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How To Wear Dress Shoes With Jeans

So you want to wear dress shoes with jeans? In this article I show you how to pull it off and most importantly... what not to do.
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Wearing dress shoes with jeans is a very common look and it bridges that gap between formal and casual.

If you’re heading to a bar, a casual date or even a casual job interview combining jeans with dress shoes simplifies an outfit but also balances formal with casual.

As a man it’s important to know the impact of a good pair of shoes. You simply can’t ignore the transformation a classic pair of dress shoes can have on any outfit.

You could wear a well-fitted t-shirt, a well-fitted pair of jeans, replace some sneakers with a good pair of dress shoes and it would dress the outfit up immediately.

Now even though wearing dress shoes with jeans isn’t a groundbreaking combination you haven’t tried before, a lot of men still get it wrong. They choose the wrong pair of shoes, they choose the wrong pair of jeans and it has a huge impact on their overall appearance.

How do you pull it off?

You need to focus on two things.

This is going to sound very simple but you need to focus on the dress shoes and the jeans that you’re wearing. Of course that sounds very simple and that’s why you’re reading this article but I want to dive a little bit deeper.

The Dress Shoes

Pay attention to the shoes that you’re wearing with your jeans. If you’re wearing cheap looking leather shoes it’s going to have a huge impact on your overall outfit.

I always say invest in shoes.

Don’t go and buy a pair of leather dress shoes for £40 at a high street stores and expect them to look classic and last you decades. You want to invest a little bit of more money in a pair of dress shoes because not only are they going to last you longer they’ll also look a lot better.

The construction of leather dress shoes is craftsmanship at it’s finest. If the leather is cheap, if the stitching isn’t strong and the sole is weak you’re not going to get a lot of wears from your shoes. But if the shoe is well made it’s going to last you years, if not decades.

Although you may be spending a little bit more money up front, a good pair of shoes can last you a long time, so you’re going to get your money’s worth in the long run. At the same time, if the shoe has what’s called a Goodyear Welted Sole you can simply resole the shoe over and over again.

goodyear welted sole

I always suggest buying a pair of dress shoes from a specialised shoemaking brand or shoemaker. The reason I say this is because their whole brand values are built around the dress shoes they produce. There are a lot to choose from and in London we’re lucky to have some of the best shoemakers in the world

Brands like Loake, Grenson, Church’s and Barker are all good places to start and it’s sometimes good to stay loyal to a brand once you’re happy with how they wear and how they look.

I’ll talk about the styles in just a moment in terms of what dress shoe you should be going for if you do want to wear it with a pair of jeans, but another thing to consider is the colour of the shoes.

You want to make sure that you choose a colour that’s versatile. Keep the detailing to a minimum and make sure the colour is something that can go with a lot of outfits.

Dark Brown, Tan and Black are the obvious choice but Cherry (a more reddish brown) is another alternative.

dress shoes colour

The Jeans

Jeans are something that we all take for granted. We think that a pair of jeans is a very casual item and we can literally just throw on a pair of jeans, feel comfortable and look good. It isn’t as easy as that.

By choosing a good pair of jeans it’s going to have a much bigger impact on how good this outfit looks.

If you’re wearing baggy jeans and you’re wearing them with a pair of cheap looking shoes, it’s not going to look stylish. It’s as simple as that.

denim

So when you choose the pair of jeans that you want to wear with this outfit make sure that you’re focusing on the fit and the type of denim.

Focusing on the length of the jeans and making sure they’re not bunching up at the shoe (or going under the shoe) is important, alongside making sure they’re slim fitting to your leg.

Opting for a darker denim will make things easier as it looks more formal but light denim can also be worn.

What Shoes Should You Choose?

So we’ve spoke about what to look for in a pair of shoes, where to potentially shop for a pair of shoes alongside the colours to go for.

But what style should you look for?

What shoes should you choose?

The Brogue

The brogue is the obvious choice. It really is the go-to shoe for wearing dress shoes with a pair of jeans. For me personally, I would opt for a tan brogue or I’d opt for a dark brown brogue because this is going to make it easier and more versatile.

