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Writer's pictureTom Goedhart

Mastering Shoe Pairings with Different Pants for Every Occasion

For those venturing into the world of fashion, a common question arises: Am I dressed right, and am I following “the rules”? Here’s the scoop on fashion: while there are guidelines and dress codes, most rules can be bent or even broken, depending on context and your confidence level. The same applies to pairing shoes with pants. Just a few years ago, who would have imagined wearing sneakers with dress pants or a suit?

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Here are some tips for selecting shoes to complement the most popular types of men’s pants. Let’s hope this advice remains relevant despite fashion's ever-changing landscape!


Chinos

Chinos are a go-to for comfort and versatility, effortlessly transitioning between casual and smart-casual styles. Therefore, pairing them with loafers or boat shoes (especially in the summer) is always a safe bet.

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However, steer clear of velvet slip-on shoes, as their texture can clash with the clean lines of chinos. As the weather cools down, consider pairing chinos with lace-up boots to add a dynamic edge to your outfit.


Joggers

Joggers, typically crafted from cotton with elastic cuffs, have become a staple, particularly among sneaker lovers. They’re all about comfort, but that can also be a drawback. Pairing joggers with slip-ons, espadrilles, or penny loafers can come off as immature and less polished.

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As joggers are closely tied to sneaker culture, opting for sleek, modern sneakers is always a winning choice.

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Additionally, suede desert boots offer a fresh, casual alternative that pairs nicely with joggers.


Dress Pants

A classic pair of derbies or brogues is essential for wearing dress pants on regular days. But what if you want to rock dress pants on the weekend? Comfort becomes paramount, so pairing dress pants with minimalist sneakers is not only acceptable but stylish (and rolling up the hems can enhance that smart-casual vibe).

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Suits

When it comes to suits, matching dress shoes are a must: basic derbies, elegant Oxfords, or relaxed brogues will do the trick. Just keep your shoes polished!

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While these traditional options are reliable, they can also feel a bit predictable. Consider stepping outside the box with trendy Chelsea boots or minimalist sneakers to showcase your style-savvy approach.

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jeans

As the most common type of pants for men, jeans can pair well with almost any footwear. In colder months, my personal favorite is wearing jeans with Chelsea boots, whether leather or suede. Alternatively, cuffed jeans with sneakers create a great look too.

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If you want to pair jeans with dress shoes, avoid overly formal styles like Oxfords to prevent a fashion faux pas. Basic lace-up derbies are the best option for a seamless look with jeans.


By keeping these shoe-pairing tips in mind, you’ll navigate the world of men’s fashion with ease and confidence. Feel free to share your own style hacks in the comments!


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