How to Match Shoes to Your Outfit

Many men assume footwear is an afterthought. They decide what clothes to throw on and casually pick a pair of shoes before heading out the door. They couldn’t be more incorrect. Clothes make the man, but shoes make the outfit. Nothing snuffs out style like a terrible choice of footwear.

Going forward, men need to get better at knowing which types of clothes go with which types of shoes. Doing so helps them avoid looking like a big no-no when meeting with friends or going on dates.

The following is an essential yet invaluable guide for doing so without being struck by analysis paralysis:


Often designed for heavy-duty work environments and rugged activities, boots can also be worn casually. The go-to combo is boots and denim. For example, a pair of Doc Martens work boots are typically worn with rolled-up slim-fit denim jeans. The same goes for Chelsea-style boots and Blundstones. Boots look good when paired with a simple white tee and flannel button-up, as well as light jackets and zip-up sweaters.


A pair of canvas hi-tops like Converse can be worn with denim, khakis, and slim-fit athletic pants. Swap hi-tops for low when wearing shorts. Since canvas shoes often come in a variety of colors, it’s crucial to find combos that complement one another. Avoid clashes unless headed someplace quirky, like a theme park or sports event. The dirtier the canvas shoes become, the more they exclusively work with denim and dark khakis.


We trust most men know they shouldn’t pair dress shoes with jeans or shorts. However, we bet many guys are overly conservative with the way they pair dress shoes with formalwear. For instance, did you know you could wear brown dress shoes with a navy blue suit? Similarly, black oxfords can go with light-colored khakis, especially if laced with red or orange shoestrings.


Every man needs a pair or two of white athletic sneakers in his closet. They should stay in his closet from September to March, only coming out in spring and summer. That’s because they work best with shorts and rarely look swell in pants. Add some flair by pairing white sneakers with colorful socks that sync with your shirt. It’s also a good idea to include white in another component of your outfit, either with sunglasses, a watchband, a belt, or graphic tee highlights.


Few types of footwear offer as much versatility as canvas slip-on Vans. They can be worn with jeans, khakis, shorts, and even dress pants. They look good in socks as well as without them. The only downside is the limited insulation, making them incompatible with cold weather conditions. Best of all, slip-ons come in a wide variety of colors and patterns, making them easy to match without putting too much thought into the matter.


Footwear made from suede covers a lot of ground, including sneakers, dress shoes, boots, and loafers. Regardless of style, suede shoes follow a similar path as leather dress shoes when it comes to what to wear with them. As a rule, never wear brown suede shoes with a black suit or black suede with a brown suit. However, feel free to wear brown suede with gray or navy blue outfits.

There’s no reason to spend lots of time wondering what kind of shoes to wear with your outfit. However, nobody should be carelessly pairing shoes with their clothing, either. Men who want to look their best have an obligation to know what kinds of footwear to wear with which types of clothes. Luckily, doing so is a simple matter of referring to the guide provided above. We hope doing so leads to elevated style and increased confidence in the days, months, and years ahead.