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  • Writer's pictureStefan S.

The ONLY 5 Shoes You Will Ever Need

You can also watch the video form of this blogpost, to learn how many suits you should own and what suits you should buy, here:

The truth is that you will only ever need 5 pairs of shoes in your wardrobe. Which means that you’re in luck, because as the old saying goes: “Your outfit is only as good as the shoes that go with it”.

Gentlemen, in today’s post, I will not only give you the answer, as to what those 5 pairs are, but I will also show you when to wear each shoe, how to perfectly match them to the rest of your outfit and where you can buy them.

Hello there! My name is Stefan and I have spent the last 10 years of my life gradually improving my style in order to boost my attractiveness and confidence. Now, I want to share my knowledge with you to help you achieve the same results in the shortest time possible.

Before we begin, I would like to give you a fair warning. It is time to get over your sneakers addiction.

No, not the chocolate bar. Let me explain.

It should come as no surprise that the majority of men nowadays are addicted to their sneakers. They wear them with sweatpants, with jeans and even with suits.

If you wear sneakers with a suit, why are you even wearing the suit to begin with? It’s negating the whole purpose. It’s like wearing a tuxedo jacket with cargo shorts. Just, don’t.

So, if you want to take your style to a whole new level, look more professional and mature, it’s time to leave sneakers behind and upgrade your shoe collection.

Let’s start with an easy one.

Shoe #1: The leather sneaker

Wait wait wait… Didn’t I just say that you should stop wearing sneakers?

Well yes… but here’s the twist.

Remember when I said that you shouldn’t wear sneakers with a suit? Yeah, well you shouldn’t wear dress shoes with jeans either.

It’s all about creating a perfect balance. And when it comes to style, each outfit can usually belong to a category such as smart casual, preppy or business formal.

And whereas sneakers have no place in the business formal category, they can work with plenty of smart casual outfits.

But not any sneaker will do.

If you want to look stylish and mature, while still wearing your trusty old sneaker, upgrade to a leather one instead.

The difference this will make in your overall look is huge.

Leather sneakers look good in a variety of different colours, with the most common being white, black and coffee brown.

And no, I’ve tried it and spilling coffee on white sneakers doesn’t work.

The biggest name in the leather sneaker industry is by far the Thursday Boot company. And while their shoes come in a very vast variety of colours and models and look very good on their website, I do not have any personal experience with them, so I cannot directly recommend them.

I got my pair from Brooks Brothers and, while I am sure that they don’t offer as many variants, the leather is indeed of high quality and the design is also very satisfactory.

Now it’s time that you ascend to the next level.

Shoe #2: The Loafer

Now, it’s time to take everything that you know about shoes, and throw it out the window.

Let me explain.

Remember when I told you that outfits come in different categories and that certain shoes belong to some categories, but not to others?

Well, that’s true… most of the time.

There is one huge exception, however. And that is the loafer.

Gentlemen, that is the reason I personally love this shoe so much. It’s quite possibly the most versatile shoe you will ever wear.

Just think about it. A smart casual outfit consisting of a pair of chinos and a polo? Yeah, loafers will do the trick.

A navy suit with a white dress shirt? Loafers are also a good option.

And since I already know that you are going to ask: Yes, you can wear loafers without socks.

Do not listen to anyone that tells you otherwise.

Loafers won’t judge you for going sockless, as they don’t care about how much your feet sweat and stink. They are your best friends. But others will judge you, so maybe get some no show socks.

Get yourself a pair made out of leather or suede and I’d personally recommend going for dark brown either way.

As to where you can buy a pair of these bad boys, you must keep one thing in mind: loafers are often reminiscent of italian style. Therefore, if you can afford it, I’d highly suggest going for something made in Italy.

This does not have to mean Loro Piana. I got my favorite pair from a local shoemaker in Rome and the quality is simply out of this world.

Speaking of out of this world, that is exactly how you will look when wearing a nice, fitted suit.

And while the loafer is an excellent option in such a case, sometimes, you need to go to even one step further.

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I want to give you my new guide with 27 tips you can start implementing today to look significantly better than your classmates or coworkers.

You can grab it for free on this website.

Shoe #3: The Monk or The Derby

Here is something that most men get wrong.

When it comes to dress shoes, you have 3 main tiers. The least formal option is the loafer.

You know that one already.

The second tier is formal enough to be worn in a business setting, a job interview or whenever you need to look extra professional, but not formal enough for certain occasions such as black tie.

This encapsulates the derby shoe and the monk strap.

Let’s discuss.

A derby is any leather dress shoe with an open lacing system and shoelaces.

On the other hand, the monk shoe is too cool for shoelaces. Instead it features straps.

And no, not the kind you use in the bedroom… Yes, I’m looking at you.

It can be either a single, a double or a triple monk.

I’ve got a pair from Lloyd shoes and one from Hugo Boss, both German companies. While you will definitely find much more qualitative leather than this, I’d say they’re both good options if you only have 100 to 200 euros to spend.

Gentlemen. When we started our journey, we were all the way down here. And slowly, but surely, we have climbed. We started with the leather sneaker, which is the perfect choice for your less formal attires. Then, we reached the loafer, which is your best option all around, as it is the most versatile. Now, we have just covered the derby and the monk shoe, which takes care of the rest of your outfits.

But there is still one more step to take.

Shoe #4: The Oxford

Did you know, that the saying “Oxfords, not brogues” makes no sense?

Why? Well simply because the term Oxford refers to any dress shoe with a closed lacing system, whereas the term broguing refers to the decorative patterns perforated into the shoe.

Therefore, Oxfords can be brogues. A more correct version would be “Oxfords, not derbies” for example — but that just doesn’t sound as catchy.

For your first Oxford, I’d definitely recommend you to go with black leather. It is the moral formal and traditional option, and you can’t really wear something like black tie with brown shoes. Afterwards, you are free to experiment with different colours.

The Oxford is the epitome of the modern gentleman’s shoe. Well… opera pumps excluded. Opera pumps are always excluded.

Truth be told, every man should have a pair of Oxfords in his wardrobe. And if you only buy one shoe from this entire list, make it an Oxford. It’s nowhere near as versatile as some of the other options, but it’s simply a shoe that can not be replaced in certain situations.

Plus, how else are you going to feel superior to everyone else? I mean you are watching this channel… But the shoes will also help.

I have my pair from the Italian shoemaker Scarosso. And let me tell you, for only 260 Euros, I doubt you will find leather and craftsmanship of this quality.

Gentlemen, believe me. Get yourself a nice pair of Oxfords, and you will dominate the world with each of your steps.

Shoe #5: The Chelsea Boot

Hear me out: The chelsea boot is the cold season version of the loafer.

Okey, that’s a pretty wild statement to make, so let me explain.

Naturally, loafers are usually worn in warmer seasons. Let’s say april to september.

At the same time, wearing a pair of boots during the summer is definitely something you can do, but probably something you shouldn’t.

As to the types of boots, you can basically choose between a chukka boot, a casual boot or a chelsea boot.

Chelseas are your best option, as they are the most stylish type of boots.

Now, you are armed with powerful knowledge. You know that you should stop wearing sneakers every day, and instead get a pair of leather sneakers, loafers, derbies or monk straps, oxfords and Chelseas.

If you are ready to take the next step, then read this blogpost next, which will teach you how to create over 300 different outfits with only 12 items.




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