How to Match Shoes With Pants (For Men)

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How to Match Shoes With Pants

How to properly match shoes with pants is a question I’m frequently asked about.

It’s a subject about which I see a lot of men make mistakes on a regular basis.

I’ve decided to clarify how to pair shoes with pants in your wardrobe once and for all.

This will include everything from color coordination to selecting the most flexible colors to get the most bang for your money when it comes to menswear.

We’re going to go into some specifics, so let’s get started.

Shorts & Shoes

To begin, we have the most casual and surely the shortest member of the pants family – a reliable pair of warm weather shorts.

Shorts might be difficult to pair with certain shoes because of their length and casual appearance.

Sneakers are the logical choice because they go with the casual vibe. When it comes to selecting a sneaker-shorts combination, my best suggestion is to keep things simple.

After all, since you’ll be showing off more leg than usual, a minimalist approach, such as a pair of slick white low tops or some comfy slip-on vans, is the easiest and safest way to go.

However, when it comes to high tops, proceed with caution.

High tops with shorts are a trend that isn’t impossible to pull off, but it all comes down to your color and pattern choices.

Shorts are typically worn for more casual events, so wearing them with dress shoes or boots is out of the question.

This does not, however, imply that you must limit yourself to footwear. There are other dressier options available, including a classic pair of loafers, such as penny loafers or suede driving moccasins, which are among my personal favorites.

If you wear them with a pair of no-show socks, loafers and shorts are a particularly fashionable combination.

Alternatively, boat shoes, which have a timeless preppy style and come in a range of fashionable color options, are a good pair.

So, how about some sandals?

You may believe that wearing sandals with shorts is perfectly fine for warm-weather attire, but please reconsider, because no one wants to see your toes.

If you’re near a body of water, however, you’re exempt. However, you could easily replace those sandals with a pair of espadrilles.

Espadrilles are fashionable slip-on shoes that are as comfy and cool as sandals but look a lot better.

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If you invest in a good pair, you’ll get so many compliments that you’ll never want to wear sandals again.

Chinos & Shoes

Next on my list, we’ll keep things both spring and summertime by discussing a pair of pants that most of you should already own.

They’re chinos, and they’re traditional, cool, and casual.

One of the best things about chinos is how adaptable they are. Depending on the style of shoe you pair them with, you can easily dress them up or down.

Loafers, like shorts, can be worn with chinos, but the key is to choose the proper fabric for the occasion.

Suede driving mocks, for example, are ideal for business casual outfits, while leather penny loafers with chinos are ideal for more formal upscale occasions.

Sneakers, especially low tops, look terrific with chinos as well. I always suggest a pair of white low tops because they work with every chino hue.

Simply switch out the upper part of your attire and you’ve got a look that can take you from Friday night to Monday morning.

You may quickly improve the look of your chinos with a pair of dress shoes if you require a more put-together look.

Dark brown dress shoes, such as Oxfords, look well with a variety of chinos, including tan, navy, and olive.

Black dress shoes, on the other hand, necessitate an added layer of thought. Unless you want to seem like you park cars for a living, I never recommend wearing black chinos.

Boots and chinos also look great together. However, it’s more of a spring or fall look. Suede chukkas are a great way to create a beautiful and seasonally suitable casual look in the warmer months.

Jeans & Shoes

Let’s move on to the pants you’re most likely to wear, and are most likely wearing right now: jeans.

Let’s start with something more casual: wearing jeans and running shoes.

Previously, this outfit would have been saved for your boomer father. But now, pairing a pair of trendy running shoes with a pair of jeans is one of my favorite fashion moves.

It absolutely reflects your individuality while also exuding a really nice, laid-back feel.

When wearing your jeans and running shoes, here’s a pro tip. To score added style points, snip the hem and show off some ankle.

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Sneakers are definitely the shoes you’ll pair with your jeans the most, as they perfectly match the laid-back mood.

You have my license to be a little more colorful than you would with chinos when choosing which ones to wear with your jeans.

However, if you wish to wear black sneakers, stick to black jeans to avoid clashing with your attire.

I like to wear jeans with low tops, but if you want to show off your high tops, I recommend having your jeans hemmed or rolling the cuff, as the pant leg should end just past the top of your high top.

Choose a pair of loafers, such as a basic brown leather penny loafer or a suede driving mock, to dress up your jeans.

The key is to have your jeans hemmed without a break or cuffed, and you should also have a tiny taper towards the ankle for a cleaner look.

Let’s speak about boots for a moment.

Boots and jeans are a stylish match made in heaven, as long as you choose the proper designs and colors.

When it comes to pairing these two items, I find that brown boots seem more casual, while black boots look more suited up and elegant.

Work boots, dress shoes, and chukkas are all affected.

Let us now turn our attention to Chelsea boots.

These should only be worn by slimmer men because they look best with slim cut or narrow jeans that taper to the ankles.

If you’re a bigger guy, avoid this style; otherwise, you’ll look like humpty dumpty, with all the weight concentrated in your stomach, hips, and thighs.

One final thought about Chelsea’s.

If you want to wear it with lighter denim washes, go for suede Chelsea’s in a brown or tan shade.

Finally, we’ll discuss dress shoes.

Dress shoes and jeans are appropriate for a variety of events, from smart casual gatherings to more formal functions.

However, you must consider the wash or shade of your jeans, since this will determine the color of dress shoes you should wear.

Black shoes look great with dark grey or black jeans. If one of the items on the upper half of your body is black, you can wear it with dark wash or white jeans.

Brown shoes, on the other hand, go with any denim shade.

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Dress Pants & Shoes

What about more formal occasions when you require a pair of pants that is dressier than both jeans and chinos?

Wool trousers, also known as dress pants, are typically paired with more formal things such as dress shirts and blazers, but if you want a more fancy casual look, a t-shirt, polo, or short sleeve button-up shirt would suffice.

Is it true that these pants may only be paired with dress shoes?

The quick answer is no, but it all depends on the situation in the end.

If you’re wearing dress pants to a more formal occasion, classic dress shoes like Oxfords, penny loafers, or monk straps are a good pair.

Remember that black shoes give an ensemble a dressier vibe, and they should only be paired with black or gray wool pants.

Brown and tan shoes will go with everything from navy to light gray and will readily accent your other colored dress pants.

If you’re going to a more casual gathering, you may certainly dress down your footwear by wearing a pair of minimalist sneakers, ideally white. It’s a casual appearance that’s both cool and stylish.

A lace-up boot is also a wonderful option if your pants are made of a heavier fabric, such as flannel or a thicker wool, since it compliments the weight of the pant well.

Finally, we must remember suits when discussing formal clothes. I’m going to make picking out your matching footwear a breeze.

Just wear dress shoes. Suits in black or charcoal, and black dress shoes.

Brown dress shoes, any other color suit.

That’s all there is to it.

How to Pair Shoes With Pants


  • Christopher

    Christopher has 9+ years of experience as a creative fashion designer who stays current with the latest trends.

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