Ultimate Guide: How To Match Shoes With Pants

I have to say I get this question a lot. So, I thought I’d take a moment to do some clearing up about how to match shoes and pants correctly. There’s a lot of confusing info out there so I want to explain how to best combine shoes and pants in your wardrobe so you feel most confident in what you wear.

This will include everything from mastering the art of color matching to selecting the most versatile pieces, so you can truly get the most bang for your buck.

Shorts

Sneakers will undoubtedly be the best choice as they seamlessly match the casual vibe of the shorts. My most essential piece of advice when choosing a combination of shorts and sneakers is to keep everything super simple. Embracing a minimalist or all white sneaker will generally be the easiest and safest way to go, especially when opting for a low-profile or slip-on sneaker.

High tops, on the other hand, are something you’ll wanna approach with caution. While high tops with shorts aren’t impossible to pull off, you really need to nail the choice of colors and designs to make it work. Never, under any circumstances, should you pair them with dress shoes or boots.

When it comes to dressier shoes, a great option would be a sleek pair of suede penny loafers or boat shoes.

Chinos

These are super versatile pieces and can easily be dressed up or down, depending on the type of shoe that you decide to pair them with. The trick lies in choosing the right fabric depending on the occassion. For example, suede driving mocs work exceptionally well for casual business looks, while leather penny loafers combined with chinos create the perfect combination for more formal and elevated situations.

Sneakers, particularly low tops, look fantastic when worn with chinos, especially white ones, and will go well with any color of chino. This ensemble can seamlessly transition from Friday night outings to Monday morning meetings simply by switching out the upper half of your outfit.

You can easily elevate the overall look with dark brown dress shoes; in particular, options like oxfords pair beautifully with numerous shades of chinos, such as tan, navy, and olive. Black dress shoes should be thoughtfully considered to successfully pull off a polished appearance.

Boots and chinos can work well together, too, but that typically lends itself to an early spring or fall aesthetic. I’d recommend going for suede chukkas during the warmer months to create a stylish and seasonally appropriate look that’ll add major flair.

Jeans

Starting off on the casual side, let’s take a moment to discuss running shoes. There was indeed a time when this style choice was often associated with a dad-like vibe. But when done right, it can genuinely feel more effortlessly chic, especially when paired with a nicely cuffed hem.

Feel free to experiment a bit more with colorful options for your sneakers; you might even consider choosing high-tops. Just be sure to either have them hemmed appropriately or roll them to a point where they stop just above the top of your high-top.

If you’re aiming to dress up your jeans a bit more, choose a more sophisticated pair of loafers in classic brown or a sleek driving moc can be a great choice. Just make sure there is no break in the fabric, or that the jeans have a slight taper for a cleaner finish.

When it comes to pairing boots with jeans, brown boots provide a laid-back, casual feel, while black options bring a more dressed-up and sophisticated touch. This rule applies to all types of boots including work boots, dress boots, and chukkas. I don’t usually recommend chelsea’s as the first go-to choice since they tend to look best with slim-fit jeans and require a careful taper at the ankle. If you happen to be on the heavier side, this particular look should generally be avoided as it really emphasizes your midsection, hip, and thigh areas.

Dress shoes paired with jeans work for so many different occasions, ranging from smart casual get-togethers to more formal events. For footwear, consider the wash or shade of your jeans, as this will help determine which color dress shoes complement your outfit best.

Black shoes work wonderfully with black or dark grey jeans, and surprisingly, they also pair well with dark washes or even white jeans if one of your top layers include black.

On the other hand, brown shoes are super versatile and can seamlessly match with every shade of denim, making them an excellent choice for any casual or semi-formal look.

Wool Trousers

These usually paired with more dignified items like dress shirts and blazers; however, you can just as easily opt for a t-shirt, polo, or a short sleeve button-up shirt if you want to achieve a more dressy/casual feel. The big question that often arises is whether these pants can only be paired with dress shoes. The short answer is no, though it ultimately depends entirely on the specific situation you’re in. If you’re wearing dress shoes for a more formal event, then you’ll want to stick with a pair of classic dress shoes like oxfords, penny loafers, or monk straps to complete your look.

Black shoes lend a more dressy feel to an outfit and really should only be paired with black or grey wool pants for the best effect. Otherwise, brown and tan dress shoes will more easily complement your other colored dress pants, as they can go with a variety of shades, from navy to dark grey.

If you’re attending a more casual get-together, you can certainly dress down your footwear with a nice pair of white minimalist sneakers. It’s a cool and stylish look that I personally love styling my clients in, it gives off such a relaxed, yet sophisticated vibe.

If your pants are made from a heavier fabric like flannel or thicker wool, then a lace-up boot serves as another fantastic option to complement the heaviness of these pants and maintain overall balance.

Suits

I’ll make the process of choosing your accompanying footwear incredibly easy:

Just opt for dress shoes.

If you’re wearing a black or charcoal suit, the best choice is a pair of black dress shoes.

Now if you decide on any other color suit, go with brown dress shoes.

It really is as simple as that.

Use this valuable information for continued success so you can attract investment from others just as you invest in yourself.

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