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New Penny Loafers from Jack Erwin

With summer fast approaching, I was in the market for a simple, handsome and elegant slip-on for casual wear. I thought about loafers from Alden and Tods, but an easy everyday shoe that I’d be wearing for walking the dog didn’t strike me as an occasion to splurge. Then I remembered Jack Erwin.

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Episode 26: When to Splurge

As a frugal consumer and creator of content that advocates living well and looking good without being a millionaire, I got called out by a follower on Instagram when I posted a picture of a new pair of Alden Chukka Boots. With a price tag of nearly $700, Alden Chukka boots aren’t cheap, and my follower had a point… to a point.

In this episode, I make the argument for when a splurge is justified. It’s all about value and what a particular item means to you. As my friend Glenn Gissler eloquently put it: value is quality over time.

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The Kenmoor: A Smart Long Wingtip from Florsheim’s Imperial Line

I know… “Florsheim.” But hear me out…

When I hear the name Florsheim, I think of shoes my dad would wear. “Old man-ish,” “conservative,” or “uncool” are some descriptives that come to mind. I wouldn’t consider Florsheim an edgy brand on the “get” list for most hipsters.

But when someone makes a smart and well-crafted long wingtip shoe with a quality leather upper, a leather lining, and a Goodyear Welted double leather sole with nice English “heft” to the thickness and width, I don’t care what the perception of the brand is.

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A New Pair of Affordable, Stylish and Grown-Up Shoes from Jack Erwin

The group of “New Disrupters” in the menswear game offering affordable solutions without the middleman is large. Once these brands establish their ability to deliver goods at a reasonable cost, what separates the men from the boys is a certain intangible and unquantifiable thing called taste. The new disrupters who actually have a level of refined taste that puts them on par with more established influential brands is a much smaller group. Ideally, the taste level filters through all levels of the brand experience, from the design and presentation of the actual merchandise to the logo and slogans to the execution of the website, which had better give first (not last) consideration to smartphone and tablet users. Jack Erwin is among this group.

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The Importance of Cedar Shoe Trees

You cannot underestimate the importance of shoes. They say a lot about us. And it’s not about expensive shoes versus inexpensive ones. It’s about well-chosen shoes that are well-tended. I apply the same degree of care to my Florsheims as I apply to my Aldens.

In addition to regular leather conditioning and shine, and maintenance and protection of the soles with taps, I also preserve the appearance and longevity of my shoes with cedar shoe trees.

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My Cordovan Chukka Boots from Alden

With many things pertaining to smarter modes in menswear, I’m often late to the party. I didn’t fully understand the pleasure (or importance) of a well-tailored suit or what went into a well-made shoe until my late 30s. When I “discovered” things like Warby Parker, J.Crew’s Ludlow suits, Kamakura or The Tie Bar, I learned that other smartasses in the menswear ether had known about them for years. I don’t claim to be inventing any wheels here, and I will never pretend to be an expert. We get there when we get there.

Another party to which I arrived late is Alden. To be clear, I’ve certainly been aware of Alden and their gold standard in American shoe and boot making for a long time. In fact, I’ve been coveting a pair of Alden’s cordovan chukka boots for several years. My new arrival to the Alden party comes in the form of actually owning a pair.

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Saving My Soles With Taps

Whether we’re willing to admit it or not, we make assessments when we look one another over. Other than the obvious signals to financial status and, of course, taste, the choices a man makes about what he puts on himself offer clues to his character.

One of those clues – something that impresses me about a man – is his shoes. It’s not about an expensive pair of shoes. I’m actually rather unimpressed with obvious displays of prestige or the perception thereof. What does impress me is when a man selects tastefully and takes care of those selections. A brilliant shine and a well-tended heel say something. Dull shoes with worn heels say something else.

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