The brogue can be worn with a suit but it can equally be dressed down with a pair of jeans.

mens brogue

This style of shoe has been around for centuries originating from parts of Ireland and the Scottish Highlands. Typically known for it’s perforated patterns in the leather more modern styles have started to become more decorative with the perforations.

If you opt for a brogue simply focus on what’s already been shared, concentrating on choosing a pair that are well made and are versatile.

The Monk Strap Shoe

If the brogue’s not for you then you can go for the Monk Strap shoe. Personally I prefer a Double Monk Strap but you can also opt for a Single Monk Strap.

monk straps jeanssingle monk strap jeans

I’ve got a tan pair of Double Monk Strap shoes and I’ll always wear them with some dark denim, and sometimes I’ll wear them with black denim as well.

The Derby Shoe (Or Oxford Shoe)

Another alternative is the Derby or the Oxford shoe. The Oxford is a little bit more formal typically worn with tailoring so you really have to take that into consideration if you’re going to opt for wearing Oxford shoes with jeans.

If you want to pull it off focus on the rest of the outfit, making sure the top half consists of more formal pieces. For example I wouldn’t wear Oxford shoes with jeans if I was wearing a t-shirt and a Harrington jacket but I’d wear them with jeans if I was wearing a button down shirt and a blazer/sports jacket.

oxford shoes

The derby is slightly more casual and also more comfortable so they’re ideal when wearing with jeans.

mens derby shoes

How do you tell the difference?

An Oxford and Derby shoe both include a vamp. With an Oxford shoe the facing which is where the eyelets are located is sewn under the vamp. This closed lacing system on an Oxford makes it a sleek looking shoe the the reason why it’s the go to for formal attire.

The Derby on the other hand has open laces which makes it more of a robust and versatile shoe. The differences are subtle but don’t be afraid to ask for help if you can’t differentiate the two.

The Loafer

If you wanted more of a casual alternative I would go for the Loafer. I personally own a pair of black leather Loafers (G.H. Bass Weejuns) and they’re one of my most versatile pairs of shoes. The Loafer is often frowned upon when placed in the ‘dress’ shoe category but opting for a well made pair of leather Loafers can still add formality to a pair of jeans.

black weejuns

Now it’s often harder to pull off black dress shoes with jeans because black leather is more of a formal shoe. Wearing Black Oxford Shoes for example would be ideal for a Tux so wearing them with jeans makes it extremely difficult. But as loafers are more of a casual shoe it means we can opt for black leather and still rock them with jeans.

loafers

The black leather loafer is something that you can wear with a pair of dark denim jeans, black denim jeans and even lighter denim.

Wearing A Belt?

Last but not least, I want to leave you with one more piece of advice. If you’re wearing a belt with this outfit, make sure that you match the leathers. If you’re wearing a pair of brown dress shoes and you’re wearing a belt, make sure that you opt for a brown belt. It’s as simple as that.

belt and shoes

It doesn’t have to be exactly the same tone, but just make sure that it’s very similar. It you’re not wearing a belt don’t worry, but the main thing you need to remember is not to clash leathers. Don’t go for a black dress shoe and wear it with a brown belt.

Wearing Jeans With Dress Shoes

So what do you think? Can you pull it off?

I really have to stress the importance of choosing the right pair of shoes and the right pair of jeans. If you wear well fitted jeans with cheap looking shoes, or ill fitting jeans with well made shoes it’s going to have a huge impact on the overall outfit.

Focus on getting some well fitted jeans in your wardrobe alongside one or two good pairs of shoes and you’ll be able to combine jeans with shoes whenever you need too.

If this helped let me know in the comments below and if you think it could help someone you know… share it with them.

Don’t forget subscribe to the YouTube channel if you haven’t already as I’m doing about three videos every single week, focusing on style, grooming, and most importantly self-improvement.

paul-mcgregor-youtube-channel

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Paul McGregor
Paul McGregor

Founder of MFM, and short course lecturer at The London College of Fashion teaching all things marketing. Read my personal blog here.

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1 COMMENT

  • James Spencer

    Liked the video> I do have double monk straps however they are black. I have not had a chance to get brown yet. I will be getting some though

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