Instagram: @OakStreetBootmakers

Every man needs a pair of heritage boots – finely crafted, rugged boots you can wear on outdoor treks, yet are not so casual you can’t dress them up when your girlfriend drags you to weekend brunch. The beauty of heritage boots is that they’re made to weather just about anything, and only get better-looking with age.

If this is your first time on the market for a nice pair of boots, look for versatility and classic colors. Ideally, you’ll want to be able to throw these boots on and head out the door confident that your getup is on point. They should also be comfortable so you actually get some wear out of them. A great place to start is Oak Street Bootmakers, a family-owned business based in Chicago.

Founded by George Vlagos, the son of a cobbler, Oak Street Bootmakers’ mission is to preserve the heritage of fine shoemaking. To that end, the company’s shoes are constructed using renowned Horween leather that undergoes 89 separate steps to yield that supple, durable finish. In short, these boots are well worth your hard-earned money.

While we’re eyeing the Brown Trench Boot, any of Oak Street Bootmakers’ shoes are worth your time.


Instagram: @OakStreetBootmakers


Why should I pay $400 for a pair of boots?

Now, there’s no denying these boots are nice. But the $426 price tag may give you sticker shock. Here’s why you should invest:

Leather quality

Ultimately, you’re paying for quality and longevity. Although you’ll find a fair amount of less expensive boots also made from leather, we can guarantee you the quality of the leather is nowhere comparable to heritage boots. Whereas the Oak Street boots are crafted from full grain leather, cheaper boots are made from corrected grain leather - leather with impurities that is treated to look better.

A lot of times the treatment to remove impurities leaves a shiny surface that flakes off with time, causing the cheaper boots to age poorly.  Quality boots, on the other hand, mold themselves to your feet and age handsomely.

Goodyear welting

Goodyear welting is considered one of the finest methods of shoe construction. It allows for a constant flow of air through the shoe, keeping it ventilated and durable so it can last upwards of 20 years. Goodyear welting also makes the shoes water-resistant and more comfortable. However, this type of shoe construction takes much longer to complete than cheaper boots.

Many cheaper boots use rubber soles, which last a year if you’re lucky.

You can re-sole your shoes

Like your boots so much you eventually wear them into the ground? No worries – just replace the sole. Goodyear welting means the boots are recraftable, extending their lifetime.


Shop the Brown Trench Boots at Oak Street Bootmakers.