The process of making an important purchase can be stressful and overwhelming for just about anyone. You take your time and research diligently to make sure you are making an informed decision. Getting started is almost the hardest part, but we look to make things easier with our newest series of interviews. We discuss an array of products from boots to vintage watches to denim and learn what should we be looking for and how much should we spend among other topics. We kick off the series with Richard Lin or better known as @doppki on Instagram. With a feed full of quality boots, Richard shares his insight into buying a pair of boots and guides us through the purchasing process.

What differentiates boot brands and styles?

I have to preface all of this by saying, by no means am I a bootmaker or an expert on what makes a great boot. Rather, I am hoping to just offer some of my experiences with boots and what I have learned over the years through reading and hearing from others.

I tend to view boot brands and styles in two main categories: formal versus casual, or put a different way, classy versus rugged. These are not terms that companies necessarily use, rather just the general impression I get when I look at a pair. If you go to companies, they will typically divide them out by categories such as work boots, hiking boots, dress boots, etc. In any case, as with most things in life, it is a spectrum and not necessarily one or another. This is how I generally approach and view the types of boots. As well, that means that just because a boot is more “classy” looking does not preclude you from wearing it on your next outdoor adventure.

Getting into the details, the quality of the leather, the type of construction, and where the boots are made are what differentiate the various brands out there. While you can look at a $400 pair of boots and find a near identical one at $100, it is very likely that the quality of the leather is poorer and the construction is such that you cannot resole/recraft over time (technical jargon: cementing versus welt). Lastly, where the boots are made obviously set some brands apart from others; and even within the same brand there can be a different line for boots that are Made in America versus elsewhere (such as the Red Wing Heritage line).

A Boot Buying Guide With Richard Lin

What should someone look for when purchasing a pair of boots? Specific details and materials?

If it is your first pair of boots, I would recommend going for something you can wear in a variety of settings. As such, finding a pair in-between formal and casual—commonly referred to as dress boots—will help you get your money’s worth in terms of usage. So what should you look for? While you should definitely pick what is pleasing to your eyes and not just what is most popular with everyone else, it just so happens that the most popular boots are ones that are absolutely beautiful. In any case, you will only wear your boots in so far as you like it yourself!

Drilling down, for a first pair I would say you should probably avoid the special or unique leathers such as rough-out, suede, and waxed; instead opt for a smooth finished leather for maximum versatility. For the leather color, a light brown to medium brown leather will typically be most versatile when compared to black, reddish, or tan colored leather. With that said, boots will always look great with a pair of nice raw denim.

Other than the aesthetics, you will want to find a pair that you can resole/recraft over the life of the boot. In my opinion, as far as boots go, nothing can be more sad than wearing in a pair of leather boots to obtain the sweet patina that everyone wants, but then finding yourself with a damaged sole that is irreplaceable. So what should you look for? A Goodyear welt is the epitome of a well-constructed boot that offers great support for your feet, but also an easy resole for a cobbler. There are also other welt construction methods that allow for future resoling, which I will simply refer you to Google for more details.

There’s a lot of jargon thrown out in the product description, what do they mean and what is the most important?

I think the jargon that was most unknown to me when I first started getting into high quality boots was the “last.” The last is essentially the form and shape of the boots. The bootmakers create a mold in the shape similar to a foot and then the upper leather is pulled over the mold to create the shape of the shoe. The last is important as it essentially deals with the “fit” of the shoe. Just as with clothes, the biggest part to dressing well is having a good fit. In the end a good fit will result in you wearing it more.

Aside from that, most other jargon I would think is pretty self-explanatory. One thing I will mention is the structured vs unstructured toe. A structured toe basically means that there is extra material in the toe box that will keep the area from collapsing over time. I note this because I personally think that an unstructured toe over time, will look more and more casual after it begins to collapse; something to keep in mind when deciding what type of boot you want.

A Boot Buying Guide With Richard Lin

How much should someone expect to spend for a quality pair? If they have $100, $200, $300, what can they expect to get in return?

At regular prices, a quality pair will likely run you $250-300. However, you can find great brands at prices $50-100 off during end-of-season sales or holiday sales. At that price, you should be able to get a boot with quality (full-grain) leather and construction at $200 or less. With that said, we all start somewhere and I began with a pair of Timberland Chelsea Boots. They lasted me almost two years, but by the time those two years came around they were totally beat. It was then that I started looking into boots that would last a lifetime and bought myself a pair of Red Wing Heritage Beckmans featuring their Featherstone leather and a Goodyear welt. I have yet to resole them as they’ve last over four years without significant damage to the sole. It was significantly more expensive, but as people tend to say, “Buy once, cry once!”

A Boot Buying Guide With Richard Lin

What brands should someone be targeting?

I personally can only speak to the following brands that also happen to be in the price range that I have been able to justify ($300-500): Red Wings, Oakstreet Bootmakers, and Allen Edmonds. All of these offer boots with Goodyear welt construction and quality leathers. Keep in mind that Red Wings and Allen Edmonds are substantially larger companies that offer multiple lines of boots that may mean some offerings may not be Made in America, may not use Goodyear welt construction, or may not use quality full-grain leathers. Oakstreet Bootmakers is a much smaller company and with that, I personally think that affords them the ability to focus on offering higher quality and unique boots that may not be as readily found in the larger companies like Red Wing and Allen Edmonds.

Other than these three, while I have no personal experience, Vibergs and Aldens tend to be very well regarded ($500+); Truman Boot Company has also been a favorite of late within the internet community that follows quality menswear.

A Boot Buying Guide With Richard Lin

Where do you think has the best selection of boots?

It is hard to provide a single company or website that has the best selection of boots. If I had to provide one, I would just say Red Wing because of their wide selection and also the history behind the company. While the history has no real bearing on what selection of boots they offer, I do think that companies with significant history tend to be the ones that other companies look to emulate or base their initial boots off of.


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