after a trip to America, got the idea to combine the slip-on leather shoe called Teser (popular amongst Norwegian fishermen) with the moccasins worn by indigenous people in North America. And in 1936, G. H. Bass created their own shoe called “Weejuns”, named after “Norwegians”. This shoe model is known to be the first kind of penny loafer, similar to what we know today.

When it comes to the colour of the penny loafer, I suggest going for dark brown leather. You can, of course, go for a black penny loafer if you want to. But because of the role penny loafers will have in your wardrobe (pairing with more of your casual outfits), dark brown offers a bit more versatility than an all black pair would.

3. Suede chukka boots

The suede chukka boots will function as your fall and winter shoes. A chukka boot is an ankle-high boot made from leather or suede, who most often come with a 2 or 3 eyelid form.

A chukka boot has the perfect balance between formal and casual. Its origin comes from the British army located in India, which used it during polo play. The name chukka comes from the time sections of a polo match, which is called a “chukka”.

It’s said that the chukka boots first came to the West in 1924 with the Duke of Windsor, who had brought with him some pairs from a visit to India.

When standing in the choice between a calf leather chukka boot and a suede leather chukka boot, I would argue for going with the suede one.

A brown suede chukka boot can be worn with almost anything. They can be combined with jeans, chinos or even more tailored trousers. Although I would stay away from pairing them with formal business suits, think navy or grey, for this occasion, your black oxfords are your go-to shoe.

4. White sneakers

It looks like white sneakers are every 16-year-old boy’s favourite shoe. The fact that the white sneaker has been on a high trend for the last 5-7 years. Doesn’t mean that they shouldn’t have a place in a shoe wardrobe that focuses more on style than on trends.

The white sneaker is a versatile shoe for the days when you don’t feel like wearing your penny loafers.

When searching for a white sneaker to get, I would advise going for a simple and slim version. A pair of low-top Converse authentics will do the job as a well-rounded sneaker for most guys’ wardrobes.

5. Slip-on sandals

For this last spot on the list, I wandered between going for a pair of espadrilles or a pair of slip-on sandals. Even though the espadrillas offer a beautiful and versatile option for the warmer days of the year, I think most guys would benefit more from having a good pair of slip-ons.

Nothing is better than having a pair of slip-on sandals for your walk to the beach when on holiday. A pair of espadrilles could fill this role as well, but I find slip-on sandals so simple, convenient and effortlessly stylish.

When trying to level up your personal style, it’s not about having the most loud clothing items; it’s about having a handful of versatile pieces that you actually want to wear. A pair of leather slip-on sandals is that kind of item; they just work, and for that, we love them.

For specific recommendations, I agree with the rest of the market (they are popular, I know) that the Birkenstock Arizonas are a great option. Although they are not the cheapest on the market, I think they offer good quality and value regardless.

This post was all about the 5 shoes every man should own to cover most of life’s different occasions.

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