Wearing jeans is nice.
Wearing your favourite shoes is great.
Wearing both at the same time is awesome.
The question is:
How do you know what shoes to wear with jeans?
Knowing this will not just make you look good. It will make you look really good.
Does this sound like something for you?
Well, then you’ve come to the right place. In this tutorial I’ll show you the 10 dress and casual men’s shoes …
… that happen to be the perfect shoes to wear with jeans. Let’s jump straight in.
The 10 Shoes to Wear With Jeans
First of all, let me tell you the most important thing about jeans:
Darker jeans have a much dressier look than lighter jeans. This, combined with the casual nature of denim, means that you can wear dark jeans with almost any type of shoes.
There are a couple of shoes that will look too dressy. Don’t despair; I’ll get to those shoes in a bit.
Here are the 10 shoes to wear with jeans in dark washes.
Sneakers with jeans is a proven casual look. Just to make it clear, we’re not talking about technical sneakers, such as the signature sneakers of LeBron James …
… or the latest running shoes from Salomon.
Good sneakers to wear with jeans should be classics. Like Chuck Taylors from Converse and the Authentic model from Vans. In other words, lace-up canvas sneakers with a low top.
To wear these men’s shoes with jeans successfully, the occasion needs to be somewhat casual.
If you have a dress code at work, casual Fridays would be the only time to wear these to the office. Otherwise, sneakers and jeans are perfect for:
- Eating out
- Everyday activities
To really nail it when wearing sneakers with jeans, make sure you match the colour of your socks with that of your pants (no white tennis socks here).
To learn more about matching sock colour and which socks to buy, click here and check out my men’s sock tutorial.
Also, if it’s a warm summer day …
… try sporting sneakers without socks, like you do when wearing shorts.
If you find it uncomfortable for any reason, put on a pair of no-show socks, also called ‘sneaker socks’. Unlike ankle socks, these look great. Because they don’t show at all (wink).
Speaking of shoes that can be worn without socks …
… slip-ons are perfect.
When it comes to slip-ons, you basically have three choices:
- Leather loafers
- Canvas loafers
- Boat shoes
Slip-ons are just the thing if in the summer. Especially if you’re looking for some nice black or brown casual shoes to wear with jeans.
By the way, brown shoes looks better with blue jeans than black jeans. That’s because brown is a warm colour and don’t match cool black pants.
Black shoes on the other hand, can be worn with both blue and black jeans.
Anyway, to get the most out of slip-on footwear, choose loafers or moccasins in leather. They handle suits and jeans equally well. But, they don’t lend themselves to business or dressy occasions where lace-up shoes are preferred.
Common types are horsebit, tassel, and penny loafers.
A thing that’s worth knowing is that, according to the book Gentleman …
… welted loafers are superior to moccasins. Both shoes are made a bit differently:
Loafers have soles and uppers made from separate pieces of material. Whereas moccasins have soles and uppers made from the same piece of leather.
You should also know that for casual and everyday wear …
… canvas loafers are a good alternative to sneakers.
With their summer feel, canvas loafers look great with pinrolled jeans (learn how to pinroll jeans here) plus a polo or a collared shirt with rolled-up sleeves.
Boat shoes are equally as casual as canvas loafers. As the name implies, these shoes were originally used when boating. A non-slip, non-marking sole and water-resistant waxed leather make them perfect for this.
Today they have become classic casual wear, no longer reserved for the docks. Boat shoes are great shoes to wear with jeans. This type also looks good with chinos if you prefer something preppier than denims.
To look your best, here’s what to do to really nail slip-ons:
If the occasion isn’t formal or business-related, lose the socks (or wear sneaker socks). Also, never wear them in winter. Rather, wear these casual shoes with jeans as often as you can in the summer.
Desert Boots, Chelsea Boots, and Dress Boots
Boots have gotten an unfair ‘casual’ label.
Of course, casual and hiking boots should never be worn in combination with jeans and a blazer.
But some boots—like desert boots, Chelsea boots, and dress boots—can.
In the spring, summer, and autumn, chukka and desert boots are perfect with jeans.
Chukka and Desert Boots
Desert boots are a type of chukka boots. Chukka’s usually have two to three pairs of eyelets, a plain leather finish, and a crepe (white) rubber sole.
Unlike Chukkas, desert boots always have suede uppers. They’re also unlined and often lighter, and so the desert boot is the one I prefer.
The next type of boot is the Chelsea boot.
Chelsea boots have a solid pedigree and date back to the Victorian era (mid-1800s). For these boots, plain leather is the only option. They can be higher than chukkas, and instead of laces, they have elastic side panels.
Another thing that’s different is their sole.
As with dress shoe soles, a Chelsea sole is usually made of stained leather or rubber. This gives them a dressier look than the white soles of chukka boots. It also makes the boots easier to take care of, since you don’t have to worry about staining the sole when polishing you boots.
Chelsea boots are best worn on rain-filled days and in colder seasons. They look great with jeans, a sweater, and a casual jacket—if casual is what you’re aiming for. However, they can be worn with a suit and coat.
If you don’t fancy the elastic sides of the Chelsea boots …
… or you’d like something a bit more watertight, open-lacing boots are the answer.
Open Lacing Dress Boots
Unlike casual boots, these boots can and must be polished to look good. You can also get them with different degrees of brogueing.
If they’re your first pair of dress boots, forget full brogues (wingtips) and half brogues. Quarter brogues are more than enough, since that means you can wear them with suits as well.
If you don’t like brogueing, boots in plain leather with a toe cap are very versatile and is what I would have chosen as my first pair of boots.
Also, open-lacing boots, like the ones in the picture, are less dressy than closed-lacing boots (we’ll get to those in a bit). That’s good news, because the open lacing makes them the perfect everyday boots to wear with jeans.
