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Beefroll loafers, by Rancourt & Co.

Shoes are something you don't want to skimp on. You get what you pay for and thus, a cheap pair of kicks could leave you limping by the end of the day. And while there are an overwhelming number of options out there, the nice thing about being a man is that you can go far on just a few classic styles. Which is why you should invest in quality pairs that will only get better looking (and more comfortable) as the years go on. We asked Kyle Rancourt of Rancourt & Co., who's been crafting fine American footwear for three generations, why men should invest in their shoes. His answer, in a word: Taste. "Most sub-$200 shoes have no taste ... every pair looks exactly the same and are made from dull, lifeless materials," says Rancourt. "Our shoes, for example, are unique—each pair is slightly different and crafted from materials that will develop appealing character over time."

Inexpensive shoes are tempting. Why spend $250 on a pair when you can find a similar pair for $85? They fit and feel okay when you first try them on, but Rancourt knows shoes, and he says those inexpensive kicks are an empty victory. "Those kind of shoes typically can't be re-soled, the leather can't be refinished properly, and when they break down prematurely—which they surely will—they end up in a dumpster," he says. "Quality shoes can be re-soled, the materials are light-years ahead of those bargain brands which makes them easy to maintain; this all equates to longevity." Meaning, you can buy a pair of $85 shoes every year or you can buy a quality pair for $250 every 10 years.

And while a good pair of shoes will only get better with age, that doesn't mean you don't need to take care of them. "I don't really buy into this idea that a beat-up, dirty pair of shoes is cool—take pride in your investment," says Rancourt. "Don't let an expensive pair of shoes go to waste because you didn't want to spend $20 on a pair of cedar shoe trees."