by James Gallichio
At least a few times every week I get an email from someone who has seen my article on socks, and wants to know “how you got your boots to look like that”, in reference to this picture:

A lot of guys want a grungy looking pair of boots like this, as evidenced by the regular calls I get for recommendations on where to buy such a boot. The sad news, however, is that you can’t buy boots like this. (Well, you probably can, but I’ll address that later).
No, a boot with a personalised worn-in, stressed leather look isn’t bought, it’s made – by you.
The Story of My Boots
When I bought these boots, they were originally intended to be worn with a suit. They are a pair of Country Road Belstone Dress Boots (no longer in production), and when new looked similar to this:

Oh, the joy of taking something beautiful and making it a beautiful mess.
I have a tendency, with just about everything that I have ever owned, to be careful, delicate and to take impeccable care of them. When I buy a new pair of shoes, or a laptop, or an SLR – or anything for that matter – I spend the first week treating them like the delicate babies that they are. I make sure not to put them near any hot liquids; I make sure that when I’m using them, I treat them with respect; and I make sure they’re always put away when I’m done with them.
Historically, this usually lasts around a week and a half, after which I generally begin to disregard their care completely, treating them as though they are just like the rest of my scarcely-cared-for possessions. Every time I acquire something new, I convince myself that I can change. “This time, it will be different. I’m gonna take such good care of this thing. In fact, it’s going to revolutionise the way I take care of everything. Watch out, old stuff, from now on I’m gonna take amazing care of you as well.”
However, despite my best efforts, the level of care I give to my possession usually follows this graph:

I have long-since resigned myself to the fact that I, simply, am not a man who enjoys having things that are impeccably cared for. I don’t want jeans that look crisp and fresh and have never been worn; I don’t want a car that I polish every time a passer-by so much as looks at it; and I don’t want boots that look pristine. I like things with character; things that looks like they’ve been places. Or, at least, this is what I tell myself to alleviate the need for me to take care of what I own.
But I digress. Back to the boots.

The answer to the original question, of how I made my boots look the way they do, is quite simple: I don’t take care of them. I bought them a size down, so that they would be tight on my foot without me having to do up the laces. I never once used a shoe horn to get into them, degrading my daily attempts at getting these boots onto my feet to a battle between gravity, friction and sheer willpower. I run in them, I jump in them, I live in them. Quite simply, you get a pair of boots that look grungy, distressed and well worn-in by accepting the fact that clothes are functional things; they are not made to be kept in vacuum-sealed vats that keeps them in mint condition forever.

Imitators Beware
The reason the distressing and wearing-in of these boots worked so well is because they are, without a doubt, high quality, well-made boots. Leather like this breathes; it constantly changes and molds itself to its wearer. Once you break in a pair of leather shoes, they become personal, and will never fit anyone else as well as they fit you.
Moreover, as I mentioned previously, there may be places where you can buy pieces that have been designed to look as though they have been worn in by the user. These can look great, but will never look as good as the genuine article.
The satisfaction of having something that is really well-worn and distressed is that you did it yourself, and it is unique to you.