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From there, Feeney and his friendly band of cobbler’s assistants will, over the course of the next few months, cut, stretch, sew, stitch and burnish into existence, not just footwear but wearable works of art; a process he’s perfected since creating his first pair of shoes over 20 years ago.

His end product is far superior to what you’ll find on a rack, for three main reasons. “First, it’s made to your specific measurements, so things you may have found difficult with generic sizing are completely ruled out,” Feeney said. “Second, the attention to detail on every step of the process far outweighs a factory setting. And lastly, the materials we use are of a superior quality, hand-selected for every single element of the shoe.”

The process is an investment of both time and money. From the first trace of your foot to unboxing, it can take anywhere between three to six months and the cost typically starts at around $2,000. So staying conservative in terms of the design is key. As far as colour, stick to black or a dark chocolate suede. 

“I always tell people to create the shoe that they are going to have to try not to wear,” said Feeney. “Too many people go crazy on the design to make it special and then never wear it because there’s too much going on. Start by filling the void of or replacing a simple staple.”

That staple might just be a stalwart style seeing a resurgence: The loafer, long a staple of Ivy League grads and swaggy Italian gentlemen.

In recent years, the loafer has been interpreted in wildly editorial ways on the runways but has evolved into something closer to its original self. “Menswear had been balls to the wall in this ‘wild style’ era. I think people started seeing the utility in having something simple and streamlined that has been around for hundreds of years. And loafers were the perfect place to start,” said GQ’s style editor Yang Goh, who has been covering the shoe’s resurgence since 2018.

Proof of its popularity: Streetwear brands like Aime Leon Dore, Noah and KITH, all of which have ties to sneaker culture, have introduced versions of it into their collections.

We’re now witnessing a full-on revival of the classics. Oxfords, derbies, monk straps and boots of all kinds are all popping up in men’s fashion influencers’ get-ready-with-me videos and NBA players’ tunnel walks.

“I think people are looking to embrace those traditional forms of menswear again, but put their own spin on it, which is heartening to see,” said Goh. He himself wears his favourite black cowboy boots almost daily. “People are also realizing that the classics are way more versatile than they might have realized. A great pair of leather Oxfords, for example, can be dressed up or down easily, and a loafer literally goes with everything: jeans, chinos, fatigues or a suit.”

Of course, price point is an important consideration. If custom isn’t in the cards just now, the midtier (around $500 and up) is loaded with amazing up-and-comers like Morjas and Blackstock & Weber, as well as a host of renowned heritage brands like Alden, Grenson, Loake and Church’s.

If you’re on a budget, it doesn’t mean you’re out of luck. “There are a lot of incredible affordable brands out there for dress shoes,” said Goh. “If you’re just starting out and want a great pair of Oxfords, you can get yourself a pair of Dr. Martens, the kind you used to wear in high school. They can fill in for dress shoes and have a bit of a punk edge to them, which is cool. For loafers, you can’t go wrong with G.H. Bass Weejuns. They won’t run you more than a couple hundred dollars and are really reliable.”

Investing in timeless footwear is never a bad idea, because here, quality matters. And there’s no such thing as a well-rounded men’s wardrobe without a good dress shoe.