Q and Answer
Chris S. writes:
What considerations are necessary in the cuff/sock/shoe colour/pattern decsisionmaking flowchart?
A good question, Chris.
We can start with this: gym socks are for gym shoes.  If you’re wearing basketball sneakers, you’re probably off to play basketball, and you should wear athletic socks to do so.  Same goes for other athletic endeavors.  I buy my gym socks at Costco, and I always buy the same kind so I don’t have to worry about losing one in the wash.
For casual wear, gym socks are dicier, but most padded athletic shoes would look silly with any socks but gym socks.  (Excepted: the simplest classic canvas and leather sneakers are usually more suited to a finer colored sock.)  If you’re wearing shorts and athletic shoes, no-show athletic socks (the kind that encircle the lowest bit of your ankle) are the most appropriate.
Once you’re wearing proper shoes, the basic rule is to match your socks, more or less, to your pants.  The basic principle behind this is that you’d rather lengthen the appearance of your legs than the appearance of your shoes.
In dress situations, you should never show bare leg.  That means that over-the-calf dress socks are best - you can buy them at most reputable men’s stores, though shorter socks are the norm.  I’ve found great pairs at great prices at the Nordstrom Rack with some regularity.  You can also find solid quality plain men’s dress socks (Gold Toes, for example) at warehouse stores like Costco.  A few pairs of plain charcoal grey and a few pairs of navy will build the foundation of your sock wardrobe.
We’re big supporters of colorful and patterned socks, generally, but stay away from novelty socks.  Argyle is a wonderful choice, with the color pallette varying by season, though we would be disinclined to pair argyle with a suit.  Obviously, too, the color, weight and feel of the sock should be consonant with the rest of your outfit, particularly your shoes and pants.  Patterned socks can be quite nice with casual pants and an odd jacket.  We’ve had good luck with sock sales at Banana Republic, which often get down to $2 or $3 per pair in-store.  These usually won’t be very tall, but that’s less important in a more casual context.
Bright socks are wonderful, but they are most effective when used as an accent in an otherwise conservatively styled outfit.  Perhaps purple socks with a navy suit and dark shoes pick out a color in your necktie, perhaps they’re just fun.  But that’s Advanced Placement dressing.  Get your no-skin-showing, no-gym-socks game tight before you start in on stuff like that.
And no socks?  We’re no Sartorialist, but we’re fine with that when the weather’s warm.  We do prefer loafer or “no show” socks, which will protect your shoes a bit from sweat and your feet a bit from blisters.

Q and Answer

Chris S. writes:

What considerations are necessary in the cuff/sock/shoe colour/pattern decsisionmaking flowchart?

A good question, Chris.

We can start with this: gym socks are for gym shoes.  If you’re wearing basketball sneakers, you’re probably off to play basketball, and you should wear athletic socks to do so.  Same goes for other athletic endeavors.  I buy my gym socks at Costco, and I always buy the same kind so I don’t have to worry about losing one in the wash.

For casual wear, gym socks are dicier, but most padded athletic shoes would look silly with any socks but gym socks.  (Excepted: the simplest classic canvas and leather sneakers are usually more suited to a finer colored sock.)  If you’re wearing shorts and athletic shoes, no-show athletic socks (the kind that encircle the lowest bit of your ankle) are the most appropriate.

Once you’re wearing proper shoes, the basic rule is to match your socks, more or less, to your pants.  The basic principle behind this is that you’d rather lengthen the appearance of your legs than the appearance of your shoes.

In dress situations, you should never show bare leg.  That means that over-the-calf dress socks are best - you can buy them at most reputable men’s stores, though shorter socks are the norm.  I’ve found great pairs at great prices at the Nordstrom Rack with some regularity.  You can also find solid quality plain men’s dress socks (Gold Toes, for example) at warehouse stores like Costco.  A few pairs of plain charcoal grey and a few pairs of navy will build the foundation of your sock wardrobe.

We’re big supporters of colorful and patterned socks, generally, but stay away from novelty socks.  Argyle is a wonderful choice, with the color pallette varying by season, though we would be disinclined to pair argyle with a suit.  Obviously, too, the color, weight and feel of the sock should be consonant with the rest of your outfit, particularly your shoes and pants.  Patterned socks can be quite nice with casual pants and an odd jacket.  We’ve had good luck with sock sales at Banana Republic, which often get down to $2 or $3 per pair in-store.  These usually won’t be very tall, but that’s less important in a more casual context.

Bright socks are wonderful, but they are most effective when used as an accent in an otherwise conservatively styled outfit.  Perhaps purple socks with a navy suit and dark shoes pick out a color in your necktie, perhaps they’re just fun.  But that’s Advanced Placement dressing.  Get your no-skin-showing, no-gym-socks game tight before you start in on stuff like that.

And no socks?  We’re no Sartorialist, but we’re fine with that when the weather’s warm.  We do prefer loafer or “no show” socks, which will protect your shoes a bit from sweat and your feet a bit from blisters.