Brogue and Derby Open-lacing Dress Shoes
When it comes to classic open-lacing leather shoes, we can basically divide them into:
- Derbies (Gibsons)
‘Open-lacing’ simply means that the shoelace eyelet tabs are mounted on top of the vamp. Oxfords, which we’ll talk about in a bit, are closed-lacing leather shoes. These have eyelet tabs that are located under the vamp.
Derbies are about as simple as shoes get. Apart from occasional toe variations, such as apron, cap, and split toes …
… there isn’t much more to these shoes.
The simplicity of open lacing dress shoes is also what makes them dressy and versatile. These will look just as much at home with a pair of jeans as with a suit.
If I had to start my wardrobe all over again, black or brown leather derbies would be the first pair of shoes I bought.
As I’ve already mentioned, brogue shoes are a type of open-lacing shoe. In fact, most open-lacing brogue shoes look much like plain derbies, but with added decoration.
The degree of embellishment differs, from long-wing brogues to quarter brogues.
Shoes with brogueing trace back to the shoes Irishmen once wore. Those older shoes also had perforations, which allowed water to drain after crossing wet terrain. Originally used as outdoor and country footwear, brogue shoes have now become everyday classics.
However, they’re not as dressy as the less decorative derbies. That’s why brogue shoes are great as shoe pair number two.
If you’re looking to wear black or brown dress shoes with jeans, I’d go for brogues.
Brogue shoes are best worn with jeans and dressy tops, such as polos and collared shirts with a well tied tie, plus a blazer or classic casual jacket.
Here’s a shoe with just as many devotees as haters. Some can’t stand the buckle fastening, which reminds them of monks in their sandals. While others simply love this cross between loafers and open-lacing shoes.
If you haven’t already decided on your pair of shoes, these could be it.
To successfully wear monkstraps with denims:
Your jeans should have a tapered cut, which means that they are fairly slim at the hems …
… and be somewhat highly hemmed, so that the jeans barely rest on the top of the shoes. The reason why your jeans have to be like this is simply because of the buckles. If you pants are too long and too wide at the hems, the buckles will snag them causing your jeans to hang in a less-than-flattering way.
Keep this In Mind When Buying Jeans
The problem with shoes and jeans is that if you don’t have the right jeans, it doesn’t matter what kind of shoes you’re wearing. You just won’t look right.
You need jeans that you can wear with as many of your shoes as possible. And to find them, follow these three steps:
STEP #1: Colour
This is the most important aspect of jeans. The general perception is that the darker the jeans, the dressier they look. Depending on your season, you should go for dark indigo washes or good old black.
Having a pair of light jeans for casual wear is understandable. But if you ever would like to wear jeans to a fancy restaurant or on a date, the darker your jeans are, the better.
Personally I prefer dark indigo jeans, because they can be washed quite a few times before they start looking distressed. Speaking of the distressed look …
STEP #2: Distressing
Your jeans should look newish if you want to get the most out of them. That is, they don’t have to be fresh from the store …
… but there should be no obvious signs of wear or distressing. This, of course, leave jeans with whiskering, patches, honeycombs, and holes and tears out of the question.
And don’t be tempted to think that this doesn’t apply to your $400 distressed Diesel designer jeans. I’m sorry to have to break the news to you, but it does.
STEP #3: Fit
So you’ve found a pair of clean, solid jeans in the perfect shade of indigo. But, how should they fit?
Here’s the short version:
Your jeans should sit around your waist without difficulties. And to make sure you’re not wearing them too high or low, aim for about 2 to 3 inches of room from your bellybutton to your pants waist.
There are several different fits available as well, ranging from baggy to skinny. We want jeans in the golden middle. Simply because they look great and fit sort of like quality dress pants.
That, of course, leaves boot-cut jeans and skinny fits out of the question. Jeans with a tapered cut in either a regular or a slim-fit version are what I’ve found to work best on most men.
A little stretch in the fabric is okay as well, since it only helps the pants sit better around your waist. Just remember to skip the fabric softener when washing them.
For the leg length, some men are lucky …
… while others aren’t—myself included.
My inseam is an odd number, which pretty much always seems to be sold out. Since cuffing or pinrolling pants isn’t a dressy or classic look, I always ask the in-house tailor to adjust the jeans length for me. Some shops do it for free, while others charge around $10 or so. Either way, it’s absolutely worth it!
That’s my three-step process for buying great jeans. Of course, you already know which 10 shoes you should wear with them …
… but did you know that there are a 2 types of shoes that don’t match jeans, ever?
Here’s the shoes you should never wear with denims:
Shoes to Wear With Jeans? Never Wear These 2
In the intro, I promised to get back to you on which shoes you should never wear with jeans. I’m not talking about sandals with socks, flip-flops, and that boring stuff. Here’s some actual advice that even the best of us can take advantage of.
We basically have two types of dress shoes that should never be worn with jeans.
- Oxfords (sometimes called Balmorals in the US)
- Closed-lacing boots
These shoes are too dressy to wear with jeans …
… and the reason why is because they’re both closed-lacing styles.
We’ve already talked about less dressy open-lacing footwear, such as derbies and chukka boots. Closed-lacing shoes and boots, on the other hand, look more elegant and are considered more formal.
Instead of the eyelet tabs being located on top of the vamp, as they are on chukkas, they are located underneath the vamp. This creates a sleek and dressy look. A look that is too dressy for jeans.
However, there’s no need to despair, because both you and I know that we have plenty of other great-looking shoes to choose from. And now you know which they are.
Now I’ve Got a Question for You …
Are you going to give any of the shoes above a shot? In case you do, which will it be?
Let me know by leaving a quick comment right now!
Perhaps you have thoughts or questions. Either way, let me know in the comment box below.
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