Port Starboard Socks*

these "rules" are always nonsensical. "short sleeved button-up shirts are always bad." "always match socks to shoes." "here's a color chart for how to combine pants and shirts."

any time you read something like this, you can completely disregard it bc it has no context pic.twitter.com/YVyYESs77Q

— derek guy (@dieworkwear) May 8, 2026

Which led to this:

To break this down:

The rule the person stated below is not even the correct "rule." The "rule," if there's even a rule, is that your socks should match your trousers. Barring that, they should be navy.

Where does this "rule" come from? It comes from the first half of the 20th… https://t.co/H6uW3CdZdZ

— derek guy (@dieworkwear) May 8, 2026

To break this down:

The rule the person stated below is not even the correct "rule." The "rule," if there's even a rule, is that your socks should match your trousers. Barring that, they should be navy.

Where does this "rule" come from? It comes from the first half of the 20th century, when much of Western male dress was shaped by the ruling class, who, at the time, still wore tailored clothing. By ruling class, I mean groups such as British aristocrats, Italian industrialists, and American WASPs who could trace their lineage back to the Mayflower.

For people in this group, proper sock choice fell into one of two categories. The first is that the socks should match the trousers: gray trousers with gray socks, tan trousers with tan socks, etc. Alternatively, navy socks were always considered correct with everything except black trousers, which required black socks.

Of course, some people broke this rule in cheeky ways, such as wearing pale lemon yellow socks with khaki chinos to add a bit of unexpected color. But the aforementioned two pairings constituted the general "rule."

When people state this as a "rule," they are trying to universalize something that was once subjective. In other words, they are trying to add a certain logic to something once practiced by the ruling class. So we invent a certain logic to this practice, such as saying wearing socks that match your trousers elongates your leg line. While this may be true (even if not for the navy sock), what we're really trying to do is make a cultural practice seem rational and scientific. This can be insidious when it applies to the practices and habits of the ruling class, because you are framing a subjective cultural practice as logically superior.

But regardless, it's no longer the case that British aristocrats, Italian industrialists, and American WASPs (Old Money) dictate the proper ways of dressing and speaking for everyone. There are plenty of groups that dress in ways that are either opposed to these groups (e.g., punks) or have nothing to do with them (e.g., avant-garde). Many of these groups possess cultural capital, which gives their style an "aura."

Therefore, you can't universalize this rule without first stating the context. Are you trying to dress like Prince Charles in 1980? Or Sid Vicious? If the latter, then the idea of matching socks to trousers makes no sense, as that's not how socks were worn in that particular group.

There's an entire cottage industry online of people proclaiming certain "style rules." "Men shouldn't wear shorts." "Here's how shirts should fit." "Here are the best color combinations." If you absorb all this advice, you end up with a very generic aesthetic, similar to how video game designers dress characters in The Sims.

IMO, if you want to figure out how to wear socks, you should identify a certain segment of culture that inspires you, whether historical or contemporary, and learn the language of that aesthetic.

About fifteen years ago, talking about this stuff was easier online because people were segmented into style communities — classic tailoring, workwear, streetwear, avant-garde — each group huddled around certain forums and blogs. These communities gave the discussions context. If you were in a community obsessed with how to dress like a 1960s Ivy League student, then no one would have to spell out the intention, as it was assumed. This made discussing the "rules" easier.

But on Twitter, there is no consensus. Therefore, it's not reasonable to proclaim things like "wear this sock with these shoes" or "this is how all pants should fit." Everything depends on how you want to dress.

When I was young I wore nothing but blue jeans. Now I am old, and wear nothing but blue jeans. When I was very young, I wore only white socks (except to church on Sunday). Now I wear only navy socks (usually with boots, so who cares?). But for a brief time, I wore the gift of neon green and yellow socks. 

They were a gift from friends who knew me well. I quickly mixed them, wearing one yellow and one green. And when people noticed, I said yes, and I have another pair like them at home.

I haven’t thought of that in over 50 years.

No, my sense of humor, and self-respect, haven’t changed since then. We are who we are.

*It’s a McGarrigle Sisters song.