Dear Ralph,

I’ve often said that clothes don’t just tell us who we are; they simultaneously tell us who we want to be and who we can never be. This is never more apparent than in the early stages of starting to dress. For those of us fortunate and unfortunate enough to have learned to dress through the Internet, where forums take the place of a discerning father and Instagram ‘likes’ take the place of the doting mother telling you how sweet you look, these growing pains must be particularly acute. Ralph, this was me.

Not only was I confronted with a staggering array of images of intensely styled men who seem to have no other purpose in life than to be photographed looking great, but there is a cacophony of experts who seem to have a direct line on the proper way of doing everything – from buttoning a vest to expounding on wool weights. Things that would have been learnt over a lifetime of dressing are condensed into listicles with the answer to all-that-ails-you never less than an online retail click away.

It is bewilderingly easy to find good style, and yet it seems that dressing well – outside of those pixel-streams-and-dreams that are at once so inspiring and infuriating – is very rare. This has been amplified for me in the way that we are able to observe trends in almost real time, able to see ideas and garments flit across screens before we see them in the streets. My distrust of the Internet and fads that gestate there is so deep that I would probably characterize myself as not having style, but having deep style prejudice. In short, I hate more clothing than I love.

And I think out of all the clothing I hate most, there is a special circle of hell reserved for the mistakes I made when I was first getting interested in dressing. There were more than a few missteps, but none that have been as hard to escape as fancy socks. They seemed to explode right around the time I started caring about how I looked – and they were an easy and affordable way to scream extravagance. I loved them. Lacking self-awareness, I cast aspersion at the sad man in the black, white or grey tube sock, wondering how any one could fail to have a bright pop of colour flash between shoe and cuff? Only later would I realize that these men weren’t spurning colour and style, they merely didn’t think their ankles had anything to say about who they were. And they were probably right.

As the fancy sock trend continued to colonize the feet of everyone, it was impossible to ride the subway without seeing some beyond-average be-suited banker, from the most well-appointed to the rubber-sole square-toed shoe-wearing variety, rocking statement socks.

There were so many statement socks around that the statement was merely one of sheepish uniformity.

But once I had sauntered into the world of cotton candy-coloured pink stripes and fluorescent argyles, could I really go back? I found out quite quickly that the answer was no. I went through a phase of wearing single-colour socks from Uniqlo, but it wasn’t long before I was back at your sock section grabbing any garish pair that was Navajo-patterned or decked out with an American flag. So when I saw these, how could I resist?

They managed to combine the simplicity of a single colour I had been hungering for, with a special bit of flash and an over-the-top show of conspicuous consumption in the herd of ponies that thundered across my ankle.

Curiously, another ankle-related trend that was insurgent when I first got interested in dressing was the sockless dress shoe. This has always seemed just gross to me, not to mention that my extremely delicate skin can’t even tolerate bare contact with my Birkenstocks. But the world of menswear was flooded with articles on how to master this trend that advocated powders and cedar foot trees and not wearing the same pair of shoes two days in a row. It seems odd that the ankle would have been the locus of so much consternation and know-how right around the time I started trawling the online menswear universe, but there you go.

I think you can probably tell that my relationship with clothes is oddly tethered to my relationship with the Internet. And I bet you can probably tell already that it is always a little bit fraught and ambiguous. Because the Internet is so overwhelmed with amateur opinions and such a vast array of images, it can be used to do nothing more than confirm our own odd impulses – impulses I am more and more inclined to follow. So for example, when I decided that I was going to wear those Birkenstocks with socks (and before you ask, yes, they were statement socks) I just had to see this picture of you to know that it was ok. And when someone inevitably chastised me for breaking the ultimate-average-persons-cardinal-rule-of-style* I smiled. The Internet had told me I was ok, even if I looked like an asshole.

Best,

S

* These are “rules” that always seem to get thrown in your face by the least stylish people imaginable, but who somehow feel compelled to point out that you’re wearing white jeans after Labour Day. It’s sort of like, how do you know that but you don’t realize that I’m never not going to wear white jeans so just fucking deal with it!