“The right shoe speaks volumes about how you view yourself and your approach to dressing,” says Adam Derrick, founder of one of the best men’s shoe brands you’ve maybe never heard of—To Boot New York.

Derrick is passionate (and right, of course) about shoes. More and more, he argues, men are now getting dressed from their feet up. “A great shoe will elevate a blah casual look and will be the right accent to the most curated outfit,” he explains. Derrick started his footwear empire in New York City's Upper West Side as a cowboy boot outpost in 1979 and has since quietly built one of the bestselling footwear collections in better men’s stores, such as Nordstrom and Saks Fifth Avenue. His secret is satisfied, loyal customers who spread the Too Boot gospel, rather than celebrity endorsements and overpriced advertising campaigns.
In this season of shoe-destroying conditions, we turned to Derrick for advice on how to maintain a great leather shoe—and how to build a collection of impressive, memorable pairs.

Shop for Quality Over Quantity (and Shop Italian)

According to Derrick, the average American man owns somewhere close to 12 pairs of shoes. But he doesn’t necessarily think most men need that many if they are being smart about their purchases. “I may be biased, but I think it’s a mistake for men to not buy quality footwear,” says Derrick. “Unlike with a shirt or a jacket, your shoes have a big job to do. They have to regularly support your entire body weight while being comfortable and encouraging you to stay active and stand tall, and look great all at the same time.”

Derrick suggests two things: First, look for a stitched sole. A stitched sole, like To Boot’s "Blake" construction, is sturdier and more practical than a glued or bonded sole. Also, he suggests buying footwear made in Italy, period. “In general, footwear made in Italy denotes a production level that is of the highest quality, with more time and attention to the details of construction and comfort.” He notes that most Italian footwear will prominently display the country of origin on the label because it’s an immense, notable measure of quality.

“Unfortunately, quality isn’t always something you can tell straight away by looking at a new shoe, but the difference will definitely be noticeable to the consumer in six months to a year,” he says.

Maintenance Is Key

Wipe, then wear. Derrick suggests wiping down your shoes with a soft cloth or paper towel before putting them on. “Dust can collect in the creases and will act as sandpaper on the leather as you walk,” he says. You could also try a all-natural product such as Shoe Rescue to keep your kicks extra refreshed.

Spray suede. “Lightly mist, not saturate, your suede shoes with a water and stain protector spray,” suggests Derrick. “And when they’re dirty, brush up the nap with a suede brush.”

Protect the color. “A good neutral cream polish will suffice for cleaning and moisturizing white leather,” says Derrick. “Only if you scuff the leather should you match the color. For polishing a burnished leather—think a shoe that has two tones rather than just being solid—he suggests using the color of the "body" of the shoe, rather than the darker burnished toe.

Always use a cedar shoe tree. “The shoe tree irons out creases and maintains the original contours,” says Derrick. “The unfinished cedar wood absorbs moisture and adds a fresh smell.
Rotate. “Don't wear the same pair of shoes two days in a row if you can help it,” advises Derrick. He says shoes should be rotated to let them completely dry out between wearings. “This more than anything prolongs the life of your shoes,” he says. “Another benefit to having a wardrobe of shoes.”

Modernize Your Options

“Even though there are more options than ever—which is great—I think it has become a lot more challenging for men to dress well today,” says Derrick. “The casualization of the workplace has got men thinking, ‘How can I still look pulled together and successful when casual Friday has become the new everyday uniform?’”