How to have the best shoes in the room

“A great shoe will elevate a blah casual look – and will be the right accent to the most curated outfit,” he says.

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 best-selling footwear collections in better men’s stores, such as Nordstrom and Saks Fifth Avenue.

His secret is satisfied, loyal customers who spread the To Boot gospel, rather than celebrity endorsements and overpriced advertising campaigns.

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,” Derrick says. “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 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 an 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,” Derrick says. “And when they’re dirty, brush up the nap with a suede brush.”

Protect the colour. “A good neutral cream polish will suffice for cleaning and moisturising white leather,” he says. “Only if you scuff the leather should you match the colour.” For polishing a burnished leather – think a shoe that has two tones rather than just being solid – he suggests using the colour 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,” Derrick says. “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,” Derrick advises. 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.”

Modernise 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,” Derrick says. “The casualisation 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’?”

Derrick suggests getting creative with bolder choices, like a streamlined sneaker, as well as circling back and modernising the classics.

“The classic tassel loafer is having a bit of a moment again,” says Derrick. “But today’s tassel loafer has a higher vamp – the front and centre part of a shoe that covers the top of the foot – so when you’re trying on a pair of loafers, look down at your feet. If you see a lot of sock showing, your vamp is too short.”

To try out the sneaker trend during your 9-to-5 shift, Derrick suggests a clean, polished calf sneaker or trainer. “Suede sneakers speak more to weekend wear,” he says.

But he stresses, “Know your audience, too. For instance, a trial lawyer appearing in court in a suit and tie does not need to be experimenting with a clean sneaker. Instead, wear a classic, straight-tip cap toe or wingtip and look the part.”