Oak Street Bootmakers

The United States was once home to a thriving collection of men’s shoe manufacturers.

But outsourcing has taken a brutal toll, whittling that number down to a thin sliver of activity. Allen Edmonds, Alden, Quoddy and Rancourt are about the last remaining options for a man seeking an American made dress shoe. And Quoddy and Rancourt really exist at the casual edge of the men’s dress shoe spectrum.

In 2009, however, a new company joined those ranks. Headquartered in Chicago, Oak Street Bookmakers has already gained significant traction among certain segments of the online style cognoscenti.  George Vlagos, son of a master cobbler, started Oak Street when he made an interesting observation. Over time, the shoes in his father’s shop hewed less to such classic offerings from Allend Edmonds and Alden and more toward essentially disposable, foreign produced versions.

Oak Street is committed to producing designs, as George puts it, “based upon classic American silhouettes.”

I’ve kept my eye on Oak Street for a few years, but its driving aesthetic always seemed a bit more blue collar/casual than classic business dress. I did briefly consider Oak Street for a pair of penny loafers, but it only offers the beefroll, and I much prefer Rancourt’s weltline version.

Earlier this year, Oak Street introduced a classic double sole wingtip offered in three colors. I was intrigued and took particular note of the bourbon version. A summer sale offered further enticement, and so I took the plunge.

Because my feet are different sizes (8E on the left and 9.5D on the right), I had to make a custom order. As a result, I wasn’t able to tap into the sale, but the good folks at Oak Street did waive the fee normally assessed for custom orders.

In a little more than eight weeks, the shoes were on my doorstep.

My first impression is that they are a beautiful pair of shoes. Although I’ve never been an eager partisan of the wingtip, these have a beauty of design that stirs even my jaded heart. The double soles are a nice touch, and the leather is top notch.

The shoes, right out of the box

However, there are some issues, and we need to look at the negative side of the ledger sheet:

  • The shoes are lighter in tone than the versions on the website. I was expecting a deeper shade, something akin to a cognac or bourbon. But they were a bit lighter than they appear online, a slightly reddish tan.
  • While the construction seems solid, it’s not perfect. The stitching on the inside of the left shoe is a bit sloppy, and there’s a pindot sized blob of darker color on the top of the right shoe. In a product that has a significant amount of handwork, I’m willing to accept a few imperfections. Others may not be as forgiving.
  • The shoes only come in medium (D) widths. For most folks, that’s not much of a concern. But when you’re paying the premium associated with a custom order, you expect a little more precision in sizing.
  • No shoe bags. If you drop five bills down on a pair of shoes (a not insubstantial sum for most of us), it’s a safe bet that they’ll include a pair of shoe bags. It’s standard practice in the industry. Over the past 15 years, I’ve purchased 19 pairs of non-athletic shoes; each came with shoe bags. But not these. Why?
Oak Street 3
Sloppy construction

So would I recommend Oak Street? I’m torn. Despite the aforementioned deficiencies, I still like the shoes, and they fill a void in my collection.

But I don’t think, given the issues I outlined, that they’re a good value at their retail price (even more for a custom job). Perhaps at $350 or under, they might be justifiable, but not at this price.

So, a qualified recommendation.

Oak Street 1

Oak Street 2

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