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The Approach to Buying New Shoes

This article has been four months in the making. I bought a new pair back in early December and I’ve been paying very close attention to them to see how they held up and to put to the test some of my criteria for “the best shoes I’ve ever bought”

What I wanted was something unlike any shoe I’d purchased before. I wanted something that worked with “almost” every outfit. I wanted something that fit well with casual and dress attire. I wanted something that would last and that would get noticed.

My previous pair was a Monk Strap by Kenneth Cole. At the time I was really just hunting for a style, brown monk strap. I found it and at a price that was less than 100$ bucks. Also, at the time I didn’t understand shoe construction or style that well.

(These but in a light brown)

What I discovered is that they aged badly. Not the good kind of age that you get on awesome antiques and sexy milfs. The bad kind. The kind that drains away at all the beauty of a thing and accentuates all the flaws. All you’re left with is a shoe that shows the world how little you cared about the build(or to learn about the build) and how little you paid for it.

(Something that ages well: Monica Belluci)

(Something that doesn’t age well: Any shoe that retails for under 100$)

So what are you looking for in a good pair of shoes? Well price is a good place to start but it’s not the one and only rule to get you in a good pair of shoes.

Let’s talk about make first.

The two things you need to know to make sure the shoes you’re holding in your hands are worth purchasing are the welting and the leather quality.

The welting is the process used to attach the vamp(also known as the upper) to the sole. Goodyear Welting is generally regarding as the best method for holding an upper to a sole. It was invented by a relative of Charles Goodyear, thus the name for the process. The only thing you should really know is that this is the only style of welting that does anything other than hold the shoe together. Goodyear welting keeps water out while helping to maximize airflow of the shoe. Airflow is one of the things that makes a shoe last. It’s also the most comfortable kind of welt because none of it is near your actual foot. This is an expensive process because it takes a long time to do and is one of the reasons your shoe may be expensive.

The other widely used and acceptable method of shoe welting is the Blake /Rapid. Again, long story short it attaches the sole to the vamp. This method makes shoes easier to resole and thus cheaper to repair. Shoes with a Blake/Rapid are also a bit cheaper because the method is quicker to employ. Both are fine and both have their benefits and cons. I wouldn’t hesitate between either really.

The leather quality is the next consideration in knowing the make of the shoe. The kind of shoe you don’t want to buy is made of something called Corrected Leather. Think about this for a moment. Leather is made of skin. Correction means eliminating flaws. What do you have to do to eliminate flaws on skin? Basically, Corrected Leather has been Frankenstined to the point where the visual imperfections a piece of flesh may have are gone. This is done with chemicals and sanding. This makes the shoe leather weak, susceptible to ugly creasing and to fading.

You want Full Grain Leather. I’m not going to get too wordy here. Just know that Full Grain is the exact opposite of Corrected. This leather lasts and that means the shoes will hold up for years and years. Seriously, research this. Some people have twenty year old shoes that have just been repaired a few times. You can’t repair cheap shoes. Here’s a link to what I mean about repairing a shoe. Good shoes can be saved. http://www.permanentstyle.co.uk/2010/08/rescuing-shoes.html

Now let’s talk style.

There are a lot of shoes out there. A lot. You need shoes that work with all your outfits and you need shoes that work in all the situations life throws at you. Now, not every piece of footwear is going to work in every single situation. I get that. Let’s not argue semantics. You know what I mean, right?

In case you don’t let me just be clear with what I mean when i’m talking about good shoes.

Gym Shoes– No. Gym shoes have only one purpose and one place to be worn… the gym. Or while exercising. I get that some people treat their gym shoe like a status symbol but please… grow up. The rest of the world doesn’t really care about your Air Jordan’s.

Sneakers– I’m looking at you Chuck Taylors. These have become the icing on the “I don’t give a shit about my appearance” cake. They get paired up with pants that are either tattered, torn, effeminately skinny or pocket covered to complete an outfit that screams “schlubby”. If done well with dark denim, the best you can do is come across as Super Casual. But usually you just end up looking like every other counter culture kid. Also, if you’re over 25 it’s time to retire your Chucks too.

Chucks with suits is NOT a thing. Try it once or twice to get it out of your system and then just stop it.

Utility Boots– Look, unless you’re mountain climbing, trekking cross country, in a warzone or building a sky scraper you don’t need boots on. Boots have a place, wear them in that place. Also, yes, I know there are dress boots but that’s not what I’m talking about. Chukkas and Desert Boots are not part of this category. They fit better in the next one.

Seasonal Footwear– I own Boat Shoes. They’re one of my favorite pairs. I’m wearing them right now. But they aren’t great shoes. They’re good. The quality of most seasonal footwear doesn’t compare to all season shoes. And more importantly, you can’t wear Boat Shoes in the winter. Seasonal footwear, by definition, lends less utility to your wardrobe than all season shoes. If possible have both, when in doubt concentrate on all season footwear first.

As far as the style of the shoe’s appearance, I’m leaning strongly toward Wingtip. Wingtips are shoes with Brogues bored into the surface (decorative holes). When this was first invented it served the same purpose as clogs before clog was a thing.  Thank the Scots and the Irish for this style.

You’ll hear phrases like Half Brogue and Quarter Brogue but all that means is that the decorative holes cover less of the shoe. Wingtips have the most. That’s why it’s considered Full Brogue.

I like this style because its the perfect middle ground between complete dressy and casual. Some people look at a wingtip oxford and think that is the height of dress but frankly the world has come to accept trashy appearances so anything not covered in multiple colors and logos must be dressy. This style will get you by for everything but standing up in a wedding or brokering peace between warring nations.

The color must be brown. Why? First of all, if you take my advice and stick with some kind of shoe with Brogues the decoration will stand out better. Brogues are hard to see on black shoes. Secondly, brown adds warmth to an outfit. People say black goes with everything but it really doesn’t. Black only looks good with more black. Brown pairs well with everything, even black. To get the most out of your footwear always go brown and specifically something not to light and not to dark. Cognac and Chestnut are frequent color shades used to name shoes. Look for that if nothing else.

But as far as the test run on my shoes is concerned this is what I ended up with. A great pair of Wingtip Oxfords from To Boot New York.

(The Windsor, as To Boot calls it)

Just a few basics from across the web about this Manufacturer. Their styles and construction methods will vary because they use a few different factories across Italy. They’re a great designer but their manufacturing standards can vary. My pair is great and most people get equally great shoes from them. Some have had issues with the Blake/Rapid attaching method used in some of their shoes. Inspect your shoes and return them if you don’t like them. Never live with something you don’t like. I suggest them highly.

Anyway, that’s my approach to buying new shoes. I’d love to hear yours.

To Boot New York