The Ultimate Guide: How To Match Shoes With Pants
I get tons of questions from guys out there on how to best combine various types of shoes with their pants — it might not seem all that hard, but it can be a little tricky to pull off with little skill.
Find out exactly what shoes pair best with your shorts, chinos, jeans and wool trousers so you feel more confident in the things you wear.
1. Shorts
Sneakers will undoubtedly be the best choice as they pair well with the casual vibe of your chino shorts. My most essential piece of advice when choosing a shorts and sneakers combo is to keep everything simple. Embracing a minimalist all white low-cut sneaker will generally be the easiest and safest way to go.
High tops, on the other hand, are something you’ll want to approach with caution. They aren’t impossible to pull off, but you really need to nail the choice of colors and design to make it work.
Never, under any circumstances, will dress shoes or boots pair well with shorts.
If you wanna dress up your short look, a great option would be a sleek pair of suede penny loafers or boat shoes.
2. Chinos
Chino pants are highly versatile and can easily be dressed up or down, depending on the type of shoe. But the trick lies in choosing the right fabric.
For example, suede driving mocs work exceptionally well for business-casual looks, while leather penny loafers combined with chinos create the perfect combination for more formal situations.
White sneakers, particularly low tops, look fantastic when worn with chinos, and will go well with any color chinos. This ensemble can seamlessly transition from Friday night on the town 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 paired with a shade of chinos in either tan, navy, or olive.
Boots and chinos can also work well together, but that typically lends itself to an early spring or fall aesthetic. I’d recommend a suede chukka during the warmer months to create a stylish and more seasonally appropriate look.
3. Jeans
Leaning into 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 give off an effortlessly chic vibe, especially when the hem of the pant is neatly cuffed.
If you’re aiming to dress up your jeans a bit more, go for a a more sophisticated pair of loafers or a sleek driving moccasin in a classic brown.
When it comes to pairing boots with jeans, brown boots in particular provide a laid-back, casual feel, while black options bring a more dressed-up and sophisticated touch. If you happen to be on the heavier side, this pairing should be avoided as it can really emphasize 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 elevated events.
Consider the wash or shade of your jeans to help determine which color dress shoes will best complement your outfit.
Black shoes work wonderfully with black or dark grey jeans, and surprisingly, they also pair well with dark colored or even white jeans if one of your tops or outer layers are also black.
4. Wool Trousers
These type of pants best work for more dignified items, like dress shirts and blazers.
If you’re wearing dress pants to formal event, then you’ll want to stick with a pair of classic dress shoes like oxfords, penny loafers, or monk straps.
Black dress shoes lend a more dressed-up appeal, which makes them best teamed with your black or grey wool pants.
If you’re attending a more casual outing, 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 a thicker wool, then a lace-up boot serves as another fantastic option to complement the heaviness of the pants and maintain overall balance.
5. Suits
I’ll make the process of choosing your accompanying footwear with suits incredibly easy:
Just wear dress shoes, it really is that simple.
Brandi is a personal stylist with over 10 years of experience helping men feel confident in their clothing. She offers tailored style solutions to solve your fashion issues, ensuring you look and feel great for any occasion.