Three things matter when you’re thinking about how to wear socks and shoes with your clothes: shape of shoe, material of shoe, fabric of sock.

I will almost always tell you that a wool sock (often in grey) goes best with whatever shoe you’re wearing unless it’s suede in which case, thin socks — actual stockings or a very fine knit are an unexpected and fresh-feeling solution.

The downside with very fine knit socks is that they’re likely to tear and quickly, so I tend to wear stockings. The other time to opt-out of wool socks and go for something thin is when your shoe is a strappy sandal.

Socks and sandals have become the most interesting solution to the ongoing, cold-weather problem of shoes sucking with pants. Something happens that makes the combo feel stale and I have spent more time than I should feel proud to admit considering what it is.

Lately, I have been thinking that it’s the combination of jacket/pants/shoes that makes what would seem like such a simple and obvious and easy-to-like pairing rub up against me uncomfortably. Like it’s too done-up or something, reads too one-note. Too simple, too formal, too obvious. Sneakers were a solve that worked for years to loosen up a formal coat, or soften a really structured one, but that combination has become so ubiquitous that it reads just as one-note. A shoe with a rubber sole (think a Birkenstock clog, or these) does something more dynamic and a boot like this one could be an answer, but that would require I buy something new, which maybe I will, but tbh, right now, it feels so much better to try to solve the problem with existing variables.

What makes a flat sandal good to wear in the Fall?

I’ve been thinking about this a bit because I have been wearing these, but something is off about them. They’re a little too flimsy perhaps. I think the key is that the top of shoe covers enough of the foot to make the sock look like it’s buckled in (which is accomplished here). You get that from an ankle strap that crosses before the arch that connects your foot to your leg on the top of your foot.

But then the sole — it has to be more durable, I think. Not necessarily chunkier, but of more substance. Like this one. But then the top half here is possibly too naked, so we’re looking for a cross between examples A and B.

A fisherman shoe is a great negotiation but for something even more sandal-y, think more like these. Or, ironically, these.

These are fisherman shoes, but also kind of sandals, and seem so out of left field away from their context (a rocky European beach?) that I think they work.

When you’re focusing specifically on the sandals, they, too, will almost always work best with wool socks unless you’re wearing strappy heels (or a short skirt/dress with tights).

Though tbh, wool works here too, but stockings look more interesting, especially if you’re wearing your strappy sandals with jeans/informal pants (like the khakis a few above).

If the sandals have platforms or just feature a more pronounced sole (like these, rendered in a pretty rigid leather too, or even these which work because they’re metallic), wool meets the weightiness of the shoe right where it wants to be met.

With a sandal akin to Birkenstocks (why do I love these?) or, actually, with kitten heel slingbacks (Chanel’s original idea), camp socks are a fun option.

Just note that they add an element of casualness to the outfit, which you can use to your advantage to pair with a suit or something else that’s fancy that you either want to dress down significantly (Birkenstocks) or lightly temper (kitten heels).

Then with loafers/brogues: this one’s the easiest because it doesn’t really matter. Any sock is going to look fine for the most part. We’ve already established that suede looks great — modern and unexpected, with a pair of stockings but then leather or velvet or calf hair (?) loafers work better with wool or cotton socks.

I like the contrast of a semi sport sock with a shoe like, say, this. On average, I actually don’t often wear loafers even though I love them because I can’t quite figure out how to look like me in them. The closest I’ve come to feel good is when I use the socks to create a stark contrast:

Recently also saw a picture somewhere of a woman in khaki slacks, with yellow socks, a brown button-down shirt, and something over her shoulders. It struck me because it was so obvious that she is not the ~kiNd oF pErSon~ who wears slacks and sweaters over her shoulders. You can offset the uptightness of the vibe by leaving your hair messy, or wearing kooky sunglasses — just breaking a “rule” in one or two other places.

Flats

If you’re wearing ballet flats, lately I find that if they’re satin/silk, or honestly, even if they’re not — if they just look like proper ballet shoes, they look great with thick wool. This is probably (definitely) a function of the way Miuccia Prada showed hers on the Miu Miu runway, which exudes a big off-duty ballet dancer energy.

I’d filter velvet (and satin!) mary janes through the same funnel.

If your flats are any fabric though really — maybe canvas or velvet, silk or satin, suede, and as a basic principle, they are supple, wool creates the most interesting contrast. It’s the soft shoe (use these as your litmus test for least soft) paired with a sock you would usually think to wear with a really structured shoe that creates this effect.

With more structured flats — Mary Janes like this or ballet flats like the ones that Chanel makes, I say go for a finer fabric for your sock. Bonded wool: fine, textured cotton: cool.

But why are we taking about this at all?

Because socks are cozy as hell.

Jeans and boots get boring quickly and it’s a pretty seductive proposition to entertain that how you pair your socks with shoes — which socks you choose, which shoes you choose — can say so much within such a small quadrant of your whole. You have barely scratched the surface of outfit yet! And to this point, how relieving.

Go on, recover the navy and black and grey and brown stuff you lived in last winter. Same you, just more personality now.